The Worst Advice I Ever Got

Roy Keely grew up being told that college was the only path that mattered. The worst advice he ever got was to chase the traditional route at all costs, even when it didn’t fit. He tried to follow it. He tried to force it. It never worked.

What did work was everything he learned outside the classroom. Roy built his career through experience, curiosity, and a willingness to step into the...

Carla McCall spent years believing the worst advice she ever got: “Don’t laugh so much.” It came early in her career and it came from someone she thought she had to listen to. The message was simple. Fit in. Blend in. Tone it down.

Carla did the opposite. Today she is the Managing Partner of AAFCPAs, a top firm known for innovation, inclusion, and a culture that actually values people f...

When Ripley Rader was told to trust consultants and experts instead of her own instincts, she almost lost sight of what made her brand special. Instead, she doubled down on her vision—building her company from a $100 Shopify template into one of fashion’s fastest-growing names.

In this episode, Ripley shares how trusting herself over “the pros” became her biggest competitive edge. She ta...

Mehrnush Saadat grew up with one message: to be somebody, you had to be a doctor, lawyer, or engineer. She followed that path into real estate law, even merging her firm with a larger one, but found herself burned out, in pain, and questioning everything. A herniated disc, a New Year’s Eve epiphany, and her passion for plant-based health led her to launch Sober ish, a cannabis and non-al...

Joy Youell was told to ‘become an expert.’ Starting college at 14, she was pushed toward hyper-specialization and a life of academia. But a detour working with the UN in Sudan—and the realization that expertise alone can isolate rather than connect—changed her path. Joy shares how leaving the pursuit of being the expert opened the door to curiosity, leadership, and a life defined by usef...

Chris Cleveland, Head of School at Wesleyan, looks back on the worst advice he ever got: “Do what makes you happy.”

On the surface, it sounds harmless—even good. But in this episode of The Worst Advice I Ever Got, Chris explains how chasing happiness alone can lead to shallow choices, and why purpose, responsibility, and faith create something deeper and more sustaining.

It’s an honest ...

Kyle followed that rule for years, becoming a decorated airline pilot by shutting his feelings down. But eventually he realized the truth: every decision we make, whether in the air or on the ground, is fueled by emotions. Suppressing them doesn’t make us stronger, it makes us weaker.

In this episode, Kyle shares how unlearning that advice changed his career, his relationships, and his ...

“The worst advice I ever got was, exercise more and eat less.”

Sammy Williams shares how that advice, repeated over and over, became a damaging mantra that pushed him toward unhealthy extremes and left him battling shame around his body. What sounds simple on the surface was actually harmful, and it took years for him to unlearn it.

In this episode, Sammy opens up about his journey to r...

What happens when the world tells you, “You don’t have to be smart if you’re pretty”?

In this episode, Teresa Caro opens up about the dangerous advice she got early in her career—and how it fueled her drive to prove her worth beyond appearances. From shifting life stages to reinventing herself through every chapter, Teresa shares hard-earned wisdom on:

• Breaking free from superfici...

What happens when the person you admire most tells you you’re not good enough?

For John Follis, it was a college professor who pulled him aside and said: “You suck at advertising. You should quit.” At 20 years old, chasing a new dream, those words almost knocked him off course.

In this episode, John shares how he pushed past that moment, built resilience through setbacks—including getti...

This week, Michael Brody-Waite shares how that well-meaning message failed him—leading to homelessness, addiction, and hopelessness by age 23. But what happened next is extraordinary. Through a 12-step program, Michael not only recovered—he built a new life from the ground up.

He went from sleeping on floors to building a company that grew 20,000%, making the Inc. 500 list, and deliveri...

When Tom Rebers was told to "charge the going rate," it sounded safe and reasonable. But playing it safe nearly cost him his business. In this episode of The Worst Advice I Ever Got, Tom shares how he learned to set his own value, stop following industry norms, and build a business that actually works for him.

If you’ve ever underpriced yourself or felt stuck following “what everyone el...

Zahra is a licensed therapist who now works with psychedelic-assisted therapy, particularly ibogaine, a plant medicine with powerful anti-addiction effects. In this episode, she shares her journey from traditional treatment centers to becoming an advocate for spiritual, mental, and emotional healing through plant medicine.

We talk about outdated recovery models, the stigma surrounding p...

That’s the worst advice Jeremy Schneider ever got — and it’s everywhere. From the headlines to social media, we’re taught investing means timing markets, chasing trends, and hoping for quick wins. Jeremy says that’s exactly why most people stay broke.

Jeremy is the founder of Personal Finance Club, a former tech entrepreneur who retired at 36, and now teaches simple, proven ways to buil...