Am I Living The Dream?


I love this phrase, “living the dream,” especially because it is almost always used in jest. Getting up every day, going to work, seeing the same people you always see, nothing really going on … you know, “living the dream!”

But what would “living the dream” really look like?

Obviously that depends entirely on what your version of “the dream” is. Some people’s dream of a house, kids, stable career and SUV might look like a nightmare to other people. Some folks dream of a small town, some a city, some “stuff,” some “experiences,” and so on.

But let’s say you’re building a dream rather than actually “living” it. What would that look like? For example, when JK Rowling was writing all the Harry Potter books, she would have “looked” just like any other person writing; in fact, she would have looked like I do now. In her case, all the magic that was to come for the rest of us — the amazing dream that she lived and shared — was entirely inside her head.

I think about this because I am working on a dream. I am building a business which, before Covid, was well on its way to helping me live out my dream of living nowhere in particular, and therefore everywhere, but mainly in London and Europe. But even then, if you spent the day at my place, you would have seen a guy in his sweatpants trying to stay focused at his desk. Had you asked, I would have said what I do for a living is something like “Help people go to soccer games in England.” And maybe, in 5 or 10 years, when my company is (I hope!) booming and I run it from my flat in London half the year and the rest of the world the other half, you might say, “Yeah, I stayed at his place when he was working on that, but I had no idea. He was just sitting at his desk and said he did something with soccer and travel.”

I also think about this because many days, especially since Covid, I feel not at all like a guy living or building a dream. I feel instead like guy in his sweatpants trying to stay focused at my desk. Nothing dreamy about it at all!

So I need to remind myself on these days that, while maybe life doesn’t look dreamy at the moment, I am in fact still on the path, still making progress, and still moving toward something meaningful and rewarding. I am still — at least I hope I am! — marching the “long road to overnight success.”

And if not — if it doesn’t work out like I hoped — then I will move on to something else. But the fact that life isn’t dreamy today doesn’t mean the dream is dead. In my case, many of the building blocks of a life spent in international travel are days sitting at home in your sweatpants.