Always Ask About the Tie

Luck doesn't just "happen"

This past week I was at an event that my girlfriend was hosting for her crypto company here in NYC. We were at a hotel in midtown, and as the event was winding down, I noticed a man in the lobby wearing a tie that looked identical to the one that we wore in my fraternity. My roommate was standing next to me, and he encouraged me to go ask the man if it was in fact the same tie. Looking over at the man once more, I could see that he was engrossed in conversation with the woman sitting next to him, “I don’t want to disturb them” I told my roommate. I also tacked on that I was feeling tired and jet-lagged after having just returned from South Africa. My roommate patted me on the back and walked away, he had tried.

As I stood in the lobby helping my girlfriend collect her things, my roommate’s words of encouragement gnawed at me. I knew he was right after all. I had nothing to lose going up to this guy and asking if he was in the same fraternity. Yeah I was tired, but it’s not like I was committing to going out, I was just asking about a tie. As I made up my mind to go over and chat I could feel a little surge of adrenaline. I put my bag down and walked up to him.

I’m certainly no Aaron Sorkin, so I’ll save you the pain of reading some boring, half made up dialogue. What I will say though is that while the man did not go to Harvard, he did in fact go to my high school. Not only that, he is also an incredibly accomplished executive in the music industry with a passion for meeting and helping young entrepreneurs. Flash forward two days, and my girlfriend and I are on his roof having cocktails discussing careers, startups etc. It was a fantastic reminder that 1) having conversations with strangers carries with it almost zero downside and unlimited upside 2) our brains are really good at coming up with excuses not to do something we don’t feel like doing and 3) we should always be trying to expand what Substack author Sahil Bloom calls our “luck surface area”. As Bloom puts it, “Much of what we come to call "luck" is actually the macro result of 1,000s of micro actions. Your daily habits put you in a position where “luck” is more likely to strike”. In this case, nobody would have faulted me had I not gone up to the guy in the hotel lobby. It would have been totally understandable to go home and pass out after a long day of work + being jet lagged. However, my luck “surface area” would have stayed the same. Luck does not just “happen” to us. We have to seek luck out. It was lucky that the gentleman in the hotel lobby went to my high school, but had I not been willing to strike up a conversation with him that “luck” would never have had a chance to present itself. In other words, always ask about the tie. Most conversations may not lead to anything, but by building the habit of having conversations you are inevitably getting closer to the one that will have a huge impact.