A Practical Choice in an Impractical World: Or Is It? With Jeremy Sweet

Episode 11 of Uncharted: Your Sidekick for Life introduces us to Jeremy Sweet, a man who might just convince you that accountants are not so bad after all.

Jeremy’s story isn’t your classic rags-to-riches tale; it’s more of a wanderer-finds-purpose journey, with a few detours, plenty of self-doubt, and a realization that sometimes, you’ve got to take the leap—even when the safety net isn’t guaranteed.

Picture this: high school Jeremy is the sports guy, the one aiming for a future that looks a lot like cleats and home runs. But dreams don’t always cooperate, and reality doesn’t send a warning email. By his senior year, the sports scholarships weren’t knocking, and Jeremy felt the sting of an unfulfilled dream. It was a quiet disappointment, the kind that settles in your chest when the future you imagined slips through your fingers. Unsure of what came next, Jeremy found himself drifting toward the next safest bet—college. It wasn’t a passionate decision, more like a reluctant nod to practicality, but it was a step forward nonetheless. He picked Texas State (back when it was still Southwest Texas) with all the intention of a “Why not?”

Accounting found him more than he found it. Turns out, he was good at it. So, he stuck with it—a practical choice in an impractical world.

Fast-forward to 2009—a year when the economy was as shaky as a toddler on roller skates. Jeremy graduated into chaos, but accounting, ever the reliable old friend, had his back. Numbers never go out of style, after all. He landed in the corporate accounting world—a steady job, a clear path. The dream, right?

Only it wasn’t. Something about staring at spreadsheets for billion-dollar companies that wouldn’t notice if he sneezed just didn’t sit right.

Jeremy craved impact, connection, and the freedom to do things his way. That’s where the real story starts: the moment he decided to leave the “partner track” safety of his firm and start his own CPA practice.

He and his wife had just had their first child, and a second was on the horizon.

Risking stability when you’re raising a family feels a lot like stepping off a cliff blindfolded. But Jeremy had something most dreamers don’t: a rock-solid partner.

His wife believed in him—and sometimes, that’s all the fuel you need.

And so, he did.

Now, Jeremy’s life looks very different. Instead of faceless corporations, he works with small businesses and individuals where $10,000 saved isn’t just a rounding error—it’s money for college funds, vacations, and family dinners.

It’s impact. It’s human.

But this episode isn’t just about careers; it’s about trust—trusting yourself, your gut, and the people in your corner. Jeremy’s leap into entrepreneurship wasn’t about knowing everything or having a bulletproof plan. It was about believing that failure isn’t the enemy—it’s just another step on the path.

As highlighted many times in our episodes, support system is key. If you're lucky enough to have a family or a good partner, you’ve hit the jackpot. If you don’t, then no matter how hard it gets, you are your own best support system.

That brings us to a question posed by Gen Z voice Trevor:

Jeremy’s answer? Trust your gut.

Natalie adds her own twist: sometimes, you have to take people at face value. Not everyone is plotting behind the scenes like a villain in a movie.

On this, I want to pause and reflect. Especially in the first years of college, we are just starting to know ourselves—navigating unfamiliar waters, new emotions, and relentless doubts. The people around you are likely going through the exact same thing. What you might perceive as "sus" could simply be fear. What feels like "deceit" might actually be insecurity.

We’re all trying our best to connect, but doubts often shrink us into smaller versions of ourselves. We are complex—and recognizing that, both in ourselves and in others, is a powerful step toward understanding.

On this matter, co-host Leon reminds us that most people are just as lost, confused, and hopeful as we are.

So, how do you handle the doubt? You listen to that quiet voice inside you, you give people a chance, and you keep moving forward—even if you’re not 100% sure where the road leads. Although we are taught differently, paths don’t have to be perfectly planned to lead somewhere meaningful. Just like Jeremy, sometimes the plan finds you along the way, shaped by small decisions, leaps of faith, and the courage to trust your gut. Sometimes, the boldest move is simply to take the next step and trust that you’ll figure it out along the way.

Now a question for you: How do you handle doubt? Do you trust your gut, lean on your circle, or pause until clarity hits?

Let us know—we’re all just trying to figure this thing called life together.

P.S.: Read Trevor's blog here—his story might resonate with you or someone you know just entering college. He opened up about his struggles with independence, loneliness, and simply finding where he fits in. It was a heartfelt conversation that warmed my heart and reminded me how easy it is to feel lost sometimes—even when we’re not.

Listen to Jeremy Sweet on Uncharted: Your Sidekick for Life – Episode 11, Season 1

Jeremy Sweet: Jeremy is a Certified Public Accountant who turned his knack for numbers into a career built on impact and connection. After starting in corporate accounting, he left the safety of the “partner track” to create his own CPA practice, focusing on helping small businesses and individuals achieve financial stability and growth. If he's your guy, check him out!

Natalie Peyton: Peyton studied theatre and film in Australia, New York and LA and performed stand-up on the “three coasts.” She honed her podcast executive skills over the last 4 years developing and producing dozens of podcasts and even hosts a children’s mindfulness bedtime program. If you would like to listen to her work, here it is: Snoriezzz

Leon Vanstone: Leon brings his curiosity and sharp interviewing skills to the table, facilitating insightful discussions with our mentors, extracting valuable lessons and insights to empower listeners on their own path to growth and achievement.

Dan Dillard: Dan, with his thoughtful approach and engaging style, delves into the minds of our mentors on the podcast, crafting compelling interviews that uncover the wisdom and experiences driving their success and impact.

This blog was written by Anais Schmidt, one of the hosts of the Uncharted Podcast. Anais is also an aspiring musician. When not in her studio, she tours Europe with Monte Mai.

If you would like to join the conversation email us at anais@foundingup.com

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