Balancing the Grind with Chris Rollings, Founder of Dare Together

Chatting with Chris Rollings, the brain behind Dare Together, it’s clear he’s had quite the journey. From the creative hustle in London to a dream job at Google, and now running his own show in Byron Bay, Chris’ career is a mix of innovation, creativity, and a bit of adventure. He’s all about pushing the envelope, whether that’s in the boardroom or on a mountain bike trail.

In our talk, he dishes on how he keeps everything in check, from family time to keeping fit with his local dads’ group. He’s a fan of staying curious and recommends a daily dose of Stoic philosophy to keep things in perspective. For Chris, life’s about taking chances, enjoying the ride, and making sure fun’s always part of the equation.

Let’s start with your background! Can you share with us your career journey and what you’re currently up to?

Sure! I started in London, cutting my teeth in the creative and advertising industry as a creative producer, I got laid off during the GFC and used the opportunity to travel the world, ending up down under.

In Australia I helped startup R/GA Sydney which led to joining Google, where I led innovation projects where I became an expert in Human Centered Design Thinking, bringing together Google’s engineering teams with our priority clients to create innovative customer facing experiences. I also launched a product for Google that supports the world’s Indigenous languages.

I am now the founder of Dare Together, my own innovation, marketing and AI consultancy. I work with both startups and established brands to help them unlock the full potential of their products, programs and campaigns with a current focus on how to think ahead, leverage AI and in these exciting but turbulent times think the way a founder would to future proof your brand. 

We’d love to know what a typical day is like for you. Could you describe a recent workday?

When I’m not travelling with work my typical day starts by having my two weasels jump in bed to wake me up (Isabel 3 and Francesca 5) then make them breakfast, hustle them out the door for drop offs and work above a kombucha and gin factory in Mullumbimby. I’m normally found on a white board, a conference call or on a deck. If I have time I’ll sneak in a swim on the way home. 

Can you define work-life balance for yourself and share with us your approach in maintaining it?

First off, as much as I love and value my career I have always made the conscious decision to prioritise life. Which probably explains travelling the world, moving to Australia and more recently moving to Byron Bay to raise “outside kids”. So far it’s panned out ok! 

On a more practical level, I love downhill mountain biking and try to get out and ride most weeks. It’s a form of meditation and is a great way to clear my head and push my boundaries and appetite for risk. My sole focus is on where my front wheel is pointed and II feel great from the adrenaline and endorphins. The rest of my time is gobbled up by my wife and kids. 

Change is constant, and it’s essential for growth. Have you made any lifestyle changes in the past year to improve your work-life balance?

Well moving to the Byron Bay area was a big one! Covid taught us a lot of things, working and living anywhere being one of them. It took a bit of getting used to but going from a 2 bed apartment in Bondi to an off grid acreage property in the Byron Hinterland but we absolutely love our new life and the lifestyle that comes with it.

I also joined a men’s group, a group of dad’s that get together every Thursday morning at sunrise to do circuit training on the beach and that was a great way to get back into exercise and build a local network with like minded people going through a similar life stage. 

We’re always on the lookout for new resources! Can you recommend any books, podcasts, or newsletters that have helped you in your journey towards balance?

I’m an avid reader of the Medium Daily Digest and if I had to pick one book it would be The Daily Stoic. Every page marks a day of the year with a quote from the world’s greatest philosophers and I traded rolling over and looking at my phone while reading a page from this book and digesting it over breakfast. It’s ancient wisdom but strangely couldn’t be more relevant today. 

Before we wrap up, do you have any final words of wisdom or insights on work, life, or balance that you’d like to share with our readers?

Work / get paid to do what you’re naturally good at and love doing and when you hear that little voice inside your head that pushes you to take a risk or do something out of your comfort zone, back yourself and go for it.

Life / Do things that push you outside your comfort zone, that make you feel alive, that get you outside and that most importantly makes the most out of the time you have with your friends and loved ones. 

Balance / Prioritise fun both in work and in life, we’re here for a good time not a long time, and good things happen to fun people.

About Author

Hey there! I'm Hao, the Editor-in-Chief at Balance the Grind. We’re on a mission to showcase healthy work-life balance through interesting stories from people all over the world, in different careers and lifestyles.