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Ask HN: What would you do if you could start over?
75 points by mathiscool11 10 months ago | hide | past | favorite | 139 comments
Does anyone here feel like they took steps that ended up unexpectedly slowing their career/progress? If you could go back 10 years with the knowledge you have now, with the sole goal of having an idea that could be a successful startup, what would you do different?

I'm looking for things such as: -College major -Career field -Bad life decisions -Relocation -Finances -General personal development (Not work/startup related, such as working out) -Career development

Please feel free to add anything you think is fit, even if it isn't on that list




Start exercising early in your life. Its net beneficial in all kinds of ways both physically and mentally.

Don't underestimate the value of repetitive processes. Automating them out of your life can be counter-productive: People bake bread, for a zen experience, sometimes, even though they've done it the same way 1000 times before.

Forgive yourself. Don't carry burdens in the past. Sure, we can all remember mortifyingly stupid, bad moments, but dwelling on them is counter productive. Of course you need to learn from them and avoid them but stewing over it at night when you should be sleeping? not helpful.

Rewards are complicated. Sometimes, the doing of it is the reward (see baking above). Sometimes, the outcome is the reward. Sometimes, the outcome is the reaction from others. Sometimes, its renumeration, sometimes it's just recognition and sometimes, there is no reward but its the BATNA. Value all of them in some way.

That said, small kids learn beneficially from SOME reward structures because before you learn to be patient to a long term goal, the short term reward builds muscle and brain memory of the task. So rewarding kids for good behaviour is not actually totally counter productive. But, contrariwise, there cannot be only winners and teaching your kid to refuse to accept second place or last is .. not helpful. If you genuinely don't win, don't pretend you won.

Habits take time. 6 weeks isn't unusual.

Don't be a dick in meetings.

Don't be contrarian for amusement value. Devil's advocating has limits.

Be kind.


I would leave jobs that weren't working out sooner. When you have a good job, it's hard to leave. But there were times when I had a good position but didn't enjoy my job or wasn't very well thought of. It's easier to be a star when you are starting out, but when you get to middle or senior management you are much more likely to be controversial or get into difficult situations that your talent isn't going to save you from. Things aren't going well and you think, well I will just work hard or try to adjust to feedback. Sometimes it is best to just move on. My favorite jobs have been fun at the start and fun years later as well.


i left two jobs that didn't work out. the problem is that the first one of those failed because i was working all alone, no team, and an overworked supervisor, and at the time i didn't know how to compensate for that (i didn't even know that it needed compensating).

it took me years to understand that i am driven by human interaction. what i am struggling now is how to translate that into advice. i mean yes, i should have looked for jobs that do pair programming. but every personality is different. how would a 25 year old know if that advice applies.

the best i can come up with is to try a few different jobs and pay attention what it is that that is fun.

but even there you can mislead yourself. i did a programming internship while studying and figured that i hated 9-5 office work. then i did foss development with roxen and pike and i absolutely loved it. but i thought it was the programming language, when in truth it probably was that i was working closely with the people that used the website i built. so i stumbled from one experience to the next without really understanding what made work fun.

i can work on side projects all alone for months at a time because i was solving problems for myself. or i can do the utmost boring work with a hands-on client. we worked together for 10 years. the most wonderful person i have ever worked with. working together made the dullest task enjoyable.

i suppose the common element is that there was a need that had to be filled. in one case it was my own, in another it was someone elses.

but how does that translate into actionable advice?


"but how does that translate into actionable advice?"

Perhaps, be aware of what you need in coworkers / end-users, and look for that?

Something that many in the tech industry completely neglect, thinking it's all about tech.

I think your comment is gold dust BTW, basically all of us need to figure out how to be HAPPY. And you've clearly stated what you need, which I think a lot of us need but don't always realise we do, which is to be important/helpful to other people. Much more important than making huge $$$$$$$$/ ££££££££££££ or being an expert in mega-cool-language-or-framework-X-which-will-inevitably-one-day-be-oboslete-however-much-we-pretend-it-wont


> Sometimes it is best to just move on. My favorite jobs have been fun at the start and fun years later as well.

Why did you quit those?


I’m 40. What I’m doing today, I wish I would have done at 30. Jiu jitsu, striving to be the absolute best version of myself, working with my hands, building other skills besides coding.

At 30, I wish I was doing this stuff at 20. Health and fitness were a priority, focusing time on things that bring ROI into life including more career oriented, less booze and idiotics.

I married and we had two kids in our 20’s, probably the best thing either of us ever did. Wish I could shift this earlier a few years as well so we’ll have more years together as they grow old and have their own families.

Sorry if confusing, on mobile.


The older I get the more I too realize that “the best time to start anything is yesterday”


There’s that, and also “I’m capable of so much more than I realize.” Too much of life is consternation about bullshit that doesn’t matter. In moments of indecisiveness, sometimes I use the “look back” tactic where I imagine a future version of myself reflecting back to this moment. Will he care? Will this have actually mattered?

Helps me get through some bs.


“I’m capable of so much more than I realize.”

Turns out I'm capable of less than I realized.


FYI there's a saying for this: https://english.stackexchange.com/questions/603690/origins-o...


"I’m 40. What I’m doing today, I wish I would have done at 30. Jiu jitsu,"

I was training yesterday and had the same conversation. I am a 48 1-strip blue belt and my body is starting to give on the wear and tear.


I'm a 2-stripe white belt. The secret to my success is that I keep showing up. Just don't ever quit.


Moving/working internationally was a dubious life decision for me (and a lot of other people I think).

While it mainly worked out in the end, there were many stretches of years on end when I stuck it out at jobs that I didn't like or had outgrown, but were difficult to move from (or start my own company) because I was on a visa and could only move to some other company that would sponsor, or move internationally.

It makes other aspects of life harder too, e.g. starting a company, buying property - sure, you can buy, but do you really want to own somewhere if you might not be allowed to live/work there in the near future? Relationships - romantic/cultural issues, and you'll leave behind all your school friends, people you grew up with. Sure, you can make new friends... but they won't be as deep, and they'll probably kind of be other misfits in the new place, like you.

