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I'm 25 years old and I am lost
309 points by mlost on Aug 14, 2014 | hide | past | web | favorite | 264 comments
I co-founded a startup couple of years back which got acquired recently. Even though it was termed an acquisition, it was really an acqui-hire. When people congratulate me on that, I know in my heart that it's not true and it doesn't really make me happy.

Now, I've quit my job at that company because I just couldn't work there any longer. And am trying to figure out what to do next.

I know for a fact that I want to run my own business and attain financial freedom but I can't risk another startup at this moment because: 1. Startups are tough and I am afraid 2. I have a few financial responsibilities towards my family which I have to take care of.

Thus, I have picked up another job which I'll join in a few weeks. It is not in a very 'sexy' or 'trendy' industry and I have no idea where it is going to take me in two years.

What do you do when you believe that you can do great things but something that you have no control over is holding you back? You believe that you are good at what you do and are meant for great things but you have to do your job even though it doesn't do justice to your capabilities. How do you cope with that? Seeing your future as an underachiever pains you. What do you do?

In the course of trying to figure it out, I spoke to my friends about this, I realised that most of them are going through the same thing. But they haven't figured out how to deal with it. I don't know if this is what they call a quarter-life crisis.

Thus, this is as much a distress call as it is a rant. And not having anyone else to turn to, I am posting it here at HN assuming that this is not just a problem for a handful of people but a general problem for people who believe in their ability to do great things (whether it is true or not is irrelevant to them).

The questions I posed here aren't the only ones I have in my mind. But, I hope I have been able to convey the message. Any help would be much appreciated. Thanks!




Why do you want to do great things? Seriously, dig into it. When I ask a lot of people in startups this question and dig long enough, it comes down to money-- they want to be rich, they want to be free.

Fact: I've met these rich/free people and they are largely working their asses off to get more rich (and presumably more free?). The ones who make it (largely) LOVE THE GAME. The few who get rich somehow but don't actually love the game of getting rich are listlessly complaining about being unhappy.

You don't love the game, it seems. The way to be happy/satisfied is to find the game that you love or learn to love the game you're playing. The latter is often what to focus on-- there people with much less interesting jobs that are satisfied with them. Whatever job you have, figure out how to be freakin' awesome at it and opportunities fall into your lap- trust me. Or be the guy who gets by, can't be happy, is always looking out the window.

All that said, don't settle for a shitty job. Get one where you're surrounded by people who impress you in an industry/market that has potential. That's where you'll find your next co-founder.

If you've got great ideas, start side projects. They turn into businesses all the time.

Reduce your burn rate ruthlessly and save $. Seriously, your car/house/clothes are too nice, and you have them because society makes you feel less successful if you don't. Happiness and stuff have virtually no correlation. Get to the point where you're downright smug about your burn rate. Smirk at people who drive BMWs.

Remember that a million years of evolution has made humanity naturally discontent-- do you think happiness/contentedness is a survival trait? Add to that the external pressure of peers who make it big, do "great things", and the river of marketing telling you that you need fancier watches, shinier cars, the newest iPhone. Being happy/content takes smarts and discipline that most people simply can't manage. Be one of the ones who can.


> Seriously, your car/house/clothes are too nice, and you have them because society makes you feel less successful if you don't.

Stuff makes me happy. Moving from a tiny apartment with a small everything to a spacious house made me much happier. It's comfortable. I now have a wonderful kitchen to cook, which I enjoy doing, that I just couldn't do as well before. I have a view out my large bay windows. It's great.

Driving a nice car is awesome, especially if you commute longer distances or like road trips. I enjoy a comfortable luxury sedan with power.

I'm much happier with nice things. Society isn't telling me I like my large flat screen tv. I am because it looks stunning on my wall.

I agree with what others say here about debt though. Don't go into debt to buy yourself a bunch of crap you don't need.


What really makes you happy is the experiences the stuff affords you. Movies and sports are enjoyable. staring at a nicely mounted TV that isn't showing any content is a fleeting novelty. The kitchen isn't enjoyable on its own. It's only wonderful because it allows you the experience of cooking. A two year old Infiniti G37 the same price as a new Honda Accord, but it comes with all wheel drive, and 330hp. Maybe its not the same status symbol as a BMW or Mercedes, but you'll have plenty of time to look at those two cars in your rearview mirror.

I think this gets to the heart of form vs. function. Don't buy things because they look cool on your wall, or in your driveway, or in your kitchen. Buy things that make it enjoyable to watch movies, comfortable to drive on long trips, and enjoyable to cook with.

Favor function over form.


You're probably about as happy as you were with less/different stuff (unless you were poor enough to be anxious about making ends meet), but maybe you're unusual. http://en.wikipedia.org/wiki/Hedonic_treadmill

On average, happiness peaks at age 20, declines until age 50, and then starts to inch up again ( http://www.economist.com/node/17722567 ).


A lot of the decline in happiness is related to starting a family. Average happiness is lower with kids (there are much higher peaks because of them, but also lower lows http://www.ted.com/talks/rufus_griscom_alisa_volkman_let_s_t...) because of all the chaos related to kids.


Average happiness sounds absolutely preposterous.


What about it sounds preposterous? Certainly happiness isn't easy to measure, but it seems like asking "On a scale of 1-10, how happy are you with your life?"(or something like it) is a really important question... And as a society, we'd like that number to be broadly high and climbing as we move forward... No?


I mean judging your own happiness against the mean or median of 300 million people who live in vastly different locations and climates, with different population densities, prevalence of poverty and opportunity, availability of social services, access to education and medical services, etc, is a meaningless exercise.


I don't think anyone was comparing happiness against other people here. It's happiness against yourself. Are you happier now than you were last year? Average happiness in this context doesn't mean the average happiness of the world, or a community. It's just how you would deem the average happiness of your life at a certain era. Yesterday I had a terrible day, but I would still say I am happy on average, I just was not happy on that particular day.


Amen. I wish I had realized at a younger age the importance of investing in nice clothes. Not only does it make a person more confident, it is literally the difference in many cases between getting a good job and a spouse and being totally ignored. Despite what your teachers and parents told you growing up, dressing well is critical to success.

Besides, why does it even matter if we enjoy something nice because society tells us it should make us happier? Yes, when I go out I DO want society to notice me and reward me. That's the reality of life- people have more respect for those who present themselves well. If the respect of others is something we value, then it makes sense to do what we can to gain that respect. Pretending that you're somehow above the rules of society is both naive and counterproductive. The bottom line is that if it makes us happier or more successful then it was a good investment.


"when I go out I DO want society to notice me and reward me"

reward you for what exactly?


Manipulating their perception of you by taking advantage of social cues.

I'm fine with people wanting to dress nicely as long as they realize it's total bullshit that people are judged by their clothes, but want to take advantage of it anyway. It's just human hacking.

I do feel a bit bad when dressing nicely, because I worry that I am contributing to the continuation of the practice of judging people by their clothing.


I don't understand this line of reasoning. When you go on a date, do you pick up the check for your SO? When you go to a bar do you buy a drink for your friends occasionally? Surely you'd rather save that money, but you have to "hack" society's rules so that they will like you.

Maybe you "hack" HR policies that reinforce the use of proper grammar by refining your resume. Or hold the door open for somebody who is behind you when you'd rather just be on your way. Society is full of norms and social cues, and I don't think it's deception to control your behavior to align yourself with them. To not do so out of some notion that we should combat human instinct is rather naive.

I think Benjamin Franklin put it best: "Eat to please thyself, but dress to please others."


It's human hacking when you recognize that the cues you're leveraging are inane and meaningless. Many people believe that the cues themselves are somehow meaningful or significant, and get caught up in the act.

How, exactly, is it naive to try to overcome illogical biases and ways of being manipulated?


Well I guess the fundamental disagreement is that I don't think these biases are best classified as illogical. Yes, if you are being completely objective, two job applicants should be judged solely on the basis of their qualifications. Yet, the one who is more polished is going to get the job ten times out of ten. Perception is simply a fundamental part of decision making, and I think the naivety lies in thinking that any of us are above catering to that perception or that we can somehow convince people to not rely on their perceptions.


It's not total bullshit. It's grounded in evolutionary psychology. We like people who are attractive because that shows that they have good genes and are therefor worth either a) mating with, or b) keeping around for other reasons. Nice clothes help make a good impression if you're in relatively good shape and your body is well proportioned. If you're 100lbs overweight, that tailored tux just makes you look like a penguin.


So you're telling me it's not total bullshit to hire someone for a coding job based on how attractive they are/seem?

Just because we have evolved heuristics for something doesn't mean those heuristics aren't stupid and irrelevant in some contexts.


"Besides, why does it even matter if we enjoy something nice because society tells us it should make us happier?"

If you REALLY enjoy it, that's great. But most of the research on the relationship between stuff/trappings and happiness finds that there isn't really any correlation. You're trained by evolution, society, and marketers to want these things, but (unless you're anomalous), they don't impact your happiness.

Meanwhile, 20% of households spend more than they make, unemployed millennials spend ~$800/month on discretionary spending, and half of american households save no money at all.


> people have more respect for those who present themselves well

If presenting yourself well means driving a luxury car, or having an expensive home, then no, I don't respect these people more than others. There are no such 'rules of society' except for materialistic people.


The subconscious mind is a very powerful thing. Even if you say you don't respect those people more than others, it doesn't mean that you don't.


Generally I respect people less for ostentatious displays of wealth (though a significant proportion of them have earned their money doing things I respect despite the sports car and bedrooms that outnumber even the guests).

Inverse snobbery is a very powerful thing too ;) But I'm probably an outlier


This is like saying "I don't respond to advertising." It sounds good in theory but pretty much falls flat on its face in reality.


Dressing nice, clean and decent is different from dressing according to the latest fashion trends. Get people to respect you for who you are, if they don't, Do you want to care about them ? do you want such people to dictate your life?


But all pleasure comes with pain/attachment/fear, the two are inseperable.

Now your decisions in life are dependent on making sure you still have those comforts that make you happy. You will miss out on adventures because you are scared that you won't have a comfy kitchen. What you own owns you too.


What about the hedonic treadmill? You say you're happy with your big TV, but wouldn't you be even happier with a still bigger TV? You like your luxury sedan for commuting, but wouldn't you be even happier if you had a Ferrari to drive on the weekends?


I like to think of it as a recursive function instead of a treadmill.

You get a TV that fits your house. But you want a bigger house. Then, the TV seems too small, the house seems bare, and your car is not nice enough for the neighbhorhood. So you get a bigger TV and fancier car.

Now, you have too much stuff in your house, it is too small again! So, you get a bigger house...


Yeah but what's the termination condition?


Death.


On the other hand, how much of your time are you willing to spend for that house, car, and TV? Because time is the commodity you're selling.


Despite enjoying my work for the most part, I'm willing to trade less than 25% of my time.

Typical hours worked in a year: 2000

52 weeks - 2 weeks vacation/sick/holiday (most have more) * 40 =2000 hrs

2000 / (365*24)=.228

Seems fair.


Probably ought to math that out with waking hours. And add in your commute. And 2000 hours = 38/week. I don't know many folks who work that little, though I supposed vacation days ought to factor into it (the average american takes 4.1). Let's nudge it up to 2400 or so.

2400 hours worked + 260 hours commuting (US avg. is 25.5min - probably average higher in startup cities?) Let's say 17 waking hours (even though people who get 7 hours of sleep are proven to be less effective on a lot of fronts, it's certainly plenty common).

(edit: average hours worked/week in US for salaried workers is 46: http://www.prdaily.com/Main/Articles/Most_employed_Americans...)

2660 / 365*17 = 43%


Why 2400 hours - that's 46 hours a week! Maybe a founder is working that much, but generally they over-work and it's proven more than the tenuous 7 hours of sleep a night thing that 45+ hours a week is bad. e.g. http://legacy.igda.org/why-crunch-modes-doesnt-work-six-less... etc. I think it's totally reasonable to work 45+ hours a week in your first year or maybe even 2. But after 3 if you're working 45+ hours a week you have a major, major problem.

Most average people are expected to work 2080 or 2087 hours a year. Seems a little disingenuous to bump it all the way to 2400 - if you're working over 45 hours a week on average you're over-working, which is far worse for your health.

Even still, using the 17 hour mark and 2087 hours it's 33.6%.


Sorry, should have referenced a source-- I edited my comment to include the source for the 46 (which is the exact average for salaried workers in the US).


That's crazy. I don't know why people do that :-(

I don't know that I would take their numbers as gospel but to be fair in the tech industry it's probably more accurate when I think of it.


I don't understand it either. I negotiated my salary for 37.5 hours a week of work. I'm happy to work a bit more when the work is interesting, but I'm going to show up late or leave early the next few days to make up for it. Alternatively, you can pay me more.

That's the deal. My work/bosses are happy with it. My co-workers seem to begrudge that they're freely giving up extra time and I'm not. I keep suggesting they stop doing that...


House can be worth a lot of time investment. It is, after all, where you live every day.

How about food? I would love to invest zero time into food, but I have to eat.


Soylent? I haven't got my shipment though.


> I'm much happier with nice things

Have you ever traveled on a shoestring in S/E Asia, Africa or South-America? I bet you're going to be a lot happier with smaller versions of your "nice things".

My second bed is part second-hand, part Ikea. My first bed was ten times as expensive. However, after some traveling I consider my second bed to be luxurious.


No thanks, a good bed and a good chair are sacred. With food, housing and all the basics covered, they should be pretty high priority. I don't understand how some people can buy a 500€ smartphone and then sleep in a shitty cheap bed.


