43, NW $17ish, still a lot unvested. Wait it out?

Recommendations

Single, no kids. Have about 8M in retirement & investment accounts, of which 5M or so is already taxed. 2M in real estate (that doesn't generate income), renting in a VHCOL area, 7M vested and 5M unvested RSUs in a non public startup (IPO maybe in a few years). Not a ton of expenses. I mostly enjoy the job but increasingly thinking about calling it quits. But it's a lot to walk away from: most of the unvested will vest in the next 2 years, and the salary is pretty good (400k+). If I retired I'd probably start my own projects that I might turn into my own company, but I don't have past experience with that.

Having trouble reasoning about the situation, what the right next move is.

Posted Sep 12, 2026, 2:26 AM UTC

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