I spent years saying "employment is better than being an entrepreneur." The moment I get a job contract, I can't handle it and start preparing my resignation.
Last year, I took 27 flights and slept in at least 20 beds across every corner of Africa. It was mostly for work.
Someone I work closely with told me something that took me weeks to digest: "Khalil, I noticed something after working with you for two years. You are always doing what needs to be done. In those two years, I saw you only once pursuing what you love doing."
I was shocked because it was true. I had never managed to verbalize it this way.
So I started analyzing what I love to do versus what I need to do. Every decision became an assessment. And the exercise brought something unexpected to the surface. There are things I thought I loved, but actually I don't.
I spent a good portion of the first few years of my entrepreneurial career saying that "employment is better than being an entrepreneur." Yet the moment I get a job contract, I can't handle it and start preparing my resignations.
But it's not an entrepreneur problem per se. Other entrepreneurs spend their whole lives chasing an exit from their companies. The moment they get hundreds of millions, they get a "post-exit identity crisis." Loom's co-founder published how his mental state became confused and directionless after the company was bought for about $975 million, despite actively chasing that outcome.
I think we don't actually want what we think we desire. The moment we get what we want, we discover that we built a whole illusion. We wanted to want it. We liked the idea of it.
Anyone else here stuck in this loop?
Posted Jun 3, 2026, 12:01 PM UTC