Not to say that it never works out... and maybe it's interesting for 2-3 years before going back home or settling some place permanently, but it can come at a pretty big cost. If moving from some third world place to a developed place, it's probably a no-brainer, but if you're moving from one developed country to another, it's quite possibly more paperwork and inconvenience than it's worth, and for the most part I wouldn't really recommend it, I think there is a lot to be said for just doing the best you can where you are, with your network, and with citizenship/no restrictions on anything.


Good comment. I worked in USA 25 yrs ago and experienced this. The key thing I think, as you alluded to, is do it for a limited time. If you're in a country which makes it hard to stay for good, or you deep down know you wouldn't want to if you could, then it's a temporary adventure and in the end the need to go "back home" or else feel rootless. In my case probably working abroad delayed meeting "the one", getting married and having kids. So now I'm an older Dad than ideally I would've been for our kids. Its not the end of the world, there are some advantages of being an older parent, but some downsides too. Also some people may delay life to the point where they don't manage to marry and have kids, which is sad if that was something they would've wanted. OTOH if you've got the itch, not going to work abroad is no good either ;). I wouldn't have missed that adventure for the world :)


I wish I'd fixed my sleep earlier, it became ten times easier to accomplish everything after I addressed my chronic insomnia.

I also wish I'd left the tech industry sooner. Now that I'm in a field that's a better fit for me, I just wish I could have the same length of career as some of my coworkers in it.


How did you fix your sleep?

I have horrible sleep hygiene and it worries my sometimes. I’ve had bad sleep habits starting as a teen so it’s been hard to break out of them.


Personally for me, my sleep started getting a lot easier and better after I started lifting weights.

I lift heavy weights for 1-2 hours every other day. My body forces me to sleep 8-9 hours/day to recover.


I don't know what he did, but for me was very basic sleep hygiene added with Cognitive Behavioral Therapy for Insomnia (CBT-I), there are several people on YouTube sharing how to do it. With their guidance, I fixed myself after years of suffering from it.

The tipping point was going to bed only when sleepy and forcing myself up at the same time every day as much as possible. Problem is, some weeks will be super rough, but I kept trying and even with an imperfect execution that made me sleepy again at bedtime, which I thought was something I had lost forever. To lay down and sleep.


Which field are you in now?


If it is okay to ask:

What helped you the most with the chronic insomnia? Do you have any advice?

Thanks


I can chime in here:

For me, it was a combination of things, here's the order I've tried: 1. Lift weights 2-3 times a week. 2. Avoid caffeine after 10:00am. 3. Stop eating like an idiot. 4. Go to the doctor and get blood work done. Turns out my hormones were all screwy. I had to get three different opinions before I found a doctor who gave me more info than "go to sleep sooner" and actually gave me some vitamins and hormone pills that helped a lot. 5. Therapy (CBT). It took me going to 3-4 therapists before I found one that jived with me.

For some people you just need to do step 1 or 2. For me it took all five. My biggest lesson is that doctors are just people to who are trying their best. Don't be afraid to see more than one or push them if you're not getting results. They can only help you as much as the feedback you give them.

It was totally worth doing all this though.


> Avoid caffeine after 10:00am

Also: Avoid caffeine for the first 90 minutes of your day.

The lifting did it with me. And going to bed at 10 every night for two years in my early 30s, because there was someone next to me I wanted go be like.


I wish I'd been diagnosed with this incurable sleep disorder and gotten treatment earlier. That and I wish I'd sold my house in 2019.


Someone told me once "...the thing about missed opportunities is there is always another one right around the corner..."

Focus on making your here and now the way you want. Do the things now that matter.

We can all imagine an idealized world where everything worked out perfectly...but how horrible would that be? To not experience all the pain to make the pleasure worthwhile. Sometimes it takes decades to realize that experience that scarred you can have a cause/effect on your life in a positive manner. In my case I know that if it hadn't been for every bad/adventurous decision I made in life led to where I am now...and there are parts of the here/now that I would not trade for any amount of money. The people I care about, my ethics, my attitude...everything would be different without the experiences that weathered me.

Stop thinking about the potential millions lost...start thinking about how you are going to lose the next million.


> Stop thinking about the potential millions lost...start thinking about how you are going to lose the next million.

:)


I would have been a lot more aggressive about finding better roles in my early career. I had 2 good experiences for 4 years each, but I could have left both jobs after 1 year and had the same career progression.

I think my upbringing focused a lot on “stick it out” and “work hard and you will get recognized exactly like you deserve.” It was a passive laborer mentality from a blue collar area.

I took a sabbatical and after some soul searching realized it was more like “sharks that stop swimming drown.” Career and compensation took off after that.


Have children would be the main one. Now I'm in my early 40s and still haven't had any yet, and it's starting to feel a bit late. I know it's technically still possible for a while, but there starts being problems for men in their mid 40s, and also now I don't have quite the energy I would have had 10 years ago.

Do everything I could to buy and hold bitcoin would be another one, and get used to buying stocks back then as well, also try to max out my 401k as often as possible. I dipped my toe into stocks and retirement then, but didn't really understand it or prioritize it enough then. Now I'm playing catch up.

I think I'd also get into streaming on Twitch. Ten years ago it was still pretty early, and if I did that and stuck with it for years I bet I could have decently well with it back then, and built up an audience for the games and whatever else I worked on. Also it would have been easier to dedicate the necessary time to it. A lot harder to do that nowadays.

For startup ideas, even though it already existed (founded May 2013 apparently), I think I'd have the best chance working on a competitor to something like Patreon. They went without any real competition for a long time, and their website never seemed all that complicated (creator page, sign up for a few different subscriptions, blog with membership tiers, I did pretty much all of that except taking money for my personal homepage I made in PHP 20 years ago) and seemed to barely evolve the entire time, so I bet I could take enough of a chunk out of it to make it worth my while.


The biggest thing for me was spending too much time worrying about dating and women. The funny thing is, that all took care of itself when I would spend the least amount of time thinking about it.

Other things I could have done to give myself a better chance with a startup:

- Embed myself in the startup scene and network

- Think of opportunities in terms of business models instead of focusing on what sounds cool or useful to me at the moment

- Don't be too skeptical. If something looks dumb but people are excited about it, maybe you're the one that is dumb.

- When you're doing business with people, be confident and always think about what you want to get out of a negotiation before going in. This could be a formal business meeting, or an informal get together. People enter into negotiations all the time. Think about what you need, who can get it for you, and if the opportunity presents itself then ask for it. There have been many times where I had the opportunity to really help myself, but I was too preoccupied with helping the other person get what they need.

