Infinite Sadness & The Dark Passenger: A Guide to Making Peace with the Chaos (Feat. Tully, Who Has No Existential Dread)

Introduction: Meet the Dark Passenger (and Tully)

There’s a strange thing that happens when you have what looks like a great life and still feel… off. You can have a loving wife, a steady job, a solid plan for the future, and even a golden retriever who worships you like a god—and yet, there’s still this lingering sadness.

That’s where the Dark Passenger comes in. Shoutout to Dexter for the term, though mine is significantly less stabby. My Dark Passenger doesn’t make me do anything sinister; it just sits there, sighing dramatically, making sure I know it’s still around.

Tully, my golden retriever, does not have a Dark Passenger. She only has a boundless enthusiasm for life, an unshakable belief that every stranger is a best friend in waiting, and a deep, unwavering commitment to making sure I never go to the bathroom alone. Maybe she’s onto something.

1. The Paradox of Sadness in a “Good” Life

We’ve all heard the stories: the successful, wealthy, seemingly perfect people who still struggle with depression. We tell ourselves, If I just had X, I’d be happy! But sometimes, you have X, Y, and Z, and you’re still staring at the ceiling at 2 AM wondering why existence feels heavy.

For me, it’s been a journey of reinvention—20 years in the Navy, then culinary school, then working as a chef, then financial advising, and now teaching. I’ve built new lives over and over again. And yet, that quiet sadness? Still there. It doesn’t pack up and leave just because you change careers or hit personal milestones.

Tully, meanwhile, does not concern herself with existential dread. She wakes up every morning like it’s the best day of her life. Maybe she’s right.

2. Understanding the Dark Passenger

The Dark Passenger isn’t really an enemy—it’s more like an annoying coworker who won’t quit. It doesn’t necessarily do anything outright destructive, but it’s always there. It shows up uninvited to moments that should be purely happy and whispers, Are you sure you’re really enjoying this?

There’s a great line about depression: It’s like having too many browser tabs open, and you can’t figure out where the music is coming from. Some of those tabs are past regrets. Some are anxieties about the future. Some are just labeled Why Am I Like This?

Tully, again, has no browser tabs open. Just a single full-screen page that says: Love. Food. Ball. Nap.

3. The Weight of the Unseen

Sometimes sadness is tied to something tangible—grief, trauma, stress. Other times, it’s just a fog that rolls in for no reason. It’s frustrating because we’re wired to solve things, and you can’t really solve a feeling.

Society often tells us to just “be grateful” or “think positive,” but that’s like telling someone with a broken leg to “just walk it off.” Sure, perspective helps, but it doesn’t erase the weight.

That’s why I try to take my cues from Tully—when things feel overwhelming, she doesn’t overanalyze. She just shakes it off (literally) and finds the next source of joy.

4. Making Friends with the Passenger (Instead of Fighting It)

Fighting sadness is exhausting. It’s like wrestling a raccoon—you’re both going to get tired, and the raccoon is going to win.

What if, instead of treating sadness like something to be defeated, we just acknowledged it? Let it sit in the passenger seat, but don’t let it drive.

Tully’s philosophy: when in doubt, nap in the sun and let life sort itself out.

5. The Role of Intrinsic Thoughts & Reframing the Narrative

We can’t always control sadness, but we can control how we respond to it. Sometimes, just stepping outside, moving, or engaging in something creative is enough to shift the narrative.

For me, writing helps. Cooking helps. Teaching (on the good days) helps. And humor definitely helps.

Tully, of course, doesn’t need a coping strategy. She just trusts that everything will be okay.

6. Balancing the Darkness with the Light

One of the biggest lessons I’ve learned is that happiness and sadness aren’t mutually exclusive. You can feel deep joy and deep sadness at the same time. Life is complex like that.

We need to allow ourselves to enjoy the good moments without guilt, just as we allow ourselves to sit with sadness without shame.

And if all else fails, find a dog who thinks you’re the best person in the world. Because no matter how much my Dark Passenger wants to tell me otherwise, Tully is absolutely convinced that I’m amazing. Maybe I should start believing her.

Closing Thoughts: Embracing the Complexity of Being Human

The truth is, I don’t have all the answers. None of us do. We’re all just figuring it out, one existential crisis at a time.

But if there’s one thing I’ve learned, it’s this: The Dark Passenger may never leave, but it doesn’t have to ruin the ride. And if you have a golden retriever by your side, it might even be a pretty great trip.