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Ask HN: Should I find a job or try to build a profitable project?
121 points by driven20 on June 9, 2019 | hide | past | favorite | 120 comments
A little about me. I'm close to 30. I recently left my job, I was burnt out. I want to take 1-2 months for myself to reflect and figure out my next steps. I'm a software developer and I have been working with various small to medium software companies for the past 4-5 years. I currently live in a small city in the south (gf and I want to move to NYC or another big city). I can build CRUD apps from the ground up. I have around $60,000 saved and with my current bills, I have a runway of 1.5-2 years. My life goal is to build a successful business and entrepreneurship has been something I have always been interested in. However, I have never successfully built anything that gained traction, so I consider myself more of a wantrepreneur.


#1 Spend my time studying and finding a new job in NYC. I'm pretty confident that if I spend my time on leetCode and networking I will land a good job. I feel like this is the safe route.

#2 Spend my time pursuing a couple ideas I have. It's nothing new or innovating, a productivity app and a yelp like service working with small businesses. Reading all the content here is super motivating and inspiring, I feel like I could make these ideas work, but it's also super risky. I don't want to spend 1-2 years working on these ideas only to look up and realized I wasted my time and money.

#3 Some combination of both? I was thinking that I can pursue my side projects and look for a new job at the same time. However, I feel like having a clear focus on one thing is important.

Similar boat to you. Had the exact same question in my life.

I decided for a totally different option, lets call it option #4:

#4 Take an "easy" programming job and use your spare time on nights/weekends to build a software business.

I chose this option because I wasn't willing to risk my savings. Plain and simple. I want to retire some day, and blowing 60k for a ~5% chance at making a profitable business wasn't worth it to me.

For sure #4. Because if you never launched anything then it will almost for sure not work the first time around. It's a skill like any other skill and you need a few tries to figure things out.

A caveat: I took an "easy" job but it turned out it was the job from Hell. Because "easy" job was surrounded by people that didn't know what they were doing. So a truly easy job might be one where everyone is overqualified and you only need to do your own thing (as opposed to expending a lot of energy explaining to people how to do the right thing, all the time, because they just don't get it).

Vote for this one as well. Also an easy way to get health insurance and 401k squared away while you're at it. OP, I suggest doing this- get a cushy 9-5 programming job and scrutinize the onboarding paperwork to ensure you're in the clear to own anything you work on in your free time if not using company resources.

Best of luck!

While I am on the same boat, there is definitely a caveat that you should aware.

Those "easy" job you think might actually be hard, because of politics/bad managements/weird policies etc. And even if you're lucky enough to get a relaxing job, the differences between those 2 jobs might damage your mindset/thinking/focus.

This is what I'm afraid of...My previous job wasn't hard. What was tiring was forcing myself to work on stuff I don't care about.

This is one of those "have my cake and eat it too" scenarios.

You want a job that inspires you and which you care about AND you want to start a business or at least pursue some side projects which you think have a shot at making you money.

I've never seen that happen, personally. Something has to give whether it's your savings (you don't work a job) or your enjoyment of your job (you keep your savings).

I think for you given you've tried the "easy" job route and found it draining... You should spend your time now finding a job which excites you and energizes you. Put your time, and effort into that. When you have spare energy, work on your side projects.

This is a sensible advice, but how do you recognize an easy programming job?

There are (at least) two ways in which a job can be "hard":

1) Technically. Having to constantly learn new things, new technologies, etc. Unable to rest on your laurels. Learning new things can be very rewarding from a career growth standpoint, but it can also leave you drained at the end of the day.

- Avoid a technically challenging job by choosing one which is in your skillset, and unlikely to change. For instance, if Java is your thing, find a back-end Java job at a big company (startups will often ask you to change roles and learn new things).

2) People. Dealing with shitty bosses / managers / coworkers can suck the "easy" out of a job and make it very challenging to get anything done.

- Try to get a feel for the leadership in your interview process. The interview should come off as warm, and inclusive, even you aren't doing well. Overly complex questions, riddles, or hide-the-ball interview tactics generally come from insecure interviewers.

It's hard to from the outside, but I would guess the biggest factor that correlates with easy is amount of red tape. The more bureaucratic, the more non-work is done in place of actual work, the easier the job.

So I'd say large corporations or government jobs would skew easier. Maybe work for a large government organization?

less then 5 days/week helps

Been there, done that. Honestly, it depends on your life goals and motivations. In my case, I tried starting a business for the wrong reasons, and realized that I'd rather be an early employee in someone else's startup; or be a co-founder in a very small team.

When I was single, a full time job and side projects were perfectly fine. Once I met my wife, I didn't have a lot of time for side projects. The relationship just took over my nights and weekends. Kids sap up most of the time now.

