Do you know why you are Searching? Really?

When you set out to run an ultramarathon, you need to understand why you’re doing it if you want any chance of finishing. This may seem trivial and obvious, but it’s not. I’m not talking about a superficial goal of simply finishing or finishing within a specific time. That won’t be enough. A race that covers 100 kilometers, 100 miles, or even 250 miles on foot means that at some point, you will find yourself so deep in the pain cave that any logical thought would tell you to stop. The only way to push through the suffering is to have a “why” so deeply rooted in your soul that you refuse to give up. You keep pushing, and eventually, things change; you begin to move a little better. The pain eases for the time being. For me, it comes down to love. I think of my late Bernese Mountain Dog Zeus’s soulful eyes, each one of my three kids, Kerry, Seamus, Cole, and my wife, Elena, who tracks me even when my race lasts through the night to the next morning. My why is that my family, even my soul animal, never gave up on me, so I will never give up on them. My why is unconditional love, of my family, the CEOs I mentor, and my students. Not money, or success, or even a time in a race. Reflect deeply on your most profound motivations. What are you trying to achieve and why? What is the reward you're seeking? I am the poster boy for someone who hit it big more than once, and every single time, the payoff lasted about 30 seconds. None of it truly made me happy. None touched the deepest part of me that hungered for connection. I was a one-man wrecking ball on a solo mission to conquer the world. And I came close. But still, I was alone and largely unhappy. I'm here to tell you that, for the most part, what you're told is a myth. The person with the most money and the most impressive resume does not win. Thomas H. Lee, the creator of private equity and a billionaire many times over, walked into his Midtown Manhattan building (which he owned), went up to his office, and into his gold-plated private bathroom, pulled out a gun, and shot himself to death. The view from the mountaintop is not what you think it is. In the class I taught last summer, we had guy after guy come for fireside chats, and when I asked them what they were most proud of in their career, none of them talked about money or deals. These were people who had conquered the world professionally. They all said it was about the people, the relationships, the connections, and ultimately above love. I hate to break it to you, but we are all going to die. The Buddhists believe that great wisdom can be obtained by meditating on one’s own death, a practice known as “Maranasati” meditation, which enables us to deepen our gratitude through a profound understanding of life's impermanence. No one on their deathbed counts their money or talks about the deals they did. They all talk about the people they are grateful for and the depth of love and connection they experienced in their lives. Doing is undoubtedly essential in sport and business, but not for the sake of the thing itself, but for your team, your family, and your dearest friends. Mentoring others has been a thousand times more meaningful than doing it myself. It turns out that a well-lived life is about service, not because it looks good to anyone else, but because it is good in how it makes you feel in your heart. The process of maturation is about moving out of selfish ends and towards living for others. You may not be able to internalize this now, but you will in time if you remain open to progressing emotionally and spiritually alongside your professional career. I wish I had understood all that at the start, rather than only towards the end of my career. There are plenty of low-risk, soul-crushing routes to “success.” I am begging you not to pursue them. Or at least look directly in the mirror and ask yourself why you want to pursue them. Is it out of fear? Out of a desire to follow the herd? Some attempt to de-risk your life? My argument is that the most significant risk in life is to be uninteresting. To fail to aspire for greatness, not in any one else’s view, but your own. To do something meaningful to YOU. That provides you with a sense of meaning in the world, of accomplishment beyond the money. That connects you deeply to other people you care about. That deepens your capacity to love, to feel empathy, to have compassion. The most recent research suggests that, at an annual income of $100,000 (when basic needs are met), the correlation between income and happiness levels off. Beyond $500,000, the correlation becomes zero or negative. People don’t go into business to make vast sums of money to achieve a deeply meaningful life. If that is their goal, they are delusional. The reason to resist following the crowd is to find that sweet spot where everything clicks into place. It's like being in the eye of a hurricane: chaotic winds swirl all around you, but where you stand it is perfectly calm. That's where you'll discover your authentic life. I am begging you to undertake that hero’s journey—to look into your soul and not just follow the crowd. In my life, the reward has never been about wealth, though wealth was a side benefit of being such a bold contrarian. The most intelligent finance people I know would argue that the only way to build something great is to go where everyone else is not. What I am asking is that you slow down, and discover and trust your voice, even — especially — if it means swimming against the current.