From Scaredy Cat to Summit: Jenny Milton's Journey to Fearless Leadership
What extreme sports taught one woman about courage, confidence, and creating your own path in male-dominated spaces
Picture this: You're standing at the top of an Alaskan mountain. The helicopter that brought you here has flown away. The slope below is steeper than anything you imagined. Your heart is racing. Your hands are shaking.
And there's absolutely no turning back.
This was Jenny "Adrenajen" Milton's reality on her 30th birthday a moment that would become a defining lesson in what it really means to face fear and come out stronger on the other side.
On a recent episode of Rooted in Your Confidence, I sat down with Jenny, a professional snow kiter, kite surfer, keynote speaker, and author, to talk about courage, resilience, and what it takes for women to thrive in spaces that weren't designed for us.
Her story? It's not what you'd expect.
The Scaredy Cat Who Became a Champion
Jenny wasn't born fearless. In fact, she was the opposite.
While her brother naturally excelled at every sport, Jenny was the kid crying on the chairlift, terrified of heights. She was the last child on her street to ride a bike without training wheels her father literally ran behind her, holding her seat while she screamed.
"I was always scared," Jenny told me, her Australian accent warm and genuine. "It never came naturally to me."
So how did this self-described scaredy cat become a professional athlete who navigates avalanche terrain in Alaska, represents Australia in downhill mountain biking, and teaches others about courage?
The answer lies in a childhood tragedy that changed everything.
When Cancer Changed the Game
At age 11, Jenny's world shifted.
Her nine-year-old brother was diagnosed with bone cancer. The prognosis was grim. The treatment was brutal.
And ultimately, he lost his leg.
But he didn't lose his spirit.
Jenny's parents owned a sports store—it's how she and her brother grew up trying every extreme sport imaginable. After her brother's amputation, the family didn't just adapt.
They innovated.
"Every sport that came in, we had to learn how to adapt the equipment so my brother could do it too," Jenny explained.
Her dad built a waterproof prosthetic leg out of PVC pipe so her brother could windsurf. The family learned to ski with him on one leg.
And here's the kicker: her brother didn't just participate. He excelled.
He became a Paralympic champion. A world record holder. The fastest man to run a marathon with crutches. He skied at 135 miles per hour on one leg.
"My brother really showed us bravery, resilience, and that there are no excuses."
"If he could overcome his fear and do this sport on one leg, well, I needed to find my courage and do it anyway."
Living in a Champion's Shadow
But there was a cost to having a superstar sibling.
For years, Jenny was known simply as "Michael Milton's sister." Every achievement was overshadowed. Every introduction led back to him.
If this sounds familiar, you're not alone.
Many women in male-dominated industries know what it's like to be defined by someone else—whether it's a more vocal colleague, a mentor who gets the credit, or simply being "the woman on the team" rather than being seen as an individual contributor.
Jenny's solution was brilliant: she chose different sports.
When her brother ski raced, she did freestyle skiing. When he windsurfed, she kite surfing. She created her own lane where she could stand out and be recognized for her unique talents.
"I think if we can find a unique path, then we can stand out," she told me. "In sport, in business, we can really stand out and hold our own."
When you can't compete on the same playing field, create your own game.
Women in Male-Dominated Industries: The Boys Trip That Changed Everything
Fast forward to Jenny's 30th birthday.
Her extreme sports retail business was thriving, and she was in Las Vegas for a trade show—one of the few female business owners in a sea of men.
At the hotel bar one evening, she overheard a group of Australian businessmen planning a heli-skiing trip to Alaska.
"Can I come with you guys?" she asked.
The response?
"No, Jen, this is a boys trip. Besides, our wives would kill us if they knew there was a girl coming."
But Jenny persisted. When someone dropped out at the last minute, one of the men approached her: "Are you serious? Do you really want to go?"
She was in.
Here's where it gets interesting: When they arrived at the heli-ski resort, the nine men told the guides they didn't want to ride with her. They wanted her in a different group.
Sometimes rejection is just redirection.
That rejection became her greatest opportunity.
Jenny was placed with Jerry, the lead guide—the top expert who opened up mountains and checked them for avalanches. While her male colleagues waited their turn, Jenny got to board the first helicopter each morning and wave goodbye.
The Moment That Defines Courage
Standing atop that first Alaskan peak, Jenny experienced what so many of us feel when opportunity meets fear.
"I was just in awe of the view," she recalled. "Wow, look where I'm standing. I'm on top of the world."
Then Jerry said, "Okay, everybody put your gear on."
And instantly, everything shifted.
"Oh my gosh, be careful what you wish for because it might just happen," Jenny thought. "How am I going to get down this mountain that looks way steeper than I ever imagined?"
The what-ifs flooded in:
What if I fall?
What if there's an avalanche?
What if I need rescue?
What if I'm not good enough?
Sound familiar?
How many times have we stood at the edge of an opportunity—qualified, prepared, ready—yet paralyzed by those same questions?
Three, Two, One, Go
Jenny strapped on her gear. The helicopter flew away.
There was no turning back.
Then she heard Jerry's voice on the radio: "Okay, Jen, your turn. I'm gonna count you in. Three, two, one, go."
She took a deep breath and dropped into the mountain.
