What should I consider before jumping from stable job to startup?


I work in finance and have a stable job with lots of growth potential. However, I have no passion here. When I think about working for a startup, my eyes light up with excitement. I'm immobilized because I'm stuck debating between the two potential career paths. What things should I consider in helping make a decision so I can march forward?

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asked Oct 21 '11 at 00:36
162 points

5 Answers


First, ask yourself how stable is your stable job. I was in a similar situation, I was an attorney in an established law firm, and I struggled with myself a lot when leaving for joining a company that might not be there anymore in one year. Guess what, a flip of the economy and my ex-employer fired 30 attorneys in one day. No advance notice. Finance does not look like a very stable industry either, at least right now.

What you call lack of stability is just the fear of switching from a known situation to something unknown, and therefore risky. Once you realize that, I think you can make a better decision by stating your priorities and aswering questions like: how long can you remain sane working at a job you are not passionate about? How much can you handle unstructured business and roller-coaster moments? How much do you care about salary and prestige?

Bottom line: working in a big corporate environment is not more stable, is just more predictable. By working for a smaller company, you sacrifice that comforting feeling for more engagement and possibly higher rewards (few startups win big, but when they do, no IB partner stands the comparison!).

Final words of advice: worst case scenario, you take the chance, go work for a startup (better, THE startup), learn a ton, fail, and come back to finance. You might lose a couple steps in the corporate ladder, but the value of the experience will be yours forever. And you grew some balls.

answered Oct 21 '11 at 05:23
829 points


There are a range of things you should think about before jumping in.

Potential Negatives:

  • Partner. If you have a partner, do they support you in the transition, are they prepared to take a complete change in lifestyle and in someways be with a completely different person ... You will be focused on different things, you will be driven, you will stressed ... are they signing up for it?
  • Family. There is only 1 thing as demanding on your time and mental capacity and that is kids (so I'm told) ... can you deal with both, are you planning kids in the next 5 years, if so think carefully.
  • Other life goals. You may not have a chance to travel as holidays are short and interupted, playing on top sports teams and doing a bunch of other stuff will likely go on hold for a few years at least, most likely 10 years or more.
  • Cashflow. For a while you may not have a consistant cashflow so signing up to ongoing things may be hard.
  • Commitments. Owning a car and owning a house may not be options for a few years, are you ok with this?
  • Daily lifestyle. While you can choose what you do and when,
  • Switch off at home time. This is something a lot of 9 to 5 workers take for granted, they don't have to worry about anything until they walk in the next day ... In a startup this normally isn't the case, you are thinking about it all day every day, and if your not then you feel like your wasting time.
  • Not understood by others. Everyone who isn't in a startup is always telling you to relax, take more time off, assumes your making millions, expects that you will have all the benefits like over time pay and sometimes get angry when you have to say "the world doesn't actually work like that" OR "I am the company, there is no 'they', its ME".
  • Social circle changes. If your social circle is made up of people who don't work for themselves then you will strike points where they ask "So what do you do?" and you answer "I run 2 software development companies" and that is the end of the conversation, they back off from you. One instance they took a dislike because I was "the enemy" (the boss) ... you find other people but it can be disconcerting the first few times.
  • There is no backup. If it has to be done, your the only one who is going to do it. Coming from a large company this can be a huge culture shock when you start realising how much was "taken care of" by other people.
  • You answer to everybody. While its true "You are your own boss" ... in reality it means that every client is now telling you what to do and pulling you in different directions.
  • You have to deal with a lot more stuff. If your an expert in a specific field then your going to get a big shock when you start having to deal with clients and employees and creditors and banks and contractors and 1000 sales people per week ... everyone wants a piece of you, all the time.
  • When it hits the fan, your the one in the front row facing up to the problem.


  • You can grow something new.
  • Your mind is alive, your always switched on even when your sick.
  • You find out what you are capable of.
  • You learn more every few months than you would every few years in another job, because there is no one else to do it...
  • You can become independantly wealthy.
  • You can define your own parameters ... well kind of.
  • You can choose who you work with.
  • You can create the environment you want around you.
  • You can meet a broad range of new people you wouldn't normally come in contact with.
  • You get treated differently, your decisions matter.
  • Other people watch you and take their lead from you.
  • You get to build what you want to build.
  • You come to get a deeper picture of how the world works because your thrown in the deep end and have to make it work.
  • You get invited to a wider range of events and gatherings.

But these are just my experiences, your likely to have your own list that looks different to mine. Really if your happy to take the pay cut and your single or have a partner who is backing you, I would recommend trying it for a few years, you can always return to corporate life, usually with more experience and thus target a better role.

answered Oct 21 '11 at 10:44
Robin Vessey
8,394 points


I sioerulsy don't understand you.

When I think about working for a startup, my eyes light up with excitement

Why? What are you running away from?

I am not disputing that working in a startup is exciting - but it should not be because it is a startup (in general) but because of what you can do there and / or the exciting product being worked on. You say nothing about "I have an idea for a startup", you seem to think that in general life in a startup is a lot better than in an established career.

Startups are hard and high risk.

Make sure you like THE startup, not A startup.

answered Oct 21 '11 at 04:15
Net Tecture
11 points
  • I didn't mean to imply that I just want to work for any startup in general. I have a genre that I am interested in. That being said, there are qualities of startups in general, that do appeal to me as well (high impact work, variability in daily jobs, etc). Thanks for your thoughts though. – Ryan 12 years ago


You should consider whether or how much you're willing to fail. I'm sure you 'fail' at your current job, but failing at the task of boot-strapping or merely working-at a startup is different. If you're like me, you consider quitting a failure of sorts. You may eventually quit your startup because of the stress. You may quit because of personal finances. You might be fired because you can't hack it! Or – what might be worst of all – maybe your startup simply dies (as almost all of them do).

Despite what Steve Jobs may have said, the world in fact would probably not be a better place if everyone followed their (work) dreams. You should consider all of the benefits of working for a startup – self-direction, flexible working times and environments, challenging projects, etc. – as just another form of compensation. How much less would you accept from your current employer if you were able to secure each of the benefits of working at a startup?

answered Oct 26 '11 at 09:17
Kenny Evitt
176 points


Everybody has ideas and would love to work for their ideas but the question is do you have a market for it? Try to find your customers for your business you are thinking about it. Talk to your friends and other people over phone and see if you have a market? If 9/10 say that your idea is great then by all means you should start you company. If 1/10 feels the need then probably you should stay in your job.

I'm saying this because one of my friends quit his job and started a start up company and it is going great till now because he did a lot of ground work before and found who his customers were and went for it.

So do your ground work and identify your market size and if you think the target market is big enough then go for it.

answered Oct 21 '11 at 10:12
128 points

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