Like many entrepreneurs, I often feel lonely, which is a weird confession coming from someone who can have an engaging conversation with a brick wall.  I’m not some tragic recluse brooding over spreadsheets in the dark. I have a full life with amazing family and friends. And yet, there’s this nagging sense that no one truly gets what it’s like inside my head.

Being an entrepreneur can be a profoundly lonely gig. We’re all out here pretending we’re fine — smiling, networking, delivering — while secretly wondering if we’re one bad decision away from selling homemade candles on the internet. My personal coping mechanism? When loneliness knocks, I don’t talk about it. I recoil in silence, grab my hard hat, dive headfirst into work, and hope no one notices I’ve mentally moved into my inbox.

Part of my issue is the need to look like an unflappable fortress for everyone else: family, team, clients. I feel often that I’m the emotional sandbag holding back the flood. And the weight of knowing that people’s paycheques, dreams, and belief systems hinge on my next move only deepens the loneliness.

I’ve written before about how entrepreneurship is basically another endurance sport. I’ve run ultramarathons for years as a lone wolf, through thunderstorms, mud, pain, and self-inflicted existential crises — and it just hit me that maybe I love these races because they mirror my life in a demented way.

During my most recent ultramarathon I overheard two guys chatting mid-climb:

Guy 1: “Yeah, my wife runs too, but just around the neighborhood.”
Guy 2: “Is she racing this weekend?”
Guy 1: “Nah, this isn’t her thing. She’s not into pain and uncertainty.”
Guy 2: “Then there’s no point trying to explain what finishing this will feel like.”

Cue the evil laugh. And that’s the thing — you can’t explain this madness. Whether it’s finishing a brutal race or dragging a project or business across the finish line, it’s the same masochistic thrill: proving you can suffer creatively and still call it passion. For me, it’s about pushing through the blisters (literal or metaphorical), finding one more drop in the tank, and chasing a legacy that’ll hopefully outlive the addictions that built it.

My only concern is that I’ve gotten too good at being alone, and perhaps I need to reintroduce the more accessible, more emotionally available me someday. Until then, I’ve got another hill to climb and a few more self-inflicted blisters to earn.