Milestone #1: First debt paid.

I don’t really know how to write this post, because I’m feeling a soupy mix of emotions as I sit down to share this story. I’m in this morass of relief, shame, deep pride, and optimism. And a little disbelief.

When I started this trading project in February 2020, my goal was ambitious: Trade my way out of about $80,000 in debt in a year. That hasn’t happened in the intervening 16 months, but there were always sub-goals, or at least an order to which I’d pay down the debts I had. The bulk of my debt is student loans, about $60k worth (a little less now). They would be paid last. I also have some credit card debt of a few thousand dollars, mostly emergency motorcycle maintenance that I’ve been steadily paying down. I’ve wanted to take care of that second.

The most urgent debt I was carrying was a personal one. I’m embarrassed to write this (it’s where those ashamed feelings are coming from), and I won’t share too many details about the person or the circumstances for privacy reasons, but this is a touchstone moment in this project, an enormous milestone, and it’s a very important moment in my life.

I began this project owing a huge debt to a former partner of mine, from a relationship that ended some years ago. There is no defensible reason for me to have put her in that position in the first place, or for the debt to have ballooned over the years the way it did, or for me to have taken so long to pay her back. And while I always had every intention of paying her back, and while over the years I’d give her a check of a few hundred dollars here, a few hundred there, for a very long time I didn’t have any real plan to clear that debt. On top of that just being an immoral thing, and something that I’m not proud of, it also affected a later relationship that meant a lot to me, and understandably so.

So I created this project to clear all of my debt, and this one first.

On Friday, 507 days after I announced the start of this project, we got coffee and I handed her a check for $14,400.

I’m still high off of it.

Some of that is money I saved over the last year. But more than $11,000 of it is from selling two items: the guitar I’d traded for (it began as a ~$250 projector and after 7 trades I sold the guitar for $1,100), and the truck I acquired through trades. I still need to make the post about the truck, so I’m doing this a little bit backwards, but the gist is that I began with a beloved-but-broken motorcycle and a $1200 lowrider pickup truck, and ended up trading, selling, buying, and trading my way to a gorgeous, powerful, and very capable Dodge Ram that I sold to a friend for an even $10k, which ended up being a very good deal for both of us.

Here are some scattered reflections as I process all of this:

  • As you can probably tell from *gestures at whole project*, I’m not a wealthy man. I have never written a check that big, not ever in my life. And still, after spending more money in one moment than I’ve ever spent, and handing over a check that will drain down my bank account, I’ve never, ever felt more wealthy. Those items I was trading, that cash I got when I sold them, it was never for me. So it doesn’t feel lost or spent. But what was mine, what I did own, was the debt. And that part is gone. It’s gone. I’m getting closer to getting rid of this negative net worth, and I just lopped off a really significant portion of it in one fell swoop. I feel physically lighter.
  • I also feel deeply capable. This project is absolutely not a sustainable investment strategy that I expect to use for the rest of my life, but I’ve watched myself show up for myself and others in ways that have been both important and effective. In the last year I’ve built a beautiful home for myself, gained admission to a doctoral program that is top-5 in my field, and, through labor and ingenuity, did the right thing and cleared an enormous personal milestone. I’m a pretty optimistic person, and I cannot remember a time when I believed in myself more than I do right now.
  • …And then some of that shame pulls me back to feelings of humility. I shouldn’t have had to do all of this, I never should have created this situation in the first place. And really the only reason I was able to do it this way—through a series of trades that took a long time to execute—is because of the grace and patience I was afforded for a very long time. Another person may have called that debt in sooner. They may have taken me to small claims court. They would not have been wrong to have done either of these things. I don’t think I did anything to deserve the grace I received, but I’m deeply appreciative, and it’s a kindness I’ll pay forward when the opportunity arises.
  • And finally, just… holy shit. Like holy fuuuuuuuccckkkk. This project! It’s WORKING. It’s working!! This has been an absolutely wild project and thank goodness that it’s not for naught.

And this: I absolutely should not have had to learn this life lesson this way, but my goodness I’ll never, ever put a partner or former partner in a position like that again. Never. I’m so sorry that I did.

After I accepted my offer of admission, and once I knew I was going to be moving out of the Bay, clearing this particular debt became even more of a priority than it had been before. I’m very glad to have taken care of this thing that was so important to me before I leave.

I’ll write up the truck post soon, because that’s a really sweet story that I want to make sure I document. In the meantime, I’ve also sold the expensive guitar I have, so I need to update about that, too. And, while my inventory is pretty much cleared out by now, I plan to keep this project alive in my new home. I still have another ~$60k to go.

And there is no reason to stop now.

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