From Dirt to Drive: Overcoming Career Challenges with a Smile

Let’s get real for a second. Behind every “Rookie of the Year” award and highlight reel is a story (or five) that’ll make you laugh, cringe, and maybe even tear up a little. For me? The biggest challenge in my career wasn’t closing deals—it was transitioning from being a W2 employee to a 1099 business owner.

Sounds simple, right? Clocking in to calling the shots. But that shift? Whew. It hit harder than a lockbox on a windy day.

When I first started in real estate, I was with a different brokerage. I came in hot—eager, motivated, and ready to work. I poured myself into every deal, stayed up late learning contracts, and took every opportunity to grow. I hustled hard and it paid off: I won Rookie of the Year in my very first year.

But here’s the plot twist… even with that shiny plaque on my desk, I felt empty. The success didn’t feel like success. I was doing the numbers, but I didn’t feel accomplished. I had come from a W2 world, where success meant structured tasks, predictable feedback, and a steady paycheck. Real estate, as a 1099 agent, was the complete opposite.

There was no one telling me what to do or how to measure success outside of sales. There was no guaranteed income. There was just… me. And I didn’t yet understand that things like networking, relationship building, and lead generation—the stuff that doesn’t come with a neat little checklist—were the new tasks.

It honestly led me into a pretty low place mentally. I was proud of the recognition, but I still felt lost. It wasn’t until I got real coaching and surrounded myself with other successful entrepreneurs that things started to shift. They helped me see that building a business requires a different mindset. It’s not about doing more—it’s about becoming more.

I had to recalibrate everything. I had to rewire my brain to realize that the “invisible” work—connecting with people, staying top-of-mind, showing up consistently—that’s the magic. That’s the stuff that compounds over time.

When Everything Wasn’t Under Control (But I Pretended It Was)

Okay, so picture this: I’m at a home showing. Things are going smoothly until I drop the key… and it vanishes through the cracks of the porch, which is completely surrounded by lattice. Cue panic.

I smiled, waved goodbye to the buyers, and then went full National Geographic under that porch—burrowing through the mulch like a determined raccoon on a mission. I was sweating, dirty, and borderline feral by the time I got that key back.

That’s when it hit me:
This is why they call me The Relentless Realtor.
Because apparently, I will literally dig through dirt to make sure a showing goes right.

Cut to my next appointment: a buyer consultation. I show up late, covered in dirt, trying to play it cool. Instead of explaining my mole-person moment, I hit them with:

“Sorry, the buyers from my last showing were super concerned about the integrity of the porch footings and I had to investigate.”

Creativity level: expert. Embarrassment level: off the charts.

How I Stay Resilient

It took me a long time to understand that there’s no such thing as failure—only wins and lessons. That’s it. Those “messy middle” moments are what mold us. Failing forward is how we grow.

My Advice to Anyone Facing Setbacks?

Stop calling it a setback. Start calling it a strategy session. Whatever is holding you back—use it. Let it teach you. Whether it’s a career hiccup or a literal fall into the mulch, it’s just part of the process.

Stay bold. Tell the truth. And if you're ever stuck under a porch, maybe keep a backup key—and a clean shirt—in the car.