S4: EP30 Rediscovering Yourself Through the Outdoors: A Journey of Healing and Growth

Let’s talk about rediscovery. You know, those moments when life kicks you down a path you never expected and leaves you wondering, what now? That’s where Anna Bailey found herself at 30, newly single after 13 years in a relationship. A breakup and a global lockdown? It’s the stuff that forces you to take a long, hard look in the mirror and ask, who am I really?

And Anna did just that. But instead of spiraling into despair, she turned to the one place that had all the answers—the great outdoors. It wasn’t about becoming some hardcore adventurer overnight, either. It was about taking those small steps out of her comfort zone, facing her fears, and finding a version of herself that she hadn’t even known existed.

Lesson #1: Small Steps Lead to Big Growth

The best part about Anna’s journey is how relatable it is. She didn’t start with some grand, mountaintop vision of herself; she started small. Her first steps into nature were familiar trails she had walked before with her brother. But each step, each hike, made her realize, I can do this. And isn’t that how it always works? You don’t wake up one day suddenly feeling ready to tackle the big stuff—you build confidence, bit by bit.

At first, she was scared. The idea of hiking alone? Terrifying. And let’s be honest, we’ve all been there. That voice in your head saying, you’re going to fail, you’re going to get hurt, you don’t belong out here. But the magic happens when you push through that noise, overpack your bag (just in case), and take that step anyway.

Anna packed everything she could think of, from raincoats to supplies for a freak snowstorm in July. Sure, it might have been a little over-the-top, but it was exactly what she needed to feel safe. And in the end, feeling prepared is what let her truly enjoy the experience.

Lesson #2: You Don’t Have to Do It Alone

The journey to self-discovery can be a lonely one, but it doesn’t have to be. Anna found her people through Instagram—women who got it, who shared her passion for nature and the confidence it brings. She connected with a community of hikers and adventurers that reminded her she wasn’t doing this alone.

She even started leading group hikes, despite being terrified every time. But that’s the thing about fear—it doesn’t go away, but we can learn to work with it. And there’s something powerful about being with people who lift you up, even when you’re scared.

Finding her tribe didn’t just make the hikes easier—it made the experience richer. There’s nothing like swapping stories with people who get you, who know the thrill of pushing your limits, even if it’s just a few steps outside your front door.

Lesson #3: It’s Okay to Turn Back, but It’s Not Okay to Stay Stuck

One of the biggest lessons Anna’s learned? You don’t have to be fearless, but you do have to be brave. Sometimes that means packing extra supplies, sharing your location with someone before you go out, or even turning back when things don’t feel right.

And there’s nothing wrong with turning back. It’s about knowing your limits and being smart about your adventures. As Anna says, “Worst case scenario, I’ve always known I can turn back.” But the point is that she went in the first place. She didn’t let the fear of failure keep her stuck.

That’s a life lesson right there, isn’t it? Whether it’s starting a new hobby, leaving a relationship, or hiking a mountain, we often get so paralyzed by the fear of failure that we never even take the first step. But as Anna shows us, you don’t have to go all the way to succeed. The success is in going.

Lesson #4: Nature Heals in Ways You Can’t Predict

It’s funny how nature can give you what you didn’t even know you needed. For Anna, being out in the wild wasn’t just about physical challenges—it was about finding mental clarity, peace, and, most importantly, herself.

After years of living on autopilot, the outdoors became her reset button. She wasn’t just healing from a breakup—she was healing from all the expectations, the routine, the noise of life that had kept her from listening to her own voice. Out there, with nothing but the wind and her thoughts, she could finally ask, what do I want?

That’s the power of stepping outside your comfort zone. Nature doesn’t judge you, doesn’t ask you to be anyone but yourself. And when you give yourself permission to embrace that space, amazing things happen.

Takeaway: The Journey Is Yours, So Own It

Anna’s story isn’t just a tale of hiking and adventure; it’s about the bigger journey we’re all on—figuring out who we are, what we want, and how we get there. Her story is proof that sometimes the answers aren’t found in books or in the advice of others, but in the quiet moments, standing on a trail, with nothing but your own heartbeat to guide you.

So, what can you take from this? Start small, push your limits, and don’t be afraid to go it alone, but remember—finding your tribe can make the journey that much sweeter. And when things get hard? Know that it’s okay to turn back, regroup, and try again.

Ultimately, this is about your journey. Whether it’s in the outdoors, in your career, or in your personal life—make it yours. Step out of the box, embrace the discomfort, and trust that the path will take you exactly where you need to go.

You’ve got this. Now go find your adventure. 🌿

Listen to Anna’s podcast episode here on substack or on all podcast platforms

https://podcasts.apple.com/gb/podcast/finding-myself-through-hiking-anna-baileys-journey/id1457720018?i=1000668447945