Why I'm Excited to Be Entering my Late 20s

This is the primetime. Time to seize the opportunities and grow the established foundations that may shape the next chapter of life.

Crossing the 25 barrier felt daunting. It felt like I needed to know some things. 21 felt like that too. These milestones are just marked by a day on a calendar as an excuse for everyone to pay attention to you and show you love (hey, I’m not complaining), but they also serve as a checkpoint for yourself. Birthdays are like New Year’s Day with a stopwatch attached. Each lap around the sun takes on a distinctive meaning relative to the past and future and the current and collective state of mind. Where am I? Where should I be? Am I what, where, and who I want to be, and how far am I away in each regard? And not only there, but am I where I thought I would be at this age relative to what I projected X years ago? Part of this exercise is healthy — setting time-bound goals with measurable outcomes that can create a notion of accountability. At the same time, tethering oneself to superficial outcomes that are generated by an ‘external’ reference point (vis-à-vis comparing the self to others) can be unproductive at minimum and brutal at its worst. So-and-so was doing this at X age — I’m not doing enough — what I’ve come to realize as I’ve gotten older is that this doesn’t motivate me, as we are all on our own journeys, and it’s best to admire others’ accomplishments rather than compare. The motivation must come from within. What have you done to nourish yourself in the last year? How did you become 1, 5, or 10% better in areas that matter to you? How have you honed in on your clarity of purpose? While comparing to others is so easy and tempting in today’s world, focusing on the self in relation to the self is, in my opinion, the best way to do it.

I’ll stop speaking in general terms — I’ll be frank. While the last few years have been filled with adventure, wonder, and joy, they have also been extremely challenging. There have been stretches of time where I felt lost. As someone with varied interests, boundless energy, and a deep desire to experience and connect, the mid-20s have been filled with chaos. From career changes and failures to lost relationships and new ones, the last few years have represented the most significant self-evolution of my life. I thought I would know who I was and what I should be doing by 25 — that didn’t happen. It took me quite a while to be okay with that. I’ve had the immense privilege of being connected with a lot of people who’ve achieved success across a variety of vectors spanning monetary to domain mastery to aligned lifestyles where passion and purpose intersect. Admittedly, it took some internal work to shift envy and insecurity to pure admiration and appreciation in this regard. Part of that shift had to be a product of changing the locus of control from external to internal. 27 was the year where this really happened for me.

Before I talk about 27, I want to touch on the 3-year story arc that I believe has built to the present day. In my 25th year, I experienced a roller coaster up-and-down that came to define a new leg of my personal journey. I had changed course, plunged headfirst into crypto (eventually into a wall), and built a whole new community. I fell in love (again) when I least expected it, I reconnected with the city that made me, and I discovered parts of myself that would plant seeds for the future. I discovered that I loved building spaces and bridges for connectivity amongst highly creative individuals. I realized that I had a real knack for it. My experience working with the EmpireDAO team at 190 Bowery came with so many lessons. EmpireDAO represented a period of immense excitement for blockchain technology — something that a lot of people wanted to tap into in different ways. It was a community that largely developed in a virtual setting, so building a physical home for it brought all sorts of benefits to bear. Human connection cannot be perfectly simulated in a digital environment (at least not yet), so bringing that enthusiasm and energy under a shared roof in the electric New York City ecosystem made a powerful impression on me. In the midst of COVID isolation and a shift to virtual and hybrid work, we had begun to lose each other. EmpireDAO brought some of us back into a reinvigorating physical reality. Then it all came crashing down, and I had to go back to the drawing board.

This is when I moved to LA. While my time there brought me new friends, put me back in touch with the natural world (I spent a lot of time in the mountains), and provided me with some peace and calm, I still felt quite lost. A lot of my friends had found clearly defined paths that they were going down. Some were getting engaged. Some had, like me, moved to new cities and were doing amazing things there. While I was happy for them, it also made me feel even more lost, and even insecure. Why wasn’t I where they were? Despite getting this advice from many people I respect, it took me time to realize why this frame was self-damaging and unhelpful. The only way to move forward was to look within and create a series of missions that aligned with the kind of guy I am. My 27th year is where I really began searching for this sense of alignment.

I give a lot of credit to my father for pointing me in a direction that felt true to my sense of self. I would say he knows me pretty well. While I was enjoying my time in LA — the lifestyle, the friends, the girlfriend, and the sense of freedom — it wasn’t fulfilling in the way that I needed it to be, and it wasn’t setting me up for the long term. What do you think about taking your love for culture, food, and community and bringing it to our work in Detroit? he challenged me, in similar words. The proposal was a big change, and not one that he was going to force on me. I had shifted gears from crypto into our core sports business — I was running the conference circuit, bringing in deal flow, cultivating strategic relationships, and learning a ton. I felt like I was beginning to use my strengths to add value in meaningful ways, but I didn’t feel a sense of extreme ownership. And one thing my dad definitely knew about me is that the sense of ownership and accountability is what really drives me. After several trips, some hard conversations, and a lot of deliberation, I accepted his challenge.

While it hasn’t always been easy, I now think of it as one of the best decisions of my life. I moved to Detroit in October of last year — I left some things behind to make this change. It felt like the 3rd major pivot in 3 years (which did not necessarily feel good). And I was not at all sure that this was the pivot that would work. It was a little scary. I had some relationships established from my time at University of Michigan and through the foundational work my family has already done there in affordable housing, but it wasn’t like New York, where many of my people were, or even like LA, where I moved in with one of my best friends. I was doing this on my own. This independence offered me an opportunity to re-invent myself and lean into the things about myself that offered the most potential for growth. The lack of social pressure led me to re-focusing on my body. I got back into the gym in a big way. I can naturally run long distances and lift heavy things, so I focused on that. In the past year, this has helped me love my physical body again. As I’ve mentioned, I also have a propensity for channeling my energy into building creative communities. My clearly defined purpose of bringing the best and brightest food, beverage, and hospitality businesses in and around Detroit together has challenged me to use my strengths to do some good and move our business forward. Last week, I hosted 200 amazing people spanning F&B, hospitality, marketing, art, government, etc. together in what will soon become Brand:Detroit’s innovation center. It represented the culmination of a lot of foundational work that I’ve been doing over the last several months. It felt good to see it all come to life in one space. The room was filled with positivity, gratitude, and, of course, delicious food and drink. It was also super validating for me — I finally feel like I’m on a path that nourishes me — physically, mentally, and spiritually. It’s a feeling I’ve been seeking for my entire adult life, because it is entirely in relation to myself.

Getting older used to feel scary, but now it suddenly feels exciting. I feel like I’m building something that’s true to who I am across multiple dimensions. This doesn’t mean that every day will be sunshine and roses — in some ways it will come with an even greater amount of struggle. But this is the kind of struggle that I love, because it is the kind that will promote continued personal growth. I would challenge everyone to internalize this — external comparison will never lead you on the path to fulfillment, only the self-work will do that. I can’t wait to see what 28 holds for me. Thank you to everyone that has entered my life in my 27th year, and especially thank you to those who have stuck by me for much longer. I feel immensely grateful today.