So, IMO:

#3 if you ever find yourself single again.

#2 before you have kids and a mortgage. This will only work if you have a good business mind or a girlfriend who's willing to help you make ends meet. If she really wants to start a family and be a full-time homemaker, it'll put a bigger strain on your relationship than you realize.

And, honestly, there's nothing wrong with #1. After quitting my job when I was 28 and in a similar situation; then getting a job right before my 30th birthday, what I can say is that carefully choosing your employer is the most important career skill to have in your situation. It takes almost a decade bouncing from jobs to know how to recognize (and stick with) a good situation, how to recognize a bad situation in the interview.

That being said, there's nothing wrong with taking 1-2 months off between jobs!

What were the wrong reasons?

Everyday I want to get up and have no employment obligation to anyone, and work on whatever I feel is interesting to me at the moment.

I was under the illusion that I could be in that situation merely by founding my own company.

The only way to really do that is to be financially independent, because once someone is paying you to do something, you can't walk away when you get bored.

You could try doing something similar to Pieter Levels' "12 startups in 12 months". He only managed to get to 5-6 startups, but from that arose nomadlist.com and remoteok.com where he's making $83k/mo now after 4 years ($10k from user subscriptions and the rest from paid ads/postings).

Forcing yourself to launch/ship a few products each within a month could be good training to not get stuck in idea phase or coding phase, and focus on getting it out. Then you can try judging how the responses are, maybe 1 will take off and the rest won't.

If you're spending a longer time developing out an idea, it's hard to actually know if the market wants it or not, unless you have actual real paying customers. So for example that yelp idea you should be aiming to have paid customers within 3 months anyways.. reduce risk by making the right moves, not hoping that you might have paid customers 1-2 years later.

I like this a lot. Tools, tricks and shortcuts to reduce experiment cycle time are invaluable. Not aware of existing tools that do a great job of this though, especially for novel, non-trivial use cases.

Thanks for the recommendation

Take that 60K, go travel the world, it will go a long long way if you are thrifty about it. See how you feel about your project when you come back or work on it while traveling. Bet you will feel different whether your projects survives or not. Ignore all this you need to buy a house garbage, do you want to spend your life investing for your retirement, for when your dick wont work or live now, that is the question. If you are disciplined enough to save 60K, that already makes you an exception to most Americans. You will be fine. You have the rest of your life to slave away and pay a mortgage, go see the world and see how your view and your priorities will change. Being exposed to many different environments and situations will definitely improve your life and your mindset for the long term. You will experience things and situations which you cannot possibly encounter while putting money into a 401K at a job or slaving away paying for an inflated house price wherever your live. Go live and stop chasing 9/10 startup ideas that actually really fail. If you do want to go the startup route. Don't risk your savings on it, risk an investors money.

This comment resonates with me. Is there a good resource for packing up your life and traveling for a while?

Background: I have a great and interesting remote job but the workload is high relative to the salary. I have 1 years salary saved. I could ask for a raise, but I would much rather spend a year traveling and improving myself.

Any specific questions? My email is in my profile if you prefer thst.

I'm currently on a five month break with my wife. The first two months were in an apartment in the south of France, currently hiking though Loch Lomond and then a couple months in Edinburgh.

It's pretty good! Probably shouldn't have waited 10 years to do this.

A break from your wife or with your wife?

I was visiting somebody recently who told me they just slept in ditches in their 20s in order to travel. They lived on peanuts and saw all of Europe. Basically, it just depends on how satisfied you can be with less luxury. Stoicism is all about that

This sounds like what Phil Knight did in Shoe Dogs...haha. This is good advice. I have traveled to Iceland, China, and I'm going to Europe this summer. Granted those were more like vacations than long term travel. Thanks for the exception comment, I know this statistically, but I also know I'm so far behind some people on HN, /r/personalfinance, and indie hackers. I know, I know... Comparison is the thief of joy. I'm living, I guess I just want more. I want to work on something I'm truly passionate about and be great.

just to add an extension to this "outside the box" idea:

with the exception of a few countries, being abroad is so much cheaper than the US.

if you plan to move to eastern europe or southeast asia, you will literally triple your runway - with $60k we're talking 5 years to succeed instead of 2.

getting out of your comfort zone will spark more creativity as well (just like shoe dog, great book btw)

if you know you want to do entrepreneurship, why consider anything else? with enough iterations, as long as you're learning and cycling quickly, you will eventually succeed.

You left your job because you were burnt out. I think you should also ask yourself what happens if you start your own project and get burnt out again before making any decision, and/or what can you do next time (either with another job or your own project) to avoid burn out.

