I think more people would regret it if they knew what they were giving up, but most would probably not make that calculation. If he had kept his corporate job and spent the initial $30k a year he could have retired early only 10 years later. Maybe less if he'd be willing to live very frugally. Then he would be free to build as many apps and games as he wanted, giving him many chances at getting a big hit.

I'm in this dilemma myself, as I've always wanted to do something more risky, but I don't want to jeapordize my ability to be financially independent at ~40. Being stuck in a potentially crummy corporate job with potentially terrible management and coworkers for another 25 years (not the case now, but things can change quickly) is the regret I want to minimize beforehand.

Moonlight unless your co owns your IP? Post traction go independent?

Seems the only reasonable option to have the cake and eat it too.

> he could have retired early only 10 years later.

That is a flawed argument. 10 years later you might not have the same drive/ambition which you have right now.

Maybe, but sounds a bit like future discounting to me. I'm just presenting my dilemma, and I don't think the solution is to be idle for 10 years and then switch to entrepeneurship overnight. More like work a normal job and try to get stuff going on the side, but don't risk your life savings for a lottery ticket.

> age would you wish you had done something like this?

Not if I was 65 and still working, because I liquidated my 401k back when I was 30 and it never panned out.

But yea, I would regret being 65 and having never built a business.

> Can you earn it all back with a good fall back plan on your expertise?

I don't know. Probably, if you were able to dramatically cut costs and go into hyper-saving mode. This can be a challenge later in life though (once kids and a mortgage take hold).

Why not throw out dirty prototypes of your top ideas every weekend to see if they gain traction?

And if you can’t earn it back, are you prepared to work until you die?

In lots of tech fields the comp packages are so high this shouldn't be an issue. With good financial planning lots of engineers could actually retire in just ~15 years or so of work.

Coding until I die? sign me up

Ageism.

Contract work, side projects that make revenue, etc.

Opportunities are always there for those who keep an open mind and a growth mindset.

Let’s not derail the thread, but there are lots of people with college educations who can still only get a minimum wage job. Opportunities are not endless, nor always there.

It’s entire possible you jump off the corporate ladder and never make it back on, your wages permanently stunted and your career prospects dimmed.

Ok let me update it. Opportunities are always there for enterprising, confident and contrarian thinkers who will take several chances with low downside and try to create new things rather than compete within existing paradigms.

Disclaimer: Not financial advice but personal observations

This discounts the high failure low success rates of entrepreneurship, which is dangerous advice in a country with a broken healthcare system and no social safety net.

Again, it’s not an OR situation. One can try doing side projects while one works full time.

Is the question of what I will think of something when I'm old really the best question? I know that this seems natural but I wonder if it is a bad way to make choices. I don't think my enjoyment when old is more valuable than my enjoyment when young.