My Countercultural Life

My Countercultural Life

I Made Money Faster Than I Could Handle It

This is something I don’t talk about lightly.

Caitlin Pyle's avatar
Caitlin Pyle
Feb 08, 2026
∙ Paid

This is something I don’t talk about lightly. I don’t even like talking about it 😅

There was a period in my life where I made money faster than my nervous system could register it. My business took off. The numbers climbed. From the outside, it looked like success… but on the inside, I was unraveling.

I worked myself into the ground, telling myself it was all temporary. I told myself this is what ambition and hustling look like. I told myself rest could come later. By the time I bought the house, the cars, the clothes, the beauty upgrades (all the proof that I had “made it”) I was more miserable than I had ever been in my life.

I had so much money and zero capacity to actually enjoy it.

My marriage fell apart, which was actually a blessing in disguise, but the divorce process wiped me out both emotionally and financially. I lost way more than assets. I lost pieces of myself I didn’t even realize I had handed over to the grind.

Eventually, I sold the business and everything stopped. And then I did something I had never done before.

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