>Stuff makes me happy

The definition of irony. Happiness will exist regardless of circumstances. No one can take it away from you. Maybe you meant, "stuff brings me pleasure"?


For your own sake, keep track of how long your happiness lasts before discontentment sets in.


I think you're confusing happiness with pride.


I'm unsure they are different for everyone.


They are. Whether everyone realises it yet or not.


Remember that a million years of evolution has made humanity naturally discontent

That about sums it up. The drive to always want more is just how humans are. If it wasn't, the human condition would never improve. However, you need to recognize it for what it is and don't let it control your own happiness.

The older I get the more I realize that doing what I want to do now is much more rewarding that doing what I think will make me happy years from now.


To be fair, if you believe in evolution, thinking of things in terms of improvement is very subjective. Evolution isn't selecting for improvement, it's selecting for survival, which may or may not be correlated with your vision of improvement. Think of cockroaches.

From a christian perspective, the natural discontent stems from the fallen nature of man. You're worldly accomplishments will never be able to satisfy that discontentment, as the two areas are unrelated.


So many straw men here...

Nobody is saying that evolution is selecting for some nebulous sense of "improvement." Reproductive success leads to traits being passed on to successive generations, and general survival is merely one precondition to reproduction. The human impulse to jockey for status is a reproductive strategy.


I really don't get this. Why do people strive to get richer??

I've chose startup grind instead of super rich Facebook jobs 3 years ago and am still living like a student and see no need to own a lot of things. Am I that "special", to me it seems completely logical to sacrifice short term rewards to be in for the long run, delayed gratification and everything.

Once I've made it, I don't see either, why I would burn myself just to have e.g. $20M instead of $10M. wtf?


That line sounds nice, but I don't think it makes sense if you break it down. You are basically saying that discontent people reproduce more than content people. Is there any evidence of that?


Historically, do you doubt that this is true? Certainly it isn't in modern times, but when we were shaped as a species? The people who worried about having enough food, a strong enough shelter, sharp enough weapons, loyal enough friends and allies-- seems like that worry would be a survival trait.


> Certainly it isn't in modern times, but when we were shaped as a species?

When discussing evolution and species, it's best to avoid the past tense. Evolution never ends, and nature is shaping us as we speak. 200,000 years ago, we wouldn't have recognized our forebears, and 200,000 years from now, we won't recognize our descendants.


Basically yes. It is a giant assumption with no actual science backing it up. Maybe there is some science that I am not aware of. So many evolutionary statements get a free pass in this regard. Someone says it, and now it is so. Where is the skepticism?


I think he's saying that content people lie around sunning themselves and get eaten by lions, or fail to store food for the winter, or whatever.


I love that first line. In my opinion it neatly sums up a few things about human behaviour.


$ is freedom, but so is lack of debt.

Zero debt + $ = great freedom.

The edge of modern Western society (those not part of the main rat race) is a place where you can truly be free and happy, but you'll be seen as fringe.

Never go into debt. Eat beans and rice. Work summer jobs as a river boat guide. Write poems. Watch the stars. Help others find peace.

Just be true to yourself and don't let modern society set expectations or guide your life.


Financial independence is something that's been purposefully pushed to the fringe of society. We've got very few people who fit the category of subsistence farmers in the West even though we have the potential for their to be a lot.

The main reason why businesses don't grow is regularly cited as the founder/owner refusing to give up control and micromanaging. One person can only micromanage so much.


Is "subsistence farmer" a metaphor for financially independent? Otherwise I don't see why people would want to be subsistence farmers.


It's good to follow one's dreams. But there is a line between living in the moment, on one side, and not planning for the future, on the other. Youngsters are in for a rough ride later on if they are too romantic about practicalities and do not take well-conceived steps towards financial independence later in life. This is true whether they have it in them to become superstars or are simply hoping to do what they do well.


>Never go into debt.

This is bad advice. Sure, don't go into debt that you can't properly service, but I've made some good money that started out as debt (large investments, etc).


You had luck on your side though. Not everyone does.


Sure, there was some luck (there was also some educated guesses involved) but I'm simply arguing against use of the word "never". Debt can be good if it is the right kind of debt.


Agreed on never. I recommend house debt, where there isn't enough cash and there's no obvious bubble, only because houses are almost sure to appreciate given inevitable population growth.


To emphasize the last paragraph: You don't become rich by obtaining lots of money. You get rich by saving lots of money. You can become financially independent before you turn 40 making $50k/year at a 9-5. You don't need to start a company, or change the world. You just need to get to a point where your investment income is equal to your expenses, and the only way to do that is by limiting your expenses.


You can become financially independent with considerably less money. I know someone who at 30 sold up, moved way into the boonies on a hobby farm. He's got enough in the bank that he can live off the interest.

Now he just potters around his farm. Grows all his own vegetables and fruit, raises chickens and cows and is getting "richer" by not spending all his interest. So him and his wife get to spend all their free time with their kids, which is what they wanted.

The reason most people will never become rich is simply because they increase their expenses the more they make.


"The reason most people will never become rich is simply because they increase their expenses the more they make."

Words of wisdom right there.

I think there is an underlying difficulty there. There's usually at least a few of your friends who also are financially well off and growing. Or perhaps your circle starts to include more well off people as you become wealthier. There is an endless social competitive pressure to be at or near the top of your peers, and the metric for measuring that is how much you own and spend. Leaving society to go on a farm, however awesome and healthy that may be, is breaking the vicious cycle that you may have been in for much of your life. And that is incredibly difficult.


With bank interest rates at < 1%, having $2 million in the bank earns < $20K/yr. He must be rich or ultra frugal.


That's why you don't put $2 million in a bank account.

This guy retired on $800k raising a family of 3 with $25k/year of passive income: http://www.mrmoneymustache.com/2012/01/13/the-shockingly-sim...


When people refer to interest they often are referring to investment gains, rather than actual bank interest.

Specifically, it is generally assumed that a diversified investment portfolio will earn ~4% after inflation on average, and by spending 4% of your portfolio balance at any time you are reasonably safe in the assumption that your money will not run out. At 3% it's all but assured that your money will not run out. These are conservative assumptions and take into account the fact that in any given year your investment performance could be significantly less than 4%


Yes, a diversified investment portfolio could perform like that in the past, when the gov't wasn't minimizing interest rates. Nowadays only with much greater risk of loss of principal.


The S&P 500 is up about 7% annually over the last 5 years, with inflation never exceeding 3% over that period. That leaves a calm 4% real return on one of the less risky investment options.


How has it done over 10 years? And that's with mega gov't help.


About the same... Over 10 years the S&P is up 83.6% excluding dividends. Going back to July so month to month comparisons are valid it looks like the annualized return is 6% excluding dividends and 8% including them.

http://dqydj.net/sp-500-return-calculator/


Agreed. With a lot of risk for that reward. The risk shows in the volatility (ups & downs) over that time, and that the gov't had to borrow several $trillion to prevent a negative return over that time.


Another option is to put the money in foreign accounts. I don't know this space at all, but interest rates at consumer banks in India are 9-12%. Even after currency exchange rates, you'd probably make >= 4%/year


That interest rate is because on average, rupee inflation has been at over 9% in the last two years, and was over 11% at the beginning of the year. http://www.tradingeconomics.com/india/inflation-cpi

If I'd opened a bank account last time I visited India, converted sterling to rupees, to saved in an Indian bank account at 12%, I'd end up less pounds than I started with.

Putting money in consumer banks in India really only makes sense if you live there.


No such thing as a free lunch, though. Plenty of people's savings went poof that way.


Why? Indian banks defaulting? Corruption/theft issues? I haven't tried this method -- just regurgitating advice other's have given me. Always thought it seemed more profitable than keeping money in US banks, and India always seemed accommodating of foreign money coming in.


For example, savers around the world were enticed by Iceland's high interest rates, and then this happened: http://en.wikipedia.org/wiki/2008%E2%80%9311_Icelandic_finan...

Turned out those savers were the suckers needed by those banks, in an attempt to remain solvent.


Forex is risky because unless you have a use for the foreign currency you are at the mercy of exchange rates. For example, INR lost 0.74% vs the USD just today.


Bank accounts are't for storing your retirement savings. Even with the current low rates you can get 3% from 20 year Treasuries. If you want more yield you'll have to take some risk, which is why diversified portfolios are always advised.


In other words you must take the risk of forgoing retirement when trying to beat inflation. In 2008 pretty much the only diversified portfolios that didn't take a huge hit were the baskets of low-risk investments.


Yes, they are financially independant to remain where they are, but they are not financially independent to do do great things, e.g. they couldn't start a company, buy a new house, send their kids to college. (except your friend became a millionaire)

This financial independence normally is temporary and normally doesn't last long. Humans crave for change, living on a pottery farm is really nice for the first 1-2 years, however, for the rest of your life? Humans are not built for that.


On the contrary, I'd argue that it's much easier for them to do those things because they have considerably more time, free capital, and flexibility than non-financially independent people.


True, you're right. Except for the college thing though. :)


But nowadays the only way your investment income will pay for your expenses is if you were rich to start with, or you take the risk of losing a big percentage of your money to earn more than 3% interest.


I'm seriously considering framing your post. It is refreshing to receive reminders that working harder to consume more products does not make us happier.


Counterpoint:

America's middle-class is increasingly eroded and the nation as a whole split into those with fuck-you money and those without.

Not having money is not a good long-term strategy as we slide into well-branded feudalism.


Not to discount the very real problem of the eroding middle class -but spending/saving habits in America are real problems. Half of Americans are saving nothing [1]. 27% of households than make over $100k/yr say the can't afford everything they need [2]. Average house size in the US has about doubled since the 60s [3].

[1] http://time.com/98152/americas-savings-city/ [2] http://www.nytimes.com/books/first/s/schor-overspent.html [3] http://www.aei-ideas.org/2014/02/todays-new-homes-are-1000-s...


I'd agree that your point is also true, and is related to mine: debt and credit are one of the strongest ropes that are being used to bind people into this system, and not carrying around debt helps a lot in being free.

Saving for saving's sake is not enough--I think it helps to divide it into "investing money so that it can 'grow' into more money" and "having enough cash in reserve to provide accounting liquidity in an emergency".

Simply hoarding gems in a mattress, for example, would not be winning strategy.


Why save? It's actually a provably bad idea to save money when the rich/government are actively undermining your savings and livelihood. Better to enjoy your money or try to actually invest it (note, not the same as saving).


> It's actually a provably bad idea to save money when the rich/government are actively undermining your savings and livelihood.

This is like arguing that it's pointless to breathe because we'll all end up dead anyway. Even in the face of governmental mischief and deliberate inflation, saving or investing money may still represent the best of competing choices.

I emphasize I'm not talking about a bank savings account -- that's really a losing proposition.


When people say save, they also mean your brokerage accounts full of index funds.


No offense, but this would kill 90% of the consumer based start ups we are all working on. Endless consumption is what has made America the best place in the world to start a business.

Just a thought.


If you're looking for a good read on some of the principles discussed in the parent, Early Retirement Extreme [1], is an excellent resource.

[1] http://www.amazon.com/dp/145360121X/?tag=oildepletiove-20


I disagree and think that people in the western world who are not starving want to do great things for other reasons which consist of: pride, ego boost, interest to face difficulties and overcome them, make history, find a goal and pursue it, mental challenge, feeling like they need to fulfill a purpose in life and many others. For me money is one of the most insignificant ones.


I want to somehow pin this post. Very well put.


THIS is why I read / love HN!


Money does correlate to happiness, so long as you have enough of it to live comfortably. Beyond that point, additional money does not increase happiness.


Amen.


There's two ways to look at this that I'll suggest, since I have a certain amount of familiarity with this.

1) You're 25 years old, and already have one acqui-hire under your belt. That's pretty impressive. Considering probably 90%? 99%? of people will never have a startup they build acquired under any circumstances, it seems weird to describe yourself as an underachiever.

There's this weird cult of young entrepreneurship, where it's implied that if you're in your 20s, you must be founding companies or you're just wasting your time.

I'll throw something out there instead - why not spend the next few years working at your day job and trying to learn how to be a better startup founder the next time you do it? Think of it like being in training for the next gig.

2) my other perspective on this:

> What do you do when you believe that you can do great things but something that you have no control over is holding you back? You believe that you are good at what you do and are meant for great things but you have to do your job even though it doesn't do justice to your capabilities.

That's called "adulthood". Sometimes you have responsibilities that limit your options or make it hard to do what you love.


"why not spend the next few years working at your day job and ..."

I realised recently that my life would be a lot better right now if I worked the so-called soul destroying corporate job because I'd have more money, work fewer hours, have less stress during work, people would expect less from me, I'd have infinitely more holidays, more work-free weekends...

Sometimes its hard to see what you've got until its gone :)

Don't get me wrong, I like being a founder and don't regret it for a minute, but when times get tough I look back and think the soul destroying corporate days were actually pretty good.

Which brings me to this: Life (usually) really is what you make of it.


Yeah, so - I/we started GridApp when I was 23. I didn't have any grand dreams about being a 20-something entrepreneur, I just came to the (accurate, as it turns out) conclusion that it was never going to be easier to completely upend my personal and professional life than it was when I was 23 - no mortgage, no SO, no debt other than student loans, no kids, etc.

When we got acquired, I assumed that I would leave as soon as I could and do it all again - but yet, I'm still here. It's interesting work, and while I miss the ability to just get things done, I find that I've been getting a lot better at dealing with problems at scale. So, for example, how DO you launch a new product to a sales and support organization with hundreds of people?

