Starting My Business: What Went Wrong (and Right)
Starting my business wasn’t what I pictured. Honestly, I didn’t picture it at all.
I didn’t grow up dreaming of entrepreneurship. I didn’t have a polished business plan or a vision board. What I had were a handful of false starts, a few bold leaps, and a persistent tug that said, “You were made to do this—even if you don’t know what ‘this’ is yet.”
That’s what this post is about: the unexpected, messy, surprisingly rewarding journey of becoming an entrepreneur. And if your path looks a little sideways too? You’re not doing it wrong.
I Didn’t Plan to Start a Business—Then I Started Four
My first “real” business was legal nurse consulting. I spent thousands on a week-long training, joined a mentorship program, made letterhead, and printed fancy brochures. I even bought suits. It looked official.
It wasn’t.
Despite all the effort, I barely landed any clients. I was scared to talk to attorneys, unsure how to show my value, and honestly—I didn’t enjoy it.
So I pivoted.
Next up: crafting. Tutus. Hair clips. Personalized headbands. Vinyl decals. Craft fairs and handmade gifts. I even named it JenGBands. It was creative and fun—until it wasn’t profitable.
Then came fitness. Group classes turned into personal training. One certification led to another. Before long, I was managing other trainers and realizing how much I loved the business side of training.
Each shift brought me closer to something that felt right. But it took time to admit it.
Lesson 1: What You Start With Isn’t What You End With
The business I run today looks nothing like the first one I started—and that’s not a mistake. It’s the natural evolution of doing, learning, and refining.
When I first launched that legal nurse consulting business, I thought I was settling into a new career path. I bought the suits. I made the brochures. I did the things. And yet, within a year, I knew deep down it wasn’t the right long-term fit.
The same thing happened with crafting. I liked what I was doing, but I didn’t love it. I wasn’t willing to scale it because I didn’t feel joy in the process anymore.
And that’s the point: the thing that gets you started doesn’t need to be the thing that carries you forever. It’s okay—and actually very normal—to evolve as you go.
In fact, most successful entrepreneurs don’t end where they begin. They shift. They adapt. They grow. So if you’re starting your business and it changes down the road, that’s not failure. That’s progress.
Lesson 2: Every Failure Gets You Closer
Looking back, none of those early businesses “succeeded” on paper. They didn’t make a ton of money. I didn’t scale them. But I would do each of them again.
Why? Because those “failures” gave me what I couldn’t have gotten any other way: experience, clarity, and a better understanding of myself.
With the legal nurse consulting business, I learned the cost of investing in something without understanding the market. With crafting, I learned that loving a hobby doesn’t automatically make it the right business. And with each, I learned what not to do next time—like undercharging or overextending myself.
So, if you’re in a season where something isn’t working? Know that it’s not wasted time. You’re learning in real-time what will work next.
Lesson 3: Don’t Undervalue What You Offer
This one hit me hard.
I used to think people would pay me based on how much time something took. If it only took me an hour, then surely I could only charge for an hour of work, right?
Wrong.
I wasn’t charging for value. I was charging for time and effort—and leaving the true worth of my skills on the table.
Whether it was consulting or crafting or training, I had a pattern: I felt guilty charging too much. I was afraid people would walk away if I asked for what I truly believed the service or product was worth. So I undercharged, overdelivered, and burned out.
Learning to price confidently is not just about math—it’s about mindset. Once I realized the transformation I was offering people, I stopped apologizing for my rates. And once I did that, I started attracting clients who respected my work and stuck around.
Lesson 4: Follow What Feels Right
If you’ve ever taken a job or gig just because it made logical sense—but your gut was screaming “no”—you’ll get this one.
There’s something powerful about following what feels aligned, even when it doesn’t look impressive on paper.
For me, training clients felt right from the start. Not because it was glamorous or high-paying at first, but because I loved doing it. I enjoyed the conversations, the process, the outcomes.
That pull is what led me to start The Solo Trainer. I didn’t set out to build a business for other trainers—I just wanted to share what I had learned. But when that idea landed, it felt different. Energizing. Clear.
That’s a signal you shouldn’t ignore.
Lesson 5: You Can’t Do It Alone
There’s a myth that you have to do everything by yourself when starting your business. That if you’re a “real” entrepreneur, you should wear every hat and hustle 24/7.
Let me be honest: I’ve tried that. It doesn’t work.
I’ve hired freelancers that didn’t pan out. I’ve overpaid for help that didn’t help. I’ve tried to DIY way too much.
Eventually, I realized that asking for help wasn’t a weakness—it was a strategy.
When I launched The Solo Trainer, I brought my husband in as COO. I leaned on experts for legal and financial guidance. I hired a coach. I focused on what I do best and found help for the rest.
If you want your business to grow, you need support. You need community. You need voices around you that sharpen and challenge and guide. Don’t isolate. Build a team—even if it’s just two of you starting out.
Final Thoughts: You Might Not Be Starting the Right Business—But Start Anyway
Here’s the truth no one tells you: starting your business doesn’t mean you’ve figured it all out.
You’ll pivot. You’ll get things wrong. You’ll have moments of doubt. But those don’t mean you’re failing—they mean you’re in it.
Today, The Solo Trainer is my fourth business. It’s the one that combines my experience, my passion, and my values. It feels like home. But I wouldn’t have found it without the three ventures that came before it.
So if you’re standing on the edge, wondering if you’re ready to start your business—know this: the only way to find your path is to take the first step.
Even if it’s the “wrong” step, it still moves you forward.
Ready to Start Your Business?
If you’re a personal trainer thinking about going independent, I created The Solo Trainer to help you do just that.
Start with this FREE Action Plan:
👉 The Solo Trainer Action Plan
What About You?
If you’ve already started your business—what surprising lessons have shaped your journey?
Drop them in the comments. I’d love to hear them.
If you’re still in the dreaming phase, check out this video:
🎥 The Realities of Starting an Independent Training Business