In your shoes, I'd first get a job, possibly more sustainable than your previous one. Then I'd start working on my side project trying to make a second income stream. BTW, startup school is starting soon, you should definitely join in and test yourself for 10 weeks.

I feel the reason for burn out was because I was working on something I don't care about. I don't necessarily think the work was extremely demanding or anything. The problem was forcing myself to work on something I don't find meaning in.

Yeah, for my next job. I'm definitely gonna search for a company that has a mission I believe in.

I live in NYC now. If I were you, I'd look for jobs now. Get one lined up or just have a good idea of what it takes to get one. Go for a corporate IT job that is 6 figs and an easy 9-5. Then I'd ask to postpone it, go on a relaxing trip with or without your gf for 1-3 months. Think about life.

Get back, move into a cheap shared studio or 1br with your gf. Work on your stuff after 5:30 and still bank money, and still live in the city. Boom.

With your runway, #2 sounds great, but try and find a different idea.

Productivity apps and yelp like services are a dime a dozen.

You'll probably waste 1-2 years, and expect to waste 3-5 more before you can replace your main source of income.

Entrepreneurship is risky and developing software is the easy part.

Yea, I'm not sure they are great ideas. My reasoning for the productivity app is because I want to build something I personally need and I haven't found a good solution. The yelp-like app is because I know I want to work with small businesses. I just don't know exactly how yet.

So, you're right. I need to spend more time on my ideas. Thanks!

Be careful with the "build X for small businesses". It's deceptive to look around at small businesses, see them using bad tools and think there's opportunity there. The truth is there's usually a reason--the small businesses aren't willing to pay for better.

It's hard to find them too, it's better to build something where they come looking for you.

Someone told me early on that dealing with small businesses was a nightmare. You'ld get Mom or Pop quibbling over a $75 bill, whereas enterprise customers will pay a $40K bill without batting an eye as long as the paperwork is in order.

Over the years I've found the enterprise side of this to be true (although it will take forever to get them to sign in the first place and they'll sometimes pay their bills so late you're gasping by the time you see the cash).

I don't have any experience with dealing with small business, maybe it's not as bad as I imagine.

I've dealt with a few small businesses and none of them ever complained about price and they all paid their bills on time. They are usually very grateful that they have someone who is interested in doing their small projects.

A lesson I learned is look for hacks to do something without writing code. It’s hard when your idea really needs it though. Then it’s more about removing features from the mvp as much as you can.

Another one is an idea journal. Then over time you have a collection of things and can choose which one is exciting.

It can be hard, but if you can get potential customers to have a conversation with you and give you money ahead of time you’ve proven you are on to something.

I’ve been wanting a framework that makes mvps easier to ship. Planning on working on one that leverages server rendered react for ui with Airbnb Hypernova, rails for data and security, aws fargate for auto scaling compute, and aurora serverless for an auto scaling sql db. Would also be nice to auto generate react/redux crud like rails does. Or just use standard rails for stuff that doesn’t need polish.

I was convinced I should build a productivity app because none of the existing apps suited me. Turns out I was an unorganised person blaming their tools. I went low tech and organised myself by writing into Bear.app, which made me realise I didn’t want to make a productivity app I just wanted to be organised.

Thanks for this insight. There is a chance I'm in this boat. I'll have to think on this.

Would you actually use the productivity app if you build it? Or you just think you might?

How long would it take to prototype it out to the point that you can start dog fooding it?

Before you write a line of code for #2, have a clear strategy for app distribution, user acquisition, free to paid conversion. It won’t just happen because you have a great product. Just remember to make a million a year, you need 10,000 people paying you $10 a month.

This. A mediocre product with a strong marketing strategy can make millions. A spectacular product with no marketing plan will make nothing or close to it.

Products that spread through word of mouth are few and far between these days. Facebook has made sure of that by snuffing out most newsfeed virality (unless you are paying them for it) such that even if your customers want to share your products with their friends, few of them will see it. Growth rarely happens by accident these days.

Do not attempt to even create a product that you are going to depend on for your livelihood without a specific marketing strategy already planned out and ready to execute. That strategy should be able to generate a positive number when when you subtract estimated, realistic customer acquisition costs from their estimated, realistic lifetime value. There is a great podcast called TheTop [1] covering a number of tech verticals where existing companies go into these numbers in specific detail. I would recommend you find an episode about a company in your vertical and listen to their numbers.

[1] http://nathanlatka.com/podcast-thetop/

I don't entirely agree with this. I think it's useful to build a proof of concept even without any follow-up plans or objectives.

Besides the fact that it'll be easier to visualize and present the idea to people, the act of building a proof of concept or a real MVP would be learning experiences themselves.