- Build yourself a reputation as someone who succeeds at getting big things done, and is fun to be around. That may sound dumb and obvious, but it's the reason LinkedIn looks the way it looks.


Unique to my psychology, but I would have prioritized finding my wife a lot more aggressively than I did.

When I was a teenager, I realized that since I was already a pretty smart and hardworking person, I was probably going to do alright in my career once it got going no matter how long it took to get there. The real risk I ran in terms of life satisfaction was ending up as one of those 80 hour a week workaholics who never carved out enough time to meet enough women to finally find the one I wanted to marry.

That was a very depressing thought, so I decided early on that I would only start taking my career seriously after I got married. Until then I'd be happy with keeping a standard 9 to 5, not trying to stand out too much in that arena, and not saving a whole lot of money (which was honestly more of a psychological thing for me than an actual reality, it turns out grabbing coffee with friends 3 times a week isn't actually that expensive).

Again, I eventually got there, but only around age 24, when I had it in me to start doing that like around age 17 or so.


I would get a job in SV in 2012-2013 instead of 2021 and made a decade of "big" money, expanded my network etc... instead of working a decade in average companies which don't care too much about software development


i know plenty of folks who wish the opposite ;)


I too know of such folks (including myself) but I think we say that only after making the bank!!!


Having an idea that could be a successful startup is very close to unimportant. Lots of ideas can be successful startups, and having them is easy. The hard part is having a ton of drive, the right mixture of personality traits, and the privilege or luck to make it happen. I think these sorts of things are largely out of your control. Maybe instead of worrying about making a mistake and missing the boat, spend some time reflecting on why you want to found a successful startup and whether something else in life wouldn't be equally fulfilling.


I let promises of being a millionaire working for a start-up drive me to eating shit for well over ten years, and it caused irreparable mental, emotional, and physical damage through stress, overwork, and self-neglect. Wanna know what I made for my trouble? $2000. All it cost me was the prime of my life, time I can never get back with people who are now gone, a lot of bad habits and missed opportunity.

Everyone wants to score big these days, but so few understand the value of slow and steady. Not saying you shouldn’t take your shots or that you should be pathologically terrified of risk or hard work, but I’ll take stability, balance, and being able to sleep at night any day of the week.

Somewhat related, be on guard for a misplaced sense of loyalty. The “old days” of you putting your life into a business and the business taking care of you, if they ever existed, started dying out a long time ago. In tech it’s virtually extinct, and in fact is actually rather risky. I’m starting to believe that sticking around for more than 5 years in this industry actually puts you at a disadvantage (unless you’re a founder or something). At any rate, don’t get too comfortable and don’t be afraid to get the hell out of there if a job is making you unhappy.


I should have started practicing self care at a much younger age. I internalized a lot of negative stereotypes of what it means to be a man when I was younger, and am still undoing the damage I've done to my health from that.

I wish I knew how important is was for me to avoid having managers who use Adderall. My most toxic work situations involved managers on that drug. I still struggle to identify them in interviews. If I go back into W2 work, I'm thinking of straight out asking prospective managers if they're on it or another similar stimulant.

I went to college with the goal of getting a job and a career, not a BS. I was in college in the 1994-1998 timeframe, and could do web development. I wish I'd gotten on the dot-com money train rather than staying in college.


This doesn't directly answer your question, but on the topic of feeling about the steps taken in the past, I have found this visual by Tim Urban helpful every time I find myself going down that rabbit hole: https://twitter.com/waitbutwhy/status/1406980353986809861


this is awesome.. thanks for the link


Whenever I think about what I could have done better 10 years ago (there's a lot!) I also remember that if I'd been more successful then, I probably wouldn't have found my way to where I am now, and I really like where I am now, and with whom. You've gotta sin to get saved, as they say.

But strictly in career terms, I wish that ten years ago I had taken full advantage of my legal right to work part-time, and gone to get a doctorate in a non-tech field. A couple years of living cheap would have given me career-mobility superpowers that I wish I had now that I'm older.


I feel the same way as your first paragraph. The path I took led me to where I am now, but I love where I am now, so perhaps that was the best path. I could say "I wish I started on my current path earlier", but who knows if the environment at the time would've manifested where I currently am if I did it differently from the start?


Startups in 20s and 30s as owner if you can hack it or at least with stock options. Either retire by early 40s or switch into larger more stable companies where your job will survive downturns. Max out the 401K and Roth IRA dollar cost averaging into stock funds. Don't try to time the market. Own real estate and when moving into a bigger home, refinance the old one for the downpayment and rent it out if its in the same town.


High school / College years:

I had lots of free time that I spent on playing games alone at home. I should have spent more time on social activities or a part time job within technology

Career:

My first job at a smaller company was so interesting that I worked there for too long (almost 10 years). That set my career back significantly and I don't have a significant network within the industry. It did not help that my second job was for a company that lacked the opportunity for me to advance as an IC.

If I could go back, I would definitely spend more time on social activities and change jobs more often to build more professional relations. The lack of a non-technical founder is one of the reasons why I haven't started my own company yet.


I feel I took steps that ended up unexpectedly slowing down my progress towards a fulfilling life. You grow up and if you're lucky you get the degree, the job, the promotion, the house, etc. The day to day of achieving these goals can make one forget that these goals are only a means to an end - a fulfilling life. If you lose sight of that, one day you'll achieve all of these goals and think "is this it? What now?". If I could start over, I'd place less importance on my career and more on everything else.


Getting my degree in university, I've had a feeling like this during every exam season. At first you have tunnel vision and a clear goal and you study for hours everyday for your exams.

Once they are over, it's like there's a weird purposeless feeling. To me it felt like I didn't know what to do with myself because all I had done before was studying so hard. I felt like I didn't know what to do for fun or what I even did in my free time before the exam season.

Obviously I'm exaggerating a bit and after a few days or so that feeling wears off. But it is a taste of how it may feel after getting the degree.


