As a guy that walked from a similar situation (next in line for CTO of a fortune 100). I would say stick out the two years. While the market is exciting right now, and yes my life has been exciting since I walked, there are times where I could have used that money. If you are two years out I would grin and bear it for that time, it will put you in a far better position when the time comes to pursue your own thing. HN and other sites can be a filtered bubble where only the success get's echoed. But the overwhelming odds are that any venture you embark on will fail. Failing is a lot easier if you have a bank account to fall back on. If I had it to do over, I would have built up my cushion a few years and then embarked on my own.

Working a few extra years to get a 1/2 million dollar sports car: NOT worth it!

Working a few extra years to get flexibility and independence: worth it!

I sucked away over a year of my life doing sales; it was soul-crushing but it gave me a very strong business-sense; I gave the Marine Corps 6 years of my life, that was soul-destroying but I came out a better leader. You have to make sacrifices to put you where you want to be. And a year, two, three, four isn't really that long; it's much better than being hungry.

tldr; Work the 300k job, live frugally/save, take what traits you can from the job, working on creative jobs can wait.

If you don't have a specific idea, you could go to hacker meetups, colleges and find groups of people with an idea and a team and join them. Offering to do some work and pay for food, servers etc. - I could sure use someone like that right now ;)

Finally if you already have 4-6 years of a similar role under your belt then you can probably move back into a similar role anytime you wish. But if not, you probably need the years on your resume in case you want back in.

Moral of the story - it's not a binary decision, you can be doing both at the same time.

Having the money will presumably give you significantly more opportunities after you do quit than if you do it while having to worry about how to make money, so it's not like sticking it out is damaging your future startup or freelancing -- it's probably helping it.

Actually, I'll make a rephrasing: I'd wait for around 12 months or until I wake up one morning with a startup idea that I can't imagine not trying out, planned in a significant amount of detail. Whichever comes first.

1) Time to jump

As long as you ask question "when should I do it", you are not ready. From my own experience,when you feel it, you know it is right time. That "feel" is a natural conclusion of a lot thinking, researching, preparing and prototyping. It is like you need to eat when you are hungry -- you will not ask "when should I eat"

2) Freelancing

Start something takes a lot of time and effort. Freelancing may take your time and energy away. I did that trying to start something on the side, which I considered a mistake.

BTW, are you hands on developer, or development manager? $300k for developer sounds high to me -- maybe you are super-star developer...

Good luck.

(..sounds like you work at Google, eh?)

I love programming and always have. I realised I needed to leave my job after I started considering changing careers. The place was completely soul crushing. I've been doing it for almost 6 months now and the funny thing is I could go back to my old job any time if I wanted to. I have no intention of doing that though.

Don't bet on this. If it happens, GREAT! If it doesn't, at least you won't be crushed. Success doesn't always happen the first time around. Sometimes it takes multiple plays before the jackpot lands.

But putting all of this aside, don't do it for money. Money is an important factor but as others have echoed on here, do it because doing what you enjoy/love outweighs what you make. Money is icing on the cake.

If you're unhappy, confident in yourself, and have enough money to be financially secure in the short term, quit. Sometimes all you need is a little incentive to do something extraordinary.

Also, if you're looking for a job in a few months, send me an email.

For me it was easy. It's about the freedom, not the money. I would rather make 60K working for myself than 300K working for someone else.

I hate having to ask someone (like when I was a kid) to have a day off or go on a vacation. When I finally made the switch 3 years ago, my life changed for the better. I love waking up every day and working on my own projects.

If you have a family and no savings, it's a different story.

I'm not that experienced but that's what I would do.