In fact thinking about what's to be included as part of the MVP and prioritizing to fit within a pre-set deadline would be extremely valuable.

Let's be honest here too, it's FUN to build a proof of concept.

This is a very, very common failure mode of new entrepreneurs. As long as you don't have any customers, any promises, or any deadlines, you can focus on the best part of being a programmer: programming. Thus people often end up postponing the customer acquisition farther and farther into the future, until they run out of savings, or just abandon the project because the bright flame of new creation has dwindled.

Running a software business sucks. You have to mete out your attention extremely carefully, and without well-vetted potential customers to build things for, building things should be very low on your priority scale.

You can achieve most of your stated MVP goals with a sketch made in Adobe XD, with a fraction of the time spent.

Everything you've said is true but I think we don't agree on what a proof of concept is.

I think of it as something that does the main purpose that looks entirely real (so has a domain and is responsive for example) but doesn't actually function. This can definitely be done in a similar amount of time as the XD sketch. Perhaps slightly longer but it'd look more real and therefore would be taken more seriously.

In fact its most important purpose is to save you from building something that does actually function.

Building a proof of concept is an incredibly expensive way to figure out what clients want. And many times you find out you're so far off that none of the project is reusable.

Also plenty of clients will take meeting without an proof of concept. And this is especially true when you have a really good idea.

I've found the opposite to be true -- easier to get a meeting if you have something to show even with a mediocre idea.

In my experience it didn't make a huge difference. More than half the time the individual didn't even want to see it. Just wanted to talk about how it would improve their business.

What is the better way to figure out what clients want? Conversations?

Yeah it takes a lot less time to have a conversation than to build an app.

Makings the cold calls and cold emails felt a lot easier with an app built but at least in my experience didn't make a big difference in response rate.

The best way is to have that problem yourself while working in at an ideal customer.

Yeah. I spent the better part of two years building something I really wanted to build that I thought people would really want to buy. Turned out I was wrong. If you're burning through your own savings you need to find out as early as possible if there actually is any real demand for your product.

This is exactly what I'm afraid of. Sorry it didn't work out for you.

I learned a lot in the process. If I ever try anything like this again I'm going to focus on validating or rejecting the idea as quickly and cheaply as possible. There are some good resources online on ways to do this.

That sucks. Did you open source it, at least?

I wrote a bunch of custom audio DSP code that I still tell myself I’m going to do something with one day.

I think this is good advice. I should think things through more...

Also, I am willing to take a pay cut if I can work on my idea, instead of working for something else. I don't need a million dollars haha.

Right now, I would be happy if I got something that pays me half as much as I used to make. Heck, if it only brought in $1,000/mo for a while I would be happy with that.

Or one person paying you 1 million...

That’s the dream. But then you’re probably limited in total addressable market.

I think "runway" (i.e. your personal savings) is a terrible idea that should be debunked and dropped by the entrepreneurial community.

You don't have runway - you have the savings to buy a house, or form the foundation for the next stage of your life.

If you build your business whilst you have a source of income then you have infinite runway - you can keep trying until your dying day or you give up.

It's only after you've tried to build your social network for dogs and failed that you look back and say "wow, that $120,000 was actually ALOT of money - it's going to take me years to make that again". AND now you don't have money to build your next great idea - Uber for petwalking.

Using your savings as "runway" is just gambling with unlikely odds.

Any "runway" that can keep you going for a year in a modern western city is ALOT of money - you're really undervaluing that money if you use it just to live whilst creating a business. And you're also assuming that you're going to be able to make that same amount of money just as easily another time - that may or may not be true at all.

I’m working and doing a side project and there are some more advantages:

I work as a web dev. I can legitimately learn on the job. That learning then benefits the side project. Example: typescript, shell, k8s, css etc.

I have less time on the side project so there is less fluffing. No docs, no unit tests, no Haskell, just getting it done with what I am proficient at. This might ironically mean I get more done than if I was full time as I’d be tempted to gold plate.

I’m exhausted when I get home and the code I write then just (about) gets the job done. It’d fail interviews big time though.

> or form the foundation for the next stage of your life

What does that mean?

> you're really undervaluing that money if you use it just to live whilst creating a business.

What would be more valuable use of that money? Do you just mean keeping it in savings account or in index fund and let the interest build up?

I'll vote for #1 and starting something on the side. The time constraint may give you more focus and you won't be gambling away more time and money on an uncertain path.

Some people seem to have a knack for getting right to the point of what needs to be done in hustling an idea and making money on it. For others, it's way too easy to spin the tires and get nowhere for weeks, then months on end. At a certain point, the feeling of getting nowhere becomes a drain itself and the likelihood of not finishing grows.

