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Uncomfortable Conversations with Josh Szeps

"How Not to Feel Like a Failure (When Fame & Fortune Aren't Enough)" with TV Host Osher Günsberg

Uncomfortable Conversations with Josh Szeps

Josh Szeps

Education, Comedy, Comedy Interviews, Self-improvement, Society & Culture

4.5905 Ratings

🗓️ 21 July 2025

⏱️ 68 minutes

🧾️ Download transcript

Summary

How do you avoid the hamster wheel of hoping that your next success will deliver happiness? How do you escape mental ruts, anxious spirals and critical self-talk?

Osher is a superstar in Australia. He was the face of Australian Idol, The Masked Singer, The Bachelor and The Bachelorette. He also happens to have, as he politely calls it, "a different brain" -- a brain prone to depression, social anxiety, obsessive compulsion, psychosis and addiction. His podcast, Better Than Yesterday, discusses sanity, recovery, parenting, and what it means to grow older without growing rigid.

This episode is a recording of a Szeps Live stream which you can watch on YouTube or Substack if you wanna see Osh 'n' Josh's purdy faces.

And just a heads-up to stay across Uncomfortable Conversations in the next few months because, as we discuss in this episode, Josh is about to deliver some killer livestreamed celebrity content during an imminent Szeps Live around-the-world tour. If you've been putting off figuring out how to download the Substack app, do it now in one click and follow this show to keep abreast of what'll be a delightful tsunami of mind-expanding chats.

Osher’s new illustrated book about mental wellness is called "So What, Now What?

Watch this conversation on YouTube. And you’re missing out on our best ad-free content if you haven’t popped over to the Uncomfy Convos Substack page.

http://twitter.com/joshzepps

http://instagram.com/joshszeps/

http://tiktok.com/@uncomfyconversations

Transcript

Click on a timestamp to play from that location

0:00.0

Gide, humans.

0:04.3

Welcome to the safe space for dangerous ideas.

0:07.7

Boy, have we got a lot of stuff coming up.

0:10.1

We got some exciting things.

0:11.5

I tells you, I tells you that for nothing.

0:13.4

Not even a shekel do you need to pay to be told that we got some incredible stuff coming up.

0:18.8

So, look, just keep an eye on the

0:21.3

old, uh, uncomfortable conversations podcast feed. Don't, uh, don't go sleeping on it. Don't go snoozing. Don't be thinking, uh, you know, my life's busy. I got shit to do. Uh, I don't need to be paying attention to old Josh. Trust me. In the coming weeks and months, you want to be paying attention to the old Josh.

0:18.2

And I'm not going to badger you

0:19.6

about downloading the substack app

0:21.3

so you can stay abreast of everything we're doing. I'm not going to harangue about how you should subscribe at least to a free subscription so you know what's coming down the pike. I don't know what's saying to that. I'm just going to say, you know, keep an eye out. Just watch out for all the things that we allude to in this episode, briefly, albeit briefly.

1:00.7

It's a recording of a live stream that I did with Oshah Ginsberg, who is undeniably the most

1:06.9

successful television host in Australia. He hosted Australian Idol for many years. He hosted

1:13.2

the masked singer. He hosted the bachelor. He hosted the Bachelorette. He's, you know, like Ryan Seacrest,

1:19.4

but plus a lot of humanity. And he also has a podcast which makes him a more sort of philosophizing

1:25.7

person who noodles on what it means to live a good life.

1:28.4

So maybe Ryan Sequest mixed with Dax Shepard, so to speak.

1:33.0

Oshah has what he politely calls a different brain.

1:37.2

It's a brain that is prone to depression and social anxiety and obsessive compulsive disorder

1:43.2

and psychosis and addiction. That's what his podcast

1:47.8

wrestles with. It's called Better Than Yesterday. It's a great listen that talks not just about

1:52.3

mental health, but also about recovery and about parenting, what it means to grow older in a

...

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