Doesn't hurt to ask yourself WHY career progress is important. If it is to be fulfilled, fine. Or perhaps at least temporarily to earn money so retirement is less of a worry and/or you have freedom in your career due to chunks of mortgage paid off early. However, plenty of people who progress far in their career become unhappy, and others who feel a failure because they didn't get promoted or have a glamorous job, are likely actually happier than they would have been if promoted. (more time with family etc). I have things in my life I wish I could have done, but nearly all of them, there were clear obstacles to doing them, not something I could have done a lot about. So I don't have many regrets. "No use crying over spilt milk" anyway. My advice is don't worry too much. Also don't develop expensive habits. Living frugally is very free-ing and less stressful, than having to have a high income to support high expectations. A lot of people talk about fitness. Obsessively so , IMHO. ITs become this massive industry. Really -don't eat too much junk food, try to walk or cycle places where possible, possibly find some sport you enjoy and do it reasonably often - seems to do the trick.


Going back to ~18-20 years old: focus more narrowly when building things. Focus overwhelmingly on business services/productivity and never go anywhere near consumer oriented services. Focus more on the process of sales generation and less on unnecessary (unintended) complexity & features.

I learned the wrong lessons from the ~1994-2001 dotcom bubble era (as a teenager) and I wasted a bunch of years correcting various wrong ideas about business that I had picked up.


I'm 55 and really have no big regrets. Do stuff you enjoy. Spend more time with friends and family. I've not started my own company, I've occasionally thought about it, but I don't think it's my thing. I don't think going back 10 or 20 years with the knowledge I have would change my decision. You need to be a certain kind of person to enjoy starting your own company, the risks are large. Having the right partner can be a factor (a co-founder that complements your skills).

Take care of your health, stay in good shape, not a lot of downside as far as I'm concerned. Sports or martial arts or something that gives you that + social aspects is IMO a good idea.

On the financial side saving + investing makes a big difference. I would start investing earlier. I don't think it'd make a huge difference though for me.

Learn how to play a musical instrument, learn more languages, learn how to dance, examples of things that can be fun and challenging.

Believe in yourself and "just do it". You're capable of a lot more than you think you are.

Career-wise try to be the best at what you do. Work on your people skills as well as your technical skills. Network and make and maintain connections and do great work and that combination will get you places. Also if your goal is to become lessay a CEO that requires a very different approach then becoming a principal engineer, or a CTO. You need to be pretty fixed on that target/driven, and have the right skills, to get there. Not for everyone.

There are many different paths that can all work out. Find yours. Most of us are very fortunate to have the sort of options that many don't.


What I wish I knew 10 years ago, and thus would have made different decisions:

- prestige and optic matter: I always maximized my interest over money; and money over prestige. Too late in life I realized once accrued, prestige can open doors, which can lead to interesting projects (and money). More concretely, I had several high-profile opportunities at FAANG and tier-1 financial institutions. Taking any of these opportunities would have made great difference in my career. Instead I worked on some random then-interesting projects. Interests come and go.

- the brain is a part of the body (duh!): people, especially those considered intellectual, often have this Cartesian division of mind and body; and they think that through sheer will, the mind can control the body. It's the opposite. the bodily state determines the operations of the mind. Caffeine and alcohol, when used consistently, do no good for the body, and thus the mind.


Every time I reflect on "what if" in my past, I get very anxious and sick, because I've made a lot of mistakes in my life. It makes me NOT appreciate the things and accomplishments I've done NOW and where I want to go in the future.

I think mistakes are a part of life, we should learn to accept them, and learn how to grow from them.


For me personally, I'd try and be more outgoing when in university. As the saying goes, it's who you know that matters in life, not what you know. And by focusing almost entirely on the academic side and solo hobbies and not getting to know anyone, I probably missed out on both friendships and career opportunities.

Other things I wish I'd done differently were:

- Getting into video creating and livestreams early on rather than writing. By the time I was posting online, the blogging world was on the way out and things like YouTube were taking off. If I'd taken it more seriously early on, I probably could have had a huge channel by now.

-Living independently in university. It seems like that's probably the best time to learn that stuff, since everyone else is in the same boat and people understand that students aren't exactly the best at healthy living.


Put everything I possibly could into a Roth IRA starting at 21.


At 21, I needed just about every dime I had to live on. If I had worked as hard as I could without affecting my grades, I could maybe have saved $2k.

In an index fund for 40 years with an average rate of return, after inflation, it would be worth about $35k.

Not enough money to make any difference at all, and to save any more would have probably had a negative rate of return because it would have negativity impacted my job prospects.

Now that I make more than enough money to save for an early retirement, I’m glad I had the experiences I did rather than save every penny I could through my 20s.


i.e., Convert your 401(k)'s to IRA, then convert the IRA to Roth via the "backdoor" that is not subject to the annual limits.


I would've focused on game engine development and gone into the game industry instead of chasing the money in web/web-adjacent tech. It's almost impossible to make that kind of change now without taking a massive pay cut and it genuinely makes me sad almost daily


I think you have to take a pay cut regardless

I worked in games ~20 years ago at my first job, and then got a huge increase when I moved outside the games industry

Games just don't pay well. I respect people who do it for the love and art of it. As far as I can see, low pay is part of the deal.

There is the outside chance of a massive hit, but most game devs aren't owners, and risk is proportional to reward


Becoming an indie game developer on spare time could make you happy


I've made several half-attempts at this over the years, but it always ends up falling to the wayside when life gets hectic. Maybe one of these days I'll finally push through though!


Could you work on an open-source game engine in your spare time, then use that to pivot across? And/or get a web-dev job in a games company and then try to get an internal transfer?


My wife has suggested the latter a few times and it definitely seems like the most realistic approach. I have a small game engine I've worked on off and on again over the last few years, but it never feels like I have enough time to make real progress


If you're into game engine development and C++, Godot is very accessible for new contributors. It's a great place to explore that stuff while also making (small or large) contributions which will actually get used and appreciated by a growing number of serious game developers.


> "Go back 10 years"

> College major

OK so we're looking for life advice here. :D If I could go back 10 years with the knowledge I have now, I wouldn't because I'll take what I have now over something potentially infinitely worse through any number of random chances. If I did, the first thing I'd do is go back another 20 years.

Seriously though (and leaving aside 'Grays Sports Almanac' style responses):

- Never stop learning. Everything in life is a lesson, and everything in life is a test.

- Just because you behave ethically towards someone doesn't mean they'll behave ethically towards you.