You don't want to find out which category you are in while burning through savings. Better to start with constraints which force that sense of urgency (lack of time.)

#3, for sure. Multiple streams of income is always a good thing to have. Nobody says you have to kill yourself working but spend an extra hour or two building your side thing.

Pro: You only live once. I've never regretted the chances I've taken and failed. I would have regretted it much more if I didn't take the chance.

Con: Statistically, you will fail. There are people out there with the same idea that are better funded, better connected and can move faster.

Pro: Internet projects are cheap. Infrastructure is cheap. Give me a $200/month budget , I could easily host your typical small software as a service app starting off with plenty of headroom.

Split the difference: Work and work on your side project. Even if you fail, you still have something to add to your portfolio.

Never risk your own money. But wasting time doesn't cost anything though. So make sure your expenses are covered, then go at it. And if you are having fun and learning stuff, then it's not a waste of time even if it fails.

But you probably don't want to do it alone. It's better to own 10% of something, then 100% of nothing. Also validate your ideas before doing actual work. For example do a kick-starter, or a signup-page, pitch the idea to possible customers.

This completely ignores the true value of time. I would give up plenty of my own money for more time.

This is what drives people eventually hiring employees for their ventures and should not be undersold as a reasonable way to think about things.

Theres opportunity cost. But you cant buy time in the past and you can not bye time in the future- only optimize it. There is only now!

Another "been there, done that". If I could give advice to my 30 year old self, without doubt, it'll be: #1. Focus on finding the right job that works for you and pays the bills. Once you are back to feeling good start a side project.

care to share how you come to that conclusion?

Chasing the "dream" of having my own business without realising what that actually requires. Then when it got difficult or boring, the next freelancing job is so much easier (and way more lucrative). Back and forth with spending savings on projects that never amounted to anything.

Slowly realised that nowadays, for us techies, there's a much better way of having a good life. Just find the right job (look long and hard), get paid well, hone your skills. I wasted a lot of time.

I could have written this exactly - lived it. Combine that with the crappy economy of 10-12 years ago, vomit.

Kids, you think you're dreaming now. Just imagine how much you'll be regretting later. Just quit your job, take some time traveling then go find another job. You'll feel better eventually.

If you're bootstrapping, be wary of the NYC burn rate: your expense base will explode and you're going to get taxed up the wazoo on your early revenue. Worst business environment I've ever had to operate in.

If you're selling primarily to a NYC audience or industry, then move there of course - get close to the customer. Otherwise you've got a lot more runway in the South....

I should have been more clear. I will only move to NYC if I get a job there.

Smart. It's more than a job though, since you're effectively investing in building relationships within an eco-system.

Certain paths make more sense in NYC; if you're selling into finance or publishing. If you're wanting to do a venture funded startup (or raise investor capital). Adtech is probably stronger there too.

Others make sense in low cost markets; bootstrapping a product for middle America. Stay cheap for that.

Pick your long term path then pick your environment.

Assuming you were an FTE, if you burned out in less than 5 years and have already held multiple positions here're some things to consider:

- Travel as soon as possible. The world will speak to you in ways a computer never can.

- If you don't go back to work right away, you may be looked at as less reliable to HR department and hiring managers later.

- If you do choose not to go back to work right away, you need to consider the opportunity cost of not getting involved with someone else's start-up right away.

- If you and your girlfriend want to move to a city, be sure she has an opportunity there to save the relationship in the case your your entrepreneurial interests don't pan out.

All of the options you suggested will likely lead to to future burn out if you don't move to a larger company. Find a job you kinda like and stay put for awhile go gain experience and relationships, and place a rock in your resume. Then you can pursue your dreams if you're able to save more or dramatically reduce cost of living relative to a city.

I think the main factor in my response is in how much you feel you're in control of your executive functions and emotions.

If you can easily re-prioritize your tasks because abstract feedback mechanisms tell you so, and you can steel yourself to strategize and make competitive choices under pressure, even when it means you may make a tradeoff that hurts someone personally, you're in a pretty good position to operate a business around any promising opportunity, and to scale it up if needed. That doesn't mean "businesspeople should be immoral," but rather "they are able to make genuinely tough decisions in an impersonal and fair manner, and are numbed to the painful parts where the livelihood of the business depends on it." (Acid test: how ruthless are you when playing board games?)

But if your mindset is more prone to meandering and getting fixated on specific problems and you get propelled by events and emotional energy around you - whether or not that adds up to a diagnosable condition, don't kid yourself. You can have a business, but it should match your personality and complement your strengths and weaknesses, and you might need a co-founder to keep you grounded. Otherwise you'll shut down or divert yourself into solving the wrong problem as soon as it gets hard.

