“If not now, when?” It’s such a powerful question, especially for someone like me who’s always analyzing risk and making decisions based on it. I can look back at a few moments in my life where this kind of take-action thinking led to the most beautiful outcomes.
When I graduated from college, my girlfriend at the time—who was a year older—moved to LA from San Francisco to be with me. I remember telling my parents, “Maybe we’ll get our own places first and ease into building a life together.” The look my father gave me said it all. “If not now, when, Grant David Friedman? If you’re going to jump into the deep end, JUMP!” Fifteen years later, that girlfriend is now my wife, we have two beautiful children, and I wouldn’t trade it for anything.
As a semi-professional gambler, I often grapple with the balance between managing my bankroll and taking calculated risks. The books all say, “Don’t risk more than 1/100th of your bankroll on any given night.” But what if you know you’re far better than your opponent? What if you have a 90% chance to win? How much would you risk? “If not now, when?”
I can think back to a night when I was invited to play in the biggest poker game in town. The players were twice my age, had ten times the money, and were well-established, but I knew I had studied the game longer and played hundreds of thousands of hands online.
After that night, I realized that, yes, I took a risk beyond my means, but I also made lifelong friends whose value far exceeds that one game. If not now, when?
Grant Friedman has orchestrated hundreds of digital asset transactions for some of the world’s most renowned individuals. www.linkedin.com/in/
For Every Jewel There is a Question:
When was the last time you took a risk?