- Saying no is as important as saying yes.

- Be kind to people when they make a mistake. Mistakes are how we learn, and besides, it's your turn next.

- Be kind to people you have power over.

- Until you take the plunge everyone will tell you not to gamble on a startup. The moment you do, everyone will tell you what you should be doing. Listen to their advice but think really hard before acting on it - after all, you ignored them before and so far it's working.

- Never underestimate the value of looking after people. Genuinely trying your best to help your clients/customers will be remembered and that's better marketing than any ad campaign.

- That said, don't be afraid to shut the door when someone takes advantage of you. Give everyone the benefit of the doubt, but remember how they treated you.

- The most difficult employee to manage is yourself, so you might have to cut yourself some slack, as an employee and as a manager.

Edit: Oh, also, if you're the kind of person who hangs out on HN and has a burning desire to start a business, it's worth seeing a psych. I'm not kidding, founders have a much higher than average chance of being diagnosed with a range of things, and it might turn out that some of the traits you thought were shameful character flaws are actually easily treatable.


1. Worry less about what's trendy or what will get you a job, in terms of the specific details. Just learn skills and learn how to learn.

2. Finish your degree as quickly as possible and don't obsess over which electives you should take. It seems like a big deal at the time, but a decade later, you'll barely remember most of them – and you can always pick up a book on the topic later in life.

3. Forget traveling and study abroad programs and instead try to live abroad. By live, I mean actually get a job there, make local friends, learn to speak the language, go grocery shopping. Traveling and study abroad programs are too structured and separated from real life.

4. You can skip job applications entirely if you focus on building a good network. Every good job I've ever gotten has come from knowing someone at the company, whereas open application jobs I've had have been (mostly) terrible.

5. Pick something small that you can do every day, and consistently do it for a long, long time. Learning 3 phrases a day in Spanish gets you to 10,000 words (which is borderline fluency) in a decade. The hard part is consistency.

6. As an extension of #5: understand that life is long. When you're 22, spending 5 years on something seems like an eternity. But it really isn't and even then, you're only 27. It's very possible to get really good at basically anything in a decade and still only be in your early thirties – but only if you be consistent and patient.

7. Worry more about work environments than about the actual content of the work. By this I mean: you may prefer thinking about programming to thinking about forestry, but if you don't enjoy sitting at a desk in an office, you're not going to enjoy the actual day-to-day existence of being a technology worker – and might instead prefer being outside all day as a forester, even if the subject matter is less interesting to you.

8. Think about startups in longer terms, not as a genius idea you need to find. Most successful founders have a unique angle and specialized knowledge that comes from working in an industry for years.


If I had to do it again, I'd avoid tech and computers and pursue the arts. That's the only reason I'm doing tech anyway: decent pay, flexible location, sometimes flexible hours. It's a just a day-job.

But I'm still not making as much money as I need. I'm still grinding to get that good-enough day job, a sinecure. I put the arts on hold while I looked for that sinecure, but still haven't found it.

I should have been pursuing the arts from the start. Had I done that, I'd still be as broke as I am now, but would have had a lot more fun.


Tech is art tho you can do both together if you have enough "art" creativity. If you don't, you actually made the right call not pursuing it.


I would brake up with her earlier.


Not allow myself to be so spooked by freshman Calculus that I switched to the least-technical major possible (American Studies), and ultimately dropped out of Stanford after two years. Now I'm 12 years in to an accidental career as a software engineer. I often think about going back to get a Computer Science degree, but there isn't any point at this level of seniority; it would just be for the love of learning. That feels like too big of a luxury for a guy nearing 40 with a family.


This is probably an unpopular opinion, but I think it's totally okay to go to school at any time even if you won't help your career and you can afford it.

I'm going to finish my cyber security masters 11 years into my web dev/software engineering career and I have no regrets because I have learned so much. I have no plans to become a cyber security analyst or anything like that. I just want to know how computers and the Internet work and how to write secure applications.


Highly agreed. It helps to go to a school where maybe there are people of similar age (usually in part time programs there are more older people). I'd say it's more impressive to finish school at an older age just due to how much more "life-management" there is then.


Coursera, MIT opencourseware, etc are great if you don't need the degree.


10 years isn't long enough, but with the "starting over" theme my biggest change would be to not take on the debt loan that I did; I'm fortunate that I've been able to support the payments and still live comfortably but it (among other decisions) has made it difficult to invest in things like a family and housing.

Education wise I likely would not have done grad school right away, at the time a 5th year masters was appealing but the shiny paper didn't really end up doing anything for my career. I enjoyed the work but I would rather have had an employer pay for it. On the flip side a PhD would appealing since I do enjoy the research process, and there are some areas in the aerospace field I would love to explore more deeply. I would likely do CS instead of AE/ME, I originally picked this field because I love aviation, but career wise I've found myself enjoying CS work much more.

I would more strongly consider ROTC; I rejections from military academies and decided to go to the university route instead (aviation generally requires a degree). I still greatly enjoy aviation but I'm not in a place financially to pursue it.


If you find people, places, institutions work or just generally a flow that you jive with, stick to it. Work, learning, exercise, friends… it all comes down to appreciating the good things you’ve got. Really deeply appreciating.

As you get older you’ll realize how rare it is. I transferred schools, but I was in a good flow at the first one so I should have stayed. (The reasons I left now seem tiny in comparison to finding good people and a good learning flow). I have a trail run that I love. Exercise is easy when I do that run because I love it.

One thing I wouldn’t change is sticking with good people. I’d try to be a better friend and lover though.

I realized recently that maintaining good connections is not just about your behavior. If someone’s behavior is about to cross a line and alienate you, you have a duty to yourself to check them before it destroys your relationship. I have lost people due to their behavior that I should never have allowed to get to the point where I had to walk away. This is especially true of family, because walking away doesn’t delete the relationship. You’ll have to continue dealing with it. There are probably five important relationships I could have saved by setting firm boundaries and just putting my foot down.


I'm a front-end developer and I sometimes wish I was a game developer instead. App development seems just not technical enough compared to video games, 3D graphics - I'm not much of a gamer but this is the most impressive use of the technology to me. I know this is a passion driven industry and because of it the salaries are worse and so are the working conditions, but I'm talking more about the perspective of working on my own product (game). I have been working on a smaller product that I did not release yet, I love the craft, but I just see how much more I would enjoy building games. But it feels like it's kinda too late to switch and making a great game requires far more resources than making a great app. I stumbled upon this path sort of by accident, by random ideas and I just kinda wish that way back then I had a random idea to make a simple game instead.