And to some extent, controlling those thoughts and feelings is something you can train up, and finding an appropriate co-founder is something you can achieve by sheer peristence, but it really sits near the top of the heap in terms of whether a commercial project with paying customers and possibly employees will be the sound thing to pursue, because there are all sorts of ways to rationalize yourself into a bad plan.

If you don't think you can do it that way, you can instead pursue a side project with the intent of turning it into your next gig - something that will at least market your skills and dreams and keep you employable even if you do not have a clue of how it would operate at scale or over the long run. And that might be preferable to grinding LeetCode.

Let me add a complication. You are at an age where most people have kids. Personally I've choose not to and went very careful to successfully not marry nor have kids, so... just saying you should calculate how that will/will-not compute into your plan.

Not planning on having kids for the time being

Start with contracting instead of getting a job. A contract will give you more flexibility to work on side projects since you have control over where and when you work while also providing cash flow. It will also teach you important skills on creating and running a business. If you can't sell yourself as a contractor, you will have a hard time selling your product.

Once you have cash flow, start with trying to sell your idea before you build it. If anyone wants your idea, hire others to help you build it and sell it. Your contract cash flow will allow you to trade your time for other's who will have skills you don't have.

Any tips on contracting? I have only got contracts through recruiters. Can you get them directly with the company?

Big companies that work with recruiters (staffing agencies) are usually just trying to hire contractors to fill a short term need. You need to create your own staffing agency if you want to compete on this.

Otherwise focus on a niche and build a brand that isn't based on your own name. That way other companies aren't assuming when they work with you they will only work with you. 1-to-1 interactions make scaling very difficult. If you've already done that, then it's time learn how to find your customers, understand their problems and how to solve them, market to them and sell. This is much easier when you focus on a niche rather than being a generalist programmer that can do anything.

Since this is an old comment, it's probably not worth going into the details here. If you're seriously interested, I'd be happy to help answer questions from my experience. Feel free to find my contact info from the website in my profile and reach out.

Don't move to NYC without a job.

I love living in NYC, have been here for 20+ years. But your $60k will disappear rapidly. If you want to be in the NYC metro area while you look for a job pick a suburb on a train line about an hour out of the City (NJ, NY east of the Hudson, maybe Long Island). Your burn rate will be much less but you'll be able to get into Manhattan and nearby business districts in a predictable amount of time for interviews and networking events (no recommendation on the train line but avoid the single track train lines).

I should have been more clear. I will only move to NYC if I get a job there.

But thank you for the extra information about NYC. That's good to know.

As someone who tried to do exactly what you are suggesting, but with considerably less runway, find a job and start the business while you have the job. It was a disaster for me trying to go all in at once. Especially in one of the most expensive cities in the world, NYC. An I was 30 when I did it. I ran into all kinds of issues that I didn't foresee. Health issues, money issues, etc etc. Now I have a job while also starting a business and its running a lot more smoothly.

Starting a business takes a high level of self control. Very few people have it. You should do a critical self assessment to make sure you have it. Since you have no job work on the business plan for your business and continue looking for a job. You will benefit from the experience even if you do not get a job. I advice that you carefully look at your self before you start the business. The big question is do you have the grit to get from nothing to a profitable business.

Nothing burns you out worse than starting a business. Get a job first. You may want to find a company not based on NYC, in order to lower your likelihood of burning out again.

#3 sounds reasonable - unless you know what that startup idea is, proved it with a handful of customers, the likelyhood of it working out is < 1%. Still, keep trying but don't assume your $60k will not be wasted & you'd not get even more burned out.

Also, if you do get a job in nyc area - try for one that pays multiple of whatever you were making down south.

Try to build your project, get full focus and become an excellent empiric, lots of resources these days for this, in your way 1. You can fail. 2. You can get traction and profit but always, 3. you will find a job, eventually, since you became expert in the field you have been working and exploring with your own spirit. This is my experience, 2 failures, both after the apps got traction but competition had more money to run operations at scale the most of the cases. Now my HV looks good because of them and my actual job is thanks to a reference who pointed me for a similar mission of my 2 failures but in different industry, I am developer and never applied to what represent my actual incomes, just do it before having kids and get some mentorship with someone senior, you will need to be confronted with reality or receive guidance on how to do things quicker or easier. Respect for taking the first and most important step.

Working for yourself makes it very easy to burn out. I'd be wary of that as you described burning out already.

re: #2

>[...] I feel like I could make these ideas work, but it's also super risky. I don't want to spend 1-2 years working on these ideas only to look up and realized I wasted my time and money.

If you can't get comfortable with that risk, you're going to have a very hard time being an entrepreneur.

