Presto Magic

Part 2

It’s always interesting to me how my stated reason for doing something can feel like a lie when I reflect back on the situation. At first, when making this realization, I’ve found that it’s easy to jump to judgment. “I just lied to myself. How could I be so stupid and shameless?!?” But this isn’t the truth either. The truth is that I wasn’t being stupid or shameless or purposefully ignorant. I was merely suffering from partial blindness. I was unaware of the full story, even if the story in question is my own to begin with. Us humans, with our high-powered brains, are exceptionally skilled at keeping secrets from ourselves. We’re experts at burying our deepest truths. We’re pros at stifling our most burning desires. We’re tacticians at keeping our riskiest secrets. We fabricate reasons why the honest life is one that’s obviously unattainable. “Sure, it’s possible to be honest in-part. But certainly not all the way. The world isn’t a place that’s built on full honesty.”The moment we convince ourselves of this illusion, we’re also giving ourselves full permission to avoid taking action. “If a fully honest life is obviously unattainable, then why even try in the first place?” So, the deep truth, the burning desire, the risky secret gets boxed up and locked away. We become honest only to the extent that it’s convenient. We might be willing to confront our deep truth only if we’re forced to do so. We might be willing to pursue our burning desire if someone else presents us with the opportunity. We might be willing to divulge the risky secret if someone else has already exposed it. Put simply, we so often wait for the world around us or another person to inform us that the conditions for living honestly are now perfect. This is precisely what happened to me. Or rather, it didn’t “happen to me,” this was the situation that I, myself, created. My unexpressed, burning desire was to step into a role as a coach for my internal teammates, portfolio company CEOs, and prospective founders. As mentioned, I was already having deep, private, personal conversations with internal & external people on a consistent & increasing basis. I derived deep meaning from these conversations. I loved them because I love people. I love going deep with people. I love understanding their stories. I love hearing about what motivates them. I love getting to know why they get out of bed in the morning. It fed my curiosity, especially because each individual is filled with so many layers of complexity and unpredictability. Everyone has a story. And they’re all unique. Everyone has something to teach. And I had an insatiable hunger to keep learning. So, as I filled my calendar with more coffee walks and lunch meetings, I found myself tilting more of my time away from my investor work. I enjoyed this work too, but just not as much as the deep conversations I was having. I didn’t crave the diligencing and analyzing and investment decision-making. It got to the point where I didn’t even crave the tasks that could be characterized as company-building. Instead, I wanted to spend all of my time conversing with people. Understanding them. Understanding their stories. When it felt like a necessity to fulfill the responsibilities of my job, understanding their businesses. But even then, getting familiar with businesses didn’t fascinate me as much as it used to. What I really wanted to do was get to know the individual. “Who was the person who created the business? Why did they do it? After all, founding a company is often an irrationally big risk. So why take the leap in the first place? And how has taking the leap changed them? How has the person who founded the business changed into the person who’s in front of me today?” These were the questions that I wanted answers to. I didn’t care so much about the company’s ARR or growth rate. Of course these are easy truths to admit to myself in retrospect. But, at the time, they felt impossibly hard to say out loud, especially to my managers. To admit that I didn’t love the investor role anymore would have been to risk everything that I’d spent my whole life working toward. I’d dedicated my whole academic & professional career to getting here. I was ascending into an even-more-promising future. Was I really just going to throw it all away? This was the Either-Or scenario that I’d convinced myself that I was facing. Either my managers would see me for my desire to shift my role to one of full-time conversation partner. Or they would fire me as they selectively heard that I no longer wanted to be an investor. “There’s no room for that position in the organization.” “What gives you the right to be a coach to our employees, and especially to our executives? You’re only 28 years old. Wow the arrogance you must have to even ask for something like that. Do you really think you’re that wise? Do you really think you’re that special?” The truth was that I did. And I knew that I had the evidence to prove it. I was having conversations with leaders of billion dollar companies on a regular basis. After listening intently to their situation, I would give advice on how I might approach their situation. I noticed that this advice would be heeded, often with favorable results. Rarely would they follow-up and give me direct credit for it though. Because, after all, who wants to admit that they took consequential advice from a 28 year old? Especially if you’re a VIP at a VIC (Very Important Company). But it’s OK, I wasn’t really in it for the credit. I was in it for the conversation. I just loved diving deep with people and offering up what I could to help them. I learned that, most of the time, what they really needed was simply someone to listen to them and ask questions. We spend so much of our lives trying to justify why we’re worthy of being listened to. I realized that maybe the biggest service I could provide is listening to someone, with my full attention, without them needing to justify why I ought to. But anyways, I was also having these sorts of conversations with my colleagues on a daily basis. Everyone in the firm. Whether someone was an IC Partner or an Analyst, I did my best to meet with them. I did my best to make time for everyone, even if it meant I’d have to work longer hours to catch up on my “investor work”. Ultimately, this felt like a worthy tradeoff for me, because these deep conversations are where I found fulfillment. I reframed the investor tasks as a tax on being able to have these conversations with smart, ambitious, thoughtful people. My willingness to do this investor work was a small price to pay to fulfill my purpose of having a positive influence on the people who were having a big ripple effect on the rest of our society. But, eventually, the demand for these conversations became overwhelming. I was neglecting my investor work to such an extent that I felt like I was drowning. I was doing my best to balance the tasks associated with my day job and that of these conversations. At the same time, I was finding an increasing draw to pursue writing. I was learning so much from all of these conversations and my own personal, introspective observations that I wanted to spend more & more of my time writing down what I was learning in order to share it with the people I cared about, as well as have it memorialized for future reference. I allowed my imagination to construct a dream scenario where my schedule would be filled with 1-on-1 meetings with colleagues, company leaders, and prospective founders. I would spend my days listening to them, strategizing with them, and helping them solve hard problems. I would spend my mornings and evenings writing what I’d learned from these interactions in order to make these insights available to a broader audience. I would be operating in my “zone of genius”, as one of my friends once put it. I created a detailed proposal of why this would be beneficial for my employer and the world (leaders feeling seen, while also receiving wise counsel, can have a ripple effect far beyond the 4 walls of their company). But I never shared it. I never even broached the subject. I was too afraid of the “Or” situation that I, or rather, my Anxiety, had created. I was too afraid to be laughed out of the room. I was too afraid to be fired. I was too afraid to hear that I might be enjoying these conversations, but they didn’t really carry much value for other people, at least not enough to justify a salary for what could be seen as just going on coffee walks and attending lunch meetings. These fears that I’d crafted ultimately paralyzed me from moving towards my dream scenario. Maybe these would have been the responses from the firm’s leaders as they rejected my proposal. But maybe they wouldn’t have been. Maybe they would have accepted it. Maybe they would’ve been stoked to have me spending more time building up the people in our organization and ecosystem. Or maybe they would have said something else. I guess I won’t know. I guess the answer to “What would have happened if I would have proposed it?” only exists in a parallel Universe. One where I had the courage to take the leap.

Part 4