Watching a documentary about Leonard Cohen, a great singer-songwriter, I was reminded of my appreciation for unique characters. I remembered an encounter from my younger years, when I shared a beer with a local drunk as he told me about his unfortunate life. I felt grateful to him because his story expanded my own understanding of life. The same was true of the conversations I had with real people—artists, businesspeople, philosophers, musicians. There is something truly amazing about meeting people with real character, people who have lived life to the fullest, people unafraid to be themselves, people who chase their passion and refuse to be molded into the box that society so often builds for us.
But if I enjoyed these exploratory conversations with strangers so much, why did I stop having them?
I’m not sure, but here are my thoughts.
Responsibility gives you a harsher, more realistic view of life
A few years after that conversation with the local drunk, I rented out an apartment to an older man who had just divorced his wife. He told me he needed a place to stay while he got his life back together. I wanted to help him, but it turned into a nightmare. A few days after moving in, he had trashed the apartment, breaking everything he could, and filled it with drug addicts and drunks. I went to the police, but they couldn’t do anything, so I had to face the problem myself—an overwhelming task for a young man with no one to help him.
After that experience, I could no longer sit down with a drunk to hear their story without thinking about the pain they may have caused others. This is just one example, but a number of such experiences have given me a harsher and more realistic perspective on people’s stories.
Thoughts are easy, action is hard
When you’ve taken action yourself—when you’ve committed to building something difficult—it becomes harder to listen to people who only talk about what they want to do, without ever taking a step forward. For example, I’ve built a few companies and I know the immense work it takes to make them succeed. It’s difficult for me now to listen to someone with no experience talk about starting a company as if it’s no big deal.
Your view of the world contracts
When you find a path to follow in life, you have to focus on deepening your knowledge and expertise in that area. As you do, you have less time for philosophical exploration. Over the past few years, I’ve become so consumed by entrepreneurship and the startup world that I rarely have truly deep, thought-provoking conversations unless they somehow connect to that obsession.
Social media doesn’t help, either. I mostly follow people in my field, so my online world is almost entirely an echo chamber of my current point of view. My perspective has become narrower, stuck in one direction.
I’m sad that I don’t have the kind of thought-provoking, original conversations I used to have when I was younger. But things change, and I’m not sure if they’ll ever go back to the way they were. Perhaps, to become a “character” yourself, you need to pick a path and commit to it completely.
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