I'm not saying I'll never start a company again, because I really want to, but I'm enjoying feeling like I'm learning how to do things better next time.


I do like your titles; CEO, CTO, Chief Scientist, Director of Development, and Mr. Database.


A lot of that was an artifact of how we got started - it wasn't quite clear who would be doing what, and so other than CEO, everyone's responsibilities were pretty amorphous.

I got saddled with "chief scientist", but practically speaking it was "technical field operations and product management", which just ends up being a lot to put on a business card.


AFAIK "chief scientist" title assumes that you, or your team of scientists are doing academic research. And that you publish results of your research.

Taking a title like that, while actually not doing it is a borderline fraud. If I'll get a resume with "scientist" or "researcher" in the title, the first thing I would look at would be published academic papers. If there are none, I will not consider this resume.


Well, the origins were far more benign than "borderline fraud" - my original role was doing product research in distributed database design and performance. I gave a lot of talks and wrote a couple of (non-acaddemic) papers on how to build widely distributed database systems, focusing on Oracle RAC.

My job evolved to be more of a business-focused role, but my title did not. The intention was never to mislead, and indeed, when asked, I never claimed to be an academic.

> Taking a title like that, while actually not doing it is a borderline fraud

That seems like a strong conclusion to draw. My title now is "Product Architect", but I'm not an architect, nor do I exclusively design products.

A quick skim through Crunchbase yields:

http://www.crunchbase.com/person/jeff-hammerbacher (bright guy, not an academic)

http://www.crunchbase.com/person/bram-cohen (not an academic)

http://www.crunchbase.com/person/chris-slowe (not really an academic)

And that's in the first 10 results. "Fraud" seems strong.


So true. I have been working in a corporate job (finance!!) for 9 years. I often dream of saving my soul and working on/founding a startup. The appeal of building something, working for myself, etc is great. But, so is the regular paycheck and benefits.

On which side is the grass greener?


On the flip side, founding a company can actually give you more time back, depending on the company. I started a consulting biz last year, and have a ton more vacation, slack days by choice, evenings and weekends than I did when working my previous full time job.


How do you started it? How long it took for you to find first clients?


I was vital enough to my full time employer that I knew they'd give me some contracting to hold them over. And, I had a couple of contacts who I knew were interested in my doing some work for them.

I started planning 3 months before I gave notice. Made sure I had 6 months' savings. Formed an LLC, talked with a business attorney and CPA, and lined up projects before my quit-date. So I was basically ready to go from day 1.


> it seems weird to describe yourself as an underachiever.

It is really not that weird.

http://en.wikipedia.org/wiki/Impostor_syndrome

What I hate, however, is knowing about imposter syndrome and letting that screw with my mind. I think, "maybe I am using imposter syndrome as a way to sneakily support my ego that is only partially supported by reality. Reality does not support my ego at the inflated levels I want to believe in." But then I think - well, I suppose I have to be smart to trick myself in such a ridiculous way, and conclude I actually am smart. That leads me to think that I am actually an intellectual imposter, and it's traditional that I take that as a truth, which my ego has temporarily decided to not believe in, for certain problem kinds.

Lately, I build on top of externally developing habits - like studying, running, meditating, eating healthy, sleeping healthy, working at a normal pace, and having confidence in my own opinions about computer science, logic, mathematics, and programming. This helps me think less about how I perceive myself and how others perceive me, but I can get knocked off my horse once in a while. I just try to remind myself that it's just time wasted that I could use studying, working, or helping other people - which is more thinking about the long long term, rather than each individual achievement.


You just described my life so well. Thank you.


The next job can absolutely be used as training for your next gig. Also, the next job can be your financial foundation as you start your next gig on the side. Running a startup should not put your family's livelihood at risk. My father is an entrepreneur and frequently had several small side projects going on at any given time while I was growing up. Right now, he's focused on building up one business, but another business he built up previously is still bringing in solid income. Several great companies started as side projects while the founders were occupied with some other "real" job: GitHub, Google (perhaps debatable, but it started while the founders were full-time students), Facebook, Basecamp, and the list goes on and on. I once read James Altucher explain that he stayed at his "real" job for two years while he built up his side business. By the time he quit to work on his startup full-time, the startup was already extremely healthy with several full-time employees and enough customers to profitably pay everyone a great salary. Of course, you'll have to talk to your new employer to work out the legality of creating side projects. But if you pursue building something up on the side, you'll be joining a long tradition of entrepreneurs who have done the same, some of whom have built companies that will be remembered for centuries.


This is good advice OP. I'm 28, have co-founded three startups, first one was "acquired" for the technology for an "undisclosed sum" (we all know what that means). I used to feel a little weird about it too, particularly because it chased the splitting of my cofounder and I; ya know what though, I built that technology and it was valuable enough to one of our customers to buy it.

That is definitely more than most founders can say. Don't let startup hype get to you.

The parent commenter said something else I want to echo: take some time and learn from other leaders right now, make money, get a good emergency fund AND a "startup fund" built. Get your hands dirty in other businesses and see what they're using spreadsheets for and what they are doing repetitively -- that's where you'll (most likely) find your next product opportunity.


I don't :) What does "undisclosed sum" mean? Does it mean you got a year's salary, 10 years', or a nominal sum like $1 for the tech and a job?


I legally cannot talk about the details of the acquisition, but it usually means "not glamorous" :)

There's much more to the story, I had blogged about it but svbtle deactivated my account for no reason and is unreachable. If you're really curious about the story I'd be happy to converse privately over email.


"Think of it like being in training for the next gig."

Amazing way to put it. I'm 25 myself and this is the only reason why I'm still working for my big corp. Payed school.


The other thing is, "working for my big corp" should teach you a lot of things, including useful stuff for a startup. With much less responsibility (e.g. you're not worried about making payroll), you have the luxury of observing and thinking about it.


This is my plan as well (also 25). I want to learn from some of the best so that when I'm a bit older I have enough world experience to build something myself. Sure I could build all sorts of apps now, but that is only fraction of the work that goes into building a sustainable business.

I used to think life was a race, but I'm really enjoying the growth and learning parts.


Learning the ins and outs of some particular industry is a great way to get ideas for the next startup. Every industry has pain points, where is the pain in your new company?

Also, 'great things' can mean different things to different people. Like building a marriage and raising children. Everyone does it, so it can't really be that big of deal. Can it? Try and see...


I'm 32 and have found that my priorities have shifted over time. I had goals of running a start-up and making work optional by 35.

I've been involved in start-ups and have been a partner in a couple.

I now have 3 kids and view my 8-6 job as an athlete views game day. I seek to perform at my highest level during work hours and then try to turn it off after. I don't miss it when I'm with my kids or my wife or friends. For me, there's more to life than work/job/running a business.

I've also come to the conclusion that I have 100% certainty of improving my kids lives through spending time with them. That time doesn't scale like running a startup, but it's guaranteed to be effective. I'll take those odds over the 1 in a million of running a startup, even if it's just improving 3 lives.


But had you successfully created a startup, you would be able to spend even more time with your kids.

Furthermore, if you were actually doing something you enjoy that 8-6 time slot, 5 days a week, wouldn't be a waste of time.


> But had you successfully created a startup, you would be able to spend even more time with your kids.

What's the measure of success? Is the measure to generate or exit with enough income to spend more time with my kids? If so, that's pretty rare I think. By "more time", I assume we mean substantially more, as in, not having work a full time job and maintain current lifestyle.

That's the 1 in a million odds I'm talking about. It's not like the lottery where you find out instantly if you win or lose. It can take a decade of extremely hard work and long hours to find out if you've succeeded at that level.

> Furthermore, if you were actually doing something you enjoy that 8-6 time slot, 5 days a week, wouldn't be a waste of time.

I enjoy it greatly. I may enjoy running a start-up that is influencing millions of lives, but maybe not. The grass is often greener. My job has visible impact on hundreds of lives and I have a decent work/life balance.


> But had you successfully created a startup, you would be able to spend even more time with your kids.

Sounds like they gave it a try and it didn't work out.

> Furthermore, if you were actually doing something you enjoy that 8-6 time slot, 5 days a week, wouldn't be a waste of time.

I didn't see where they called it a waste of time or didn't enjoy it?


Nice... 3 kids at 32! Sounds like you made that your "startup" instead. Happy to hear you've decided to commit to making that successful. :-)


>meant for great things

This part of your post sticks out like a sore thumb. What "things?" How will you know when the "things" you have "done" are "great" enough? What makes you think you are "meant" for them? What does "meant" mean? Was your birth heralded by a double rainbow or something?

I'm betting that "great" is defined relative to some imagined ideal that you can never reach, or which you will constantly shift to ensure your own continuing dissatisfaction.

Decide what you want.


This makes sense to me. In a lot of way, the current generation seems to have a lot of folks suffering from 'special snowflake' syndrome. It is drilled into people at school, 'you are special! You are destined for greatness!" But the reality is that they don't tell you theat most of the great things in life are free...

A good family and children, personal happiness, friendships, love. These things make a person happy and satisfied. Even relationships I've had when waiting tables and the pride I took in doing that work was extremely satisfying (even if the hours were bad and the pay mediocre). But that was because of my attitude and goals, not because of the work.

Now, I work at a very very large software company doing interesting, challenging work and am paid well for it. Despite all my great coworkers and satisfaction in doing my job, they are not going to keep me company or be my real friends at the end of the day.

Work to live, my friend, don't live to work.


Yeah, that stuck out to me as well. Thinking like that is a sign that there may be larger issues at play here. Truly satisfied and happy people don't believe themselves to have been destined for greatness in any such manner - even though they may or may not be as "great" as anyone else. And conversely, truly "great" people, are often the benefactors of circumstance and luck more than anything else. Focusing on attaining the greatness that you were destined to achieve is a recipe for lifelong disappointment.


Not attempting greatness, because of risk of disappointment?...I feel something is missing there. I don't have any answers yet though. There must be a third way.


There's an important distinction between simply being ambitious about achieving greatness, and feeling as though you were destined, or meant, to achieve greatness. The former accounts for failure, while the latter does not.


I'd be careful about falling into the HN echo chamber. Lots of the most important and interesting technical work I've done has come in boring/traditional companies and industries.

To be perfectly frank, I don't think you can learn the true craft of software development (you didn't say you were a developer but I am so it's my perspective) at least without a few stints in the "real" world.

I've also found the meme that big corps. are full of bad employees and startups are full of the best and brightest to be completely untrue. At this early stage in your career if you can't learn something from a traditional job you aren't trying hard enough.

Also, you've been in the working world for one of the high times in our industry. Those don't last, and startup scenes dry up. This won't be your last move in/out of that world.


Just want to preface this: the following contains a giant wad of sarcastic tone and is mildly accosting; this comes from my own internal dialogue with myself about this same issue. My internal voice doesn't take my real voice very seriously. It's not meant to be unkind whatsoever.

---

There's something called Y-Generation; you're it.

Good for you, you think you're special. And your friends all think they're special. Guess what? I think I'm the most special of everyone. Yup... this is our plight, and frankly, we just need to get the hell over it. :)

If I really believe I'm capable of doing great things (which I do), then there's no reason I shouldn't be doing them. But for some reason... shrug Excuses -- my biggest one, ultimately, is that because I think I'm sooooo smart, and capable of suuuuch grand things, I'm scared shitless of trying and failing and realizing that maybe I'm not quite as exceptional as I thought. Poor little baby ego, awwww.... Keep putting up a front though.

You managed to say the sentence "Thus, I have picked up another job which I'll join in a few weeks." Do you have friends who don't work in tech? Like, for real? Normally... in the real world... you don't just "pick up" a job as if you were going shopping. Spoiled goddamn brats, the whole bunch of us!

My suggestion is to go find a local pub with good staff and good regulars that you can relate to. Go there more and more often until you're blowing all your money getting tanked every night of the week. If you keep that up long enough, and then push it just a little bit longer, you'll either figure out you're exactly where you belong, or you'll get so fed up that you'll end up back exactly where you are now. But this time you'll have something to run away from.


This is extremely poor advice whether meant to be unkind or not.

Alcoholism is not amusing.

Also you are projecting your inner thought onto others just as the original poster is projecting his feelings onto those of his peers in order to find self-justification.

Obstacles over which you you think you have no control is usually an emotional response. Separate from your emotions. When I am feeling negative emotions, I try to see them as a separate event, not a part of you, and I watch them.

This removes their power as commandments one must follow or believe in, but rather they are just passing objects, like a leaf floating past you in the wind. The leaf doesn’t control you, and neither do negative emotions.

Viewed existentially most "obstacles or powers" affecting us beyond our reach are not really so. And those that are, just are. Better to accept them.


Did you really suggest to OP he try becoming an alcoholic? Like as real life career advice?


Why would you suggest something that's such a bad idea? If you're trying to be funny, it's not very.


It might help to change the way you "score" your life. I'm suggesting that because your comment suggests you are mentally evaluating your progress against some internal metric and seeing failure rather than progress. Allow me to share an example that my own daughter (Also in her 20's) went through.

She was 'failing' at getting a job, for the summer. She had made over a dozen attempts and not a single offer. The lack of success was putting a huge damper on her ability to motivate herself to try again. When we talked I suggested that perhaps rather than "failing" to get a job in an attempt she "succeeded" in learning something new. By letting the 'end goal' of getting a job go for a minute, and concentrating on things to learn, she when from failing 12 times to get a job to succeeding in learning 12 new things. Different spin on the same circumstance. And before you say "But Chuck, isn't that just a mind game you play on yourself?" The answer is no it isn't, you really are learning new things and recognizing that is important, like the App on this site recently called 'RememberWIN' that is the key, realizing you are making progress even when it doesn't feel like it.

