Plan for much higher income taxes.
Than the OP is paying now? If it’s mostly portfolio gains, taxes should go down.
I would be looking very carefully at expenses in your shoes. It’s probably doable, assuming you have social security coming, but an extra 10-20k in spend can make a huge difference in success rates and at these spend levels and lots of free time, can happen fairly easily. You’re at the threshold where that extra can make a big difference over time.
We have a higher spend rate than you, but a lot of our spend tails off and isn’t subject to inflation. If a mortgage is a big chunk of that spend, it’s worth running the numbers and understanding the impact of inflation and this spend going away. You also want to be sure you understand your tax liability, healthcare/dental and other expenses over time.
I think the best part of your situation is that you’re FI and could always pull the trigger if you wanted to. It just might require some adjustments.
Another thought—there are lots of options for fractional CFOs, which could be an alternative to a full time position. And if you’re good at your job, I think finding another position at C level is more doable than you think, it may just not be at your current rate. I left private equity at the beginning of the year and we were always looking for good c suite people.
If you’re not miserable, I’d personally stick it out for a few more years and see if there’s an exit that might be interesting. That also gives you better clarity on current market shenanigans. I was miserable and pulled the plug, but the current conditions definitely give me pause.
Also, IMO, value those private investments at zero in your head. It doesn’t matter what someone puts on a valuation—they are worth nothing until an exit.
You’re in a great place and a lot depends on your risk tolerance and willingness to cut expenses if necessary.