u/Mixolytian

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.

As a kid I aspired to ... something. Some fate or destiny alone with the fearsome and mysterious beauty of the world, somewhere I can only remember on nights like this, now in this music, in these scenes of a people alive with the artistry of living, sophisticated or refined, possessed of some quality that I or we have lost, abandoned suddenly, or that it abandoned us. I'm left with alienation alone, that same which my heroes struggled to express in poetic thought, but lacking any of their genius or sensibility, approximating only their loneliness, I falter. Looking back I witness me formed into this man through misguided romantic notions about the world, lost in higher possibilities of the human spirit with no thoughts or panic at the broader slaughterhouse reality, meanwhile stumbling at every stepping stone and not once squaring to catch myself, no heed to warnings of the coming maladjusted present, this marooned future, this haunting of a world that never was but only imagined. And now each day's attempts at reorientation exhaust me to the point of madness, and then - a son! A crackling imp with truth or lies required steadily applied and me with scant idea which to tell. Should he build a wall of Jewish gold to insulate against the coming tide, or seek a peace beyond the oppression of his appetites, friendless and misunderstood? Which nightmare is preferred, and how can a father wager the two with each a banishment to the anguished meaninglessness of modern life? Which least evil can I pursue for such a one as this, pure-hearted and overflowing with a perfect love, angelic benevolence reflected in the shining beauty of his innocent skin? What God prepared such a being for such a place, and how in my confusion would I conspire with so reckless a creator in setting him on some or another course? And if nobility of spirit be born from suffering, what father could wish such tuition upon his child, pure of soul, of perfect trust and love and hope? And what of my own dreams? For still I am myself that child.