In "The psychology of Money" the author warns the reader to don't make bets that need to go perfectly to plan. Creating a project every month until somethings sticks, requires that at least one of them can become a sustainable business. But if you can't achieve that, its very difficult to catch up to your peers or re-enter the workforce.
I spent the last 5 years working in Big Tech and have a large amount in savings where I plan on leaving, not b/c it make sense financially, but I just need something fresh in my life. Even if that fresh thing fails horribly, I have more than I need for retirement due to low lifestyle costs and careful saving.
What makes it so hard to reenter the workforce?
The ones that stayed out for a while, lost their ‘drive’ to reenter. They tasted the good life of no leetcode or on-call duties.
They make enough to support themselves but still less than half of what they could make in tech.
They realize their good life isn’t on the right trajectory and would like to reenter, but just don’t want to put in the effort, especially since the roles available to them are behind their friends that didn’t take a break
TL;DR: part time basically pauses careers.
My experience, working part time for 6 months, is that my side projects have differentiated me from other candidates, and get me a foot in the door for interviews. They usually say most candidates are the exact same, and the only way to differentiate and get an edge is: Perfect GPA; Successful projects; Sought after niche skills; Leadership experience.
But I've also had 2 relatively successful side projects (and tens of failed ones), so without those I'm not sure how I'd go
Spend your 30-40 hours at your job, drop to part time (3 x 10 hour days if you can) up-skill at your job, and use the extra 2 days to build stuff. Its very do-able
This is probably the way to go. Having _some_ income drastically improves the equation in your favor (due to tax laws and compounding growth).
Unfortunately, when I did this, I struggled balancing my time between the work as well as wondering if my startup failed b/c I half-assed it working part time or if its just not a viable business..