Let’s be honest: horseback travel sounds dreamy. Windswept hair, magical views, the majestic clip-clop of hooves on a trail… until you’re sweating through your breeches, gripping the reins for dear life, and flying headfirst into a ditch wondering what life choices brought you here.

Yep, I’ve been there.

When I started riding, I thought I was prepared. I had the right attitude, the YouTube tutorials, even the breeches that made me feel like a professional (spoiler: I wasn’t). But as it turns out, the trail doesn’t care what you think you know—it will humble you, teach you, and maybe even toss you a few times for good measure.

So here it is: my collection of big mistakes and the great (sometimes painful) lessons they taught me.

The “Fashion Over Function” Fail

One time, I wore my “cute” breeches because we were filming, and hey, looking good on a horse is half the job, right? Wrong. Thirty minutes into the ride, that synthetic fabric turned into a personal sauna. My thighs were screaming, my skin was on fire, and I could barely sit in the saddle without whimpering.

💡Lesson: Comfort is king. If your riding pants are torturing you before you hit trot, throw them in the garbage and never look back. Pain isn’t aesthetic.

“I Watched a YouTube Video, I’m Basically a Pro”

I had mentally rehearsed emergency stops a million times. Visualized it. Practiced it in slow-mo. I was ready. Then one day, the horse bolted, and I… completely blacked out. I became a panicked spaghetti noodle, yanking and squeezing everything in the wrong direction. Ended up in a ditch. Again.

💡Lesson: No amount of internet scrolling prepares you for the real thing. In a crisis, your calm head is your parachute. Panic = dirt nap.

The “I Can Ride Anything” Overconfidence Spiral

After a few solid months at my stable, I was feeling myself. I could canter. I could steer. I even looked relaxed in photos. So naturally, I took off in an open field with a new horse, thinking, what could go wrong?

Well. This horse had a speed setting I wasn’t aware existed. We were galloping like we were late to the apocalypse. I panicked. Guess where I ended up? Yep. Ditch.

💡Lesson: Just because you can ride a horse doesn’t mean you can ride every horse. Each one has their own vibes, buttons, and “don’t you dare” list. Humility > heroism.

The “Picnic Pack” Strategy

In my early rides, I packed like I was going on a lazy Sunday outing: snacks, extra hoodie, lip balm… but somehow forgot gloves, water, or sunscreen. Priorities? Nonexistent.

💡Lesson: You’re not going on a cute picnic. You’re sweating, moving, riding for hours. Ditch the nonsense and pack like you’re Bear Grylls—but make it equestrian.

The Reins (and Saddle) of Doom

In the beginning, I wasn’t just holding the reins—I was also clinging to the saddle for dear life. Honestly, the saddle probably got more attention than the reins. My grip was so intense, my left hand was sore for days. At one point, I couldn’t even open a door without wincing like I’d just come out of arm day at the gym.

💡Lesson: Death-gripping the saddle doesn’t make you safer—it just makes you sore. Horses feel everything, including your panic. Loosen the grip, breathe, and let the horse do what it does best: carry you forward (preferably not into a bush).

So, What’s the Point?

Every mistake I made felt like a disaster in the moment—but in hindsight, they were the best lessons I’ve ever had. The trail humbles you, sharpens you, and keeps you honest. It doesn’t care about your Instagram game or your new boots. It wants your presence, your patience, and your sense of humor.

And let’s face it—falling in a ditch is funny eventually.

Your Turn

Tell me your funniest, messiest, most humbling trail mistake. 💌 We’ve all got one. Let’s laugh, learn, and remember: if you haven’t made a fool of yourself on horseback… are you even doing it right?