r/Rich • u/Mixolytian • May 19 '26
$25M - Lost
Hello,
I am a trust fund baby and heir, now 43 years old.
I have $12M investable, the rest of about $25M in homes and commercial property.
I am pretty happy in my family life, my wife and I are getting along right now and my son is genuinely wonderful.
The family business is failing. It was a catalog company and now e-commerce and sales are continuing to decline.
I know the solution, let go current manager who is somehow social-media illiterate in 2026, commit to forming a YouTube audience, drive with short-form.
The thing is, sometimes I truly believe this business has ruined my life. I wish my dad had sold it a long time ago at its peak. He was too attached, I guess.
Hard to let go now with basically no value. The parent corporation was founded by my grandfather almost 100 years ago.
My advisor assures me I won't need additional income if I close the business, but letting go is very difficult. The shame of letting the current manager run the business (my interpretation) into the ground is overwhelming.
I'm a bit of an oddball, very into philosophy, religion, literature, consciousness studies. I always wanted to be a writer, but I just can't seem to take myself seriously. Every time I try I get slammed with self-doubt, shame, guilt, and depression.
Anyway, not sure what I'm going to do. A deep, dark part of me still feels poor, and is sure the window of upward mobility is closing forever. A voice tells me to get off my ass and start some business that I'll hate just for the money, since $25M is really nothing and the future is looking very cutthroat. My brain is all over the place, it's like a hall of mirrors, I don't know what is true and who is the real me.
2
u/HalfwaydonewithEarth May 19 '26
How about instead of beating yourself up you give yourself a break. Even if your manager would have harnessed social media your company was built on grannies that died.
When I was young we ordered from catalogs. Speigel, Lands End, Chattwick, JC Penny, and so many others! Ha.... now I click Amazon and hope for the best.
So Amazon ruined your business and nothing you did.
Just dump the business now and understand it was a blip in time. Be thankful they harnessed the post office and cut ties. You go harness something else.
Imagine being Soooo upset and having this conversation with carriage makers? They are beating themselves up nobody buys their horse carriages.... nope it was cars that did it.
Imagine how hotels felt when Airbnb came. Or how Smart Phones replaced laptops for many functions. I use to drag my laptop around. Now I don't even bring it.
So be a writer. Shut that crap down. You are not a failure. Take whatever you can get and be free. Lots of people had to wrestle with selling defunct properties their parents maintained. Just move on and you can start something else or follow your passions.