Ten years in business deserves a celebration.
But I’m not going to give you the highlight reel. The milestones. The “look how far I’ve come” post.
Instead, I’m giving you the real story: 10 failures that shaped everything I know about leadership, building, and scaling a business that actually lasts.
Because here’s the truth—the wins are easy to celebrate. It’s the messy, expensive, gut-wrenching failures that actually teach you how to lead.
So here they are. One failure for every year I’ve been in business.
10 Failures That Taught Me More Than Success Ever Could: Celebrating 10 Years in Business
Failure #1: Hitting Six Figures & Burnt Out
Year one was “successful” by every external metric. I left my six-figure corporate job with some savings and a line of credit—gave myself six months to make it work.
I made six figures. I was fully booked. I looked like I had it figured out.
I was also the worst boss I’d ever had.
Eight coaching calls a day. Working weekends. No boundaries between work and life. I’d wake up thinking about work and fall asleep the same way. In corporate, I had these natural boundaries—everyone left by 6pm, you didn’t work most weekends. But in my business? There was nothing stopping me from working myself into the ground.
The lesson: For highly ambitious women (the type I am, the type I work with), the problem isn’t lack of motivation. It’s that we drive ourselves too hard. Burnout doesn’t come from working hard—it comes from working without rhythm, without recovery. You need to learn how to redline and how to restore. There are seasons for growth and long hours, but you can’t operate that way forever without breaking.
Failure #2: Deleting Domains and Throwing Away Years of SEO Equity
My first business was called “Winning Defined by You: Coaching, Consulting, and Facilitation” because I had no idea what I was doing and figured if I put it all in the name, I’d be covered.
After year one, I realized that name wasn’t going to cut it. So I rebranded to “Winning Academy.”
And here’s where I messed up: I deleted my original domain. Deleted my social accounts. Threw away everything I’d built.
I didn’t understand how SEO worked. I didn’t understand the online space. All that work I’d put in—YouTube videos, guest writing for Forbes Coaches Council, building searchability—gone.
Now those Forbes backlinks? They’re broken. Dead ends. And I can’t get them back.
The lesson: Every time you start from scratch, you’re throwing away equity. Refinement beats reinvention. Build on what exists instead of burning it down and starting over.
Failure #3: Building a Successful Consultancy That Still Felt Like the Wrong Job
After those first couple of years, I built a thriving leadership development consultancy. I worked with big brand names, facilitated trainings, developed programs.
Good revenue. Great clients. From the outside, it looked like I’d made it.
But it didn’t feel aligned. I was doing work I was good at—not work I was meant to do.
I realized I’d just traded my corporate job for another job. Different title, same constraints. I had simply replicated a structure I thought I’d escaped.
The lesson: Revenue without alignment is just an expensive job you gave yourself. Sometimes the bravest thing you can do is close what’s working to create space for what’s right.
Failure #4: Holding Onto Old Contracts (and Identities) Way Past Their Expiration Date
Closing the consultancy wasn’t immediate.
I held onto old contracts. Old clients. Old versions of myself because they felt safe. Familiar. Even when I knew they weren’t serving me anymore.
Letting go takes time. And I stayed too long.
The lesson: Holding on fragments your energy and dilutes your impact. The longer you wait to let go, the more it costs you in focus, clarity, and momentum. When something’s done, it’s done—honor that instead of dragging it out.
Failure #5: Spreading Myself Too Thin and Watching Revenue Contract
Too many offers. Too many directions. Too many things I thought I “should” be doing.
In 2023 my revenue contracted—not because the market changed, but because my energy was scattered everywhere except where it mattered.
When you’re pulled in too many directions, nothing gets the attention it deserves. Everything suffers.
The lesson: When you’re doing too much, you create energy leaks. It’s not about market conditions. it’s about where you’re placing your focus. Simplification isn’t a nice-to-have. It’s the strategy.
Failure #6: Wasting Money on Ads, Launches, and Offers That Went Nowhere
Not every investment pays off.
Some ads flopped. Some launches barely covered costs. Some offers took years—not weeks—to refine.
I’ve wasted 10’s of thousands of dollars and have learned through trial and error, through expensive lessons that taught me more than any course could.
The lesson: These aren’t mistakes. They’re tuition. Mastery is built through lived experience, not hacks. Every “failed” launch, every ad that didn’t convert, every offer that needed refinement—those are the things that actually teach you how to build something that lasts.
Failure #7: Hiring Support Exposed My Leadership Gaps
I thought hiring would solve my problems.
It didn’t. It exposed every gap in my leadership I didn’t know I had.
Unclear communication. Misaligned expectations. Delegation without systems or clarity. Financial oversight issues. Even with years of leadership experience in corporate I’ve made costly mistakes when it comes to hiring.
The lesson: The right support amplifies your vision—but only if you’re able to lead. Team problems are almost always leadership problems in disguise. Hiring doesn’t eliminate the work—it changes it. You need clear processes, boundaries, accountability, and the willingness to own your role as a leader.
