July 26, 2025

The Solitude of Unemployability

I’m subscribed to a lot of mailing lists.

One of them is from Shane Parrish.

Another is from Naval Ravikant.

It just so happens that today I read Shane’s message and Naval’s message back to back.

Each message is about completely different things, but there was an overlap that struck me.

Here’s a relevant excerpt from Naval:

I think once people experience working on something that they care about with people that they really like in a way they’re self-motivated, they’re unemployable. They can’t go back to a normal job with a manager and a boss and check-ins and nine-to-five and “Show up this day, this week, sit in this desk, commute at this time.”

And here’s a Schopenhauer quote that Shane shared:

Schopenhauer on the relationship between freedom and solitude:

“He who does not enjoy solitude will not love freedom.”

Here’s the thing...

Building and running a durable business is largely a solitary act.

Especially for soloists, obvs.

But what’s even more solitary is when it’s actually successful and you have the freedom to do what you want, when you want.

Why?

Because there’s no one to tell you what to do.

No one to answer to.

The old cliche that “It’s lonely at the top“ is true even (especially?) in a company of one.

Before you start chasing freedom, it’s worth considering whether that’s really what you want.

Yours,

—J