Often times we come across situations in life with asymmetric risk: where the reward of a choice meaningfully outweighs its risk of failure. Single decisions could achieve our dreams in mere moments - as if our life is like a game of chess, and we’ve found the winning move. But whether in chess, business, or life, understanding when a move could push you forward is paramount to capitalizing on your goals. It’s not about gambling recklessly, but recognizing when the benefit to cost ratio is immense. And when you find these moments, you find your edge. It’s authentic, powerful, and long-lasting.

Of course, risk isn’t always objective. What feels impossible to one person may be trivial to another. Risk tolerance, resources, and experience all shape how we perceive asymmetric risk. For example, some people prioritize stability above all else: they’d rather preserve life rather than wager it. This often leads to stagnation and longer timelines for change, because risk happens slowly over a period of time. Others are driven by curiosity, competitiveness, a need to see what else is possible. It’s not necessarily recklessness, because these traits are controlled by calculated decision, but urgency and conviction.

Entrepreneurs live in asymmetric risk. In fact, it’s their job. They have to look at products or ideas and calculate - not just financially, but existentially - whether the reward is worth the effort. If an investment is small compared to the possible gain, then it’s worth doing. Even if it fails. Especially if it fails. Because asymmetric risk isn’t always about getting it right. Professional entrepreneurs realize that failure is often the more valuable outcome.

Sometimes you take the shot and you just miss. Terribly. But you walk away better for it: sharper, clearer, and more capable. Failure from asymmetric risk isn’t a miscalculation, but a data point. After all, wisdom and experience are built off the numerous risks taken in our lives - most of which didn’t pay off - but all of which pushed us further than where we started.

Human progress doesn’t happen without asymmetric risk. It never has. The first boat, the first flight, the moon landing, none of it was safe. Each step forward came with the understanding that the reward would justify the unknown, risk that could change the world itself. These moments have become chapters in the human story, in the grand chronicle of our existence. And when they don’t, they simply become foundations for those who try next.

But there’s no formula for knowing when to act. And no one can tell you what’s worth risking except yourself. If you never act, you’ll never change. So, what will you do? Will you wait for the perfect moment? Or, will you take the asymmetric risk and jump, evolving in the process? Because the greatest risks in life aren’t the ones we take - they’re the ones we never do.