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Di Westaway: from ‘mid-wife crisis’ to woman on top of the world

Di Westaway: from ‘mid-wife crisis’ to woman on top of the world

Sixteen years ago, Di was a tired, wrung-out working mother-of-three trapped in an unhappy marriage.

BY Business Chicks, 10 min READ

Premium member Di Westaway is one of the wildest women we know, but 16 years ago, she nearly lost it.

She was a tired, wrung-out working mother-of-three fighting forty. Out of the blue, her friend’s personal trainer invited her to climb an extreme mountain in Argentina. She took the leap, and it completely transformed her life.

“I chose this wild adventure to escape my miserable life. I hoped it would get me fit and happy again. But little did I know it would transform my life,” Di says.

“I failed to reach the top of Mt Aconcagua on that first adventure, but I learned how to manage stress and turn obstacles into opportunities, as well as how to wee into a zip-lock bag, among other, similarly important, survival skills.”

Fast forward to 2017, Di is a world-record holder and CEO of a social enterprise that has raised nearly $20 million for charity. Her Wild Women On Top movement has transformed the lives of millions around the world. Di inspires and empowers women to get outdoors, experience nature and improve their mental and physical health through shared hiking adventures. Coastrek, also founded by Di, has inspired nearly 25,000 trekkers, mostly women, and raised nearly $20m for The Fred Hollows Foundation.

Di has also been recognised as a NSW finalist in the 2017 Telstra Business Women’s Awards in the For Purpose and Social Enterprise category. We spoke to her ahead of the awards night next week to reflect on her success and find out what’s next for this adventure junkie.

What did you want to be when you were younger?

I wanted to be an Olympic gymnast, and then an acrobatic dancer. Now when I grow up, I want to be a kick-arse rock climber.

What inspired you to climb Mt Aconcagua in Argentina?

It was more about desperation than inspiration, but I climbed Mt Aconcagua to escape my mid-wife crisis. I was on the guilty working mum treadmill in a dysfunctional relationship, and this extreme adventure gave me hope.

How did this decision affect your life as you knew it at the time?

I went from miserable to marvellous, when I realised that having a compelling adventure with friends was enough to chase the blues away and keep me wildly happy, despite leading a very busy life in a very busted relationship.

Tell us about your social enterprise, Wild Women on Top.

Wild Women On Top inspires and empowers women to lead adventurous lives they love. We get women off the couch and into nature with their friends and help them be ‘heroes’ again. Our Coastrek adventurous journey teaches women how to prioritise their health and happiness as a way of becoming better mums and happier humans.

Why do you think Coastrek been such a success?

Coastrek is a winner because it connects women with their feminine powers while removing the guilt they feel when having fun. By inspiring and empowering women to go hiking with friends for charity, Coastrek makes women feel good about themselves.
It rejuvenates and re-energises us, so we tell our friends about it, and it spreads. It’s the winning combination of Wild Women On Top energy, stunning coastal tracks, treats and trails as well as a feel-good cause that transforms millions of lives through The Fred Hollows Foundation.

I am also an ‘Energizer bunny’ who’s good at finding kindred spirits and supporting them to lead. I believe in lifting others up, and I always try to recruit people smarter than me. I’m a planner and a dreamer and I never, never, never give up.

What has been the hardest lesson you’ve learned along the way?

The hardest lessons come from learning to lead. This requires more empathy than I was born with, and I’m constantly learning about what makes women tick.  I’ve learned to see feedback as fertiliser for growth, and I try hard every day to help others manage stress better.  I’ve used lessons from extreme adventure to help me overcome daily life challenges including a traumatic divorce and business partnership challenges. But I know that together we achieve more, and I’m passionate about building strong teams.

What’s the best thing about what you do?

I feel very lucky to have found my passion and purpose while I’m still young enough to make a difference. Every day I get to help women step into their feminine powers by leading adventurous lives they love. I get to leap outside my comfort zone in life and business, and this makes life both challenging and fulfilling.

How important is mental health and self-care to you as an entrepreneur?

Mental health comes from self-care and without it, your ability to make a difference is limited. I am a Chief Adventure Chick leading a social enterprise and to be authentic, it’s essential for me to live the brand. That means daily movement outdoors, a bit of puffing and regular micro-hiking adventures. But the great thing about hiking is that it’s fitness, fun, friends, and family all rolled into one beautiful ball, so that makes it super efficient. I also often have ‘walkie-talkies’ with friends in nature to brainstorm issues and have tough conversations. It’s a win win win.

What would you say to anyone who is struggling in life and thinking about making a change?

Just do it! You’ll discover you’re much stronger than you ever imagined and that you’re excited and energised by the journey. But don’t be afraid to ask for help and don’t do it alone. The first lesson Emma Isaacs taught me was to find the right buddy for business, and it’s is the same in life.

How did you find the process of applying for a Telstra Business Women’s Award? We’ve heard it’s tough!

Applying for the Telstra Business Awards is a trek, but it’s soooooo worth it. You’re forced to reflect on your journey and to focus on what you’ve achieved. For a futurist like me, that’s something I would never otherwise do – I’m so busy planning the next adventure that I don’t stop to reflect on the last one, but reflection is good for us.

What did you learn from that process about yourself and your business?

I learned that personal stories and numbers matter, and that you need both if you want to capture and share your achievements.
I realised that getting 25,000 people, mostly women, hiking for health and raising nearly $20 million for charity is something to be truly proud of and a big deal!

Why did you first join Business Chicks?

I met Emma Isaacs in the early days of my business about 12 years ago, and she blew me away. Her deep understanding of human nature and how to support women in their goals and dreams was remarkable. I went to a speed networking event and have been hooked ever since.

What do you love about Business Chicks?

Business Chicks is awesome because it inspires and empowers women to achieve their potential, to step up and support each other so that together we can really make a difference in life and business. The culture that Emma Isaacs has developed is truly magic, and I am in awe of her ability to reach out so effectively. She and Business Chicks have been a game-changer for me.

What are your bold goals for the future?

I want to reach out to millions of women globally to inspire and empower them to lead adventurous lives they love. This means learning how to use digital to build local communities of women who support each other to get active.

connect  Connect with Di here, and follow her on Instagram and Twitter.


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