Against the Grain

On Saturday, I spent the afternoon walking around downtown Chicago wandering about taking pictures; a much-needed break from work. After a nice stroll, I ended up meeting with a friend to check out an exhibit at the Museum of Contemporary Art. As we walked around the museum, we got to talking about life, where we’ve been over the last few years, and what’s next.

Part of our conversation—a continuation of a thread from the night before—was about trusting in the undefinable magic of the universe. That thing that, when you’re certain there’s no way out of a situation, taps you on the shoulder and says “here you go, you’re going to be fine.” We laughed at all of the times we’d spend several days in a state of absolute panic, only for something to work out the next day.

While keeping this in mind is essential when you’re working on your own or trying to build a business, it’s one of those things that only really helps in retrospect. In some sense, the rush of not knowing if you’ll pull something off is part of why you keep doing it. Fear in the right context is an incredible motivator. After so many times going through it, though, you start to ask “is it worth it?”

I’ll admit, I’ve definitely had fantasies of hanging up the towel and taking a full-time job. I hesitate, though, because I consider what that means in the long-run. Sure, it can be tough at times, but each successive step forward has proven—even if I’m oblivious to it in the moment—that it does get better. The more time you invest, the better you get. The more you get a feel for how you want to do things (and why). Full-control is wonderful, but it comes at a price.

Believing in what you’re doing and forging ahead is tough. When the majority of the people around you are living the normal, 9-5 life, it can be discouraging to think about where you are now vs. where you could be. The short-term is a son of a bitch. It really boils down to mental strength and what’s in your heart. If you know without a doubt that being on your own is what you should be doing—and your situation is improving, even if slowly—then it’s best to stick with it.

When I’m feeling doubtful, I like to ask myself “how will you feel about your choices when you’re about to die?” It’s grim, certainly, but really puts everything into focus. If I could look back on a life where I listened to my heart and went for it, regardless of result, would I regret it? As long as the answer is “nope,” I’ve resolved to keep moving ahead. My friend made an excellent point during our chat: “we’re all just tiny specks sitting on another speck, none of this really matters.”

I think he’s on to something.