I am a web programmer with a family and all the accompanying expenses. I am trying to decide whether to:

  • develop my dream start-up (which will take at least 7 months) with no guarantee of success, or
  • continue with my current occupation making simple stuff and dragging clients to work with me normally.

If you were in my position what would you do?

  • 3
    I never was in your situation but I would say: make your dream come true :) And also: I would just take advice from people who were in the exact same situation as you. People who never took the risky step mostly don't know what they are talking about :) You are lucky to have a higher goal and you should try to make it reality :) Commented Feb 18, 2015 at 9:29
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    There is also a Stack Exchange site for startups. You might find some relevant info there. Commented Feb 18, 2015 at 15:56
  • 5
    It's better to regret the things you did, than the things you wish you had done.
    – JohnFx
    Commented Feb 18, 2015 at 16:10
  • 1
    You might find more experienced answers on brightjourney.com, which was an Area 51 stack exchange before they shut it down.
    – Chloe
    Commented Feb 19, 2015 at 0:06
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    Don't spend 7 months on the startup. Spend 10 days on a minimum product, then try to presell it to people you don't know. You will find out quickly if it's a good idea or not. Google "Ghetto validation": google.com/search?q=ghetto+validation Commented Feb 19, 2015 at 12:34

7 Answers 7


My general rule of thumb with start-ups is don't quit your day job until you can afford to quit your day job. If you were a single man, or your wife also could provide income for the family, then you would have more flexibility but if you are the single income provider I suggest a more cautious route.

It may be frustrating to deal with the drudgery of work, but if you really want to see that start up I would suggest getting started to work on it with what you can while working at your other job, until you have enough money saved and enough work done that you can fully launch the start-up full time. It will be a lot of work, (so would a start-up) but it is less risky, especially considering your family situation.

If you really hate what you are doing, I would suggest looking for other opportunities in your field of work. Maybe there is something that you have overlooked, and don't hesitate to apply for jobs you are not sure if you are qualified for-- as long as it doesn't involve time away from your current job an application is fairly painless and the worst case is you keep doing what you are still doing.

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    Just be careful of employment contracts which give the rights to anything you work on (even in your own time) to your employer. And definitely don't work on the start-up at work.
    – Bobson
    Commented Feb 19, 2015 at 12:33
  • @bobson I don't disagree with you, exactly, but I think this fear is largely unfounded. This has always been a concern of mine, so I've kept an eye out for stories about employers "stealing" an employee's invention due to loosely-written contracts. I really haven't seen an abusive situation to date. As long as you're not working at Widgets1.0 and working on Widgets2.0 in your spare time, you should be fine. The one exception I've seen is Universities. They seem to lay claim to employee inventions more than any other type of business. Commented Feb 20, 2015 at 18:20
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    @JamesBeninger - Depends how successful you are. If you leave to become the next Facebook or Twitter, they might just want to pursue it. Something to keep in mind even if in most cases it isn't worth their time to care.
    – Bobson
    Commented Feb 20, 2015 at 19:46

I did this 20 years ago. I wanted desperately to quit my job, but my wife wouldn't let me -- not because she thought it would fail, but just because she thought it would take longer than I thought. It took us 2 or 3 years to get to roughly half my previous salary as a software engineer. It's been my full time job for 15 years now.

It's much better to not have enough time to finish X, Y, or Z on your startup than to have finished it and be waiting for someone to show up and pay.

  1. I agree with "Don't quit your day job until you are very confident your startup can support you and is making money".

  2. Validate your startup idea early. In the words of the Lean Startup movement, "Fail Early". This is absolutely critical. Starting a company requires extreme confidence. Succeeding requires extreme humility and a willingness to face your mistakes (because how else can you improve?). You've clearly got the confidence. Now you need to to be realistic and look at "What could go wrong?" and "How will I know that this is working?"

  3. There are some parts of a startup that require what I call "Calendar Time". It's just elapsed time for things like:

    1. You tweaked your landing page and you're A/B testing whether that improves things. And you wait for a week or two.

    2. You are waiting for a contractor to finish something on your website's Payment feature.

  4. Read The Lean Startup (and similar books) to get an idea of all the things you'll need to do. You'll need to:

    1. Verify that the customer's pain exists.
    2. Verify they'll pay more for your solution than it costs you to crease (including sales marketing and support).
    3. Figure out how to reach them with your marketing.
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    I really like the insight that you bring into this situation. The information you have shared is quite invaluable to anyone reading even if they are not currently considering starting their own business. I am very glad to hear that it all worked out in the end!
    – MonkeyZeus
    Commented Feb 19, 2015 at 15:58

I did this a couple of years ago, and boy do I regret it. After many months of delayed, and new faces coming onto the team for a short period before leaving, there wasn't much hope to ever complete the project. I ended up accumulating debt (About 4.5 grand) that I am still paying off because I chased my dream.

