POST 2: “I Said I’d Never Wake Up Dumb”

I used to tell myself…no matter what happens, I’ll always know how to make money. Like, maybe I’d be broke. Maybe distracted. Maybe stuck in a foreign country with one bar of Wi-Fi and a fever. But not dumb. Never that.

I had systems. I had clients. I had six email accounts and the kind of momentum you can only build when you’re slightly delusional and chronically unmedicated. I wasn’t thriving, but I was clever.

Then I hit my 30s. And I woke up thin. Not stupid exactly. But… thinned out.

Like someone had quietly siphoned off all the easy wins, the cheap flips, the hustle-energy that got me through my 20s. And left just the shell. The form of someone who used to be sharp.

I used to run a mapping company. Remapping Services. Best client Vivint ever had. Then Covid happened and so did a full collapse of everything that felt like it might one day stabilize. ADHD went untreated. My skin broke out. My living situation devolved into a glorified garage with a broken 1983 Vanagon that I called my “project.” I was the project.

That’s around when my sister stopped speaking to me. Because my best friend…who lost his dad, then found my sister at the funeral…decided to take comfort in her married body. Now they have a kid. I never got the memo. He was my best friend. She was my sister. Now they’re a couple with a toddler, and I’m a guy in Thailand trying to decide if he should sell a yurt stake to fix a $4,000 hot tub to stay ranked on Airbnb.

The condo I bought for $79k with seller financing, back when I was still believing in passive income and magical spreadsheets, sold during Covid for $129k because of a $17k special assessment. It made $4,200 a month. They sell for $280k now. That one still stings.

I still have the triplex. And the illegal backyard yurt that wasn’t supposed to be real, but kind of is. I couldn’t afford to build the whole thing, so I gave my friend 25%. Then the hot tub died, so I gave him another 25% just so he’d buy a new one. Because if you don’t have a hot tub, you don’t show up in the Airbnb algorithm. And if you don’t show up, you don’t exist.

I made $37,000 this year. More than last year. Still didn’t help. The $3,800/month mortgage repayment plan just ended. I’m out of foreclosure. Technically.

But I still feel like I’m failing. Like a used-up business card.

Now I sit in a rented hotel-style room that kind of feels like mine, wondering what version of me still has earning power.

Do I:

Meanwhile my mom wants me to just “get a normal job.” My dad pretends to forget what I do entirely. And I pretend to be okay with both.

I don't know what I do. I only know I used to.