To quit or not to quit…

This is the next big thing on my mind… When do you bite the bullet and tell your boss that you’re walking out the door?

I’ve got two conflicting ideas in my head at this point in time.

1. Tell the boss that I’m leaving now so I can spend all my time building my own business
2. Wait until I’m making good money through my own business so that I don’t need the other income anymore

Both have pro’s and con’s.

If I stay at my job and put 50 hours a week into doing projects there, sure I’ll get paid but I also won’t have either the time to build my own business or the drive to build it because money won’t be that important.

If I quit my job now before I’m making money through my own business, I’ll have the time and motivation to keep build the business fast but at the same time, I’ll be putting my family at risk.

I only have enough in savings right now to keep going for a month or two and I don’t know if the risk is worth it.

It’s a tough call…

If anyone reading this has been in this situation before, please comment on this. I’d love to hear your thoughts.


  1. Michael says

    That’s a tough call to make. You have to look after your family but sometimes, you just have to take the leap.

    Have you even tried getting new clients yet? Do you know how successful you’re going to be?

    • The Lucky Stiff says

      I’ve tried… A bit. I’m not going to pretend like I’m the worlds best salesman but I’ve chatted with a few people, asked them what they’re looking for, how I could help them.

      The response has been positive but consistent – “Love to work with you but now is not the right time…”

      I don’t know if they’re being polite or if they really mean it.

      I guess there’s only one way to tell.

  2. C0d3_5NiP3R says

    I was in a similar situation although I decided against making the move. I have a wife and 2 kids, and found it would be too stressful to make the move now since this next job will require 1 week of travel per month, the rest I’d be working remotely from my home office.

    Maybe just re-evaluate in the Fall, and in the meantime, work on perfecting your plan for your business.

    • The Lucky Stiff says

      Thanks for the message mate. It’s good to hear from someone who’s been in the same position and who made the call. In hindsight, do you think it was the right decision?

  3. Hunter says

    Sounds like you need a Junior Software Developer in training that doesn’t want any pay and just wants to learn, help, and to be a part of something bigger *cough* *hint* *cough*

    • The Lucky Stiff says

      Haha… Thanks for the offer but at the moment, I don’t think it would work. I can hardly manage my own time, let alone the time of someone else.

      If I ever do get this up and running and to a point where I have enough work to keep an enthusiastic junior developer entertained, you’ll be the first person I contact about it.

  4. Fergus says

    Not sure where to start with this reply … I ran my own business for about 10 years (I’m back in corporate now) and there’s probably about 30 questions that are important; I’m not going to go through them ’cause most seem silly, like “what age are you?”; what’s important to realise is that many people will tell you there’s not a correct answer to what you should do. Unfortunately you come realise that’s bullshit, there is a correct answer. Being successful is about understanding that and making evaluative choices based it.

    You’ve already started your company, so that’s a given. Your basic mission now is to decide what is of value. If you have no clear idea, you will stuggle and I suggest you find a large market sector you can bury yourself in, simply trading time for cash. For example, web development, mobile development (although I’m sure you will realise you need something more specific); taking into account the potential customer base around you. Failing that, get work as a contractor. It has balance between steady, novel and flexible, and it can pay very well if you have the right skillset.

    If you do have a clear idea, your next job it to evaluate what assets you have (e.g. money, time, knowledge, friends, family) and figure out which are to be traded in return for this thing. Building something requires resources that you can trade, if you have none you will fail. The best you can hope for in that scenario is that someone will see the value, steal it from you and throw you a bone.

    Which brings us to your exit strategy. Right now that’s simply mental masturbation; indulge in it when you have something to exit. I’m sorry to say that both WebBrokers and IPO are dead ends (and am not going to try and explain why). Someone will no doubt eventually mention the idea of private investment too; this is more viable but it’s very unlikely that it’s valid 2 months into your business unless you have a golden, patentable idea.

    To end on a more positive note (apologies for my brusque nature), the timing of your venture is good and if you have the above (i.e. a clear idea and resources) then you have all the chance in the world for success. Remember, it really is about “what is of value”, I mean, that’s why you left your previous job, right?

    Good luck.

  5. Martin says

    So, have you reached a decision? I would be delighted to know what your decision was, and how things are going for you. I find myself in a similar position.

  6. Bruno Della Motta says

    Well… If the question wasn’t already solved and I’m allowed to give my opinion, if I were you, I’d do: a realistic business model forecasting when my own enterprise will be profitable; keep working as an employer untill I save the amount necessary to cover me and my family in order to survive the unprofitable stage of my own enterprise (with maybe a 20% increase in the time necessary for “failsafe” reasons, despite having no real “failsafe” for those kinds of thing; in the meantime, I’d be planning my enterprise and trying to close deals to make it feasible, so when I quit my job I wouldn’t be with “empty hands”.

