Chasing self-love: three months in Medellín, and the company it built
There was a feeling inside of me I could not escape. A feeling that I was off balance, not fully aligned — and that if I didn't find intentionality, I would compromise the potential of my future self.
I felt the residue from past traumas clouding the path. Demons I had not yet engaged with became clearer. Jealousy of someone else's success. Lack of financial discipline — try counting the months you spent more than you earned. Addiction in the form of any material thing or substance you can't let go of. Insecurity, the kind where your actions don't quite line up with the person you want to be.
The decision was simple. Engage, or stay stuck. So I sat with my therapist, told him I was re-reading The Way of the Superior Man and reading Your Money or Your Life for the first time, and he asked me a question I couldn't unhear:
"Have you ever put the same energy into yourself that you put into the home you remodeled?"
How you allocate your life energy is a reflection of how you want to live your life. I'd allocated mine almost entirely outward.
The detachment
Within a few weeks, I sold my car and over half of my closet. The car was a liability in a used-car market; getting rid of it was a net gain plus the bonus of no more insurance. The clothes were clutter I'd been carrying through every apartment move. Cutting was liberating.
I added it up — the way Your Money or Your Life trains you to.
From the reset accounting
~$3,400
freed up in roughly six weeks — enough to:
- Cover three months of rent + groceries in Medellín, twice over
- Pay for a Cartagena flight, a Medellín loft in Provenza, and 6–8 hours of weekly Spanish school for a quarter
- Erase the monthly insurance line that had quietly bled the budget for two years
The point isn't that $3,400 is a lot of money. The point is what it represents: time, attention, and surface area for the next decision.
The five goals
I sat down and wrote five things. Not aspirational. Operational. The order matters.
A trip to Cartagena was the first move. AirBnB arbitrage — host my place while I rent another — was the financial scaffolding. I closed two travel-nurse stays and a marathon runner before the flight took off.
Three months in Colombia
Cartagena was a beach city. Beautiful, but not the energy I came for. So I added Medellín to the trip, flew up for a few days, and knew within 48 hours I was coming back to live there.
I went home long enough to renew the passport, then returned to a two-story loft up the street from Provenza — gym in the building, grocery in walking distance, the most popular zona in the city. I'd curated an environment that made the next part possible.
The next part was a fast. No sex, no Instagram, limited drinking. Not as performance — as catalyst. Avoiding convenient bandages exposes the wounds and gives them air to heal. Controlling urges was the work; the result was time I'd never had before — time for Spanish, time for the gym, time to walk around a city I was just learning the streets of.
I almost never spoke English. It took two months to navigate normal life in Spanish. The phrase I'd say when people asked is one I still use: "puedo decir lo que necesito" — I can say what I need.
Five cities in three months: Cartagena, Santa Marta, Santa Fe, Guatape, Medellín as the home base. Three peoples — Rollos from Bogotá, Paisas from Medellín, Costanias from the coast. Colombia straddles the equator, which is to say it has the kind of weather that lets everything grow. The people grew on me too. Many of them gave me — without knowing they were giving it — permission to live a life free of the traumas I'd been carrying.
The coffee
Income stream number five was the one I didn't see coming.
When I'd flown back to Chicago to renew the passport, I'd hopped on my bike and visited Metric, Stumptown, and a handful of other local roasters. I asked questions. Then I started reaching out to suppliers in Medellín — not as a customer, but as someone who wanted to understand the whole chain.
When I returned, I went to the farms. Spent days watching the process from end to end.
The roasting is the part of the chain where a small operator can actually control the product and the margin. That's where I wanted to be.
When I flew back to Chicago, I called Kevin Bradford — a fellow Dayton alum, a brother in Kappa Alpha Psi, and (we'd discovered years earlier) somebody who shares my birthday. We co-founded Work In Progress Coffee Roasters.
What it became
The full case study lives at /builds/work-in-progress — the version with the post-mortem. The short version is this:
We made money. We closed it on purpose. The lesson — profitable doesn't mean sustainable; sustainable means the calendar agrees with the spreadsheet — was worth more than the run.
What I'd say to you
The honest through-line: I couldn't have built Work In Progress without selling the car. Couldn't have sold the car without the fast. Couldn't have done the fast without Medellín. Couldn't have gone to Medellín without writing the five goals down. And couldn't have written the five goals down without the therapist's question.
Each step was small. Each step was specific. None of it was a grand reinvention — it was a sequence of operational decisions stacked over six weeks, then three months, then the year after.
You don't reset your life. You free up the surface area. The new thing shows up because you made room for it.
If you're sitting on that same restless feeling — the one that says you're off balance — start by tallying. Tally last month's spending against the version of yourself you want to be. Tally your closet. Tally the relationships you keep maintaining out of obligation. The number isn't the point. The act of seeing the number is.
Then sell what you don't need. Write down five things. Buy the ticket.
The rest is just doing the work in front of you.
📬 Get in touch · Originally drafted on Medium, July 2022