Is there a version of you that feels unattainable? For David Gerard, it was becoming a full-time magician. So he did it slowly. Twelve years slowly. VP at Sequoia-backed startups during the day, performing shows at night, catching 3 AM flights from Kansas back to his job. The double life was the bridge. He built the thing he actually wanted one night at a time while keeping the safe life going, until the gap closed enough to jump.

And the magic wasn't the only thing he was keeping hidden. David buried his mental health struggles for decades. When he finally started talking about it, he did the same thing. Told one therapist. Then 20 people. Then 50. Then 100. He calls it "opening the aperture of fear slowly." It became his approach for everything. Not one dramatic leap. Just a longer, quieter path toward his authentic self.

Now, he’s directed the #1 rated show in Las Vegas, has consulted for America's Got Talent for four seasons, performs 100+ nights a year for companies like Google, coaches executives on presence, and runs men's groups. He talks about switching from “gasoline” to “solar” as a fuel source, choosing 1,000 real relationships over hundreds of thousands of followers, and why the secrets you keep are the ones that cost you the most. He also reads Connor's mind at the end. Just stay for that part.

Chapters

00:00:00 Intro — Magic as armor, authenticity as freedom
00:01:26 From external validation to internal fuel
00:04:00 The 12-year runway — Marketing by day, magic by night
00:06:34 Breaking the container — The Dunkin' moment
00:07:43 Creating awe for a living — The magician's mindset
00:08:52 Relationships over reach — Building a career without fame
00:10:13 Fear as a compass — Micro-dosing on authenticity
00:12:56 Magic became armor — Pennsylvania in the early 90s
00:15:24 Practice enables presence — The subconscious mind
00:16:06 TGIF at Google — The American Idol of leadership
00:18:30 Red, yellow, green — The simplest coaching tool
00:23:09 The spiritual practice — Meditation and men's work
00:31:18 The career transition — From stage to facilitation
00:34:55 Magical moments keep coming — The Tetris game of life
00:48:56 Assumptions and repositioning — The magician as marketer
00:45:42 Feedback as fuel — Taking notes from people you want to become
00:54:24 Borrowing confidence — Faith from others when you don't have it
00:56:16 Resources for the journey — Books and practices that matter
00:58:08 The magic trick — A coincidence you won't believe

IS THIS WORKING?!

What if the most interesting thing about work isn't what we do—but what it does to us?

Is This Working?! is about meaningful work and the messy humans who do it. Host Connor Diemand-Yauman talks to the leaders, builders, and creatives navigating the chaos through the moments they question everything and show up anyway.

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