This is especially important in the 'do great things' sort of arc because frankly it is generally impossible in normal circumstances to do something truly great in fewer than 5 or 10 years[1] and it is generally impossible to do great things alone. That means you have to find some folks who can be part of it, communicate a vision and a plan to achieving that vision, and then executing on that plan. All of that takes time.

Because of that the only productive way to 'score' your progress is by noting successes in 'found a great web designer' person or 'sales person type' or 'engineer' or 'mathematician' what ever. Assembling the folks who you will want to be the team will take time as well.

When I have something that it going to take a 'long' time to get done I try to write out the history of that in reverse with options, example lets says it is "deliver an electric vehicle", so just before that you've got the "car passed all its manufacturing approvals and tests". Before that you've got "opened manufacturing plant", before that you've got "designed manufacturing plant", before that you've got "found a parcel to build the plant", before that you've got "closed funding to buy a parcel", etc and walking back to where you are now with just an idea and you'll have a series of milestones you can work on between now and then.

The trick is that people see things happen when suddenly "all this stuff comes together" but for that to happen "all this stuff" has to be converging. If you plan for that you can understand when things are converging and when they aren't and that helps inform where you are needed most at any given time in the process.

[1] This arises from the fact that there are lots of smart people out there and 'great things you can do in a year' have all been taken. Times of war and disaster however offer accelerated schedules since there are lot of people already motivated to do something and leading them to do something great is then possible in a shorter period of time.


"What do you do when you believe that you can do great things but something that you have no control over is holding you back?"

Whoever taught you that made a mistake. This is very typical of our generation (yes me included) we all think we can be the president if we just work hard at it. While all our parents heard was: "You know when you work hard you might own a house, with a garden even!"

Happiness is reality minus expectation. (http://waitbutwhy.com/2013/09/why-generation-y-yuppies-are-u...)

And you, your expectations are too big. Yes you can change reality but how hard do you have to work to make it match your expectations of greatness? Perhaps you should just learn to be content with what you have, be happy, who knows what comes on your path. Your alternative is facing a high chance of never being happy with yourself and your achievements.

I'm half way through this book: http://www.amazon.com/Guide-Good-Life-Ancient-Stoic/dp/01953... On the advice of the HN crowd. So far I'm liking the message. Try, regularly, to imagine life without the things you hold dear. Try to want the things you already have.


Some realize it later than others, but life is long. There's a lot of emphasis on carpe diem, live today like it's your last, etc. That's actually a very good way to get anxious about what you're doing today when you could be doing it tomorrow. Sounds like procrastination, I know.

The thing is, putting things off makes sense. You can't do everything you could ever want today, or tomorrow, or this week, or next. But you also have several decades to do things. I think my greatest peace of mind comes from the knowledge of three things:

- I have plenty of time. And if I die suddenly from disease or accident or whatever, the bad thing will be death, not “I didn't do everything!” - I won't ever do everything I want to. My mind is coming up with new things that might be interesting to explore on a reasonably regular basis. But that's okay. The things I choose are what make my life distinct from that of others. - What I want to do is going to constantly change. More of a corollary to the previous one, but what I'm doing today will have inevitable influence on what I want to do tomorrow.

Choosing to focus on taking care of your family now doesn't mean you'll never have another opportunity to attain financial freedom. That opportunity may take a different shape than what you're thinking of right now though. Sometimes it's good to just let things settle for a while before launching into the Next Big Thing. Sometimes you let things settle out and you realize the Next Big Thing wasn't what you originally had in mind. That's what makes things fun ;)


I have 2 kids under 2 and I am working on 2 startups at once. That is basically like having 4 babies. I don't believe you should necessarily wait for the right time, for any kind of baby. There may never be an ideal time. If you have something you are passionate about you go for it. If you don't then you bide your time.

I have gone through periods of burn out and extreme passion about my startups. Sometimes it's nice to have a steady paying job and be stress free for a while. That's you biding your time until the right idea/opportunity comes along.

I went through an acquihire myself. Don't feel bad, startups are a longshot, and to see any positive outcome is much better than nothing. I worked for that company for 2 years, became frustrated, had an idea I was excited about, and then started something new.

So my advice is, take the stress-free job until you build up the passion to work on something new. And then do it.

EDIT: typo


Are those two actual startups, or more like two mirco "startups"? In other words, are you trying to get both of these startups to grow massively fast, or are these just businesses to cover your living expenses?


Sorry for the delay in response... I would call them actual startups.

For one I raised $1.7m in money over the years several years ago, but then had to scale it back due to lack of success. I pivoted it to a site that now has millions of visitors per month, but I run it solo trying to figure out how to make money and grow it.

The other company is just two us, my cofounder and I created a social media analytics platform and we have done about $150k of revenue in bootstrap mode in the past year or so. We are now trying to push a product to the masses and may look for funding soon.


This is not a definition of "actual" startups, just of those who have an imperative to grow "massively fast", usually because they have taken external, primarily VC, funding.

A startup is a new business that is still investigating what kind of product it is going to sell, and to which audience.


Genuinely curious, why do you think this is an important distinction?


When I was 21 I started a company with 4 other people that lasted about 2 years before we ran out of money. After that I went to work for an insurance company. At the age of 26, the contacts I made from my startup started to blossom, and I got back into a trendy company that I stayed at for 6 years before breaking off on my own again around the age of 32.

Here's the thing, I was worried about going backwards in my carrier when I went to work for the insurance company, but instead it taught me discipline and gave me the chance to learn from veteran programmers. I would not trade in those years for a new startup firm.

Don't feel like you're giving up just because you have to step back a bit. Use it as a chance to get a different perspective on our industry.


What do you do when you believe that you can do great things but something that you have no control over is holding you back? You believe that you are good at what you do and are meant for great things but you have to do your job even though it doesn't do justice to your capabilities. How do you cope with that? Seeing your future as an underachiever pains you. What do you do?

This is what I call the "hero myth." We're all inculcated with the idea that there is a heroic destiny before us from a young age. The stories we read, the movies we watch, the parents and educators who teach us beseech us to "believe in yourself and you can do anything." This seductive myth gives us the escape hatch from reality that lets us believe we are special and that everyone else is normal. It's a terrible myth and responsible for many summer blockbuster movies and burning out many bright, young people.

It's bullshit. Do things. Enjoy your time doing them. Don't worry about what other people think. Every person who has done great things is feeding the tulips right now. You will one day too.

As for dealing with having responsibilities: get used to it. It doesn't limit you. You have be more tactical with your time and learn to cut away all of the fluff and focus. It tests you to learn what you truly appreciate.


I think it's important to remember that in the world of the Internet, "running your own business" doesn't have to be "a startup." I'm 32, and had a similar realization a couple years back. I hated having bosses. I don't know if my ideas were the best, but I feel like I tend to have good gut instincts. I was tired of not having control of what I was doing.

I worked at a small web shop, a big ad agency, and a tiny remote-only web thing. I saw what people were doing, and what was out there, and knew that I knew enough that I could survive.

The hardest part was making the leap. To say "OK, I design and develop websites under my own flag," and then to find people. Having worked in the industry for a while, I had contacts, and so far (knock on wood) I haven't really had to do a lot of marketing. It's all mostly word-of-mouth. Build something, do a great job, get remembered/recommended, repeat.

Even though when you first get started you'll take a couple projects you might not be thrilled with to get your feet underneath you, soon enough you'll be raising your rates, getting to say no to projects your not interested, and maybe even working on small product-like projects too to mix in with your client-work. That's what I'm doing, I also co-lead development of a little CMS called Statamic. I use it on a lot of my clients' sites (if they're OK with it), and using it lets me improve it, while improving it helps me sell it.

It's not glamorous. It will probably never net me a 7-figure-profit for a year. But it's fun, challenging, and rewarding. You don't have to build a product that makes hundreds or thousands of people happy. You can build one site for one person and they'll be just as thrilled. And on top of that, all the challenges of business are there too. You get to pay taxes and everything. :)

You also mentioned family obligations. For me, being self-employed helps with that too. If something comes up, I can walk away from my desk and go help out — whether it's picking up the kids, or just meeting my wife for lunch if she's having a bad day.

Self-employment is risk, but it's a calculated risk that balances with freedom. If I want to make more, I take on more projects. The hardest part I've found is turning that off. ("You mean working 80 hours pays me 80 hours!? SIGN ME UP!" — that just leads to burn out.)

Anyway, I know Hacker News is more startup-focused, and that you're probably more interested in that, but I wanted to throw my two cents in that there are other things you can do relating to the Internet that are just as interesting and just as rewarding.


> If I want to make more, I take on more projects.

Or you can increase the transactions per customer. You don't have to have more projects/clients to make more money. There are only so many projects you'll be able to work on.

However, if you already have 10 - 15 customers, and you increase the # of transactions per customer, you can reach 7 figure revenue per year.


I guess I don't fully understand what you're saying here. For me, a "project" is "I'm going to do something for you, and you'll pay me." The only way I could gain more money that way is by raising my rate. (My projects are one-to-one.)

Otherwise, time becomes the biggest limitation. I've toyed with the idea of hiring people to work for me, but I really like sleeping at night, and I'm not sure that I can do that if I'm worrying about being able to pay people. I've heard that more people will spawn more projects and more money, but time and time again I come back to the thinking: I'm not unhappy with what I have now. No need to rock the boat.

Time, as always, will tell.


I think he means upselling and/or offering more paid services/products to the same customers. Hosting, a new theme, regular blog posts (outsourced, of course), plugins for social networks, integration with whatever, constant monitoring, etc. - ideally on a subscription basis. This way, you can make more money with the same number of clients.


Many parts of this write up have a resounding similarity to my journey! Thanks for sharing.


I was feeling the much same way when I was 27. I had a lot of ambitions, but my financial obligations (and weak resume at the time) prevented me from doing what I thought I was capable of.

I saved up some money, then took the best paying, most flexible–yet reliable–part time work I could find. I got really lucky and found a boss who was very understanding of my situation.

For the next few years I was fairly broke, but by having a steady part time job, I was able to swing back and forth between developing new skills, working on my own SAAS business, and freelancing when things got tight.

My business didn't hockey stick, but it had a steady bootstrapped upward incline. When it was making enough to pay the bills, I stopped freelancing, then eventually quit my part time job.

I traveled overseas a bunch, toured with my crappy band a few times, did all the other stuff on my bucket list, then bought a house and had a kid. Business is still good and consistent. I'm not rich, but I'm not poor either.

I'm 35 now. I spend my days hanging out with my son and answering the occasional email, hacking at night or whenever. I've never been happier than I am these days.

Sometimes, I wish I could travel back in time 10 years so that I could tell younger myself, "hey, things will turn out really well." Would've made the trip here a lot easier.


Thank you.


Welcome to the human condition.

I received some advice a number of years ago which has stuck with me, and served me well.

If there's something you want to do with your life... Don't talk about it. Don't think about it. You'll do so forever.

Just do it. You'll be 50 before you know what the hell happened.


Exactly this.

Another advice from a book, which stuck with me: "If you have the desire to do something, do it, because if you wait too long, you will find that the desire has left you long ago."

I have done everything I wanted to do in my 20s. I have a technical/developer background but left my startup career, with no job offer or backup nets, became a SAG actor, and a whole lot more. I even wrote and published a bunch of eBooks on this too.

BEST MOVE EVER.

I now have professional resumes in 3 different industries. Acting, Sales, and Startups. Great diversification. I even joined another startup years later doing something much more fun. The career gap came up, but I just told it like it is. You will find open-minded people who want to work with you.

Now I'm in my early 30s, happily getting ready to settle down. Just follow your heart. It's healthy and normal to yearn for great things. That is because YOU are pure greatness. Those who take action will distinguish themselves from those who don't.

What do I want to do in my thirties? Be a life coach to share my experience to those who find value. Be a great father/life partner. Learn to surf.


You might have Imposter Syndrome. Take a step back, and make a list of all your accomplishments. This is not about being self-centered, it's about taking a honest view of your life. During the day-to-day shuffle, with short-term deadlines and other obligations, it's easy to forget about the long path you've taken to get to where you are.

You co-founded a company that was acquired - how many people can say that? Even if it was an acqui-hire, does that really make a difference? Why do you feel that this accomplishment is not worthy of praise?

You didn't like working at the parent company and so you left to find different work. What is wrong with that? I would bet that most people on HN have been through a similar circumstance. If you don't like working at a certain place and don't fit it, it's not necessarily your fault or anyone's "fault".

Furthermore, you had the ability and confidence to leave a job you did not like and take a job that perhaps will be a better fit. Why does it matter that it's not in a "sexy" or "trendy" industry? Reading just the big headline stories on HN or other tech websites will leave you a bubble where it seems like everyone is working for an ultra-trendy hipster startup that will be "the next big thing", when in reality many software developers work in more mundane industries but are still very technically astute and have a fulfilling life.

If it's something you can do day after day and it doesn't bother you, in my mind that is great. Don't compare yourself to what others want, compare yourself to what you want.

Which leads me to my next point: Why do you believe that you are an underachiever? Compared to what benchmark? There is nothing wrong with being ambitious - motivation often provides the drive to succeed. But if you are always left wanting more, then you never really get to savour the reward from your efforts and hard work.

Take a step back and try to figure out what really fulfills you in life. Work is often treated as a means to an end, and there's nothing wrong that. However, some people really do relish work and for them, that is an end in an unto itself. But if that's not what fulfills you, you shouldn't try to pigeon-hole yourself into someone else's goals by way of comparison.