  7. Brent says

    I’m struggling with this sort of decision right now… without the worries of a family. Leaving a stable and well paying job to pursue my own interests feels akin to jumping off a cliff without knowing if you are wearing a parachute or not.

    We all have dreams of doing our own thing, but the key is to have the ambition and the courage to follow them.. It seems I continually put off my dreams for more security and tell myself I’ll get around to it next month, when things are better and I have more money saved, etc … But the truth is that those months turn to years and you’ll eventually find that “10 years have got behind you” (pardon the Floyd reference) and you still haven’t made the leap. If you aren’t doing anything today to try to achieve your dreams you will never get any closer to them…

    I hope you are still not struggling with your decision. I, for one, know that my courage is building daily and I’ll eventually figure out that I am wearing a parachute.

  8. Nicolas says

    I quit my job about three years ago. I am very happy about it. I didn’t have any business plan, I just quit my job, called people and told them I was available for freelance work. I did not earn as much money as I would if I had continued to work for that company but I earned back one thing that I will never trade back again : freedom.

    I want to take vacations ? I don’t ask, I just take vacations. I want to take a university course part time ? I don’t ask, I just take a university course. I want to take tuesday and friday off to work on a silly project with a friend ? I don’t ask, I just take tuesday and friday off. I want to go lunch with my girlfriend ? I don’t ask, I go take a lunch with my girlfriend.

    My girlfriend still have a regular job and we talk a lot about her quitting her day job and going freelance. But I think now she’s just not ready for it. But sometimes it makes me upset how much her job is controlling her life.

    People don’t realize how much their job is sucking their life out of them. Everybody should quit and try starting a company at least one time in their life. What’s the worst case: you go back to a regular job if it doesn’t turn out as you planned.

  9. Snail Walker says

    I was born in a very poor village , I have been though a lot of hard times . I still remember when i was 10 years old, we only get to eat meat once 6 months. I started my own business when i was 19. I cooperated with a programmer to do that project for about 6 years until the business ended. Even though that business didn’t last long. But we have made enough money to spent for the next 10 years without doing anything. Im talking about living in Thailand. It’s not expensive to live here , More importantly it makes me a quite happy life. I don’t really feel comfortable to live in my home country China. i started to learn Ruby on rails recently and i have seen a lot of posts about you. Apparently , you’re a capable man. I don’t understand why a capable man like you can risk your family under this kind of circumstances ? Are you spending like lots of $$$$$ ?

    The benefit of being a freelancer is that having a lot of freedom ,you can do what you like to do. During these 6 years I have learned English,Thai and I’m currently learning rails for my online tourism business . I believe that The pursuit of knowledge is far preferable to the blind pursuit of riches.
    The first brings wealth, and the latter ends in a loss of life. Anyway for a Chinese boy like me can even made it through , I don’t see any problem of a capable guy like you that can risk your family unless you are having a kind of luxury lifestyle .

    But your situation is kind of unique , Is that rushy you have to quick the job right now and you only have the saving for one or two month , Are you sure that can make profit in 2 month from your own business . What if not, Can you still handle that risk. Before starting a business you have to be ready for the worst situation , If you are ready for the failure , there is nothing to fear , just give it a try !

  10. says

    Skip to the end for the specific answer :)

    I made a similar choice 8 years ago. While working at an established software company for 7 years as a developer/team lead/pm I couldn’t help but wonder whether the grass is greener on independent side of the lawn. So one day I parted with the company for a fresh start on my own and convinced a coworker of mine to do the same. I didn’t have any savings or a good plan, just wanted to make my own decisions.

    We looked for decently sized freelance jobs and we did find some but it was far from adequate. The earnings were very modest, about ten times less my previous salary, just on the brink of keeping ourselves fed. We worked in this mode for about two years until one of the customers invited us to work on his project exclusively with regular payments. We kept a degree of independence so this was a welcome compromise.

    The customer was very supportive to the projects we started making on our own after his system moved from active development to maintenance. As we worked in a specific niche we were able to accumulate lots of relevant experience and ended up creating a product solving typical needs of this niche. We established a company around this product and were able to attract a decent amount of customers. In the end I became frustrated with administrative duties which distracted me from hands-on development.

    So I made this choice for a second time. I left the company, this time with a pretty decent savings which allowed me to live for a year while contemplating what to do next. I wasn’t emotionally ready for founding a new business, so eventually I started looking for startup jobs. The reason for that is the good mixture of dynamics, challenges, fresh technologies and team work startups usually present. Downsides are of course the inherent stability risk, overtimes, intense working rhythm. After working for a year in a startup, here I am again, thinking about founding a new business. Looks like it becomes an addiction.

