Has anyone ended up regretting quitting a good job for their own business?

If you take the leap and regret it, what is to prevent you from getting another good job? You'll probably regret it if you don't take the chance, so I'd go for it.

The answer typically depends on the circumstances and how much is at risk. If you have a family to support and your startup does not succeed (especially in this difficult job market) then regret will likely set in.

I haven't regretted quitting a good job to start a business, but I miss certain things about that job: being on a large team, office camaraderie, a dependence on a nice salary and not worrying at all about money (we're bootstrapped so we're constantly worried about money both for the business and personally,) people always taking my calls and responding because i was from a name-brand company. All that said, I was just remarking to my wife today that I wouldn't trade anything for the flexibility I have now running my own business.

What are you optimizing for? Income? Learning? Benefits? Status? Long-term family stability?

In a quest to optimize for learning and connections, I quit my cushy corp gig to found a startup. I cut my income from 120k w/ benefits to 54k w/ no benefits.

I didn't regret it for a second because I learned a ton and I met a slew of new and fascinating people (aside from launching a product, building a team, raising money, getting customers, etc.)

The world is full of well-paying gigs for smart people. Go do your startup.

> I have a great job that pays very well, offers excellent benefits, and has a good work-life balance. That said, my partner and I have spent the last few years building our business and have, for a while now, been at the point where it really deserves our full attention. Quitting would cut my income by a little more than half.

Imagine you're working full time on your own business and you get an offer for [your current job] at twice your current income with excellent benefits. Do you take it?

You may try to quit your job gradually -- talk to your boss and explain that you cannot dedicate as much time to your job anymore and can work only ~3 day per week (with reduction of pay of course). When (if) your new business really picks up -- you would be able to make safe transition to your full-time start-up involvement.

I'll never forget what a wise entrepreneur once said to me as I was scared of going out on my own:

"You have nothing to lose. If you quit your job and start your own company, and fail, you'll be much better off than if you hadn't. If you go look for a new job, you will have run your own company. Would an employer rather hire someone who hasn't run their own company, or someone who has?"

Running your own company definitely brings with it valuable lessons. If I were to get a job today, I would have a completely new perspective on the concerns of my superiors, and what really matters in a company's day-to-day operations. Before working for myself, I didn't feel any motivation at my job because I often felt I could make better decisions than my superiors. If it came down to me needing to get a job, I would clearly know whether this was really true or not.

If my math is correct, your company - which you run when you aren't at your job - makes you as much money as your job does? QUIT!

I quited so-so, but still my own, business and started work full time (first time in my life) due visa related stuff and i regret i went this way (although, do not have much choose). And I would say working full time kill any creativeness and it stops keeping you "fit" business-wise. So I'd say - go ahead if there is no other "dependencies".

For myself, absolutely not. I've never regretted quitting a job, or making almost any life change. Not that things have always gone well, but looking back and second-guessing yourself is just totally a recipe for misery and the worst kind of depressive introspection.

I suspect that if you need to ask this question on HN, then you are not ready to quit.

However, you have a valuable side-business, have you thought about trying to staff trusted people in or have your partner run it, with you as part-time consultant?

If your relationship with people at your day job is as solid as you imply, you might want to take an unpaid leave of absence, and spend 6 months trying to drive your side-business to the point where you don't have any further doubts.

Don't underestimate the importance of a near-passive income that you control. For most of us, starting your own business is the only viable way to attain this, and ensure continued income when you decide to retire.

I took the leap a couple years ago, started a startup, ran out of cash, and got a day job again.

Incinerating your savings at a startup only to end up back as a cube warrior is pretty sobering. Even so, I never looked back on the (great) job I had with regret. Aside from not seeing some good friends every day, I didn't miss it at all, and now I'm at a far better gig than I was at the last time I was a happy wage slave. And I'm lucky to have gained some amazing experiences and a big network for the next time around.

I'm sticking to the HN party line on this one and saying that good things will come from taking a risk on what you really want to do.

Thanks for the amazing feedback, everybody.

I think the point that a lot of you have said-- essentially, "so what if you fail? You can find another job" -- really resonates with me.

I'm leaning towards doing this now because I have no kids or mortgage at this point. I really appreciate all the good responses in this thread. It's definitely a scary, but exciting, time as we consider it.

The one other factor is the drop in total income. The hope is that's temporary though-- our goal is that more time spent building the business will pay off in spades.

There's something about getting the support of people who have been in similar situations that helps with this kind of thing. Even online here, it's reassuring. So thank you all again for that.

Well no and no. After working for the man for 11 years, I started my own business. Some very good years and some lean years (15 years) later I was enticed to go working for someone whom I knew and respected. That was great. But then the business was sold and I didn't get on with the new owners so I took another job and lasted just 5 weeks. Quit and started up another business, now up and running for 6 years. Looking back, I am much happier being my own boss. If I see an opportunity I can go for it. Money is not the most important factor. Freedom is!

I have a coworker that quit his job, got broke trying their own business (he argues he chose his cofounder poorly), but he got his old post back, so in a way he regrets it, but he had his chance and didn't miss on opportunities that much.

I should ask him, but my take is that it shows that you don't risk as much as you believe if you take risks and are good enough.