There's always people who luck into an amazing business and business model, but realistically, you're going to have to put some resources in before you figure out if there's value. Even if it's just mocks and time spent talking to folks (do both those before coding anything though!)

Oh, and yelp is a terrible business -- the coding is straightforward. Your problem there is entirely how do you seed a site with reviews and businesses. Typically, two-sided marketplaces are some of the hardest businesses to create.

I totally agree with the risk comment.

Also, my idea is to onboard small businesses slowly. Maybe, adopting and building out features/tools for one business at a time. Until the project is more completed and I can focus on scaling the onboarding.

The problem isn't onboarding. The problem is that without a pool of users, the site is worthless to businesses. The fundamental question you have to answer is -- assume you can friends and family a couple businesses, fine -- why does business 7 pay you money, or even do anything at all for you? Or business 8, or 9, or 10...

Small businesses are barraged with calls from vendors like you.

Well it's not that black and white. Can op make the application/business appealing as a single sided marketplace to begin with? Maybe. If there is 1 side that can find value without having the other side onboard then there you go. Doesn't mean it's going to be easy. Still hard, but just address the challenges as they come.

op, take a couple months to build your product (considering this is a CRUD-like app) and then face the distribution problem.

I wouldn't make any decisions while burnt out. Take some time and recover.

Then I think you need to think about where you want to go in your career. Do you enjoy development and want to do nothing else? Don't start a business, because you'll end up doing a lot of other things. Are you interested in the control and passionate about your solution of your own business? Then start a company.

Note that there's many other routes, some outlined in other comments. In particular I spent years as a contractor/consultant on my own. It paid the bills and gave me a ton of freedom.

Any links or resources on getting started as a contractor/consultant?


Is a good one, though high level.

For nuts and bolts I don't have a good recommendation, other than take other software contractors to lunch and take a lot of notes.

Work part time to pay the bills and spend the rest of your time working on your projects. The $60,000 of yours will disappear faster than you think. You'll eventually spend money on the business I assume.

Do you have recommendations on where I can find part-time work?

If you post your email / contact info on your profile, I can reach out with some ideas. I work in NYC and happy to connect you with people depending on your interest areas / skillset.

Updated my profile to contain my email. Thanks!

you need to put it in the "about" field, the "email" field is just for password reset emails etc and not public.

Either through your network or do some freelancing. If you go the freelancing route you'll have the extra benefit of having a relatively straightforward way of developing other business skills you'll need like sales. Just be sure not to let it take up all your time if you're going for a different business model :)

I’m in a similar position and have an option #4 that would be my own preferred route, but I’ve only recently started thinking about it.

#4 Partner in as a tech lead or cofounder on someone else’s early stage idea.

The question is how to find that person. Angle list? Product Hunt? Who has some ideas?

I think once you’re working among the right group, you might find more startup founders to work with in a way that is inline with what you seem to want.

Before you have settle down and start a family...

#3 or #2.

You could also attempt to build an MVP (#2) and try to raise a small amount of money so you can de-risk yourself a bit.

If you have to set aside time to start a business you shouldn't go that route. An idea should take over your life before you consider making it your day job.


You are burned out. Rest / have some fun and fall in love. When an idea hits you run with it. If nothing inspires you and you get bored with rest go find a job.

I’m making a similar choice myself. I just graduated though and I don’t think it’s responsible to chase a pipe dream while I have student debt and family responsibilities without at least having more experience.

Badly wanting to be convinced otherwise though, but it’s hard when people are depending on you...

I highly recommend reading the book "Company of One" by Paul Jarvis if you are considering going the entrepreneurship route

If you aren't 100% sure if your ideas are any good, they probably aren't, and it's better to just get a job.

Pick an idea and try to make it work. There's useful advice to be found here and elsewhere on the web, but your own experience trumps all that. You'll learn a lot, and if/when you decide to return to the corporate world you'll be in an advantaged position to do so.

Well if you’re happy with a prior that sees you fail after a year’s effort 95% of the time; you should do a startup (don’t kid yourself about better odds). Perhaps if you were capable of putting in 5 years of pivoting trying and failing your odds start to look much better.

Otherwise, get a job.

I wish I had more experience, because then I could help you more. I unfortunately am in a similar situation and have less work experience than you do. My sources will mostly be from my studies and HN. I hope some people will amend my thoughts or challenge them strongly.

Some hopefully helpful thoughts:

1) Is it for fun or profit? You can't have both motivations

One thing you should think about with #2 is the overjustification effect [1]. I think there's a cognitive dissonance effect at play [2]. In practical terms, ask yourself: are you having a side project because you like to do it, or because you want to make money and "scratching your own itch" is simply a marketing tactic of understanding your users? If you say: well, both! Then you're prone to the overjustification effect and you might sap a lot of intrinsic motivation away.