I’d worry way less about what other people thought of me and focused instead on quieting down the insecure voice in my own head. I might not be anymore successful financially or politically, but I certainly destroyed several professional relationships that could’ve grown into meaningful friendships or partnerships.


Push for what I wanted. I took a lot of the options out of my plate by assuming that what people and institutions said were final, as if buying stuff in Walmart.

But almost everything is negotiable, and you can almost always bend rules, create exceptions, etc. As Jack Sparrow says, they are more like guidelines.

Relatedly, I would encourage myself to follow my gut much more. The trends I missed I did because I ignored my gut, not because I wasn't aware of it.

Finally, I second the exercise comment. I think we are not thought well and early enough about how to keep our body in good physical form and avoid injuries.


10 years, not enough. Once there are children in the picture, one has to be cautious.

25 years, yes. I'd probably drop out of university faster than I did, and work harder at building a web-based business rather than chasing girls.


When I went to that conference in like 2011 where the guy who created Dogecoin made fun of it and said it was an indication of how idiotic crypto was, instead of thinking to myself, "Yeah, that makes sense," I should have bought as much of it as possible.

Jokes aside, I feel like the last 10 years have largely been like that. The more you took massive nonsensical risks, the more likely you were to be handsomely rewarded. So, basically, everything I did that I considered "prudent" 10 years ago, I'd do the opposite.


I bought a machine to mine dogecoin in (2013?) and just never hooked it up... no ragrets =(

I was into the silly subreddit at the time, when they sponsored the racecar. Seemed like a fun time. Turns out they actually hit the moon after all...


Specialise I guess. I've done a bit of everything but once I get to a certain level of competency I start losing interest, I don't dump it entirely but something else catches my eye. I've always been jealous of folk that get into something straight from school and become a master of that craft over the next 50 years. Finding work and my place in the world has always been part of my life and to have that solved I feel would be a lot off my mind and simply a case of me telling myself to stick with what I'm doing. The world is just such an interesting place!


I am the same. I am searching for a career or job that will reward people like us. There is value in having a breadth of experience, knowledge, and network, but it seems harder to pitch yourself this way.


The amount of jobs I have been rejected from because I know a bit of so many things as opposed to being a master of one thing...


Should’ve talked to my doctor ages ago about my chronic nausea and stomach pain and pressed them until they discovered the cause was my Pentium 4 gallbladder.

Wasted a lot of time being sick for no good reason that I can’t get back.


In retrospect, I should've been more aggressive and risk taking with life decisions in my early teens and early twenties. Now with two small kids and a mortgage, I no longer have the flexibility to take massive risks.

All the risky moves that I made so far in life ended up being ok. Stressful, terrifying, but I always came out ok somehow.

Couple of examples:

- Moved to a lesser developed country at 19 to be with a girl.

- Bought two homes at the same time, was broke for a while.

- Moved back to my home country & bought a house in a crazy market.

- Joined a startup as the third employee.


I never would of joined Palantir out of university. I was on an awful team, and it shaped my world to be negative for a long time. I was exploited and got less out of the experience then I would have elsewhere. If I could do it again, I would of tried to join Amazon, Apple, or Google. Feeling financially safe matters a lot, especially if you want to take a risk like starting a business. So my advice to myself would be: Fuck your ethics (in large part). Make money at a innovative tech company so you can learn and be financial safe.


Didn't you fuck your ethics by joining Palantir? How doubling down on it would have been better?


> Palantir

> ethics

wow


Not get married, not have kids, job hop, take a high paying job in a high cost area to later switch to a low cost area, focus more on healthy living. That's probably most of it.


You really wish you didn't get married and have kids? Or is that depression talking, which you might need to get some help with? Do you love your family? And do they love you back? Most likely yes and yes? ;)


I do regret having kids and getting married. I love my family. Love isn’t the issue. I would much prefer my freedom.


Apparently, many people feel that way. ;) What's that old saying about a marriage being "something everyone not in one wants to get into, and everyone in one wants to get out of". ;) Yeah, one does lose a lot of freedom particularly once kids arrive, but then, it seems totally worth it to me. I'd be bored and lonely without my lovely family that's for sure (despite some pretty full-on over-and-above and restrictive caring responsibilities). I hope you can be happy :) I see frustration with your life in your posts sometimes, and just hope that people on here are saying helpful and kind things.


I will choose the right major for university. I chose Civil Engineering because my uncle is successful in the industry, I thought he would take care of my career, but this is stupid. I changed my career to Machine Learning Engineer after graduating from the university. 4 years of learning Civil Engineering is a waste of time. People should follow their passion in the first place. Now I am a 5 year experienced MLE and a happy programmer, everything is fine.


I’d put even more emphasis on getting into the right companies, spend more time at companies that worked for me, and spend less time at companies that weren’t working out.


Focused on a particular industry and domain instead of jumping between industries on each contract.

All of us can write code - that's not a hard skill to find. But combining code with strong domain knowledge and a deep understanding of a specific industry is what turns the ability to code into a super power.

I'm a couple of years into this now, but if I'd began 10 years ago I would be so much further ahead.


On the other hand, this limits the number of jobs available to you by a factor of 10 or 20, depending on how large the industry is.


Done grad school immediately after undergrad, rather than waiting until my 2nd kid was on the way.

Missing that time with my kids was so... amazingly... stupid.


I would have avoided the hype train and intellectual amazement for computers.

Treating startup ideas as an over-achieving school project, wasted a lot of time.

Getting a clear handle on what kinds of problems I can make computers solve and what is unrealistic theory, would have saved a lot of time and angst.

Because my ideas for programs, are orthogonal to the direction of the computing industry.

Therefore it would have been better if I went into finance.


I would probably have gone to school, gone into a different field entirely. Later on if I decided I hated it I could always shift over to software, but the opposite is not as feasible. It would have also probably helped my social life as well. I got independence young, but it came at the cost of isolation.

Probably should have taken better care of my health, but I’m not too mad about that one quite yet.


Lawrence said it best in the movie Office Space.


