22 April, 2023. Leaving Winnipeg again. It’s a long story. This trip flies YWG-YYG-ORD-FCO, which is Winnipeg to Toronto to Chicago to Rome. If you’re keeping score, that’s +1 time zone, -1 time zone, then +7 time zones.
I always like saying goodbye to Winnipeg. It’s not you, it’s me. Okay, to a large degree, it’s you – but also me. I love to travel, sometimes I just sit still long enough that I forget.
I wrote about this on Facebook, but in case Elon Musk buys it and deletes me or otherwise makes it suck, here’s what I said:
A few years ago when it seemed like everyone was turning 50, my friend Ian McCausland decided to mark the occasion by taking headshots of 50 people who were turning 50 in the same year as he was, and to talk to them about what it meant. Many people talked about reaching a place where they had more free time, or a successful career, or kids having moved away from home, or things they would treat themselves to now that they were able. Normal stuff for people having moved into the second half of life. But when we talked before doing my headshots, one of my reflections as I spoke to Ian surprised me a little. It was to the effect that it brings a realization about some of the things you probably won’t get do in your lifetime. Now, “bucket lists” are a trope, and I don’t think I know anyone actually working through one, but I’d venture to guess that all of us have hopes and dreams for our lives – some realized, some not.
In my twenties, I wanted to travel, and to see the world. I’d been to Hong Kong, China, and Macau, where I celebrated my 21st birthday. I couldn’t get enough of experiencing other cultures, and I wanted that to be a way of life for me. I had my eye on one particular “job” for the mid/late 1980s – one it turns out that a friend I would meet a couple of decades later (Andrew Jones, who’s been traveling the world ever since) was doing at the time.
First I had to finish college, then finish paying for it. And get married. And start a career, have kids, then start another career, build up a business, do some freelance work, start another company, and… here I am in my fifties. I’m happy with the company we’re running, and I love the freedom of working flexible hours from home so I can work from my patio all summer long. But still. There are things I wanted to do but never did.
I told Walter J. Hildebrand recently about this realization, and explained that if I were to talk to my twenty-something self, and if he asked how much of the world I had seen, my answer would disappoint him. I’d tell him I’d seen a lot of Canada West of Montreal, and I’d been all over the USA and to a few places in Mexico, at least briefly. But North America wouldn’t cut it, as far as he was concerned. My reasons all sounded a bit lame to him, but of course he wanted different things than I do – though not completely different.
In high school, I had been fascinated by the Renaissance. Leonardo Da Vinci fascinated me, and I loved the idea of living in an age of discovery and rebirth and contributing to it as he had. The realization in the early 2000s that I actually was living in such a time now did not significantly reduce this fascination, which somewhere along the line had morphed into an overall longing to visit Italy, not just for a quick tour, but long enough to absorb the culture and appreciate its history, and to learn from both.
This is all by way of explanation of how I came to find myself a few days ago eating pizza one evening just outside Rome, in the medieval village of Tivoli, Italy, in the shade of a 15th century fortress with four towers. Because why wouldn’t I?
As it turns out, it’s not too late to do things in your fifties that you’ve always wanted to do. In fact, there may be no better time. I had enough Aeroplan miles to book a flight, and with eight days’ notice, I stuffed my things into a backpack the way my twenty-something self would have done, and loaded my laptop and work things into a day pack the way my twenty-something self had not yet conceived of, and somewhere over the Atlantic, it started to become real. I’m not on vacation, I’m still working – remotely, as usual. But in the off-hours, I’m living the dream for a little while. But as I told my family, “Don’t worry, I’ll be back for Winnipeg Folk Festival.”
Since this is neither a beginning nor an end, here continueth the journey.
