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The Light Watkins Show

294: How to Know When It’s Time to Let Go: Sean Hoess on Building Wanderlust, Burning Out, and Starting Over

The Light Watkins Show

Light Watkins

Self-improvement, Religion & Spirituality, Society & Culture, Education

4.9960 Ratings

🗓️ 5 June 2025

⏱️ 84 minutes

🧾️ Download transcript

Summary

In this episode, Light Watkins sits down with Sean Hoess, co-founder of Wanderlust—the global wellness festival that once redefined how people experienced yoga, music, and community. Sean shares his winding journey from burnt-out New York City lawyer to record label co-founder, and eventually to the unlikely creator of a worldwide movement focused on mindfulness and well-being. But what happens when your dream job starts to feel like just another grind? Sean gets real about the pressures of s...

Transcript

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0:00.0

2019 was an extremely tough year and it was all about like trying to restructure and it was super

0:09.0

painful and we had to let a bunch of people go and tried to refocus on what I sort of saw as like

0:14.5

what's the magic the magic is these festivals right and a few of them so we were going to come back

0:19.4

in 2020 with a i suppose it was a vision that

0:22.6

was much more pure and close to what the original 2012-2013 version of wanderless would have been

0:29.4

and then i've had this final moment of like i had found new investors the thing was coming around

0:35.7

to being a stable vision of what I think at least

0:38.7

living up to that integrity and the values and the authenticity that I think we always wanted

0:43.0

to have it. And then COVID happened. Sort of like a one-two punch. And man, that was, I guess,

0:49.8

different for me because it was like, whoa, this isn't in my control at all. There's nothing

0:55.8

I can do about this. There's like a virus sweeping the world. We can't gather. No one can gather.

1:02.5

And the brakes just got slammed on by the world. I felt like it was the first time in 20 years,

1:06.9

I was forced to stop and consider what the hell that I'm doing with my life and why I'm actually here.

1:14.8

Because the rest of it had just been kind of like entrepreneurial like go go.

1:18.9

And of course in service the causes that were I still deeply believe in.

1:22.9

And I think we're really good for humanity.

1:25.1

But still just go, go, go.

1:29.0

And then stop.

1:30.0

Stop.

1:38.0

Most people chase success thinking that it's going to make them feel fulfilled inside.

1:42.4

Sean Hess actually reached success more than once,

1:46.0

and each time it left them feeling more and more disconnected.

...

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