After a couple of cautious, shaky turns, she went head over heels—tumbling in the snow, one of her worst-case scenarios playing out in real time.
But here's what happened next: she landed back on her feet and kept riding.
"If I'd been a skier, all my skis would have flown off," she said. "But because I was snowboarding, it stayed on. And because I was into sport, I had good balance."
When she reached the bottom, the men were cheering. Maybe they thought she'd done it on purpose—some Australian trick.
Jenny came to a stop and burst into tears.
"These were tears of fear. These were tears of accomplishment, of being so proud of myself, of being so scared and doing it anyway."
"And even when something went wrong, having the skills to continue."
Leadership Lessons From Extreme Sports: Why Women Make Mountains Safer (And Boardrooms Better)
During her avalanche training, Jenny learned a statistic that every woman in leadership should know:
Groups with women are statistically less likely to be caught in avalanches.
Why?
Because women tend to be more observant. More likely to check weather reports. More willing to point out red flags that men might overlook in their eagerness to "just go for it."
"A woman can bring a really unique perspective," Jenny explained. "We might point out that there was an avalanche on that other mountain on the same aspect. We might notice the temperature has changed since yesterday. That's two red flags."
This is why heli-ski operations make sure to have female guides. That perspective saves lives.
And it's why diverse leadership teams make better decisions. Why companies with women in senior roles show better risk management. Why your voice—even when it's the minority opinion—has strategic value.
Our caution isn't weakness. It's survival intelligence.
Our different perspective isn't a limitation. It's a competitive advantage.
Confidence Through Courage: The Framework—Ready, Mindset, Go
Jenny teaches a three-step framework based on that countdown on the mountain:
Ready
Make the decision. No more fence-sitting.
You want that promotion. That project. That opportunity. You're ready.
Mindset
What mindset do you need to achieve that goal? Jenny has a whole collection:
The Skydiver Mindset: Just jump, even if you're scared
The MacGyver Mindset: Adapt and innovate with what you have
The Mountain Climber Mindset: Slow and steady, step by step
"Knowledge builds confidence," Jenny said. "Empower yourself with the skills and information you need."
Go
Take action. Let the adrenaline pump. Find your courage.
Go scared. Go anyway.
"Just go forward and make that move, girl, because you've got this," Jenny said with the kind of conviction that makes you believe her.
The Truth About Being Fearless
Here's something Jenny said that stopped me in my tracks:
"When people use the word fearless, I'm not a big fan of that word. Because if we are fearless, we'll put ourselves in danger. It's not a safe place to be."
She's right. Fear serves a purpose.
It makes us observant. It activates our adrenaline, which is actually a superpower:
Our eyesight gets better
We become stronger
We're able to focus more intensely
The progression is simple:
Fear is the problem
Courage and adrenaline are the solution
Confidence is the reward
"You can't have courage without adrenaline."
"And you can't just take a pill or eat something and make yourself confident. Confidence is the reward we get. The more times you overcome your fear and find that courage, the more confidence you get."
What It Means to Be Rooted
When I asked Jenny what it means to be "rooted in confidence," her answer was perfect:
"I think of a tree. A tree needs to have strong roots in order to not be blown over and to grow. Confidence is something we all want, but we can't just instantly have it. The more times you overcome your fear and find that courage, the more confidence you get. And then you become grounded and rooted, and you can use that confidence in so many other areas in your life."
Those roots develop each time you face fear and discover you can handle it.
They ground you. They stabilize you for the next challenge.
The Invitation
Jenny's story isn't just about sports—it's a reflection of what every woman faces when she's the only one in the room.
Her journey from scaredy cat to champion reminds us of something crucial:
Your fear doesn't disqualify you. Your different approach isn't a disadvantage. Your measured perspective isn't weakness.
Women don't need to toughen up or play the game like everyone else. We need to trust our own strategy—and own the power in how we lead.
We need to recognize that our unique perspective—the way we see red flags, ask different questions, and insist on preparation—makes everything we touch safer, smarter, and more successful.
The mountains are waiting. The boardrooms are waiting. The opportunities are waiting.
There's a helicopter ready to take you to the top. The question isn't whether you'll be afraid when you get there.
The question is: will you go anyway?
Connect With Jenny
Want to learn more about Jenny Milton's work or experience a women's adventure camp in Alaska?
Website: Adrenogen.com
Instagram: @adrenogen
Children's Books: Gale and the Red Kite of Courage and Gale and the Wind Warriors
Jenny is also available for keynote speaking on leadership, resilience, and turning fear into fuel.
Your Turn
You know that moment—the countdown before the leap. We've all had one.
What's your "three, two, one, go" story?
What mountain are you standing on top of right now, trying to decide if you'll take that first turn?
Drop a comment below or share this post with a woman who needs to hear it today. Sometimes knowing someone else made it down the mountain is exactly the push we need to begin our own descent.
Ready? What's the key? Mindset. Now what? Go.
This story is part of the Rooted in Your Confidence series, where women redefining leadership share what it means to stay, thrive, and lead with truth. This blog post is based on Episode 2, Session 2 of the Rooted in Your Confidence podcast. Listen to the full conversation with Jenny Milton [link to episode] for even more insights on courage, leadership, and creating your own path.