Being lost is pretty much normal at your age. You've only just (what, 3 years ago?) finished college. You haven't yet experienced enough of the world to know what you want to do for the next 10 or so years.

Take the day job, save money, travel, enjoy life, meet people. You don't have to set such enormous expectations for yourself - you'll always end up disappointed in what you do (like you are now).

Find something you like enough to do as a hobby, and grow it into something more. And go easy on yourself.


I'd say there's 3 things to consider

* You should be really proud of your achievements so far, an acqui-hire is no joke.

* I understand you may be afraid of starting or joining a risky startup. But what have you got to lose? At age 25, you can live a scrappy life, there's no social pressure not be a salary man anymore these days, especially in a startup scene where it's so normal. You're young and can take the risk.

* Third, the only point that really matters in my opinion, is the people you have to provide for. If there's no way around it, there's no way around it. I know what that's like and I respect that. Just make sure to check your assumtions carefully. I'd had to take care of my sick dad for a long time, but wouldn't throw away an opportunity I really believed in, as he'd hate himself if he was an obstacle, and he'd still have my mom and my bro, and I'd still be able to support him partially. Talk to those who you support, and consider if they really depend on you. Sometimes there's room to juggle both, sometimes it's possible to find an alternative caretaker.

Lastly, there's quite a few startups that are challenging and do pay decently from the get go. Bitcoin is a fun space for example, and Bitpay and Coinbase pay well, yet exist in a challenging and ever in-flux ecosystem.


Minimize your expenses, encircle yourself with close friends, spend time outside, buy a small plot of land and plant some trees, seriously, I think most of the tech/starup scene is a forest through the trees problem. Most "successful" people work themselves to death "preparing for life" during their best years. You are 25 man, relax, travel, find someone with REAL problems and put a smile on their face.


I can only give you some advice with what has worked for me. I'm 29 now, I've been programming something I'm very passionate about for the past 4 years, earning just enough on the side to work on that. Last year, it took a big conversation with my girlfriend to accept that it was time to set aside the project for a bit and start working as a freelancer. For the first time I took a serious attempt at making a good CV/portfolio website and reached out through several channels to get some work. What worked in the end was to work though consultancies (which I had a grudge against). They gave me good connections which then gave me new work without the consultancy. I learned what I was worth per hour (much more than I used to ask). And because I did small jobs it was also very dynamic. The work wasnt always fun, but to develop myself like this was very much fun! And guess what, I grew a LOT in this time, my coding got better, mostly because I had to deal with lots of real life demands. My toolbox grew. My confidence grew. My professionality grew. My wallet grew. Then after bout a year I switched back to doing as little as possible and working on my own project. It took some effort, determination and time, because I had build up some responsibilities, and they tend to keep going for a while, but you also don't have to cut it all. Just keep the best :) .. right now I'm in a sweet spot of 1 day of well paid work and 4 days of doing my own project. And if you don't know what product to build next, I would suggest following your heart first, finding you passion, find what drives you. Give yourself the freedom to explore that. Because that's what will keep you going and motivated. And once you've found that... THAN it's time to find a way to make a living with it, preferable while helping others in the process. Good luck!


>4 days of doing my own project

May I ask what kind of project it is?


It is a framework for the semantic web. It allows on the fly setup of data structures which you can then instantly use. It comes with pre installed datatypes and visualisations (both 2d and 3d), but user made datatypes can also be shared with eachother. It also comes with a reasoning engine so you can do some AI stuff. I set out to make an interactive nonlineair book, and figured out I need and want to make this. It took a bit longer than anticipated, but the framework is getting pretty steady now, and I can soon make a lot more with it than just the book I made it for. Hoping to put it to use with some test projects in the next 12 months. Will post on show HN once something worthy comes out. Tnx for asking!


Hunker down in the new job for a couple of years, don't fall for needless lifestyle upgrades just because you have a salary now (Mr Money Moustache methodology) and come back to a start up in a couple of years if you want to with a bit of cash under your belt and a new perspective.

Good luck what ever you choose, it's likely that there are no bad choices right now which is why you're feeling like this.


As long as you wake up in the morning with something to look forward to, something you are going to feel good about doing in the future, you will be able to get through anything. The whole thing about 'wasting the crucial years of your life' applied to a time which has now passed. The Y Combinator observation that it's getting cheaper every day to start something potentially world-changing by making something a lot of people really want is not going to go away, just because you're older. Yes, your energy and health may decline in the coming years, but that could happen even if you were working on the startup of your dreams right now. Never imagine that you're going to miss the boat: when you're feeling ready to do another startup, that will be the right time for you. This notion of whether you have a 'window' in your 'lifespan years' as far as starting startups is concerned might have once been 100% true, but if anyone tells you it's still true now, you cannot use expect the past to be a reliable guide.


Life doesn't have an award ceremony at the end, so any measurement you make of your success is pressure you're putting on yourself. Nobody else, including your family, cares about the "great" things you could be doing.

Unless you subscribe to one of the many religions that tell you that there IS an award ceremony after you die, you can rest assured that your presence here has absolutely no point or goal. To some people this is extremely depressing, but I firmly believe this and it's the most liberating thing in the world. There is nobody I have to impress, no goal I have to meet, and no level of success I have to achieve before I'm happy.

That's liberating because my life is more like play than work. You ever play a pick-up game of a fun sport, where you don't keep score and you just enjoy the competition with friends for its own sake? That is ALWAYS better than organized competition with awards and a goal, and I've done both.

I'm not saying check out and smoke pot all day, unless that's really your thing long term (probably isn't). But nobody gives a shit about how successful you are but you.

  I met a traveller from an antique land
 Who said: "Two vast and trunkless legs of stone
 Stand in the desert. Near them, on the sand,
 Half sunk, a shattered visage lies, whose frown,
 And wrinkled lip, and sneer of cold command,
 Tell that its sculptor well those passions read
 Which yet survive, stamped on these lifeless things,
 The hand that mocked them and the heart that fed:
 And on the pedestal these words appear:
 'My name is Ozymandias, king of kings:
 Look on my works, ye Mighty, and despair!'
 Nothing beside remains. Round the decay
 Of that colossal wreck, boundless and bare
 The lone and level sands stretch far away."


I understand this is easier said than done, but stop living in the future and start enjoying the present. One way this can be achieved is by setting short term realistic goals; learn a skill, volunteer, help others, meet new people, etc.

This might sound cheesy, but fulfillment and happiness are usually achieved in the process of working towards your goal, and are rarely found after an accomplishment.


Hi, I am 28 years old, I never started my own startup but want to, I do not consider myself a underachiever cause there are young people making billion dollar deals, if you live for the news/press/media you will always fell a underachiever, the car of your dreams, the teenage singer that sold a million albums, you got the point.

You need to reflect what's most important for you, what makes you happy, is it money? Is it helping the other? Is it reading books? Does being happy mean having buck loads of money? Do you feel alone? Do you feel good about yourself being alone? Do you like the company you have? Partner, family, friends?

We live in a amazingly connected world with billions of people, so while you are brushing your teeth there will be people practicing gymnastics, people winning gold medals, launching new programming languages and selling million dollars companies, it's fine, you can't keep up with everyone, don't compare yourself, don't envy, the key is to understand what makes you happy, in a peace state of mind.


1. Startups are tough and I am afraid.

> This will never change. Conquer your fears and do it.

2. I have a few financial responsibilities towards my family which I have to take care of.

> Manage these as you work to own #1.

You're 25. What a great age to be! To be young enough to take risks, fail, and get back up and begin again. In my experience, most of those who were/are successful in their endeavors, were at the brink of financial failure and dealing with both issues you mention, when the risks paid off quite literally overnight. Of course startups can be absolutely huge undertakings, but the risks and rewards involved are the reasons we go after them.

Don't miss out on a chance at your passion because you were too afraid or intimidated. Regret sucks. There are just as many lessons (or more) in failure as there are in success for the next project you take on. Regret has nothing to offer but regret. It's a complete waste.

Go after what makes you happy--no matter what and never ever stop. Anything less and you will remain unfulfilled as you mention in your opening statement. Go get it and good luck!


You're young and sounds like you have done very well.

I think taking care of your financial responsibilities is wise and responsible. Just keep plodding on.

Picking up another job is not an easy thing to do in this current economic situation, so I would be pleased about this! Non-sexy and non-trendy industries are still important. Working in farming is not very sexy or trendy but people always need food. Just because it isn't trendy doesn't mean it isn't important.

The difficulty is that the things we want to do are put off by the things that we HAVE to do. We unfortunately have no control over a lot of the things that are holding us back, but probably just need to accept that we have no control over them and carry on anyway. If we have no control over them, there's nothing you can do.

Try working on things on the side that do do justice to your capabilities, even if the main thing you are doing perhaps doesn't. The main thing will cover your financial responsibilities whilst you scheme to escape it. That should keep things in balance.


I'm 23, and I'm in the same position as you. It might be a generational problem. http://www.huffingtonpost.com/wait-but-why/generation-y-unha...

I also think we are tuned to focus on the future and all its glory and not focus on the present, especially in an environment that is all about "becoming the next big thing." So, one suggestion is to focus and be mindful of the present because if your head is always in the future or in the past, then you will be always unhappy. I see this present mind advice everywhere, but it is easier said than done. I don't have nearly the success you have, and I go through the same issues. "Why can't I start up a company and get it going? Why am I just working at a company? Why don't I get all the cool perks like Facebook employees? Is this going to be my life? Am I going to find someone to settle down with?" These questions naw at my core, but I am starting to find ways to avoid them.

One of the best ways to focus on the present is to exercise. When I mean exercise, I mean the gasping for air at the end exercise, which I accomplish via basketball. I only just starting realizing how truly blissful I am after a game of basketball because all I can focus on is getting air into my lunges. Nothing else matters at that point. My mind is forced to clear out because the need for oxygen has taken over.

The other one is to be introspect and read about this kind of stuff. I journal almost every day about my experiences, my emotions and that exercise helps me be more mindful of myself. I bet just writing this HN post felt good for you! Once in a while on HN, I will see articles posted about mindfulness and behaving in a zen-like manner, such as http://zenhabits.net/toolset/ and http://nyti.ms/1ld9lfU. A lot of this stuff is very nebulous, but the more you read and the more you write, the more it solidifies.


>It might be a generational problem.

I am 32 and I am in a similar confusion.


Can you say what exactly is not under your control? I hear that frequently, but most times people misinterpret their feeling out of control with not having the ability to control things in their life.

At 25 I was married, had a house, a riding mower, 3 cars, and everything felt out of control. I had pretty much the same crisis. At that point I was making good money, but my stuff owned me. So, I sold the stuff and started to take control.

One year later, I was debt free and had tons of options. I could have put my few possessions in storage and lived in Costa Rica or backpacked across Europe. I didn't do that, but I could have, and that made a huge difference in my mental state.


> I have no idea where it is going to take me in two years

No one knows the future. The best experiences of my life have been things I hadn't even thought about a year before they happened.

> You believe that you are good at what you do and are meant for great things but you have to do your job even though it doesn't do justice to your capabilities

Spend one hour per day working on your own project idea. Maybe it will turn into something, maybe not. But at least it will be something you own and you'll learn a lot from it. Does it suck that progress will be slow? Yes. But 1 hour per day over the course of two years can add up to something pretty impressive.


"I don't know if this is what they call a quarter-life crisis."

This is what happens to most post-college grads. You're led to believe that you are the smartest most capable person in the world and that _you will_ make a difference.

Then you get a real job and and eventually come to understand how the world really works.

I'd say:

1. Put your family first. They are likely the only one that will not give up on you in the long run.

2. Pursue what you enjoy. It's a long life (hopefully) and you will do great things _because_ you love what you do.

3. Plan the future. You will end up _somewhere_ is 5 years. The destination can be determined by planning.


It's my point of view but why center your life around your job ? You already have done one impressive things for your age.

My advice would be do what you please, maybe take a job and learn things asides and live.

With such a resume you will not have problemes to find a job, why not just live ? Travel , meet people , try to learn things and skills.

And there is two things in life , things that you control and things that you can't control. Don't worry about the second part. Enjoy yourself and don't forget to laugh and have fun. Life is hort.

Even i you are the best in something, you may not achieve renown because of unluck or politic.

Find something / someone that you like and do it. An other things is that as long people that you respect, respect you tell the others to f* off. You don't have anything to prove to anyone.

Once you will realise this you will be more peaceful. Life is short enjoy , go out your circle of confort.

I worked in a lot of menial job (doorman was the worst for some aspect, having some drunk rich kids spent your monthly wage in one night) but you may find in something interesting in it (for me it was networking my contacts and practice undercover hypnotism on asshole drunk people).

Live. and don't forget to laugh :

For life is quite absurd

And death's the final word

You must always face the curtain with a bow

Forget about your sin - give the audience a grin

Enjoy it - it's your last chance anyhow.

So always look on the bright side of death...

(Whistle)

a-Just before you draw your terminal breath... (Whistle)

Life's a piece of shit, when you look at it

Life's a laugh and death's a joke, it's true

You'll see its all a show, keep 'em laughin as you go

Just remember that the last laugh is on you

https://www.youtube.com/watch?v=JrdEMERq8MA#t=21


Sounds like you are a perfectionist in nature :) Perfectionist tend to be rarely "happy" with their achievements and are always striving for more. It is very hard to be fulfilled with such a mindset. I would suggest checking out this book with some more information on being a perfectionist http://www.amazon.com/gp/product/B004BKJB6Y/ref=oh_aui_d_det...


