You’ve been there before—the feeling like you are drifting in an ocean with no motor or rudder, just floating and moving wherever the current and wind decide to take you. This unsettled feeling is something we rarely seek in life. I mean, why would we? We work tirelessly to establish roots, grounding ourselves in comfort, security, and the basics of life that calm our nervous systems. We never intentionally seek the feeling of being untethered.
But we should. Maybe there's value in throwing ourselves into that world—no strings attached, just being out there with zero plans, moving through life to see what it offers.
Initially, I didn't think this was a good idea or something I'd recommend. However, having lived in this space for the past several months, I now have a different opinion—you might want to hear me out.
When I left my previous job (no need to mention them), I went full steam into my writing, speaking, and diving into my companies. It was, and remains a fantastic opportunity. The freedom to do what I wanted and be where I wished was liberating. For the first time in over three decades, I could pursue my desires without the constraints of a boss, board, or obligations to shareholders. I only answered to myself. The euphoria was great, but it was a process to get there. Unwiring your brain to dig deep into what you want to do is a beautiful exploration.
You've probably experienced hints of this before—at least I have—when you go on vacation. If you're like me, it takes a day or two after arriving at your destination to clear your mind of all the clutter. Emails, calls, and trivial requests that can clearly wait until you get back fill your thoughts and suck time out of your adventures. There's a magic moment toward the end of your trip, where you *finally* decompress, relax, and benefit from the time off—only to board a plane and be thrown into the chaos of 'catching up' from your time away. Then you tell yourself, "Maybe I should just not go next time and save the stress of reentry."
But have you ever considered what happens when you truly disconnect? Stay in that unplugged space; what happens? I hadn't until I lived through it. Now, I have a radical take on it: Run at it.
Once you see that you can surf, play tennis, travel, and do what you want when you want, there comes a moment when you almost get lost in your life. The standard work structure of Monday through Friday gives way to a constant 'what day is it?' mentality. I started measuring my weeks by when football was on TV, knowing that college was on Saturday and the NFL was on Sunday and Monday.
Welcome to Being Untethered
When you cross into this abyss, you quickly find you can get lost in your head and life. You begin questioning your confidence and abilities and having pretty scary conversations with yourself. You start questioning everything, worrying about what's next, whether the phone will ring again, and on and on. I began forcing conversations, trying to insert myself into places that didn’t feel right, like taking company positions because I felt like I needed to. The anxiety is real, the fear is real, and the self-doubt is paralyzing.
That led to me working out less, eating worse, and drifting down some dark paths.
Then, I remembered one of the best stories of all time that Oprah told me personally—a story I've seen her talk about for decades. It's about her role in "The Color Purple." The story is so powerful that we put it on a wall in Harpo for all to see. I won’t recant the story here, but I'll say I was in a place of surrender. (It's worth a Google if you don’t know it.)
That’s when the phone rang. It was my closest friend in my life, Scott. He needed some help with a few projects in Nashville. Of course, I did it for him—things spanning the world of inventory management, fashion, music, and racing. I never thought I’d be doing any of those jobs in a million lifetimes. But, as the universe dictates, things happen for a reason and at a time that is perfect for you. And I did it for him, not realizing the gift he was offering.
Given that we both have gone through life-changing moments—my stroke, his horrific racing accident—we agreed if we were ever going to do anything together, now would be the time. We talked for decades about doing something, but we both never knew how to make it happen, given what we were doing in our careers. The timing now seemed divine.
When I started, I knew very little about racing, much like TV business, the Cable Business, The satellites business, or a sports league, but I knew I could learn. Scott acquired a company that put on the Grand Prix in Nashville for the prior three years (that's a race for you non-gear heads). When he assumed control earlier this year, It’s safe to say the company setup was, well…. less than optimal. From the onset, the goal was simple: Execute the race this year in 2024, which at the time seemed easy enough.
The odds were not in our favor, and with each passing week, they seemed to double down against us. Everything from the local government to businesses who doubted we could do what we were saying, you name it, and it was every day. The phone would ring, which would be just another issue and problem. We had to change the entire location of the race, AFTER we had put tickets on sale for a race that was downtown! It was full-on. If we were going to save this race, we had to both dive into the deep end holding lead weights.
We both knew there was only one way through this: do what we both know how to do—fix it.
Practicing many of the things I've written about here and in Forbes, the entire Grand Prix team focused on the next right thing—with one goal: to have the most successful race in this event's history.
Calling in every favor, spending thousands of hours with the team, and thinking about every detail, we just concluded the most successful event the race has ever seen. We saw over 100,000 people downtown for the kickoff event. We had over 40,000 on the property at the speedway, sellouts across the board in many areas of the track, and the race was all-time. It set INDYCAR records with the number of passes lead changes, and more; then to cap it all off, a Nashville resident won! It was one of the hardest turnarounds we’ve ever attempted. The drivers, the press, everyone was gobsmacked by the weekend.
Monday morning post-race was surreal. The world felt a bit lighter; we dropped some lead weights and were catching our breath. Then I started playing back the weekend.
As the field went green on Sunday afternoon, hearing 27 INDYCAR roar out of turn four, I was overwhelmed by the events leading up to that moment. How in the world did I get here? Why am I totally invested in this moment and this sport? Why am I standing on this starting grid? Max, one of my long-time friends and a huge race fan, and some of my closest friends from MB came, who knew as much as I did when I started about racing - zero. I felt like I was having an out-of-body experience. What in the world was happening?
When I really started to think about how it happened, it was clear—I was untethered. I was almost a free spirit when I got the call. I was moving through life, open to what was next without judgment. Placing my ego aside and not caring what others, the press, or anyone would think or say put me into a place where I could lean in and be open to whatever was next. And therein lies the gift.
I have written about moving through businesses by starting with 'yes' so much. Start with yes and lean in, but it's much easier said than done when you're grounded and have some balance. When you're off-center and adrift, you tend to overthink and not heed your advice. Indeed, for me, that was the case.
Today, I look at what we as a team have accomplished and whom I've had a chance to connect, meet, and work with. It’s an entirely new world of people, partners, and friends I've made. One door that has opened now is a thousand more, unlocked, waiting for me to walk through. The opportunity to leverage and build what we have is limited to what we can manifest, so let’s think big. We shifted how events are viewed, promoted, and consumed. There’s no going back; there's only one way forward now—2025 has to beat this year.
The people I have met on this nine-month journey will be friends and colleagues I'll have for a long time, regardless of what's next. That is a certainty. The other certainty is that if I had planned for this to happen, there is zero chance it would have materialized. I'd be in my own head about myself and wouldn't allow myself to hear others or even take the shot to lean in. My ego would have taken over, and I’m sure I’d just be looking online for the next Oklahoma Sooner kickoff time.
That’s where the gift of being untethered comes in. No ties, no ego, very, very quiet with yourself—so quiet, it's scary. What is that voice saying? What are the whispers? I was scared at times—very. We are wired to constantly focus and think about the outcomes, wanting to know how things will end. I wish I could have known the gifts on the other side when I was in the middle, drifting toward who knows where, but if I had, I wouldn't have enjoyed the sweet moment of success this weekend.
I'm not 100% sure I'd throw myself into that state again. Still, if I do find myself in that place, I'll lean into the insecurity of the period, answer the phone, and see where the universal currents and wind take me—trusting they have my best interest at hand all the time as they always do.
But, you never know - maybe that’s the key; being untethered is what opens all the doors. Only you know the answer for you.
Love! Congrats, the weekend was AMAZING! Had to edit my profile with this pic of you!
Great insight and perspective ⭐️