Would I Do It Again?

Would I do it all over again?

Is that a trick question? You know how I feel about questions. In many ways, I value the question more than the answer. How many times have you heard me pontificate about people insisting that they have the right answer, only to discover that they were asking the wrong question?

But I’ll bite.

Would I do what again?

Or, as someone more famous than me once asked: it depends on what “it” is.

If you are asking whether I would duplicate the last fourteen months—or perhaps the last two or three years—the answer is undoubtedly no.

I would not duplicate it.

I would have tried much harder to make the money we had saved over a lifetime last longer. I would have had a budget. I would have prepared better for medical emergencies, although even in hindsight I’m not convinced that adequate insurance was available to us.

I would have handled some relationships differently. I would have made some of the boys earn my trust, respect and love a little more slowly. I would have been more careful about giving money away.

One thing I was woefully unprepared for was understanding what our money meant in Colombia.

We considered ourselves people of modest means, and by American standards we were. To some of our Colombian friends, we looked filthy rich.

We genuinely thought that we were helping people. Sometimes I still believe that we did. Sometimes generosity got mixed up with affection, expectation and our own desire to make people happy. I don’t have a neat accounting ledger that tells me which gifts were good decisions and which were expensive mistakes.

I no longer know if I wish that I did or if I’m glad that I don’t.

I also would have understood that visiting a country for weeks or months at a time, staying in Airbnbs, eating out, traveling around and making friends—with the very best of intentions—was not really due diligence for moving there.

It was an extended vacay in drag.

Or maybe just performance art.

We called it due diligence because that sounded good. It legitimized the crazy fantasy. I know that I wrote and spoke that phrase more than once.

It wasn’t a lie. We tried. We had a plan. We had goals. We had an objective. We did not want to fail.

But due diligence is what you do before experience teaches you what you didn’t know enough to ask.

You don’t learn a new culture in a few months. I’m not sure that you can learn one in a couple of years. And you certainly cannot know what it will be like to grow old despite your best intentions, get sick again after a lifetime of bizarre illnesses, run short of money and become dependent on systems and people you barely understood when you arrived.

Things started out swimmingly.

We had money.

What we didn’t have was a budget.

Or insurance for a crisis.

Our health was pretty good, all things considered. We could get on a plane or a bus and go somewhere simply because we wanted to see it. We never got to the coasts, but we explored a lot of Andean Colombia. We stayed in different cities. We visited pueblos. We ate well. Almost every place we slept had a hot shower, luxurious living for many Colombians.

We met people we had known only online and discovered that we actually liked each other in real life, too. So many of them remain in our lives—or perhaps more accurately, we remain in theirs.

Life was good. The adventure was incredible.

Our financial mentor warned me before we left: “It’s not as much money as you think, Jon.”

She was right.

Rich people can live on a vacation like this all the time. Middle-class people may get to do it for a week or two every year. People of modest means like us might get to do it once in a lifetime. Truly poor people are lucky if they even get to dream it.

And my Gawd, what a lifetime experience it has been.

Colombia was exotic to me. I don’t care whether that is the politically correct way to put it or not. Exotic is subjective, and to a gay farm boy from Kansas, Colombia was exotic.

The climate. The biodiversity. Great cities and quaint pueblos. Modern comfort and rural simplicity. Mountains and jungle and beaches.

And young people who lived and touched and related to one another differently than I was accustomed to.

Especially that last part.

Somewhere around here, the question started getting away from me.

The relationships Michael and I formed in Colombia became one of the most important parts of the experience, and one of the hardest to explain in ways that make sense either outside or inside Colombian culture.

Money was inevitably part of some of those relationships. It created time and mobility. It allowed us to invite someone to dinner who could not afford the restaurant, or say, “Let’s go spend a few days exploring that pueblo,” when the answer otherwise had to be, “I can’t afford it.”

Sometimes we paid.

Sometimes we helped.

Sometimes, I admit that we overdid it.

But what mattered most wasn’t just what we bought.

It was what happened while we were together.

Affection and intimacy. New friendships. The strange and wonderful ways that relationships here developed across enormous differences in age, culture, money, sexuality and lived experience.