I know how you feel.

I've worked at a couple of startups, two groups at Apple, two groups at Google and now at Twitter. I've learned two things chasing a feeling of fulfillment, like you seem to be:

1. You can't expect your job to give you the all of the fulfillment you need.

2. The most fulfilling work is the kind of work that's just challenging enough, but not too challenging--http://en.wikipedia.org/wiki/Flow_(psychology)


'Even though it was termed an acquisition, it was really an acqui-hire.'

What the hell is the difference? Someone was interested enough in your company to buy it. This is a very superficial distinction and irrelevant.

All of these voices telling you you should be crushing it are coming from within, and actually originate in some sort of arrogance/insecurity where you simultaneously believe you are amazing but are also not sure of it, and the only way to prove it to yourself for sure is to prove it to other people.

I spent my 20s with a debilitating chronic neurological illness, to the point where I was totally unable to live up to what I originally thought my potential to be. Even though this used to be a source of great distress for me, I eventually learned to stop struggling. Instead of fighting it, I began to understand that on each and every day I'm only the person I am that day, and only have the capabilities that I have that day. I let myself off the hook, and things became a lot easier as a result.

And if you think it's different for you because you don't have a neurological disease, you're wrong. You too only have to be the most amazing person you can be today. If you find that to be distinctly un-amazing, that's ok - you might be different tomorrow.

Remember too there are those out there who are in a much worse position than you are. Keep perspective. It is easy to lose sight of that in the tech bubble where everyone is always crushing it 100% of the time. (They aren't, and you don't have to either.)


You're 25 and still to young to worry about 'responsibilities', I'm 34 and have similar feelings and my appetite for adventure and greatness may just have to sit on the back burner for a few years if I want to settle down and have a family.

If your family care about you then they'll know you'll pay them back at some point.

If you've got something and feel that you're destined for greatness don't hide it away, it'll only make you miserable.

Live the dream whilst you can.


The exact same thing happened to me - startup, acquihire, quitting the acquirer, and joining a less sexy company, though in my case I got the bonus of moving to Switzerland.

You mention the desire and the ability to do great things, but not having the opportunity to follow through because of circumstances. It was the exact same feeling that led me to leave Silicon Valley, and I struggled for a long time with it before coming to a simple conclusion. Here's what I decided:

Greatness is a consequence, not an aim.

Have you ever read Man's Search for Meaning by Victor Frankl? If not, read it now. It will convince you immediately that the same is true of happiness. You cannot simply wake up one morning, say "I want to be happy," and become happy through the mere force of your desire. You need to be living correctly; acting rightly; communicating and connecting well.

Likewise, naked ambition will not make you great. You have to shape that ambition with goals and methods and plans. Only once you are fully engaged in something you believe in will you be able to achieve the result you desire.

In other words, pursuing your will to greatness directly will only depress you, and won't make you any more successful. The way to greatness is developing your interests to the fullest, and working hard to gain expertise. Eventually, you will find an opportunity that you can seize, and your success will be a natural consequence of becoming fully engaged in the creative process.

Until then, know that you will eventually find your castle in the sky, after and because you have built the foundations under it.


I am 27 and going through the same thing, it seems no matter where I work until I can truly setup the structure or foundation for a project I never feel like I am working on something glorious because I think it wasn't put together well or sloppy; I have worked at places where I believe it was put together well so I'm not always putting down code I inherit. The way that I keep sane is I try to stay positive by going to meetups and being with other people who are excited about the more advanced things and have the same type of hunger for purpose. At home I also work on personal projects and explore new things and I would recommend that. I quit my job like you a year after the startup I was with was acquired because they really didn't care about the tech aspect of it and joined a new one but I am not really challenged (even thought they needed to hire a senior software engineer) and try to lose myself in my routine so the day goes by quick. I think what I am going to have to do for purpose is do more open-source projects or build small apps of my own. I would recommend that. Focus on your family too and your non-tech life, remembering how valuable they are in helping you not think of this. There are tons of us like you.


I'm Anny. I am 25 too and I'm facing situation like yours and I am also lost. I don't have any fancy advice but I want to share some stuff that may work with you as it works with me.

For sure in the future I know that I will have my own business. But Right now I'm trying to get a new job. Also I have to maintain the responsibility that I have to support my family. It is very tough life. I was very suffered. I recently just realised that yeah suffering demands to be suffered, we have to experience it and never hold back, but once when we done with it we just let it go and look for positive possibility and pursue it.

I was very miserable for past months and just recover from letting those shit go. I choose to be thankfully happy not miserably lost. I am now having job interview with Amazon AWS and Google. I keep positivity high but expectation low and still keep looking for, again, positive possibility. I keep telling myself that always believe in yourself, always look for positive possibility, focus and pursue! Lifehacking is fun after all :)

here are some of my stories. I wrote it couple weeks ago when I was super miserable and I didn't know what to do.

http://fleurblanc.tumblr.com/

Enjoy lifehacking!


What do you do when you believe that you can do great things but something that you have no control over is holding you back? You believe that you are good at what you do and are meant for great things but you have to do your job even though it doesn't do justice to your capabilities. How do you cope with that? Seeing your future as an underachiever pains you. What do you do?

Problem Solve. Swallow your pride and do what needs to be done. "Being Great" is not the ego trip you think it is. You get there by doing hard things for a long time while people act like you are crazy, stupid, etc. It isn't all about your ego. Set your ego aside.

If you really believe you can "do great things" than start doing 'great things." But, you know, I think you and I maybe interpret that phrase differently. If you are actually awesome, that will eventually shine through. But it won't be a picnic. You don't get the valor without doing the hard work first.

So, even while you work a regular job, you can make plans for another startup and work on pursuing financial freedom. Paying the bills now, even though it isn't doing something sexy or trendy or ego-enhancing, is part of pursuing financial freedom.


You are 25 years old, you have your whole life ahead of you, you are still wet behind the ears in terms of learning your chosen profession and in life experience - frankly this is the bleat of a spoilt child ... "I could be great but someone else is stopping me from being so". "I'm going to under-achieve yah di yah".

Stop whining and grow up would be my advice. Life is about taking knocks, getting up and getting on with it - sure ask advice but its hardly a "crisis"

Speaking from a perspective of being close to 60 years old and having worked in IT for 38 years. considerably longer than you have been alive, my observation is that what has truly mattered has been the people I have met, the friendships I have made, my family and my children.

Great things ... cough ... dont come from yet another better version of Javascript or some other re-churn or regurgitation of yet another way of presenting mobile/web data content or whatever is fashionable.

In your context - great things are defined by adding something of fundamental value to your chosen professional discipline or field. That comes from damn hard work, intellectual rigour, a willingness to face and overcome obstacles, vision and often sheer bloody-mindedness


Hi,

I'm 25 too, I've been like you and I'm starting to getting out of this 'crisis'.

Like you I lived awesome things in the last 5 years, things that I would have never think I will accomplish.

I don't have a solution for you, but for me what's worked is reading books (non-fiction). In a book, you will generally find a condensed version of the life of the author and that's great. In a few hours you'll understand what he went through, how he did this or that and what they learned from that experience.

And that's great because at 25, your lack of experience doesn't help you make choices.

Here is a few books I can recommend you:

- Choose Yourself (James Altucher & Dick Costolo) - It's mostly about how to become your own boss, but there's a few chapter that are really useful when your a bit 'lost' or in 'crisis'

- The Obstacle is the Way (Ryan Holiday) - Really great reading!

- Satisfaction (Gregory Berns) - I'm in the first chapter but it's seems to be a good book.

These books are really easy to read.

If you don't like reading, listen to James Altucher podcast https://itunes.apple.com/us/podcast/ask-altucher/id868149214...


I know for a fact that I want to run my own business and attain financial freedom but I can't risk another startup at this moment because: 1. Startups are tough and I am afraid 2. I have a few financial responsibilities towards my family which I have to take care of.

I just turned 30 two weeks ago. I am married, have three children and a mortgage. I am leaving the government in December to build my start-up (visidraft.com) into a successful business.

The reality is, beyond a certain point your responsibilities will not shrink. The key questions once past that point are: Is your family on board; and is the risk probably worth the payoff? If you can answer yes to the first and maybe/yes to the second then your mind should be eased.

Beyond that though, it sounds like you need to figure out where you want to be and then set a path for how to get there. The fact that you had a positive in your favor liquidation event is massive and you should not spit at that. Maybe your path requires you slogging at a regular job for a little while, building up a war-chest to bootstrap the next project.

Bottom line is: you need to find a place that you want to be in the future and then determine what your vectors are to get there.


Don't beat yourself up too much. Doing great stuff takes time, you learned a sh*t load from your last company and next time you can avoid some of the mistakes. As irritating as it is to endure - doing a mediocre job should give you some respite, time to think and the ability save some cash.

Aim to save the maximum humanly possible (reduce spend/be frugal) to give you potential budget or run-way for your next project. Start it while you are employed, work on it when you are at work. Be a terrible employee while more-or-less still looking good... but vest your time in new projects or ideas, or exposing yourself to where you might find them (not pointless crap like most other bad employees do).

Personally, I am in the latter stages of 'medicore job' period after a very similar gig at a fairly similar age (few yrs older). I am hitting 70% net wage savings rate and have one project in-hand progressing reasonably well and a bigger/ambitious project in the works. I spend the majority of my work day working on these projects while still delivering for my job - I really dislike working for someone else but, as a means to an end, this is pretty cushy.


Actually working for someone really isn't that bad.

I had my own company for about 8 years and had quite a lot of fun doing it. The money wasn't great, but the freedom to do what I wanted was nice. Or so I thought at the time. I probably put in 60+ hours a week. I was constantly thinking about it. I rarely took long vacations simply because there really wasn't anyone to answer the phone when I wasn't there.

Then I gave it up, and went to work for client of mine and now had the freedom to actually take a couple weeks off. And to actually work on interesting projects without worrying about my paycheck. I had a wife and a 1 year old daughter and being able to leave the office and forget about work until tomorrow was wonderful. And it wasn't something I was able to do at my company.

After 13 years doing that, I've gone out on my own again. Consulting for my old employer and picking up a couple new gigs. Its not going to make me rich, but that's not important to me.

Anyways, enjoy the different kind of freedom of working for someone else. Maybe you'll find you like it. Maybe you wont. But at least you'll have some more experience under your belt.


If you're still feeling stuck after all of these great answers, feel free to hit me up over email (should be on my profile) and we can setup a time to skype and dig into this. I've been told I'm a good listener and ask good questions, so let's see what we can unearth about your situation. No charge and no funny business. I've just had my own experiences with being lost and want to help.

-Samuel


You'll get a lot of advice on money from self-righteous spendthrifts, or workaholic try-hards like myself projecting their own image on to you -- but this is about you.

What makes you happy ... dig really deeply into this question by:

0) Acknowledging that you are free to do whatever you want (really!)

1) Seeking out and being around people you admire

2) Trying brand new (scary) things

3) Practicing collecting data about your state of mind and happiness, and pursuing behaviors that improve it.

4) Acknowledging that unhappiness and happiness can exist in a healthy balance which both motivates and rewards you.

5) Do what you want.

6) Accept that your goals and ideas about happiness will change over time and aren't static

Right now I'm an over-working, game loving, big spender. And right now its pretty fun because I have the confidence to love this lifestyle for what it is -- pretty silly. Its not who I am nor who I will be forever. I've also been a survivalist and outdoor photographer for magazines, a car-living homeless person, a Master's student, a startup-er, and most recently a researching for one of those big SV companies.

You'll find it. You'll do great. Don't be afraid.


The questions I read were in the 4th paragraph where you talk about not being in control.

There's a range of possibilities that you are more in control of things than you think. Is it The opinions of others? Perhaps take a needed vacation to travel. Travel alone to reflect or just not think about it. Perhaps someone is actively trying to control you for what they think is best for you?

I believe in a 25 year old crisis. Because you still have people out there who think they inspire you, or want to influence and guide you. Or you are legally an adult but there's all these older folks to still see you and treat you as a kid. Or you overcompensate for it by out-adulting the adults. Or you are self-aware of your age and how your accomplishments overshadow those who are older than you. You have surpassed them in some ways yet still try to find meaning in life. I think that's what I'd call something like the quarter life crisis.

I guess no matter what age you're at, it's time that matters in how you invest it and appreciate it. I want to control time!


You're so young, enjoy the ride.

Cultivate a rich life and identity outside of work. It's hard but what we do doesn't have to be what defines us.


Why ?


Look at it this way: just the fact that you know you're "lost" puts you way, way, way ahead of the pack. "The pack" being, of course, all these kids working for Google, Twitter, Uber, etc who think they're on some glorious "path" to meaning and success just because they're doing something instantly recognizable and buzzworthy.


I think reframing the way you're thinking about this would help.

Instead of saying "I'm annoyed that I can't do these things arg" why not say "I've made a decision to do Y because, and I'm going to make the most of that." Next, try to evaluate whether you are succeeding in that role. Are you learning? Growing? Maybe you're not coding as much but you're learning a crap-ton about how NOT to do things, or about a business domain that has a bunch of meaty problems you can solve later.

Look hard at the things you really want that make you happy (spending time with family, creating things, etc) weigh them, and use that as a new target.

Unfortunately your conundrum is a constant struggle throughout life for those that want to have an impact. First, breathe and relax, and know that it is impossible to do everything all the time. Second, realize that you have a bunch of time left, and there is no formula that determines when in life you can have an impact or be successful. You'll be just fine.


> How do you cope with that? Seeing your future as an underachiever pains you. What do you do?

