OMY syndrome, but 2024 looks like the year

From what I read, half of New Yorkers are asking that same question.

NY-ers have forever been asking themselves this question. Past 35 years I've been asking myself this question. People come for the amazing opportunities, but I can't vouch for why they stay. I plan to keep a simple crash pad in the city, for at least the next 4-5 years, as I'll likely have some part-time business and charitable interests to attend to.
 
Call me crazy, but I am trying to figure out if I can retire on $2500/month with 15K in 401k. LOL.

Seriously, though, my inclination would be to offer to just step out of the way and let the next generation have a chance to grow and earn. Yours is done, you will be fine, stop accumulating, start your new life, and let someone else have a chance at opportunity.


Just my thoughts.

Trust, I am actively trying to step out of the way! I'm too old to advance any further - yes, age discrimination is very much still a thing. And my eager younger replacement is nervous, but capable and ready to fly under their own power. Conditions could not be better for my exit.
 
Any kids to worry about? What does your wife want you to do in retirement?

How long is your pay out period for your deferred comp? Probably not much you can do about taxes, especially for the real estate sale and deferred comp. Regardless it sounds like you are in great shape.

I’m 53 and expect similar numbers and spend need/want when I get to 60 and hopefully also receive an offer to leave. Also in a very HCOL and likely won’t leave. I’m amazed people can live on $40k/year but realize I live in a bubble.

Nothing to worry about on the kids/family front, maybe some grad school bills to fill, but nothing major. Wife just wants me to enjoy the fruits of my labor - she appreciates how hard I've worked and how much I've sacrificed, and she wants me to detox from my career, chill out, and spend more time with her and fam.

Def comp, RSU's, etc. will fully vest upon retirement, pay out (i.e. taxable events) over 3-4 years. With the r.e. there are creative potential solutions (special trusts, 1031 exchanges, Opportunity Zone investments, etc.), gonna need professional guidance on that for sure.

Yup, the bubble is real. Scary how isolated we can become without even realizing it.
 
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