United Polaris Suite on a 787-10

…And Yet, I was lonely.

April 14, 2023

Not gonna lie, friends, I’m writing this from my luxurious suite overlooking the glittering lights of Las Vegas. Here I am, attending the NAB Show 2023 – a prominent industry event for broadcasting professionals – and I’m loving every minute of it. I’m traveling for work, meeting fascinating people, and even indulging in some first-class flights (which, as an aviator at heart, makes me giddy with excitement).

Flying is my favorite part of any trip. I was so excited I couldn’t sleep the night before. It was going to get to fly on one of my favorite planes: the 787-10 in United Polaris Class. I got to Chicago, dropped my bags and made it to my gate all in 15 minutes. I go on the aircraft, ordered a vodka tonic, and then a profound realization struck me. An uneasy one… As the plane raced down the runway and the force of lift overcame gravity, I thought, “You’re on your own, kid. You always have been.”

…here’s the thing: even though I’m living the life I’ve always dreamed of, there’s still something missing – the friends I imagined would be with me on this journey. Back in 2016, I had a vision of reaching this point in my life, traveling to cool places, and sharing these experiences with my closest friends. We’d laugh, explore, and create memories that would last a lifetime.

Unfortunately, reality hasn’t quite aligned with that vision. Sure, I have a fantastic group of friends, but many of them are on different paths in life. Most aren’t entrepreneurs, and the ones who are tend to focus on local businesses, which means they don’t travel as often. So, as I sit here in this incredible city, I can’t help but feel a bit lonely.

To be honest, my mom usually accompanies me on my trips. I grew up watching her work tirelessly, never taking a break, and I vowed to work hard so that she wouldn’t have to. In many ways, I’ve achieved that goal by giving her a well-deserved break, but this is the first trip in a long time that she hasn’t joined me on.

A few days ago, she suggested inviting some friends along, and I did. I even offered a place to stay in my swanky suite. But, as it turned out, no one could make it.

Now, I know these are first-world problems. I’m incredibly grateful for the life I lead, the places I’ve been, and the experiences I’ve had. But, like anyone else, I’m only human. And this human is feeling the weight of loneliness.

Maybe this is stirring up past wounds when I’d pay for friends to join me on trips only to find out they weren’t genuine. Maybe it’s a reminder that entrepreneurship can be a lonely journey. Or maybe it’s the realization that “Team SBG” isn’t quite what I had envisioned – it’s just Sidney and his mom.

Or maybe… as I sit here in this spacious suite, I’m faced with a choice. I can either be upset that my current reality doesn’t quite match the vision I had in 2016, or I can embrace the now. I can transform this uncomfortable feeling into a positive one, creating an experience that’s even better than what I dreamed of because this isn’t a dream – this is the now.

So, I’ll continue to embrace this journey, cherish the connections I have, and learn to find joy in my own company. After all, sometimes the most significant personal growth comes from embracing life’s bittersweet moments and making the best of them.

Here’s to the highs and lows, the laughter and tears, and the journey of living the dream – no matter what form it takes.

Keep Climbing,