For myself? I work out what I want to achieve and go work on it. There are several problems I'm interested in at the moment: visual IDEs and complexity, computer aided research planning, local-proxy based encryption, sousveillance as a peer to peer service...

Do I have a job in any of these areas? Well, yeah, one. But that's besides the point - I don't stop working on the others because I don't get paid for them, I just tinker at home. If I lost my job on the one I'm working on at the moment I wouldn't be in a 'The world is over, can't work on what I love.' position, I'd just find someone else to pay me to work on something that interests me.

I feel like you're maybe feeling lost because you want to work on great things but don't know what those are. Might be wrong? The worry there is that great things isn't a thing you can steer towards, it's a magnitude - and in so far as that magnitude lines up with someone's values it's an opinion. You could almost call the want to work on great things an expression of longing for a goal.

So:

What interests you? What problems keep you up at night? What has hurt you in your life? What might you like to help others with? What have you enjoyed and would like to see more of in the world?

What are your current strengths? How well do those fit addressing the earlier problems? What do you have to do to make them fit better?

I feel like sitting down for a few hours with a sheet of paper and answering those sorts of questions might make you feel a bit better. Even if you can't think how to steer A towards B immediately, you at least have a starting point to begin looking into what you'd need then.


1. Freelance until you figure it out. Just pick up short term contracts if you can.

2. Spend time with family and friends.

3. Find a way to help others. Get out of yourself for a bit.

4. See a therapist. There's no shame in getting an emotional 'tune up'.

5. Life is longer than you realize. And harder than you imagine. Start being good to yourself.

6. Remember that difficult times don't create character. They reveal it.


> What do you do when you believe that you can do great things but something that you have no control over is holding you back? You believe that you are good at what you do and are meant for great things but you have to do your job even though it doesn't do justice to your capabilities. How do you cope with that? Seeing your future as an underachiever pains you. What do you do?

It sounds like your someone with ambition. You know you're capable of great things and wouldn't be satisfied with anything less. I'm like that too and I thought a lot about it.

IMO, the ultimate goal is to be happy, so the natural question is how these ambitions translate to happiness and whether you could do better by taking another approach to happiness.

Other approaches might work for other people, but I suspect that they wouldn't work for people with true ambitions. I suspect that people with true ambitions are so driven and motivated to do big things that they won't really be able to rid themselves of these thoughts. If you try to settle down into some nice relaxing lifestyle where you should be happy, you'll always be haunted by the thoughts that you could/should be doing something better.

Note: I'm saying "suspect" a lot because I'm only 21 and am not too confident in this hypothesis.

So if you're ambitions are a core part of you, I suspect that it's best to pursue them. And if you need to get yourself some stability in the short term, don't worry about it. Do what you can with what you have, and think long-term.

- - -

Also, I hate the idea that smart and ambitious people can't pursue their ambitions because they need to pay the bills. I wrote about it here - https://medium.com/p/f4902d078f58. I think you'll be able to relate.


May I prescribe a course in reading? Read Zola's Germinal. Read Moby Dick. Leaves of Grass. Pride and Prejudice. King Lear. Les Miserables. Lysistrata. The Odyssey. Anything great. We all (for reasonable values of 'all') yearn. It's the human condition. "true ambitions" suggests a fairly naive view of the world.

To put this in context. Almost everyone who ever lived has died of starvation, a broken leg, an infection, or by being eaten, if they somehow made it through childbirth and the next 3 years of helplessness. Everyone. Even today, most people work selling shoes or insurance, or assembling things in a factory for 12 hours. As I stand here at my expensive stand up desk, outside some guy is driving a lawn mower around with a bandana around his face to inadequately protect him from the flying dust. I hope your mental model of all these people is not a lack of 'true ambition'.

We all yearn. I guess you can put yourself on a pedestal and conclude that you are different than everyone else, or recognize your brother/sisterhood, and try to learn what life is about. You have 80 years left if you are extremely, outrageously lucky. I'm not saying don't strive, but I am arguing for perspective into the human condition.

We all yearn. Life is limited. The air is beautiful today, and your wife wants some attention. Live it, instead of lamenting that you are such an incredibly special snowflake that being at the very, very top of opportunity for humans in the history of the world just isn't good enough for you. The people that just died in Typhoon Halong deserved more. We all do, but we don't get it. Take what you can, embrace the bittersweet, and live. It's all going away soon.

I think you'll be happier that way.

To the person I am replying to: I am more riffing off the things you said, than replying to you specifically. You may be perfectly happy. No disrespect intended.

edit: I yearn too. I'm not dismissing the feelings of the OP, but pointing out that it is pretty darn universal. I've found that viewpoint incredibly helpful for my own life; perhaps the people reading will as well.


You're listening to your gut! I'd say that's a pretty good start. Most people ignore what their gut is saying while they make the "comfortable" safe choice.

I would try to shift your mindset. Nothing is permanent, nothing is forever, and there is no perfect situation.

Try to view life as a series of choices. Right now you're choosing stability and that's fine. When your financial situation improves, you'll be able to make another choice.

Plus there is always bootstrapping on the side :)

Learn what you can out of your new situation and try to view it in the most positive light. It's not your ideal situation, but ask yourself "What can I learn from this experience?" and it will be easier to digest. A stable company has the potential to teach you about leadership, the structure of successful companies, how strategy scales beyond 3 people in a room, and you also have the potential to form friendships and relationships along the way.


I fell into a similar frame of mind a few months back.

I've been running a tech business since I was in school, it's all I've ever known. Ten years on it's not like a startup any more, it's a daily slog and I dislike it immensely.

Friends and family think I've done well even getting this far but all I see is the lack of real growth for the past few years. I thought I would be a lot further ahead than this.

So I'm now doing my best to stop feeling sorry for myself. I've started helping my wife progress her career and it feels far better than anything I've ever done for myself. It gives me a reason to carry on with my boring job every day, knowing that doing so brings in enough money to give someone else the chance to follow their dreams.

I don't think I'll ever give up on my own dreams but at least if I can help someone else in the mean time I'll never have to say that it was all for nothing.


Make 'peace' with your 'current' situation.

This does not mean 'accepting' it and 'acknowledging' that mediocrity is all you're bound to. This means that for the time being, you will make the 'best' of the opportunity 'at hand', you will work for a better one to present itself while eliminating all the negativity and irritation associated with the present.

Changing your mental state, to become a catalyst for progress instead of a shackle, is the actual problem and the real challenge. Work on this point, the rest is relatively clearer (side projects, another startup, better offer, fancier pay, more exciting challenges/problems to solve etc...).

I'm in the same position, at the same age, battling the same demons. The above is my realization after a prolonged phase of depression. 'Work with what you have to reach what you couldn't before'.


My mom always told me do what you love and the money will follow. Sounds trite but I've spent the last six years going 50/50 between working as a professional skydiver and traveling internationally. Now I am successfully transitioning to web design so I can travel full time.

If it isn't fulfilling then don't do it.


I completely agree with this; however, there is another way to approach the situation. I recently went through almost the exact same experience OP did and decided to cut everything extraneous out of my life and take a remote dev job. This has allowed me to slow life down, re-focus on the things that matter in life and build up my bank account. THIS gives me the freedom to go and create and build and run whatever I want if I so choose.

So, don't feel bad doing a job. Nothing is beneath you, and everything is always a stepping stone between where you are now and where you will be later.


First off, good for you for asking for help and advice. Too many people keep to themselves and stagnate. Learning to ask for help is something that took me nearly a decade to understand was okay.

5 months ago, I posted something very similar here: https://news.ycombinator.com/item?id=7398968

I'm only 26, so I can't give you the wise advice that others in this community can, but I'll say that I just stuck it out, and things got better. I was in a job I really didn't like, I was personally unhappy, and felt very alone.

Simply as a process of time, continuing to get better at my craft, and continuing to poke on my network, I now am in a much better place, working on something I'm excited about with a team I really respect. I don't even like calling it a job.

I think a lot of us are going through the same thing you are, especially people our age when we look at the web and see all these other people our age who are far more successful. Just remember that if you see some 26-year-old millionaire on the front page of TechCrunch, it's because that person is an exception, not the rule. You don't have to size yourself up against their level of success, or even what you perceive as their happiness.

Live your life. Find and follow your path. You're always doing what's in your heart, so listen to it. You cannot run from your own nature, so take time to sit with it, discover it, and fall in love with your own desires. If you truly know yourself, and can discover what you truly, deeply want to do, I think you'll be happy. Just know that there's no timeline on when you discover it. I still haven't found my "thing", but I'm happy because I know I'm getting closer to it.

My email is in my profile. Please reach out if you need someone to talk to. I'm sure there are many others (older, wiser heads) here who would offer the same.


I've found that as I do what I know is my obligation to do, while still reaching for what I feel is my dream, that things seem to almost conspire to move me in routes that actually enhance, rather than detract from, what I really wanted.

Keep the vision of what you want liquid. Go in a general direction. Role with the punches and don't swing at every pitch. Try and use your distinct perspective to give you insights that others do not have.

While the journey might take longer, or may not be as conventional, if you stick at it my experience has been that things work for me when I stay at things regardless of how distant or implausible they may appear at any given point.

I'm only speaking from my own experience, but every seeming downside I've had has, after enough time and experience, actually appeared to be a boost rather than a drag on my long term aspirations.


Please read: 'Thinking Fast and Slow' by Daniel Kahneman (Note: the last 1/3 of this book is quite arduous and not really related to your issues...).

'Thinking Fast and Slow' changed the way I think about everything. In fact I need to read it again.

I like you have had perhaps two periods of feeling incredible inadequate since I moved to London 3 years ago. The quarter-life crisis is well recognised if you do a quick search.

One thing is certain: Money != Happiness. Last time I received a pay rise I requested a day off every fortnight. That day I get so much done, it is unbelievable. Just that day makes me happy. My aim is to keep reducing the number of days I spend sitting in offices.

> I'm 25 years old and I am lost

I can easily look back and apply the same sentence to the way I've felt at times.

Good luck!

PS email me if you would like more advice. I mull over this sort of stuff almost indefinitely.


Why do you want to run your own business? What are the positives you hope to gain from doing that? I spent my mid-twenties convinced that I wanted to found a startup and live that life, but having recently emerged in my 30s I've realised that what I actually wanted was the freedom to make my own choices about what I work on and how. I never cared about entrepreneurship.

I left the startup world behind and my life satisfaction went through the roof - I no longer felt guilty for not crushing it 100%, or that I hadn't sold a successful company by the age of 24. I'm not saying this is the answer for you, but it's never a bad thing to get some perspective. Get out of the bubble - take a road trip around some states, maybe. Take a break from Hacker News. You and your friends might be chasing the wrong thing.


> I've realised that what I actually wanted was the freedom to make my own choices about what I work on and how.

What are ways to accomplish this without running your own business?


Not OP, but not every business is a startup. Freelancing or building a consultancy might give you freedom without a 90% failure rate.


First, you need to get over the popular idea that the only way to do something great is to create a start up which gets bought for millions of dollars. That's really flashy and everybody likes having millions of dollars, but there's plenty of other ways to do great, important things.

It sounds like you're not excited about your new job. I understand that you took it anyway because you have financial obligations to your family, and that's great. But the solution is obvious; look for another job and/or do something you ARE excited about in your spare time.

It's up to you if you don't actively dislike the job you're taking, it just doesn't excite you, then maybe doing that full time and working on something exciting in your spare time is the way to go.

If you find your new job miserable, then look for a new one.


My advice will likely be laughed at, but I chose to follow Jesus Christ. Start with the Book of John. I'm 45 now, and have been following him since age 20.

I have friends who are millionaires, and one who is close to a billionaire. I don't think they are any happier than I am, and in fact my relationships are much better than most of theirs. It's weird, but when you do finally have tonnes in the bank, and you've had your fill of partying and the good life, it becomes a bit tiring. Then the question becomes "now what?".

Also, what do you do with your guilt?

Once you get the meaning of life sorted, everything else makes sense. Whether you are rich or poor, healthy or sick, or

This is, of course, just my opinion. I respect a person's right to believe whatever they want, all I ask is they respect my right to believe whatever I want.


This is good advice, and I'd like to broaden it to include any deity. If it feels good, you can take a minute or two at the end of the day to say thanks to colleagues, to a friend or what have you. You can thank Hephaestus for a good day's work, or Hera for your family.


>Then the question becomes "now what?".

Well, if you are a billionaire you can pursue just about any answer to that question. If you are poor, all you can do is hope that the answer is within your reach.


If you are a follower of Christ your hope is in something greater, and it is within reach no matter if you are rich or poor.


You'll have wasted half of your life. Why wait? It's not an either-or.


Man, I have the answers to the "now what" but not the money to pursue them. I can't imagine having that much money and not having big plans for improving the world.


Firstly, don't be ashamed of your acqui-hire - that's a hard thing to pull off and you should be proud that you didn't fall over like 99% of all startup companies do.

Secondly, take some time for yourself. Assuming the terms of the acquisition were favourable, you should have a fair amount of financial freedom (at least for a few months). Take some time to travel and see parts of the world that are new to you. For me, travel is a very effective "reset" that helps me examine my life and the world more holistically.

After founding a startup and working hard to see it succeed, you're probably used to a fast-paced cadence and it's hard to relax into a less high-producing role. Time box your relaxing so you don't feel like you're just giving up - but give yourself some space to live.



