Lessons From the Inflatable Bouncy Castle of Life (and Other Things I Learned from Chris Webb)

I didn’t really want to start a podcast.

No, really!

Not because I don’t love talking to people (I do) or have something to say (arguably too much). But because the world probably doesn’t need another 40-something man sitting at a microphone trying to solve everyone else's problems.

Yet here we are – and I’m already so glad we are. Because the first episode of Toby Martin’s Happy Place reminded me that we do need to talk about this stuff. Especially with people like Chris Webb.

Chris is an estate agency consultant. No, the estate agency consultant – a bit of a powerhouse in the property industry, and an Olympic-grade competitor when it comes to inflatable obstacle courses (don’t ask). But behind the carefully curated social media presence – which he openly acknowledges – is someone who’s thought deeply about what happiness means, how to create it, and why it’s sometimes really bloody hard to hang onto.

So, what did I learn from spending an hour in Chris’s happy place (spoiler: it smells like fruity ice cream)?

1. Authenticity takes practice.

Chris was honest about the fact that, for a long time, he felt pressure to present a polished version of himself online – all shiny wins and airbrushed success. But these days, he’s leaning into being real. Not for attention, not for applause, but because it just feels better.

“Some things are great, some things are terrible. And that’s fine.”

Lesson? You don’t have to share every scar to be authentic. But letting people see the cracks can actually help you feel more whole.

2. Comparison really is the thief of joy.

One of my favourite moments was when Chris talked about no longer letting someone else’s progress make him feel like he’s falling behind. It’s such a common trap – especially when social media gives us front-row seats to everyone else’s highlight reel.

Instead, he now approaches success as a shared experience, not a zero-sum game.

“Them doing better has no regard on me in any way… we can all take a step forward and that’s okay.”

Note to self: the only race worth running is the one you actually want to be in.

3. You can’t be happy if you don’t know what makes you happy.

Chris has done the work. He’s figured out his “happy ingredients”: helping people, meeting people, and travelling. If those things are on the menu, he’s probably in a good place.

That clarity didn’t come from a motivational meme. It came from reflecting on the low moments and asking: what do I actually love doing?

If you don’t know what lights you up – take the time to figure it out. It’s the difference between coasting and creating.

4. Movement matters.

We touched on how easy it is to let your day be swallowed by desk time, but Chris has built non-negotiable movement into his routine – walks, workouts, anything that gets him out of his head and into his body.

“You are the most important thing in your business – look after yourself first.”

And yes, he listens to audiobooks Monday to Thursday and podcasts on Fridays. The man even schedules his light relief. Iconic.

5. Don’t overthink it – just invite the bloody people.

Whether it’s launching a podcast, inviting someone to join your Facebook group, or taking your first stab at something new – Chris reminded me how easy it is to talk ourselves out of action. We build these big mental monsters when actually... it’s just a click.

“I don’t overthink things anymore. I just get on with it.”

I’m trying that this week. Feel free to hold me accountable.

Final thought:

I asked Chris to leave us with a note of encouragement. What he said hit me like a slap and a hug at the same time:

“No one’s thinking about you. They’re thinking about themselves. So do what you want. Start the podcast. Go on the trip. Live the life. No one’s stopping you but you.”

Mic. Drop.

Thanks for joining me in my happy place. Go check out the full episode with Chris Webb wherever you get your podcasts – and if it made you think, smile, or belt out Bon Jovi in your car, do let me know.

We’re just getting started.

— Toby