I have a job interview tomorrow

Sounds trivial, right?

No.

A mid-career job interview — when you’re searching, not when you’re being headhunted — is not trivial.

I’m thinking it’s kinda like trying to start a new relationship after your decades-long marriage ended, not that I ever went through that experience. I hope I never will.

My analogy is a little misplaced because in the almost two decades of my career I was never with a single employer. I tried different things. I started in the glamorous world of investment banking and then experimented. My experiments were many. Most failed. Among other things, I failed as an entrepreneur.

This is the problem with entrepreneurship: it’s painful enough to fail and then you realize that the scar is there to stay. Once you step away from the corporate world, you’re no longer as employable as you used to be. Most companies want to see a clean, linear path. They’ll compliment you for your “interesting background”, but they won’t hire you. So you find yourself in this awkward position: overqualified for many 9 to 5 jobs, but underqualified for senior positions.

I’ve been solving my struggles by doing consulting work but there are limits to solo-consulting.

Then there is the question of me being picky. I’m very picky. I have to be excited about what I do. I have to like the people who I work with. I often think of myself as a humble person. I am in some ways. But I underestimate my own ego. When my…