[dangus]

“more freedom to keep building”

This is the disconnect to me. This phrase has tech industry cult vibes to me.

I don’t see “freedom” and “building” as words that mesh together.

I see “building” as something I’m obligated to do to pay my bills. I do it because it’s preferable to other forms of labor. As soon as I have the financial means to stop doing it, I’m out.

[collingreen]

Hardly a cult. So you don't like building things. Fine. Nothing wrong with that. Plenty of folks, however, do love building things. When I dream of freedom unlocked by money I love the idea of building things still; the difference is building what I want, how I want it, without being trapped.

[dangus]

There’s a big difference between “building things for fun and accomplishment” and taking on the intense obligations of continuing to be a CTO when a major exit is on the table.

I totally understand that there are people who relish in the challenge, feeling needed and important to their team, and the prestige and visibility, but I don’t really understand what their brains are doing and what.

OP talked about the luxury of being able to fly out the grandparents to help out taking care of the kids when things get busy at work. That doesn’t sound like freedom to me.

[collingreen]

I agree with you there - that doesn't sound like my kind of freedom either (Id rather have the freedom to shape work better).