“Do you think she meant to wear those two different shoes together, or is it more of a Friday experiment gone wrong?”

That’s the first thing Erin Whitaker ever said to me. We were standing in line at a coffee shop off Mill Avenue, waiting for what felt like an eternity because the barista was deep in a philosophical debate—or possibly a break-up conversation—with the customer ahead of us. Erin, with her sunglasses perched on top of her head like a life-long invitation to spontaneity, just turned and dropped that observation out of nowhere. I laughed, awkwardly, but it was the kind of laugh that sneaks up on you before you can filter it. You know, the honest kind.

We didn’t know it then, but that one-liner sparked a friendship that altered the trajectory of my life, and—to be honest—my definition of courage, connection, and joy.

The Girl with the Cactus-Like Resilience

It’s funny how some people are like a monsoon rainstorm—unexpected but entirely necessary. Erin was that for me. Before her, I’d thought of myself as plenty adventurous. I hiked the jagged trails of Camelback Mountain. I could comfortably use the phrase “desert modernism” in casual conversation. I had a carefully-cultivated network and a solid routine. But Erin? She lived as though the world might spontaneously combust if she didn’t squeeze the most out of it.

Raised on a communal farm somewhere on the New Mexico-Texas border (the exact location fell victim to Erin’s lifelong anti-GPS stance), she spoke like she just wandered off the set of an indie road trip movie. She had this gift for syncing up with life’s chaos instead of resisting it, like one of those cacti you see thriving against all odds in the middle of the desert. I was immediately both baffled and inspired by her.

How She Flipped My Script

It didn’t take long before Erin made herself at home in my neat little world, which is to say she completely upended it. For instance, there was the time she invited me to tandem paraglide off a cliff—not after months of mental preparation, but because we passed a sign about it while driving out to Sedona to “find cool rocks.” Then there was the time she persuaded me to play my first-ever open mic night, despite the fact that my only audience before this was my shower tiles and a judgmental neighbor’s dog.

And yes, I hear you. This might sound like she was just an adrenaline junkie in disguise. But what made Erin’s friendship transformative wasn’t the activities. It was her way of making the unfamiliar feel inviting, as if the unknown was always just a chapter of discovery waiting to be read. She had this knack for holding up a mirror until I saw strength in myself that I didn’t even know was there. One minute, we’d be joking about something trivial, and the next, she’d drop these nuggets of wisdom, like: “You don’t prove you’re brave by avoiding fear. You prove it by taking yourself along for the ride.”

I started showing up differently in every part of my life. When a marketing pitch flopped, I didn’t beat myself up the way I used to. In fact, failure stopped feeling like evidence of inadequacy and started looking like a badge of experience. Even in relationships, whether romantic or otherwise, Erin showed me that the connections that mattered most weren’t the ones I tiptoed around but the ones I pursued unapologetically.

Lessons in Choosing the Journey

Now, I know what you’re thinking—“That’s all well and inspiring, Nate, but what do I do with this IF I don’t have an Erin around to coach me through my next existential meltdown?”

Trust me, I hear you. Not all of us have a fearless road trip guru with a cowboy hat and a knack for fixing flat tires. But here are a few Erin-approved principles I’ve carried into my life. Maybe they’ll spark something for you, too:

  1. Get Comfortable with (Small) Discomfort
    Erin used to call growth “the itch before the stretch.” Sure, some things look uncomfortable at first—a solo vacation, a blind date, or even having that tough conversation with your sibling about boundaries. But you don’t need to leap into the deep end. Start small. Say “yes” to micro-challenges and build from there.

  2. Let Joy Be the Goal, Not the Outcome
    One of the biggest Erin takeaways? Life doesn’t need to be an endless check-list of what’s productive or profitable. Try this: Tack a sticky note somewhere you’ll see every day—write “What’s one thing you did just for joy this week?” And yes, karaoke counts.

  3. Reframe ‘No’ as Nudging You Toward ‘Yes’
    Erin took rejection like someone refusing their turn at dodgeball—it was just another way of saying you’re still in the game. A bad date doesn’t cancel out your romance potential. A failed pitch doesn’t sideline your ambition. So say “no hard feelings” and keep your eyes peeled for the better “yes” that’s coming.

  4. Make Like a Cactus
    Translation? Be resilient but not hard. Erin didn’t sugarcoat the challenges—she just chose to find all the ways challenges could enrich her. Adapt to your environment but still leave space for softness and connection. Remember that even in the harshest conditions, cacti know how to bloom.

The Big Takeaway

Here’s the thing about Erin—she didn’t “change my life” by handing me a blueprint for success. She changed it by showing me how to trust not just the desert paths but my own instincts while walking them. What started as a casual friendship became a masterclass in authenticity, risk-taking, and leaning unapologetically into what we love.

So whether your Erin is a bold friend who refuses to play by the rules, or maybe you’re becoming your own Erin one day at a time, my advice is this: Don’t hold yourself back because the path looks unfamiliar. Lean into it, have fun, and for the love of all things caffeinated, don’t be scared to comment on someone’s mismatched shoes. You never know where a throwaway observation might take you.