I’ll be honest—failing at my first business was one of the hardest things I’ve ever been through.
I didn’t just lose money. I lost confidence, sleep, and, at times, hope. To top it off, I was drowning in debt with no clear way out.
It felt like the end of the road for me as an entrepreneur. Maybe I didn’t have what it takes. Maybe I wasn’t cut out for this after all.
But here’s the thing: failure wasn’t where my story ended—it was where it started.
Looking back now, I see how that first failure taught me lessons I couldn’t have learned any other way.
If you’re in a similar place—feeling stuck, defeated, or unsure how to move forward—let me share what I’ve learned along the way.
You may be closer to your breakthrough than you think.
When I started my first business, I thought I had to wear every hat. Marketing, sales, customer service—you name it, I did it.
At first, it felt empowering. But eventually, it became overwhelming. I was stretched so thin that I couldn’t focus on the big picture.
Worse, I made mistakes because I was too busy juggling a dozen things at once.
When I launched my second business, I did something different: I asked for help.
I surrounded myself with people who were better than me in areas where I struggled.
Instead of wasting hours trying to design a logo or figure out bookkeeping, I hired experts who could do it faster and better.
Not only did this free up my time to focus on what I was good at, but it also made my business stronger overall.
Collaboration became a game-changer, and letting go of the need to do it all was one of the smartest moves I ever made.
When my first business collapsed, I was embarrassed. I felt like I had let everyone down—my family, my friends, even myself.
I remember one night in particular. I was sitting at my kitchen table, staring at a stack of overdue bills, feeling completely defeated.
That’s when my dad called. He’s not one for long speeches, but he said something that stuck with me: “You didn’t fail. You learned.”
At first, I didn’t believe him. But over time, I started to see what he meant.
In my first business, I didn’t pay enough attention to cash flow.
I assumed sales would always cover expenses, and when they didn’t, I was caught off guard. That mistake haunted me—until I used it as fuel for my next venture.
In my second business, I made cash flow a top priority. I tracked every dollar coming in and going out, planned for slow months, and built an emergency fund early on.
As a result, my business stayed stable even when we hit bumps in the road.
That failure taught me lessons I couldn’t have learned any other way—and those lessons became the foundation of my success.
My first business was built around something I was passionate about. Everyone always says, “Follow your passion!” so that’s exactly what I did.
But here’s what no one told me: passion alone isn’t enough.
I poured my heart into a product I loved, but I didn’t stop to think about whether other people actually needed it.
I assumed that because it mattered to me, it would matter to everyone else too. Spoiler alert—it didn’t.
By the time I realized this, it was too late. Sales were barely trickling in, and I couldn’t afford to keep the lights on.
When I started my next business, I approached things differently.
Instead of asking, “What do I want to do?” I started asking, “What problem can I solve?”
I paid attention to the frustrations people around me were facing—the little complaints they had about their day-to-day lives—and built a business around fixing one of those problems.
This time, people didn’t just like what I was offering; they needed it.
In my first business, I avoided anything that made me uncomfortable.
I hated sales calls, so I’d hide behind email. I was terrified of rejection, so I’d underprice my services just to avoid hearing “no.”
And when things didn’t go as planned, I’d distract myself with busywork instead of facing the real issues head-on.
Looking back, that avoidance was one of the main reasons my business failed.
When I launched my second business, I made a promise to myself: no more hiding.
I started pitching to clients I thought were out of my league.
I asked for help even when it felt awkward. I raised my prices and stood firm, even when people pushed back.
Every time I leaned into discomfort, I grew—and so did my business.
Over time, what once felt impossible became second nature, and the results were worth every uneasy moment.
In my first business, I thought success was all about the numbers. More sales, more clients, more revenue—that’s what I believed would determine whether I made it.
But here’s the truth: people don’t buy from businesses; they buy from people they trust. And trust isn’t built through one-off transactions.
When I started my second business, I approached things differently.
Instead of chasing quick wins, I focused on building genuine relationships with my customers and partners.
I took the time to really listen to them—not just about what they wanted to buy, but about their challenges, goals, and stories.
I made it a point to follow up after every purchase, not to sell something else, but to check in and see how they were doing.
It worked.
Studies show that 65% of a company’s business comes from existing customers—something I learned firsthand when those relationships turned into repeat clients and referrals that kept my business growing steadily.
It wasn’t about selling more; it was about showing up for people in a way that mattered.
After my first business failed, I carried the weight of it everywhere I went.
Every missed opportunity, every bad decision—I replayed them over and over in my head, beating myself up for not being “good enough” to make it work.
It was exhausting. And more than that, it held me back.
I was so afraid of failing again that I almost didn’t try at all. I second-guessed every idea, hesitated on every move, and let self-doubt keep me stuck for far too long.
But then something shifted. I realized that no one else was judging me as harshly as I was judging myself.
The people who cared about me didn’t see me as a failure—they saw someone who had taken a risk and learned from it.
I decided to do the same.
I gave myself permission to move on, mistakes and all. I stopped seeing my failure as a reflection of my worth and started seeing it for what it really was: part of the journey.
Letting go of that shame didn’t just help me emotionally—it gave me the freedom to try again with a clear mind and an open heart.
In my first business, I wasted so much time waiting. Waiting until I felt ready.
Waiting until I had all the answers. Waiting for the stars to align before I made my next move.
The truth? There’s no such thing as the perfect time. There will always be unanswered questions, risks to take, and things you don’t know yet.
With my second business, I stopped waiting and started doing. I launched before I felt ready, learned as I went, and figured out solutions to problems as they came up.
Every mistake taught me something valuable. Progress didn’t come from waiting—it came from starting, even when the path wasn’t clear.
If there’s one thing I’ve learned, it’s this: action beats perfection every time.
Failure is never easy. It’s messy, it’s humbling, and sometimes it feels like the end of the road. But it doesn’t have to be.
The truth is, failure isn’t the opposite of success—it’s part of it. Every misstep, every setback, every lesson learned brings you closer to the version of yourself capable of thriving.
What matters most isn’t that you failed; it’s what you do next. Will you let it define you, or will you use it to grow?
If you’re willing to reflect, adapt, and take that next brave step forward, there’s no limit to what you can achieve.
Success isn’t about avoiding failure—it’s about learning how to rise after every fall.
And sometimes, the comeback is even greater than the dream you started with.
The post I failed at my first business and was drowning in debt. Here’s how I made my next one a roaring success appeared first on Small Business Bonfire.
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