    The findings of these 8 years: First of all, it is fun. Very hard, very nervous, but real fun. The overall experience is actually freaking awesome! I architected complex systems, implemented those with my teams, learned from mistakes, did better next time. Established process, honed it until it worked, interviewed and hired people, built teams, communicated with customers, made sales, solved problems, wow!

    Second, the amount of technologies I was able to learn and use on production is immense. There is just no way something similar would be possible while working for an employer. This gave my skills so much boost I can’t stop looking for more :)

    Third, rather contradictory, I became overqualified for a typical development position and at the same time underqualified to take an expert role in any particular technology. The years of self-reliance earned me a pretty unique and holistic set of skills. This makes me good in the same areas established companies rarely have much interest in.

    Which leads to the fourth: I don’t really consider looking for a job in an established software company any more. It’s just makes too little sense. Instead, I’m looking to found a new business while keeping my ear open to startup jobs where my skill set may be really indispensable.

    And the specific answer…
    …which seems not to be relevant to you any more looking at your later posts, but might still be helpful for others:

    If you got savings for only two months and a wife and kids to care of, don’t do it. Two months is just too little time to be safe.

    If you or your partner got sales skills that might be ok, but don’t delude yourself if you don’t. It’s one thing to make a product and quite another to sell it. Customers often like to go slow when an offer is complex enough, so a decent sales pipeline is essential to get things going. It takes time to build one and preferably someone who knows how to do it.

    Alternative option is to apply for investment which might be a good choice since you got the product ready. Some research I did shows the average time to get funding is about six months these days. This can be done while still working for an employer and is a much safer strategy. It’s not about making all the money right away. Having created a business once, be sure you’ll be doing it again.

    Of course your experience is yours alone and it’s you who has to make the decision. Be sure that working on your own can be a great adventure. Risky and not always lucrative, but lots of fun. As Snail Walker said above, make yourself ready and give it a try.

    BTW, @Snail Walker, your story is intriguing, let me know if you’d care to talk more; reach me at Skype by the name nicnilov.

  11. GregsBetterHalf1982 says

    Save up a little dough ray me and take the plunge. :) Keep the wife happy with lots of foot rubs. Thanks for taking us on this journey!

  12. Duder McGee says

    Quit my job three years ago to start a company. My first one failed, my second one is still running and moderately successful.

    When I quit, I had about 1.5 years of “personal runway” stashed away, so the risk was a lot lower. I also worked on my first company for a few months during nights and weekends while I was still proving out my company.

    I took a pretty cautious approach. I quit when I knew that to grow my business, I’d have to give it my fulltime effort. I burned the boats and have no regrets (even though that first company eventually failed).

    If you only have a month of personal runway, it will definitely make you hungry, but realistically it might not be enough to get your business off the ground. I’d work on your business nights and weekends, save up a bit, and then quit.

  13. Aaron Gray says

    I was in this exact same situation not too long ago. What I ended up doing was easing myself into entrepreneurship so I could keep food on the table without burning my savings. I found a 25 hour a week job as a remote contractor on a 6 month project, told them I could start in two weeks, and signed that contract. Then I gave my employer a two weeks notice and quit the 50 hour a week employee job. That gave me a safety net of guaranteed work, and I could spend my other time either building a product of my own, or hunting for other hourly projects. It worked great.

    I’ll be praying for your new adventure. :-)

  14. Roi says

    I made this decision in December 2012. I was the lead dev at successful agency in San Francisco – my partner was the lead designer. We decided together we would like to start our own company.

    I started 2013 off as self employed, he decided he was going to wait for the right time. Save up some money, pay off some debts, ect…

    Well, almost two years later it’s still not the right time. He’s making a fraction of what I am and is incredibly unhappy with his job.

    It defiantly could have gone the opposite, but I am glad I took the plunge to “the dark side” as we used to call it!

  15. says

    Don’t do anything, unless you **know** it is what you have to do.

    (or is the right thing to do, whichever speaks to you more. know being the operative word)

    That’s the short of it. The shorter of the longer version is that you have to see that decisions are a way of forcing a situation. Any decision you make comes back to bite you. Because you forced it.

    Every situation has something to teach you and when you learn the lesson, the situation changes. In other words life knows what is best for you, and you only ever think you do.

    PS. don’t usually do this, but you did ask. And a lot of good ruby stuff came from your ways, so this by way of thanks.
    PPS: yes, have been in the situation for many many years. When it stopped it first took me to become a carpenter, shop and b&b keeper , and when i came back to coding years later, all was very vey new.

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