On Respectability.

Respectable people rarely change the world

Phil Knight, in his memoir Shoe Dog, recalls that his father was obsessed with one thing: respectability. Good schools. Good job. Picture-perfect family. Something you could talk about, better yet, brag about, at dinner parties.

Respectability is seductive. It feels safe. It feels like progress. It convinces you that you’re on the right path. But here’s the thing: respectable people rarely change the world.

Founders aren’t respectable. They’re scrappy. They’re fine with failing, often and in public. They live with rejection, embarrassment, and risk in a way that respectable paths never require.

That was my problem early on. I was raised to believe a respectable career was the goal, and that running a business was, at best, a backup plan. Deep down I always wanted to build, but instead I played it safe. I climbed the corporate ladder. I told myself I was being smart. I was hitting all of the “milestones”: max your 401k, save and invest in stocks, buy a house, etc.

Then one day, I’d had enough. I was in my late 20’s and if I was going to try something different, it’d have to be now. I wasn’t brave enough to quit and start something of my own, but I thought I could at least get closer to the fire. So I joined an early-stage startup, just to get a taste. Worst case scenario, I come back to consulting.

That taste ruined me, in the best way possible. I loved it. I can’t stomach the thought of a corporate job anymore. My body rejects it.

That tiny step towards building was all it took.

Since then, I’ve bought and run a small business. I’ve started a podcast and a newsletter. And now I’m diving into building for SMBs.

So to hell with respectability. To hell with the “right path.” I don’t want a life that looks good on paper, I want a life where I can build something that leaves a mark.

This essay is my second step in that direction.

If you feel the same, reach out. Let’s talk.

- Cyrus

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“Let those who wish have their respectability- I wanted freedom, freedom to indulge in whatever caprice struck my fancy, freedom to search in the farthermost corners of the earth for the beautiful, the joyous, and the romantic.” ― Richard Halliburton

“Respectability is a curse; it is an “evil” that corrodes the mind and heart. It creeps upon one unknowingly and destroys love.” ― Jiddu Krishnamurti

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