Failure #8: Trying to Scale Complexity Instead of Simplifying
2025 was my best revenue year to date.
But it didn’t always feel how I wanted it to feel.
This year I implemented a bunch of new and creative sales strategies—different micro offers, new approaches, multiple things at once. And they worked. Clients got great results. Revenue was strong.
But there was too much busyness. Too much franticness for me. My system doesn’t thrive in that environment.
Some people can sell multiple things at once, fly all over the place, juggle a million moving parts. My system doesn’t enjoy that. I like clarity. I like focus. I like going deep and putting out really good work.
The lesson: Simple scales. Complex fails. Even when complexity “works,” if it doesn’t align with how you’re wired, it’s unsustainable. 2026 is about doing less, better—and actually building a business model around what works for me, not what works for someone else.
Failure #9: Forgetting to Do Less, Better (Again)
This one’s connected to #8, but it deserves its own mention because it’s a pattern I keep having to correct.
I know simplicity is the answer. I’ve learned this lesson before. And yet I keep finding myself in seasons where I’ve overcomplicated things again.
This year proved it: even when revenue is strong, if the model feels frantic, something needs to change.
The lesson: You can know something intellectually and still need to re-learn it in practice. Doing less, better isn’t a one-time decision—it’s a discipline you have to return to again and again.
Failure #10: Forgetting the Weight of My Own Experience
This is the big one. And it came to light while working with a mentor earlier this year.
I forgot. I forgot the weight of my experience and the depth of what I bring to the work.
When I shut down my leadership development consultancy, I kind of left all of that in the past. I didn’t see how my almost 20 years of leadership experience—running operations for multimillion-dollar organizations, training across North America, developing programs that scaled, opening new locations—connected to what I do now.
I help people codify their brilliance, package it into scalable offers, and position it to sell. But I was treating my background like it was normal. Like it didn’t matter.
And my mentor called me on it. I remember being irritated with myself, annoyed that I’d lost the plot.
Because here’s the truth: what I do today isn’t something I read in one book or learned at one weekend seminar. It’s literally decades of experience—the failures I’m sharing here, the trial and error, the breadcrumbs that all led me here.
The lesson: Your body of work didn’t arrive by accident. Every failure, every pivot, every lesson learned adds weight to what you do. When you forget that—when you treat your expertise as “normal”—you diminish your authority. The work is to remember. To honor the full scope of what you carry.
A Practice to Close the Year: The Brag List
If you’ve forgotten the weight of your own experience, here’s what I want you to do:
Create a brag list.
Go back as far as you can and write down everything that’s braggable. The wins. The failures. The experiences that shaped you—even the ones that didn’t work out.
I’m proud that I got married in Peru on top of a mountain by a shaman, even though that relationship ended in divorce. It was a bold, out-of-the-box experience that taught me something about myself.
That’s part of my journey. Part of my story. And those things—all of them—make me unique. No one else can replicate that.
So create your brag list. Sit with it. Recognize yourself for everything you bring to your work and the people you serve.
Because that’s what makes you different. That’s what makes you irreplaceable.
What 10 Years (and 10 Failures) Actually Taught Me
Here’s what I know after a decade in business:
The failures matter just as much as than the wins. The pivots teach you more than the straight lines. And the moments where you had to choose between what looked good and what felt right? Those are the ones that actually build the business—and the leader.
I’m not the same entrepreneur I was in year one. I don’t hustle the same way. I don’t say yes to the same things. I don’t measure success by the same metrics.
And that’s the point.
Ten years doesn’t give you all the answers. But it does give you the discernment to know when something’s aligned and when it’s not. When to push and when to rest. When to hold on and when to let go.
If you’re in the middle of your own journey right now—whether it’s year one or year ten—my hope is that these failures remind you that the messy parts aren’t mistakes. They’re the curriculum.
Listen to the full episode on Season 2 finale of The Soulful CEO Path podcast. It’s not a polished retrospective. It’s the raw, honest, messy story of what building a business for a decade actually looks like.
🎧 Listen to the full episode here
Before you go—here are the 5 most-listened-to episodes of 2025:
If you’re looking for something to listen to over the holidays (or you missed any of these), here’s your binge list:
- Behind The Scenes With Kristin Constable: The Human & The Founder Of Soulful CEO – Listen
- Why You Need an Ownable Body of Work – Listen
- How to Host a Sold-Out Conference from Scratch: Lessons in Leadership, Mindset & Experience – Listen
- Activating the Next Generation of Leaders: Confidence, Voice & Vision with Lauren MacKinnon – Listen
- Work-Life Balance vs. Integration: Rethinking Success with Andrea Barr – Listen
And if you want to go deeper on the strategies, mindset shifts, and identity work it takes to build a business you’re actually known for, join me in KNOWN—my free Telegram community for soul-led entrepreneurs who are redefining what leadership looks like.
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