2) Generalists tend to earn less money

There was a recent thread on HN that made me believe that specialists will fare better in big(ger) companies and generalists will fare better in small ones. Since big(ger) companies tend to have more resources, specialists tend to be paid better salaries. I presume your entrepreneurial motivation is in part financial. Being an entrepreneur prepares you to be a generalist [3].

3) With that said more motivated people are more competitive and earn more

This is a bit of a tricky one. It has been my observation that CS students who enrolled into university and were passioned about coding tended to be more competitive on the job market than the average CS student (if I have to believe my LinkedIn, which has +500 connections and +100 recent graduated programmers on it).

One confounding factor, however, with competition is not that you simply have to be motivated. There is a certain baseline of motivation depending on whom your competition is. For example, the gaming industry is a more competitive industry simply because employees are more motivated (I read it somewhere, I do not have the source). Another confounding factor is that the distribution of wealth regarding an industry matters. If you are the 50th percentile earner in the compiler industry, you'll earn a lot more than if you are the 50th percentile earner in the game development industry (with its many indie companies that are underfunded).

What I described here I'd equate as (with the strong assumption that people their ability to learn is similar and they are at a similar level as you):

wealth = motivation_percentile * wealth_distribution_percentile

motivation_percentile: your motivation ranked to that of peers who are in the same industry. A simple metric is: amount of hours worked on relatively high focus.

This is a long way of saying: do you know how motivated you are compared to your competition? And do you know the wealth distribution of what job and/or app you're getting into? In terms of entrepreneurship on wealth distribution: education is less lucrative than healthcare, for example. A heuristic following from this: if you can find a boring industry that you're excited by, then your chances of success are higher.

4) How many product market fits are you able to validate?

It took Rovio games 52 games in order to produce Angry Birds [4]. I am not sure if this is a fair comparison as many industries are different and the average amount of tries to make it big can vary. However, based on stories of most entrepreneurs, I think it is safe to assume that this number tends to be bigger than 10. I hope other people could get some good statistics on this, I couldn't find any.

[1] https://en.wikipedia.org/wiki/Overjustification_effect

[2] https://youtu.be/h6HLDV0T5Q8?t=488

[3] https://news.ycombinator.com/item?id=20094242

[4] https://en.wikipedia.org/wiki/Rovio_Entertainment#cite_note-...

If you're serious about it, there is another option. You can move to Europe or Asia and live cheap while working on your business. I make ~$1,000 a month doing freelance work 30 hours a month. The rest of the time I spend working on my project ideas. My living expenses are ~$400 and I spend another $100-200 on project ideas.

I live in a dirt-cheap country and I find it hard to believe that you can survive on $400/month. Do you take a trip back home? Do you factor in the price of your laptop/phone? Does this include clothes/medical expenses? Also, what country are you living in?

I don't take trips back home, I don't have a phone, I don't have health insurance, I have one pair of clothes and gym clothes. I have an 10 year old x200 ThinkPad that cost $90. It's very fast, I use Arch Linux+Libreboot+Vim. I've live in Ukraine, Moldova, Macedonia, Romania and Serbia. Normally I stay in Ukraine or Moldova though. My expenses are between $150-250 for housing (I live in youth hostels or Airbnb, I travel with my brother and a friend so we split the cost), $165 for food, and ~$20 for the gym.

Very cool. What kind of work do you do? Also, do you speak Russian or just basic Russian to barely get by?

I can't speak any language other than English. I've never had any issues. You can generally get what you mean across by pointing and/or shaking your head

Love to know more about you. Anyway to connect or blogging ?

I've never found myself interesting enough to start a blog. I might write a post on what I've been doing/how to survive as a 'digital nomad'. I think I'm in a unique situation since I've been doing this since I was 18. I was inspired by https://levels.io/eighteen/, but I know when I made the decision I wish there was more info/people talking about how they do it

link is great. thanks for sharing. pls lmk if you write anything.

That sounds fun, but my gf probably wouldn't like this. haha Luckily, I'm in a very low cost of living area already.

> “Live in New York City once, but leave before it makes you hard. Live in Northern California once, but leave before it makes you soft.”

From “Advice, like youth, probably just wasted on the young” by Mary Schmich

Haha, I ran across this quote before. I like it. Thanks

I highly advise u choose safe routine, while spend your spare time on side projects. You can always find sparks on HN or Indiehackers websites, or some Internet Marketing related forums.

Do you know PHP and wordpress? I personally have a very big project idea, but only need a very very high level technique involving design a wordpress plugin using PHP, if this can be done, it would be a very good side project and passive. (no need big investment, the plugin is the main goal)

good luck to u and your family.

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