Diplo on Mastery, Music, and Reinvention: Why Fear of Failure is Fuel

"If you take everything from me, I still have the motivation to start over again and build something." — Diplo

When you think of Diplo, you probably think of the Grammy-winning DJ who’s headlined global festivals, broken genre boundaries, and produced chart-topping hits with the likes of Beyoncé, M.I.A., and Sia. But underneath the fame, beats, and flamboyant stage persona is Wes Pentz — a relentlessly curious creator who built an empire not by chasing virality, but by leaning into failure, reinvention, and the grind.

In his wide-ranging conversation on the Finding Mastery podcast with high-performance psychologist Dr. Michael Gervais, Diplo opened up about creativity, fatherhood, psychedelics, and why staying curious is more important than chasing success.

🎛️ Curiosity is the Compass

Diplo’s artistic journey didn’t start in clubs — it began in the swamps of Florida, navigating small towns, odd jobs, and chaotic adolescence. Moving frequently as a kid (thanks to his father’s work), he developed a deep sense of independence and emotional intelligence. “I could just be dropped anywhere,” he said. “That was a gift I can’t teach.”

But the constant uprooting gave him something else too: an insatiable curiosity.

“I was always a student,” Diplo shared. “I want to explore. I want to see what people do. What people are.”

That explorer mindset led him from pumping gas and making sandwiches at Subway to anthropology studies at Temple University to producing one of the most iconic tracks of the 2000s — Paper Planes with M.I.A.

🌀 Reinvention Without Fear

What separates Diplo from the pack isn't just his versatility — it’s his willingness to start over.

“I’ve always found the freedom to just take a huge turn and never be afraid of it,” he said. “Some projects might work, some might not. But if you believe in your vision, you can make anything happen with music.”

This ability to take left turns — from EDM to dancehall to country — comes from a deep comfort with failure. He’s not precious about past success. He treats each new direction like a blank slate.

“Even today, take everything from me — I still feel like I can start over and build something.”

🎯 Why Mastery Isn’t the Goal

Despite decades at the top of the music industry, Diplo doesn’t consider himself a master. “I’ve never reached mastery. That’s the beauty of it,” he told Gervais. “My process is always happening. It’s never finished.”

He’s put in his 10,000 hours (and then some), but sees mastery as a moving target — not a title you earn, but a mindset you live in.

The way Diplo frames it, success is a trap if you define it by external metrics: views, likes, streams, status. “You can get caught in that algorithm. I did — and it didn’t make me happy,” he admitted. “Now I focus on being better. On making better art. That’s it.”

👨‍👦 Fatherhood, Psychedelics, and Staying Human

One of the most touching arcs of the conversation was Diplo reflecting on fatherhood. As someone who didn’t feel emotionally supported by his own dad, he’s determined to break the cycle:

“I want my kids to always feel like they’re enough. That they don’t need to do more to be more.”

Parenting, like music, has become part of his internal growth practice. It also fuels his commitment to staying grounded — despite the celebrity and chaos.

To stay open and centered, Diplo uses microdoses of psychedelics — not to escape, but to enhance his self-awareness. “It helps me connect with people. To be more myself with fans. To stay soft,” he said.

🧠 The Art of Staying in the Game

With over two decades in a notoriously fickle industry, Diplo attributes his longevity to two things:

1. Staying curious.

   “Inspiration is everywhere,” he says. Even in the algorithm, even in the weird corners of the internet.

2. Building the right team.

   “Art is business. 90% of it is logistics. You need people who believe in you and can help you do the things you’re not good at.”

But most of all, Diplo is proof that you don’t have to chase relevance if you stay in pursuit of something deeper — meaning, exploration, and creative truth.

Final Word to Creators

If you're a wantrepreneur or creator stuck between ideas, unsure of your next move, Diplo's story offers this reminder:

“You’re never going to win chasing other people’s success. But if you stay true, adapt, and keep working, you’ll create something the world didn’t know it needed.”