Unfortunately, anything can happen when you choose to pursue a goal. It can get delayed, stopped, or outright fail. At the bare minimum, you would best be prepared to deal with delays, competing products, and outright failures. If you say "I have enough money to last me 12 months and I expect to take 7 months", then you best be prepared to answer:

  • How quickly can you get a job if you need to?
  • How do you prepare to deal with delays? What about delays caused by restructuring your time so that you don't go bankrupt?
  • How do you prepare to deal with a competing product that is superior?
  • How do you prepare to deal with corporate bullies who will try to steal or mimic your product?
  • How do you know when the project has failed?

These are just a handful of ideas, and there are plenty more that would need to be addressed.

Probably the best thing that I have seen a few friends do is to ask for reduced hours. Working part time allows you more time while reducing, but not eliminating, the pay. Even better is that depending on your company, you could ask to go back to full time if your startup didn't work out.

Another option is to do what I'm doing currently: Find a job with lots of downtime. My job is critical and the market here is starved of good techs. Even then, I have a solid 2-4 hours of work each day. The other 4-6 hours I can spend on my personal projects that may eventually lead into a startup. If you plan to do this though, make sure to read your agreements carefully. There may be restrictions on copyright and the likes by working on a personal project on company property. If you do plan to go this route, you might want to consult a lawyer (like I did) to make sure you won't get screwed later.

  • Yeah, this is the most common failing - it usually takes years even if you're on the right track. And let's face it, most programmers don't really have a problem with over-estimating, rather the opposite :D A great answer :)
    – Luaan
    Commented Feb 19, 2015 at 17:04

No one can make this decision for you.

Involve your wife and truly value and heed her thoughts on the situation.

Succeeding in such an endeavor without her full support/consent will bring an unwanted undertone into your marriage.

I am personally more reserved and in your situation I would stick with my job until my start-up can stand on its own. I know it would require more work but at least it wouldn't put my family in an all-or-nothing situation.

It's tempting to reach for what you don't have but sometimes it worthwhile to stand back and be truly grateful for everything you do have.


I quit my job 8 years ago with a wife and a new baby to start an agency. We aimed to do client work to pay the bills, and meanwhile work on a portfolio of products which we could sell.

We had around 5 years of extremely tough times, sometimes not enough money to buy food, and the revenue breathing down our necks. It was highly, highly stressful.

The next 3 years were a little better, still stressful and a lot of hard knocks and lessons to learn.

This last year has been wonderful.

Creating a startup will teach you things you never realised you needed to learn. It will break you down and remake you.

If you decide to go for it, make sure your wife is on board. Maintain an emergency fund, and don't eat into it. Save for tax, even if that means you can't eat. Don't expect to go on holiday for at least 5 years. Cut your expenses down to a shoestring. Get really good at finance. Practice envelope budgeting. Don't eat out. Work hard, talk to people, network.

If you and your wife can get through the pain it will be worth it, but don't expect anything like an easy ride.


From a talk by entrepreneur and investor Gary Vaynerchuk:

@2:37: Look yourself in the mirror and ask yourself: "What do I want to do every day for the rest of my life?" Do that. I promise you can monetize that shit.

@12:04: I don't want to hear about this "9 to 5, I don't have time" thing. If you want this, if you have a passion, work 9 to 5, spend a couple hours with your family, 7[pm] to 2 in the morning it's plenty of time to do damage. But that's it; it's not gonna happen any other way.

@You work 9 to 6, you get home, you kiss the dog, and you go to town. Everybody has time. Stop watching fucking Lost. If you want this, if you want bling-bling, if you want to buy the Jets, work. That's how you get it.

  • 6
    The ability to follow this schedule depends largely on personal circumstances. For example assuming 1h commute and 0.5 for shower/exercise etc. it leaves 5h for sleep and 1h for family. In addition proposed time contains 15h of creative work. Usually people need 7-8h of sleep, less they cognitive ability suffer. It is not uncommon to be productive only for a few hours in cognitive work. At the end for most people 15h/5h is not sustainable lifestyle (if not dangerous) for many people and can result in quick burnout. (Yes, there might be some exceptions - Edison slept 5h but Einstein 10-11h).
    – User
    Commented Feb 20, 2015 at 5:26
  • @User: I agree; Gary is "a bit" of a promoter. On the other hand, once taken by a passion, you'd be surprised how resourceful, focused and productive you become. Commented Feb 20, 2015 at 7:01

The final decision must be made by you, but from personal finance perspective it's the high risk investment.

  • you invest the money in startup (the money you need for living in the time you don't work)
  • you may get very high win (if your startup becomes a little star)
  • you may loose everything (you get no win from startup)

The first consideration is, do you have enough money to invest? You need money for much more that 7 months, because the money won't flow immediately. At best you should have finantial reserves for 18-24 months.

The second, do you wish to risk? You can place a deadline, for example if after 18 months you're still on minus, you give up and return to the normal work. It will mean you've worked for 18 months for nothing, while having expences, so it's effectively a lost.

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