People often talk about success stories, but the truth is that most meaningful growth comes from the parts that don’t work out the way you hoped. Failure is uncomfortable, yes, but it’s also clarifying. It shows you what you value, what you’re capable of rebuilding, and what you need to adjust moving forward. Here are a few of the lessons I’ve learned from my own missteps and messy middles along the way.
- The first major failure in my side hustle
Back in graduate school, I started a company called Extreme Professional Makeovers. The idea was to help people rebuild their resumes and navigate career choices. I thought it was brilliant. The only problem: I had no money, no marketing knowledge, and no real plan beyond hanging flyers around campus. I ended up with exactly one client. One. I finally realized the business wasn’t failing because the idea was bad, but because my bandwidth and resources were nowhere near what were needed.
So I pivoted. I took a far less glamorous but much more realistic job as a tutor at the learning resource center. And honestly, it was the right move. That early failure taught me the value of timing, readiness, and starting where you actually are—not where you wish you were.
- The times I wanted to quit
This part is easy: yes, I’ve wanted to quit. Pretty much every single day at some point. That’s the truth of long-term leadership. I’m the CEO and founder of a company I started 15 years ago, and even with all the impact and meaning, the thoughts still surface. The trick is not to fear them. You notice the thought, validate that this is hard, and then gently bring your attention back to the next task at hand. If you ever truly need to quit, you’ll know. Until then, you keep going.
- How I structure risk so it won’t ruin me
The only risks I take now are ones I know I can recover from. When we started offering prescribing services, we hired just one prescriber. No sweeping launches, no big overhead. We treated it like a pilot. We watched, we learned, we adjusted. Only once we saw the model work did we expand.
Start small, observe reality, refine. That’s how you take bold steps without letting one miscalculated move topple everything you’ve built. The key is not getting stuck in analysis paralysis. The only way to know is to go.
- The mistakes I only understood in hindsight
I could list many, but hiring mistakes stand out the most. In the early years, I got swept up by shiny, charismatic personalities and impressive resumes. I didn’t ask the harder questions about whether they genuinely had the skills, stamina, humility, and alignment needed for the work. I learned the hard way that a great story does not equal a great fit. Now I look for what’s under the hood, not what sparkles at the surface.
- The small successes that kept me moving
When I feel stuck, I go straight to patient testimonials. They are the anchor that reconnects me to the why behind all the noise, stress, and decision-making. Just yesterday, a parent wrote: “My therapist helped my daughter overcome many fears and her ADHD and depression. Now she is happier and more confident.” Reading messages like that snaps everything into place. Yep, it is worth it.
- What I tell people who are afraid to fail
From my own experience, it is much scarier to not act and live with regret than it is to fail. Failure means you tried. It means you were brave enough to step into the arena. If you fail, you get information. If you never try, you get nothing but what-ifs. Go you for trying.
- How failure has clarified my business
I genuinely believe each recoverable failure is an opportunity to refine what you do. It’s how you grow. But the real challenge is building a culture where people aren’t afraid to bring failures to light. If everyone hides their mistakes to avoid embarrassment, you get all the pain with none of the learning. When failure is openly examined, it becomes a powerful tool for sharpening who you are as a business and what you want to stand for.
The bottom line
Failure is not the opposite of success; it’s part of the process that leads you there. Every stumble has shaped me into a clearer, steadier leader. And if there’s one universal truth I’ve learned, it’s this: the only truly dangerous mistake is refusing to learn from the ones you’ve already made.