Every day, make it new.

Every person is another world. Treat them accordingly, and meet some of them.

You can solve a surprising number of your problems by not carrying them around.

Dig one hole, if you want to find water. (Dig many, if you want to endlessly weed.)

Don't polish a turd. Work on things of true value.

Progress is the glacial fruit of long constancy. Failure is abrupt, and you rarely see it coming.


In terms of career; don’t get comfortable. If you are comfortable then you’re not being challenged enough, and if you’re not being challenged enough then you’re not growing at a decent rate.

It’s ok to be comfortable absolutely, but if you’re looking to advance your career then do not get comfortable.


2014....let's see.... I'd finish the move that took years too long, and saved a ton of money in the process.

I'd have coded up a BitGrid and had chips done a decade ago, instead of just starting on it now

I want to go back to the 1980s, after high school, but before life wore me down. Marry the same girl, but 15 years sooner.


Like 17 years ago I wrote an article describing how to capture frontend telemetry to a server. I thought it was a really simple, stupid idea and just left it at an article. Now RUM is an entire industry. I could have invented it if I'd been entrepreneurial or knew the right people.


I might work a little less. If you plot money and time, you gotta wonder what the optimum is. There are always crunch times when you need to get something done to advance something, but there are diminishing returns in putting in endless hours every day for long periods.


Knowing what I know now I would write enterprise grade tools to completely commoditize front end developers. I don’t mean framework nonsense, so developers can pretend to be developing, but a real business solution that entirely writes the frontend for noncoder product owners with a focus on performance, accessibility, and small output.

The 99% goal of frontend browser developers is to connect to data from some backend database and put text on screen. Yes, that is beyond stupid trivial, like conjuring the insane strength required to lift a paperclip. Nonetheless, it seems very few people can figure it out. The compile target of the browser is the DOM, which irrationally scares the shit out of most people. The DOM is just an in-memory data structure accessed via a standard API.

Imagine how much employers would be willing to pay if some application can eliminate 90% of their frontend developers and produce superior output with a lower cost of maintenance.


I'll throw you an up-vote, perhaps somewhat in irony.

I left uni in 1992 and went to work for a company -using- a tool pretty much exactly as you describe. I've spent 31 years now solving problems, building software and training others in the tool. We're a tiny team, our closest competitor spends upwards of 50 mil a year on development. We outsell them in our space with 2 people developing.

So the tool you describe exists, and there are low-thousands of very small companies (or one-man operations) dominating their industries.

So tiny front end developer teams, check. Superior output, check. Lower cost of maintainence check. How much are employers willing to pay? Next to nothing.

I've heard every excuse under the sun. Some are more material than others. But ultimately it boils down to risk. Stepping outside Microsoft/Apple/mainstream tools has existential risk at managerial level.

Programmers don't like it cause the focus is on results, not coding fun. It very much favours people who are making a product to sell, not writing code by the hour.

The makers have never spent a dime on marketing. Their Web site is terrible. Their users tend not talk too loudly about it because the competitive advantage is material.

So employers don't want it. Programers dont want it. Self-employed folk love it.


You would spend 10 years trying to make this huge software work well in so many edge cases that you would look for posts like this to tell people to not waste 10 years doing what you did :)


No edge cases. Understanding the DOM is easy.


The edge cases aren't in the DOM, they are in the software being developed. By your reply it seems that you never tried to take this idea out of paper?


Well I'd tell you that this already exists. It works well and drives a bunch of software in industries you've never heard of.

I'd also tell you not to do it because there's no money in selling tools to developers that makes developing easier, with fewer people. Indeed programmers are exactly not the target audience. The sweet spot is empowering one-man operations who find a niche and dominate it.

But you're right in one sense, all the value is in solving the edge case. All the grunt work is taken care of, so what's left is programming in the corners.


I wouldn't build on others APIs. Figure out a way to own the content itself or not at all.

I would commit to things more fervently rather than trying to decide if it's good value to commit. There is a lot of value to be had in commiting that can outweigh flexibility


Pursue more of the interesting opportunities when young, and don't let women get in the way - they're effectively unlimited in supply.

Opportunities to get in on something like the dot-com boom having ~all the relevant skills? Far fewer per lifetime.


Really some kind of oldschool advice from a granddad. So much wrong with this.

Let's start with the simple one, we don't know that the OP is a guy interested in women.


  > Really some kind of oldschool advice from a granddad. So much wrong with this.
  >
  > Let's start with the simple one, we don't know that the OP is a guy interested in women.
Hey genius, it's advice to myself if I could hypothetically start over.

Are we reading the same thread? "What would you do if you could start over?"


Hey, sorry, was not tried to be disrespectful to you. See my other answer. Just feels like that way of saying is very old school and for me only related to disrespect to women.


Would it change anything about the advice if OP was a woman interested in men, or any other permutation?


I am sorry, maybe we lived in a different time. I only have heard an advice "don't let women get in a way, they are unlimited in supply" from very disrespectful man back in the days. That is all.

Or is that a joke? Not very funny anymore. I have met a lot of smart women. My wife is definitely one of them. I wish I have met her in my 20.


We lived in the same time. Each person can talk about their own experience, a man has better advices for another man.

You're creating drama where should have none. His life advice to himself is to not focus too much/too early in women (or sex, love, ...), this is a great advice.


Start investing in stocks early. The initial years of my career, most of my investment went into real estate, which have provided nowhere near the kind of returns that I've got from stocks in the last decade or so.


Any recommendations on getting started here? I'm also early in my career, but dumping almost the entirety of my salary into a plain old savings account.


Choose an online firm such as Charles Schwab or Fidelity. Find a mutual fund that tracks the S&P 500. Put money in there when you can. If you're young and want to take more risk for a chance at higher returns, you certainly can. But the idea behind the simple S&P 500 mutual fund is that the mutual fund will be comprised of the top 500 companies in the market and so your gains will pretty much match the gains of the market itself. It's a simple way to just put money into the market and get safe returns. You can read "The Little Book of Common Sense Investing" by John Bogle for more details on this. I actually have about an 80/20 split between two funds. The 80 would be towards the S&P 500 and the 20 would be towards the equivalent but for international markets.


I would cut out alcohol from regular consumption much earlier.