Part of the reason you are lost is because you have no experience. You are trying to solve problems with startups, but the quality and profitability of the problems you can solve at 25 is not that high. Simply because you have not seen enough. The other part of the reason is that our (I am 28) generation has a lot of freedom and a lot of free time too, we are having troubles dealing with that, many just waste time/freedom on useless stuff (carrier, facebook, TV, etc.), others “waste” it thinking of how to obtain a better future (financial freedom, sounds a bell?). My advice is: go out, go have some fun; meanwhile get good at whatever job you are doing and I ensure you that in a couple of years you will have seen lots of profitable/interesting problems worth solving.



"I know for a fact that I want to run my own business and attain financial freedom"

This is really cool to have that mindset. I'm also building my own business right now while I'm working for another startup.

But are you sure that this is what you want? Why do you want this? Will it make you happier? If so, why? So many people are on the top and yet they are unhappy.

I _know_ I will be downvoted for this, but I can only suggest you to pray about it. My rationale for praying is simply this:

1. If God doesn't exist, I only lost a couple of minutes.

2. If God does exist and what's told about him in the Bible is true, he will hear me.

There's nothing much to lose in both case. Only a potential win. I prayed all my life and I saw answers to them so often. I can assure you God loves you and he really cares about your future. Ask him about it. :-)

God bless.


>There's nothing much to lose in both case. Only a potential win.

Just like astrology and power crystals.


A guy with an acqui-hire under his belt describes himself as an underachiever -- I don't think you realise how insulting that might be to other ambitious people who are in much, much humbler places :)

Grab that bag of money and go travel if you can. Have a good time, you deserve it.


Sounds like you pine for social status.

When you get older you'll see that it doesn't mean much. Once you achieve the status you've set your eyes on today, some higher status will beckon. The treadmill will never stop.

You can find happiness in work only if you find happiness in the work itself. Not only because of some monetary or prestige-based result.

Prestige chasing is not a recent phenomenon, but it is certainly more common now than it was in the past.

My father and engineers of his era entered the field for the love of making things. Yes, it provided a solid middle class job, but their aspirations were to work on some machine they were fascinated with, and to provide for their families. Becoming a millionaire or billionaire was not in the realm of possibility.

And yet they were so happy and content.

In my own generation many engineers are filled with angst. The stories of rich engineers fills them with envy ... and sometimes drive.

Because some engineer made it, you feel your good grades mean you can make it.

But success in business is not often linked to your engineering chops. And sometimes its not even linked to your hard work.

You need a combination of a lot of different traits.

And even with the traits you might be born in the wrong country and not make it.

But it is no loss to not make it. Happiness is not guaranteed by commercial success.

And many without commercial success are happier than those with commercial success.

As one of many who turned down a Google job long before it reached its lofty current share price, I have often had reason to question my life choices. My former colleagues who took the Google jobs are very comfortable (understatement). Sometimes I have pangs of regret. But they pass.

My regrets are mostly not for myself, but for my wife and family. I see missed opportunities where I could have helped the people I love.

But I am fortunate that my family really doesn't need my help that much. My wife is self sufficient (actually makes more than I do). My extended family can take care of itself, even if I have to lend money every once in a while (which hurts).

I focus on these things. I also try to do those things which make me happy--like going to meetups that I enjoy (Go, Docker, CoreOS, Clojure, etc.), playing video games, watching movies, hanging out with friends. When I do these things with my rich friends, I realize our happiness is not materially different from moment to moment.

Really our subjective wellbeing is exactly the same when we are living in the current moment. Only if I contemplate my mistakes of the past, or the possibilities of the future does my happiness and theirs diverge. Otherwise we are traveling along the graph, parallel to the time axis, with two almost co-incident lines. In times of volatility their line may even dip below my line ... deaths ... bad days with spouse ... etc. Mine may soar above theirs sometimes ... a great meal, the birth of my nephew ... meeting a cute puppy ... giving some money to someone I know will use it well.

We will all have some ups and some downs. You are in the downs right now.

The downs happen a lot in our twenties because we don't understand at that age that our brain is sometimes like a state machine. We have to manage the state transitions from bad states to good states using conscious actions, applied whenever we find ourselves in an unwanted state.

You will soon realize what you need to transition from bad mood to good mood.

For example, if I am hit with melancholy I do several things which 99% of the time guarantee a cure. First I run or lift weights till exhaustion, and then I eat a big meal with a friend and discuss some interesting topics. And then I come home and give my wife a tight squeeze and sleep. In the morning usually I will have transitioned to being upbeat again.

You will find for yourself what your transition processes are. Just try some stuff.

Good luck.


I think you should chill out for a while. Travel and experience other places, people and cultures. Read meaningful books which provide you thoughtful insight on the vagaries of life. IMO you will appreciate the smaller, more meaningful things in life, which is actually what makes people happy rather than materialistic endeavors (there's nothing inherently wrong in being materialistic, it just doesn't give people long term happiness. See this: http://en.wikipedia.org/wiki/Positive_psychology)


I'm 46 and rode the Web revolution to a great career, working for some amazing places, and I'm still worried about some of these things. I've done a lot of things I'm really proud of, and I still don't feel done, so trust me, this never goes away and maybe it doesn't even make you lost, just searching.

One approach I can suggest: in my generation if you wanted to change the world you went into nonprofits, which is what I did. You don't have to build a startup on one of your own ideas to make a difference. What are your causes? What do you care about?


Just because your current job isn't in a sexy or trendy industry doesn't make it bad. You can learn a lot about working with people and business even if you're somewhere in the bowels of a large multinational corporation. I know I have. Also, there are really excellent developers in companies like that, too, not just in startups in the valley. Even if this job isn't for you, a couple years in a place like that isn't very long in big scheme of things. You might get ideas for some sort of B2B startup that you wouldn't have otherwise.


Try not to focus on yourself and inward. Focus outward. There is no right answer to "what should I do" but it is also the wrong question. Instead I would read Viktor Frankl and ask "what does life expect from you." Maybe it demands you work a job that you are not passionate about right now. This job won't be forever. Maybe the world right now demands you quit your job and work on a great idea and seize a great opportunity. Only you can answer these questions, but make sure you are asking the right questions.


I'm hearing a bit of Impostor syndrome there...sometimes just bringing this to a conscious level can help counteract it.

I find that it also helps to remind myself that life is managed not cured.

So you're working a non startup gig for a while - there is zero shame as that. If you've got your heart set on a startup long term then see it as a tactical retreat whilst you gather your strength and evaluate options. Chance are it might just help you - sometimes its better to bid your time and attack from a position of strength than charge at the problem blindly.


As you know this yourself, all "startups" are not risky. early stage startups are risky. "Startups" that have reached a growth stage are not necessarily risky (that scaling phase is about throwing gasoline in the fire). Your compensation package, role and type of work you do at any of these companies is on par with that of a big company. Many metropolitan areas are filled with companies that fit this profile... why work at a crappy place when you can get steady income from a safe place & fun place?


You have more freedom than you think to do great and interesting work in the job you have now. Just don't wait to be asked, you just invent without being asked to invent.

You just need initiate and bootstrap the idea yourself on the side quietly, then when ready for demo, show it to your boss and ask for some sponsorship to keep working on it (you gotta make sure it has clear business impact for them) Most reasonable bosses will allow for some time invested in new and interesting ideas. If your boss always shoots it down then find a new boss.


Start learning about meditation, but like, for real. I went through the same "mid life crisis" (I'm 23) and it helped me immensely. Especially vipassana. I'm still a massive massive newbie but I can get a tiny tiny grasp of what true happiness is. Startups are an amazing work environment but they're also incredibly stressful and sometimes just shade away what's the real meaning of life. Building startups, optimizing UI/UX, etc etc etc is NOT real life. Just my 2 cents


Some great comments here. I'll add a few favorite quotes that I think are relevant:

On doing great things:

"It turns out that for all their diversity, the strikingly successful groups in America today share three traits that, together, propel success. The first is a superiority complex — a deep-seated belief in their exceptionality. The second appears to be the opposite — insecurity, a feeling that you or what you’ve done is not good enough. The third is impulse control.

The way to develop this package of qualities — not that it’s easy, or that everyone would want to — is through grit. It requires turning the ability to work hard, to persevere and to overcome adversity into a source of personal superiority. This kind of superiority complex isn’t ethnically or religiously exclusive. It’s the pride a person takes in his own strength of will."

On resilience:

"They use difficulty as a catalyst to deepen purpose, recommit to values, increase discipline, respond with creativity and heighten productive paranoia — translating fear into extensive preparation and calm, clearheaded action. Resilience, not luck, is the signature of greatness.

... turn it into “one of the best things that ever happened,” to not let it become a psychological prison.

The 10Xers exercise productive paranoia, combined with empirical creativity and fanatic discipline, to create huge margins of safety. If you stay in the game long enough, good luck tends to return, but if you get knocked out, you’ll never have the chance to be lucky again. Luck favors the persistent, but you can persist only if you survive."

On finding happiness:

"Forget about finding your passion. Instead, focus on finding big problems. Putting problems at the center of our decision-making changes everything. It's not about the self anymore. It's about what you can do and how you can be a valuable contributor. People working on the biggest problems are compensated in the biggest ways. I don't mean this in a strict financial sense, but in a deeply human sense. For one, it shifts your attention from you to others and the wider world. You stop dwelling. You become less self-absorbed. Ironically, we become happier if we worry less about what makes us happy. "

Best of luck to you.


Working at a regular company can provide you ideas for your next project. Find out how things are done, figure out how they could be done better. Your next startup should solve a problem for someone, why not solve a problem faced by your employer and its peers? In fact, there's a problem right there - a capable person like you doesn't want to work for a company like that - why? There is a problem there. Much bigger than what I had in mind when I started this comment.


I would take 'enjoy the ride' a step further. Use the ride. If you are never anything but a successful entrepreneur you will fail:

1) To be a good boss to anyone except the elite talent 2) To understand how/why gears of productivity can grind to a halt as you get layers of management beneath 3) To have a vantage point to appreciate what you achieve later. 4) To meet anyone who you can say forever was there for you when things weren't going rockstar sexy.


You're only 25 years old. You have the world at your feet. Not only that, but you're accomplishing great things.

You will have these transitions in life. They are not failures. They are the closings and beginnings of chapters.

Before you know it, you'll be approaching the end of the book. But right now, you're young. Take more (positive) risks. Enjoy everything, knowing you have plenty of options. And definitely don't waste any of your youth on self-pity.


> How do you cope with that?

Don't underestimate the Mental Game aspect of this personal challenge. An unusually good read on this subject, Way of the Seal by Mark Divine. Here's a recent interview> https://www.youtube.com/watch?v=T_bDMEUF7F8

Mindset is crucial. And a 24-36 month game plan to pay-off debt, salt-way cash, & plot your next move is a smart strategic play.


I'm your age. All you need to do is find your passion and work on it after your day job. If you don't like your day job find another one.

Money alone doesn't bring happiness because happiness comes from within and not from external sources.

Email me if you'd like to talk more.

You'll get all sorts of advice on HN but at the end of the day all that matters is that you're happy and excited to work on your goals everyday while providing for your family.


Great things never came from comfort zones. If you want to reach your goal of financial freedom you're going to have to put yourself back out there.


If need money, start freelancing or get a job. With a job, you can build a small sidebiz and when you're ready to make the jump you'll have either existing revenue from your new product or freelancing gigs.

I've been doing this for last few years. I currently have a startup that has very little funding but I have cashflow from consulting, so it's not that risky (can still pay the bills)


Startups will always be tough and you'll probably always be afraid.

Take care of your financial situation and push on with your new startup.

It is easy to feel panicked when facing a situation you want to change, but I'm sure if you reflect upon your life you've felt that way before and made it through. Problems ahead can often seem insurmountable but few things in life actually are.


The Universe is much bigger than you. Go with the flow. Have your ambitious goals as an intention, but take what you are getting now with peace. In the end, your achievement or lack of, hardly matters. Your living of your life with peace, matters. Be attentive and opportunities that suit your intention will knock on your door. Until then, don't sweat.


I think you need to (1) find a significant other and (2) partake in debauchery. I say this because you seem to be myopically focused on business/success, and despite doing pretty well for yourself, you've derived almost no satisfaction. Maybe you need someone to share your life with. And maybe you need to step outside of your own thoughts. Live!


It's possible to be happier with less, plain and simple. What did people living with far less throughout human history do? I guess you think they were just miserable, that we've reached happiness as a society through comfort goods. I think you're just a wimpy comfort junkie with no imagination.


35 here and still lost. Basically lost faith the direction civilization is going. Currently trying a radical shift in 'career' paths; leaving tech & entering organic gardening. Seems to be going well, but I still feel like I have no idea what I'm doing. Good luck to us all.


If you want to be independent, try to come up with an idea for a real business (not a funded tech startup) that you can implement with software, and spend 2 hours a night (or just a few nights a week) on it for a month. By the end of that month you should be able to sell it to someone.


Holy crap man, this is almost the exact same boat I'm in (except I'm 26) and I feel the exact same way.

I find my biggest problem is a lack energy / motivation to start that next thing. I really have no clue where the fuck it came from... a few years ago I could work endlessly...


You're burned out. Be very afraid of this.

If you can afford to, take a long vacation. If you can't, try to find something that brings you joy and do that thing every single day, without fail. Beware of burnout, it can cost you years.


diction says a lot about frame of mind. the negativity wont let you think differently here, but its definitely possible.

one foot in front of the other. get rid of the fear, its pointless after the first time - you have a network and a net under you.


You sound somewhat anxious and depressed, feelings I know well.

It will help you to have some tools to deal with these problems. CBT and DBT are two such tools, and can help you manage your thoughts and mood. Counselors teach these tools.


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