Watching a documentary about Leonard Cohen, a great singer songwriter, I was reminded of my enjoyment and appreciation for unique characters. I remember encountering a local drunk in my younger years and sharing a beer with him while he told me of his unfortunate life. I was grateful to him because his story expanded my own understanding of life and the same was true about all conversations I would have with real people, artists, business people, philosophers, musicians etc. There is just something truly amazing about meeting people with true character, people who have lived their life to the limits, people who are unafraid to be themselves, people who chase their passion, people who do not fall into the normal box that society usually moulds us into.

But if I enjoyed these exploratory discussions with strangers so much then why did I stop having them?

I’m not sure, but these are my thoughts on the matter.

Responsibility gives you a harsh and realistic view on life.
A few years after my nice conversation with the local drunk I was renting out an apartment and I rented it out to an older man who had just divorced his wife and told me he was looking for a place to stay while he got his life back together. I wanted to help him but it ended up as a nightmare, a few days after he moved in the apartment he had destroyed the apartment, breaking everything that he could and he had filled the apartment with drug addicts and drunks. I went to the police and they couldn’t do anything to help me and so I had to face the problem myself which was not an easy task for a young man who had no one to help him. After that experience I could no longer sit down with a drunk to learn about their story without thinking about what pain they had caused for someone else in their lives. This is just one example but a number of random experiences gives you a harsher and more realistic view about the stories of people.

Thoughts are easy, action is difficult
If you have taken action yourself and committed to creating something difficult and challenging it is difficult to listen to people that have never taken action talking about all the things that they want to do. So for example, I have built a few companies and I know the amount of work needed to make them a work so it’s difficult for me to listen to somebody with no experience talking about starting a company like it’s no problem.

Your view of the world contracts
When you find the path to follow in life, you have to start expanding your knowledge about that path and as you do that you will have less time for philosophical exploration. So basically over the last few years I have become so obsessed with entrepreneurship and the startup world that I just haven’t had time to have truly deep and giving conversations with people unless they are somehow connected with that obsession. Social media isn’t helping because I mostly follow people associated with my obsession my view of the world online almost only reflects my current point of view, my view of the world has become stuck in one direction.

I’m sad that I don’t have as thought provoking and original conversations as I used to as a young man but things change and I am unsure if they will ever revert to how they used to be. Or perhaps to become a character yourself you will have to pick a path to follow and commit to it.