My business pivot failed

Rebuilding Chillpreneur: Why I’m Choosing a Lifestyle-First Business (Again)

After stepping away, pivoting, and trying something completely different, I’m officially rebuilding Chillpreneur and this time, it’s more aligned than ever.

This post is the beginning of a new chapter. One rooted in ease, fun, lifestyle, and building a business that actually fits the person running it.

What Chillpreneur Has Always Been About

At its core, Chillpreneur was never about hustling harder or building a business that consumes your life. It has always been about:

  • Building a lifestyle-first business

  • Making marketing, content, and sales feel easy and natural

  • Designing systems that align with your most authentic self

  • Creating income in a way that supports your life — not the other way around

For me, that authenticity looks like spending time with friends, surfing, skating, creating, and letting life inspire the business — not being trapped inside it.

Why My Business Pivot Didn’t Work

Over the last year, I stepped into a completely different career direction. I ran a physical content studio, worked in production, managed large projects, and tried a much more hands-on, high-pressure way of working.

While I’m deeply grateful for what that chapter taught me, the truth is simple:
It wasn’t how I’m built to work.

Running a physical business with high overheads, constant logistics, and being “on” all the time pulled me away from what I value most — freedom, creativity, and flexibility.

Trying something new wasn’t a mistake. It was necessary clarity.

The Lifestyle Shift That Changed Everything

After a challenging year personally and professionally, my partner and I made a big decision — we moved from Melbourne to Queensland.

That move changed everything.

Living by the beach, slowing down, picking up surfing, and reconnecting with myself reminded me just how deeply ingrained the Chillpreneur philosophy is in who I am. I didn’t just teach lifestyle-first business — I lived it, and I missed it.

Sometimes you don’t realise what you’ve built until you step away from it.

What Rebuilding Chillpreneur Looks Like Now

This new era of Chillpreneur isn’t about “building in public” for the sake of it. It’s about documenting life as it actually is:

  • Rebuilding a business you once closed

  • Exploring new hobbies and identities in your 30s

  • Creating content that feels fun again

  • Letting lifestyle lead, and business follow

Chillpreneur is returning as a philosophy, a way of being, and a reminder that success doesn’t have to feel heavy to be sustainable.

The Chillpreneur Diaries: A New Series

This blog post (and the video that inspired it) marks the start of The Chillpreneur Diaries — a long-form series where I’ll be sharing the behind-the-scenes of rebuilding my business, my lifestyle, and myself.

No hustle culture.
No forced strategies.
Just real life, aligned work, and building something that feels good.

If you’ve ever felt called to step away, pivot, or rebuild in a way that honours who you’re becoming you’re in the right place.

Erin Henry