Streaks, Hot and Cold

I admit, I love thinking big. At times, before I’ve taken my first step, I’m dreaming of my hundredth step. I believe there’s value in this mindset, especially when building positive momentum and racking up wins.

Unfortunately, we all go through periods when success seems harder to come by. We’re likely not as smart as we think we are when things are going our way, and not as incompetent as we feel when all our shots seem to clink off the rim. Many of my successes in life have come after faltering time and time again, long after most people thought I should have moved on. It’s not that I wanted to spend six years raising money for my first fund or lose countless deals before building a reputation as a desirable business partner. My plan as a young adult wasn’t to spend years training as an engineer, only to become a doctor; and to spend a decade training as a physician, only to go into finance; to spend a decade building my first business, only to leave it at its peak to start my second business.

In the most challenging of times, I’m a huge fan of stringing together small wins. We live in a society that glamorizes grandeur, extreme feats, and champions. We love debates about who is the Greatest of All Time (GOAT). We gravitate toward awards and honors, whether all-star teams or Oscars. But this mindset doesn’t lend itself to celebrating meaningful milestones that seem banal compared to the highest peaks of our lives. Yet it’s the small victories in life that keep us in the game and provide us the opportunity—and energy—to persevere.

Small wins are surprisingly powerful. They supply a surge of confidence and motivation. Momentum gradually builds up and negative emotions dissipate, providing the energy to take on the next challenge. And by celebrating even the little things, we help create a slow-and-steady habit of reaching goals. We get into a more realistic rhythm of progress. There will be trying times, and it’s easy to let yourself get lost in the daily grind. But small steps still count as movements forward; they still put you among the active (versus the passive). Celebrate those little wins. If you do, you’ll earn bigger victories down the road.

Along my journey of raising capital, there were investors who initially declined a meeting, only to agree to meet years later. They didn’t initially fund us, though they did offer encouragement, they did indicate that we were making progress. In a binary mindset of winning or losing a client, one could classify any meeting that did not result in an account as a failure. But I saw these instances as small victories.

My initial business engagements were limited. In my early days of starting my first venture business, I was rarely included on the board of directors in the companies I was heavily involved with. But being included at all was a tangible step forward. Most other firms and companies in my ecosystem saw me as an insignificant member of our community. Yet, to me, each small victory meant something deeply personal and meaningful, even with little or no outside validation.

Although I’m more established now, I still go through cold streaks, through periods when events just don’t go my way. At those times, I find ways to succeed at smaller projects. I take note of small accomplishments, even if it’s as simple as completing a workout. Or I find small tasks to complete. Finishing anything, putting a period on even the shortest sentence, is meaningful. And I’m mindful to congratulate—and learn—from others. I encourage them as a way of celebrating their small victories.

By taking these modest actions, I start my own hot streak of small victories. Retraining my brain to create and recognize success—even if the achievements pale in comparison to what others might be doing or what I might have done in the past—sets me on the right track. This mindset ultimately translates into larger opportunities and victories over time, often when we least expect them.

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How to Manage Multiple Business Obligations with Joy and Purpose

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Alignment in Business—And in Life