And I assure you: Whenever you are pondering "taking it easy and spending time with family", there will be yet another cool thing to give you an excuse not to.

1) You can never get back your kid's childhood no mater how hard you work.

2) The time to take big financial risks for big financial rewards was before you had a family, particularly before you had a kid.

3) Getting a new well paying job at a big tech company in the event that your AI asperations don't come to fruition is likely going to be a challenge. At least that is my understanding from what I read about the current economic landscape.

The way people talk about AI powered everything reminds me of how people talked about block chain powered everything a few years ago. Don't get me wrong, I love working with Claude but I get the distinct impression that many marketing people confuse a case statement as being "Powered by AI". I use AI code assist every day but I'm not going to bet the farm on joining/founding a startup that is "Zillow for <something> powered by AI".

But probably not to just “get startup experience”. Having a kid is a time to not upset your routines if you can manage it. Startups have very wide variance in experiences compared to roles at big company in my experience. Just switching jobs would be difficult.

I had a cushy year at a comfortable job when my first kid was born. I did more the founder thing (write a career changing book) when my second kid was born.

2. Will also statistically fail and won’t offer you income.

3. Guaranteed money.

So better take it easy now and wait for next once in a life-time opportunity. There will always be more. And if there is not stability is much more needed.

Stay in big tech (baby or no baby) for interesting work. Id aim to get the skills to be chased if passionate. Also gaining skills fits around family life more than being chucked on a plane last minute for client meeting.

You and your partner have already achieved your first life goal as a human, work on the next two, then everything else is a bonus.

Enjoy yourself until it’s time to help with your, hopefully, nine grandchildren.

1 and 2 are now trending essentially to 0.

3. Will get harder to get a job in the years to come.

Stay at your role, build a small side project if you can. Don't leave.