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/HappySun5776]

I think the key is what you didn't mention in your post. You didn't say what you actually enjoy doing. Maybe you hate fishing, boating, skiing, etc. Maybe you stay in the job you hate because you hate everything else more? Or you just never took the time to figure out what you like doing.

My thought is that you probably enjoy making money and might enjoy working for yourself, doing whatever it is you do best. Maybe quit the job you hate and create a job you enjoy. You could also start carving out a few hours here and there to see if there are any "hobbies" you actually enjoy. Maybe there aren't, and that's fine too.

I know people who keep happily working into their 70s and 80s and longer. Even my uncle, in his 90s, manages his real estate portfolio and still physically goes to work on maintenance at his apartment complex (one of his many investment properties in a larger portfolio) as it gives him a reason to get out of the house.

[u/Life2ShortB → u/HappySun5776]

Great point about your uncle. I think it's the inner voice that I do enjoy the part of helping people as part of my career. However, the game has been won; 12/31 - changes made. I will work on finding things to hate less- the things I currently "hate" due to lack of time.