Reasons That I, a Billionaire, Am Still Miserable

The yacht’s Wi-Fi became weak for almost forty-five seconds while crossing the Mediterranean, forcing me to experience what experts call “a thought.”

My personal chef interpreted “comfort food” as “deconstructed truffle-infused childhood,” when what I wanted was a grilled cheese sandwich.

I accidentally wore last season’s cashmere to an event where everyone else was wearing this season’s cashmere, and now I have to fake my own death.

My therapist insists that “buying another island” is not a healthy coping mechanism, despite overwhelming anecdotal evidence that it sounds extremely relaxing.

One of my houses has gone completely unvisited for so long that I am beginning to suspect it has developed its own culture.

A stranger on the internet referred to me as “mid.”

My assistant asked which Ferrari I meant, and I had to spend twelve emotionally exhausting seconds remembering.

The private jet landed at the wrong private terminal, causing an inconvenience statistically indistinguishable from ordinary life but spiritually catastrophic.

I found out my college roommate, who became an elementary-school teacher, genuinely laughs more than I do.

The algorithm keeps recommending videos titled “Ten Habits of Billionaires,” as though I need to optimize my morning routine even further.

My children only call when they need something, which, in fairness, may be because I raised them to outsource all human interaction.

I spent $18 million on a painting that now makes me feel judged every time I walk past it.

There are now so many people whose full-time job is agreeing with me that I have no earthly idea whether I’m funny.

The tailor looked at me with pity when I said I wanted my pants to make me appear “approachable.”

The concierge greeted me by name before my own cousin did.

I keep reading articles about how money can’t buy happiness, and I resent how aggressively peer-reviewed my life has become.

Every birthday gift I receive is either impossible to surprise me with or another watch.

The family office sent me a quarterly report titled “Legacy Planning,” which is an extraordinarily elegant way of reminding me that I will, in fact, die.

The barista smiled more warmly at the man ordering a small coffee than at me, and for one irrational second I considered buying the café.

Despite controlling companies, foundations, investments, real estate, aircraft, and enough liquid assets to alter the GDP of a small nation, I still occasionally wake up at 3:17 a.m. convinced everyone secretly hates me.

Money turns out to be remarkably effective at solving money problems. The other ones are apparently their own department.

Please don’t mistake this for a request for sympathy. I’m mostly just annoyed that the penthouse echoes.