When Things Don’t Go Your Way

Most entrepreneurs love to talk about success—those shiny highlight reels filled with fame, freedom, and financial wins. It’s attractive, magnetic even. You picture yourself next to them, sipping margaritas on a tropical beach, celebrating the dream come true.

But what about when things don’t go your way?

Where are the videos of entrepreneurs working two or three jobs to keep the lights on? Where are the stories of chasing kids away from a dining room desk because the nursery took over your home office? Where are the real, unfiltered accounts of what this journey looks like?

I consider myself a glass-half-full guy. I’m an optimist—but also a realist. And if you're a landscape architect like me, you probably relate. We chose this profession for its precision: draw a line, solve a problem, get a beautiful result. Rise ÷ Run = Slope. Simple math, right?

But when you tack on “entrepreneur” or “small business owner” to your title, that precision starts to smudge. Things don’t go to plan. That perfect line becomes a blur. Your days shift from line weights and layouts to late nights stressing about budgets, insurance renewals, and juggling a dozen hats—designer, estimator, sales rep, client therapist.

Sound familiar?

Let me toss you a lifeline.

I’ve been there. My path has been anything but straight—cross-country moves chasing the dream, launching a business from a basement, walking away from the stability of a good job at 34. It’s gritty. It’s hard. It’s isolating.

But you don’t have to do this alone.

Yes, you’re your boss—but you don’t have to be your only co-worker. When I co-founded our Plans for the Future course with Greg, it was born from a shared belief that “iron sharpens iron.” We began as professional peers, but over time, we developed a partnership built on honesty, mutual growth, and hard-earned wisdom.

Plans for the Future is more than a course—it’s a place to learn from our mistakes, hear the stories behind the glossy project photos, and get real about the terror (and triumph) of small business ownership.

Because maybe we’ve been telling the wrong story.

What if failure is magnetic, too?

Because through failure, we don’t just build success—we gain wisdom. And wisdom will carry you further than any paycheck or project portfolio.

So if you’re a landscape designer, an architect, or someone just trying to figure out the business side of design, join us. Share your story. Ask your questions. Let’s build something better—together.

👉 [Join our free private Facebook group here]
👉 [Check out the Plans for the Future course]

You don’t need all the answers to keep going—you just need a community that’s been there too