The only thing I would have done differently is change jobs more frequently and been less afraid to negotiate harder. I stayed in one place too long.


I’d probably go into finance. Seeing the TC my friends brother in law is clearing in his early 30s is nutty. I’m taking $1m BONUSES


Finance as a SWE or something like a quant?


Probably gtfo of an emotionally abusive/manipulative life situation by enlisting.


The same thing, just faster, with more confidence, gusto, and pep in my step


Take the internship at Google.


Rebel more.

Learn to love learning, earlier in life.

Less sunk cost fallacy.

Everything in moderation, law of diminishing returns.


I'm in my late 30s. Some recommendations:

- If you want to have kids one day, better get them early.

- In times with low tax rates, invest. Especially in property.

- Start investing ASAP (ETF). DCA.

- Don't do daytrading.

- In your 20s, feel free to do risky / hard jobs. E.g. found a startup, get into one of the large consulting companies. This takes a lot energy but opens the door to powerful social networks and high income jobs.

- Take care about your surroundings (e.g. community, relationships). Your environment has more impact on you than you think. Surround yourself with those bragging success narcissists and you will enter a questionable spiral yourself.

- Reflect about yourself to learn what really drives you. Writing your own eulogy helps.

- Stay true to your values.

- Surround yourself with people that share your values.

- Invest in social networks. It's a loot harder to make good friends later in life than e.g. in university. Most chances lie in people that don't belong to your best friends (weak ties).

- When you can have either one chocolate bar today or two bars tomorrow, better aim for those two bars tomorrow. Not always (have some fun today!) but most often. One night stands, big cars, bagging stuff... Usually cool for the moment but worthless over time.


Plant more seeds, sooner.

Arts along with relationships take time to cultivate.


Buy a shitload of crypto.

Smoke less

Waste less time

Explore more of the world

Arrange certain finances earlier.


Take the internship at Google in 2012.


I would have more kids.


If you don't mind my asking - how many kids do you have? And why did you choose that number?


Warned John McAfee about 9/11


I went through some comments, and they give the worst advices. Those are not advices, those just lost opportunities. Or simply regrets. Like my mom likes to say "I knew that was coming!", how the fuck did she knew anything? Sure a lot of people in 80 thought about investing in IT stock, but they did not. Sure a lot of people thought about buying bitcoin for a cent, but they did not. And you know what? Those who did, they might be not with us anymore, or maybe they are living happy live, and not going to post anything here.

I would not change a thing in my life! I am happy where I am.

2002 - went to get my math degree in Russia. Knew close to nothing about software development.

At that period of time, I was thinking about I wish I had a car, so I could work as a taxi driver, and make some money. I should have started collecting for a car a while back.

2005 - sold my first tiny program to a small factory. later got my first job as software engineer.

At that time I was pretty happy, that I did not have a car, and actually spent that time learning more than university could give me. And was able to make some money. That summer I also worked at construction.

2010 - got my first remote job for a company outside of Russia. Started making 5x times more than I used to.

At that time I was thinking, that I should have done it before. But hey, I did not have knowledge and experience. I am glad that I have spent that time not only working, but also learning, getting into community, got Microsoft MVP and MSP awards.

2011 - got a job in Microsoft, moved to USA. If you look at how many big macs I could buy in USA vs Russia, my salary probably went down maybe 2-5 times (if it matters it was $54,000USD in Russia vs $92,000USD in USA).

Was thinking every day, if moving out of Russia was a good idea or not, because Microsoft salary in Redmond was not the best at that time. But you know what? Now I am definitely glad that I moved away from Russia!

2013 - moved from Microsoft to Splunk. Best job I ever landed.

Certainly was thinking that I am so late in the game now. All those kids from college making so much money. And I am in getting close to 30, and only started working for a real company. All those smart people around me. Regretting that I invested more than 10 years in Microsoft technologies, when all the startups in Linux and cool languages like nodejs (it was very popular that year).

2017 - joined Stripe for just a year.

Definitely was thinking that I made a mistake joining them. Great company. I was on the wrong team. The manager could not explained me correctly what the team was doing - "hey you worked for Splunk, that includes Search - we doing something related to search" - turns out that was data engineering. But! Usually I would dedicate 40 hours + unlimited a week for a company I work for. But in case of Stripe my project was sooo boring for me, that I started building my own company while riding a bus everyday 40 minutes one way and 40 minutes another, and in the evening.

2017 (end of the year) - sold my first license for the software I have built.

2018 - left Stripe. I started working 80-100 hours a week. For at least two years. That was not a hobby anymore. There was a stress about starting my own company knowing nothing, and every day fighting with something new and unknown.

2024 - I am making Google Principal Engineer total salary and work for myself. I am very happy and don't want to change a thing. Because every single thing brought me to a place where I am right now.

I went thought painful divorce (happily married now, again). My dad recently died, and I could not go to Russia, because of situation right now. One of my dogs recently died. There is a lot of shit happening around me. But I am happy.

But yes, there is one thing, that I kept saying that I would change. If you want to have kids - make them in your 20. But you know? If I had a kid, I would probably be in a different place right now. Maybe I just did not want to have kids, that is the reason why I kept saying that.

My point is, do not look back. There is going to be so many people who would say, if only I was 10 year younger, or if I knew 10 years ago. Just 2 years ago we were saying that there could be nothing bigger than FFANG, but hey OpenAI came out of nowhere. Maybe OpenAI is going to die next year as a company, and sure there is going to be somebody like my mom who would say "I knew that was coming!" How the fuck did you knew?!


> I went through some comments, and they give the worst advices. Those are not advices, those just lost opportunities. Or simply regrets. L

OP wasn’t asking for “advice”, but for things you would do if you could start over, so why the were you expecting? It’s also pretty rich deriding comments that actually answer the post while dumping a fucking essay of your life story which doesn’t even respond to the stated question.


I believe my comment provides a good answer to a question. I pointed a several period of the times where I was thinking that I should had mad a different turn. Only left I believe the important stuff.


And sorry. I guess that paragraph does sound a little aggressive. I am just throwing out there, whatever you think you should have done differently, don’t think about it. Move on.


Congratulations on building your own company! Out of curiosity, may I know what it is?


Thanks! I wrote about it on HN a while back and answered a few questions https://news.ycombinator.com/item?id=35569380




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