We’re halfway through Season 5, so this week it’s just me: no guest, no script, and fresh out of a therapy session. I’m talking about something that’s been quietly holding me back since I started building She Who Dares Wins full-time, and that’s uncertainty.

I spent years on construction sites where things went wrong every day, and I thrived on it. But it turns out that handling uncertainty on a job site is very different from handling it when it’s tied to you, your achievements and the thing you’re building. In this episode I share how that showed up for me. I kept going back and forth on the clothing line because I’d told myself it would be the “stable income”. I kept reaching for a Plan B, and I fell into exhausting loops of going back to things I didn’t really want to do.

I won’t pretend there are three easy steps to fix it, because there aren’t. What I can share is what’s helping: slowing down, checking why I’m making a decision, and learning to trust myself when things go wrong. And if you take one thing from this episode: the incredible women who sit on the sofa didn’t have it all figured out either. You’re not alone.

In this episode

• What’s new at She Who Dares Wins: the film production side and the launch of Dare Club
• Our first Dare: a cold-water dip and sauna challenge (coming soon to YouTube)
• Why a career in engineering didn’t prepare me for uncertainty in my own business
• ADHD, high stakes, and the flip side nobody talks about: paralysis and second-guessing
• The clothing line, Plan Bs, and confusing “certainty” with what I actually want
• Why trying to fix uncertainty is impossible, and why knowing you’re sensitive to it helps
• Slowing down and asking: am I doing this out of fear, or for the right reasons?
• How many of us give up on a new career too soon because of that horrible feeling
• What every guest’s story has in common: you get through it, with a win or a lesson

Key takeaways

• Uncertainty in business is unavoidable and will always feel uncomfortable. The aim is to get used to the feeling, not to make it go away.
• Notice when a decision is really an attempt to create certainty rather than something that fits what you want.
• Building trust with yourself, and accepting that things will go wrong, takes a lot of the pressure off.
• Sometimes understanding why something shows up is enough, without needing to fix it.

Join Dare Club

Dare Club is our new community that gets women out of their comfort zones, with a Dare series on YouTube and in-person events planned for 2027. Sign up at www.shewhodareswins.com to get the weekly newsletter every Wednesday, with a mini dare and a few things that brought me joy that week.

Watch on YouTube

Every episode is also on YouTube. Search She Who Dares Wins Podcast to see the conversations in full.

Coming up

A wonderful guest next week, more fabulous guests to finish Season 5, and then we start shooting Season 6!

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In this episode of She Who Dares Wiggles, I'm joined by Stephanie, Olympic marathon runner, one-to-one run coach and mum. She never dreamed of the Olympics, but after a marathon ballot she expected to lose, a pandemic and a run of injuries, she ended up on the start line in Tokyo. We talk about the races, the setbacks, and why starting her own business may have been the bigger dare.

Timestamps

0:00 From Hedge Fund Admin to Olympic Marathoner

1:35 The Biggest Dare: Starting a Coaching Business

3:24 Early Athletic Roots and School Sports

8:02 The Berlin Marathon Ballot That Changed Everything

12:34 Chasing the Olympic Qualifying Standard

15:09 Valencia: A High-Stakes Olympic Qualifier

24:21 The Olympic Trials at Kew Gardens

39:10 Running the Olympics with a Fractured Shin

💬 KEY TAKEAWAYS - You don't need a big dream to end up somewhere extraordinary. Small steps add up. - You won't tick off every training session, and that's okay. Flexibility beats perfection. - Get a diagnosis, make a plan, and use cross-training to stay fit through injury. - Stand in your value when you start something new. Prices can rise without losing clients. - Accountability helps: bring a friend along to the thing you've been putting off.

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This week on She Who Dares Wins, I'm joined by Squash: adventurer, speaker and high-performance coach.

Squash grew up on a farm planning to be a vet, until a ski season, a view of Mont Blanc and a group of adventure-racing friends changed everything. We talk about how she bluffed her way into BBC and BMW backing to become the first British woman to paraglide off the summit of Mont Blanc, and what happened when she reached the top of Everest without doing what she'd set out to do.

Then she gets honest about becoming a mum, the years that tested her most, and the simple tools that carried her through: breath, routine, the right people and one small next step.

If you've ever felt you should be coping better, or you're waiting to see the whole path before you begin, this conversation is for you.

KEY TAKEAWAYS

- When you can't see the way, find one more step, and do it on repeat

- A "failure" can still be the best story you tell

- "And" is more useful than "but": you can be grateful and struggling at once

- Other people often see your strengths before you do

- Growth comes from discomfort, so say thank you to it

- Small basics (breath, sleep, movement, a routine) hold up the big things

IN THIS EPISODE

0:00 Welcome and the story behind the name "Squash"

1:14 Growing up on a farm and unconditional love

3:02 From farmer to future vet

5:34 The cow that changed her mind

6:59 A ski season and a view of Mont Blanc

10:34 Hitting the wall: "find one more step"

13:00 When did you last do something for the first time?

16:02 Nothing is ever wasted

19:39 Three dreams, one wild plan

22:57 Bluffing the BBC and BMW

24:10 Taking off from the top of Mont Blanc

28:05 "They don't make stuff up"

30:00 GoPro, debt and the Everest "failure"

33:57 Summit day and the way down

38:59 Public speaking and the energy before a talk

44:24 Motherhood: the part nobody posts about

46:25 Simple daily practices that actually work

50:25 The breath that changes everything

52:54 "If your knickers are right, your day goes right"

59:25 When things fall apart, they're falling together

1:04:04 The dare: leave everyone a gift

QUOTES FROM THE EPISODE

"The only thing you've got to do is find one more step and do it on repeat."

"When you think you're done, you're nowhere near done."

"If your knickers are right, your day goes right."

THE DARE

Squash's challenge to you: leave everyone you meet a little better than you found them, and have the one brave conversation you've been putting off.

MENTIONED IN THIS EPISODE

- Mont Blanc and Mount Everest

- The BBC, BMW and GoPro, who backed her early expeditions

- The Salomon 36-hour adventure race

- The Obstacle Is the Way (the book I mention, by Ryan Holiday)

CONNECT WITH THE SHOW

www.shewhodareswins.com

Join Dare club: Here

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If this episode helped you, send it to someone who needs a reminder that they're stronger than they think. A rating or review helps more women find the show.

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