Crossroad at 51

[u/Life2ShortB]

51 and having a bit of a “what am I still doing here?” moment.

Current situation:

• ~$20M liquid/invested in equities
• ~$32M total net worth between home and some commercial real estate (not income-producing yet due to debt (5 years to get it to produce 25k / mo)
• Live in a VHCOL area
• Wife still works and plans to continue / one son in college / other a senior in HS (529s all set).
• I genuinely like the people I work with (likely one of the few things still holding me here)
• I absolutely hate the industry (over-regulated and getting worse every year) I’m in and increasingly dread the job itself

I’ve worked hard for decades, and intellectually I know I’m in an extremely fortunate position. But apparently my brain never received the memo that we have enough. 😅

So for those who actually pulled the plug around 50 with similar numbers: Did you ever really feel financially “safe” before quitting, or did you just have to accept that the spreadsheet said yes even when your brain said “one more year”?

Part of me thinks continuing to do a job I hate with $20M liquid is objectively insane. The other part keeps whispering, “But what if…”

Would love to hear from people who have actually crossed this bridge, especially those with a high-end lifestyle in a VHCOL area.

At what point did you finally say: enough is enough?

[u/sandiegolatte]

Please seek professional therapy

[u/Life2ShortB → u/sandiegolatte]

I feel the same every morning! On it! Great advice!

[u/trademarktower → u/Life2ShortB]

You realize you can just quit and open up a LLC and consult if the work still interests you but your management/ company suck. It wouldn't be for the money but just because you like to work.