My husband and I share the addiction of entrepreneurship.
It’s thrilling (and exhausting) to launch businesses. We’ve fallen flat on our faces at times, but we agreed early on that wallowing and judgment won’t move us forward. Instead, we see mistakes as a type of tuition in our ongoing DIY entrepreneurial educational journey. There’s the “ouch” moment of a misstep, but after the gut punch of a business setback, our next step is always a shared line: “Well, that was the cost of a seminar.”
We’ve repeated it in unison on multiple occasions. I encourage you to adopt this line, too.
Anyone who has stepped beyond the “big idea” passion talks and embraced, “OK, let’s make this actually work,” confronts the competency cliff. How do I climb this? What if I fall? Entrepreneurship is a fierce inner battle between your doubts and your determination.
And you’re going to fall. Every entrepreneur does. The competency cliff feels overwhelming because you’re looking straight up at the peak, but what actually happens is messier and more forgiving. You scramble up a bit, slide back down, find a different route, maybe sit on a ledge and catch your breath. One day you’re Googling “how to write a business plan” and the next you’re helping a friend figure out their pricing strategy. The climb happens gradually, almost without you noticing, until you look around and realize you’ve gotten higher than you ever thought you would.
In our quest to climb that cliff, my husband and I have written checks for coaches, attended workshops, paid for certifications and ultimately recognized that sometimes the universe just sends the invoice for our “schooling” directly in the form of a mistake.
Accept it. Pay the “tuition” and extract all the value you can get from the class. You didn’t fail. You just invested in getting better.
Here are some tips on getting the most out of your “tuition payments” to the DIY Entrepreneurial Academy.
Look for the pattern, not just the pain
Entrepreneurial setbacks often feel isolated, like a freak accident or one-time miscalculation. But when you pause and look at your history, you may start to notice a theme: overpromising, underpricing, skipping due diligence, ignoring gut instincts. The pain usually points to a recurring vulnerability.
Patterns are valuable because they show you where your thinking or systems need to evolve. One mistake is survivable. Ten in the same category means you’ve just discovered a curriculum you didn’t realize you were enrolled in. Your job is to learn that lesson well enough that it stops repeating.
Sometimes the pattern is tied to your ego. It happens to all of us. Talk to a mentor who has known you over time. They might spot what you’re too close to see. For instance, do you have shiny object syndrome? You get a wild new idea during a slow week and suddenly your whole team is knee-deep in a rebrand. It’s exciting. It feels productive. But often, it’s a clever way to avoid the hard, boring work of optimization. Catching this pattern early can save you from building castles in the air while the foundation below cracks from neglect.
Are you holding on too long?
You have a heart. You have logic. And you need both. But there needs to be a balance. Think about situations you’ve had — maybe underperforming employees or outdated systems — where you knew it was time to make a change, but you delayed due to feelings, not logic. You gave second chances and hoped for a turnaround, avoiding the hard conversation. Each time, the delay made the damage worse.
Now you recognize the pattern: Your desire to be kind or fair often overrides your responsibility to act decisively. The root cause isn’t naivety. It’s pain avoidance. You’re hoping problems solve themselves so you won’t have to be the bad guy. Entrepreneurship doesn’t shelter you from pain. You have to establish criteria outside of your emotions and stick to it.
The insight here is that leadership means making clean, timely decisions — not perfect ones. Create a process for reviewing performance and value regularly. Set exit criteria in advance. When you catch yourself stalling, remember that the kindest thing for your team and business is often clarity.
Has your greatest strength morphed into a liability?
Your greatest business strength can sometimes morph into your biggest liability. Maybe you’re naturally detail-oriented, which helped you in the beginning when you launched. But now that same trait has you micromanaging every step of your employees and second-guessing decisions that should take minutes.
Or maybe your willingness to say yes got you those crucial early clients. Now you’re spread so thin that quality is suffering and you can’t serve anyone well. Your superpower became your kryptonite, and you didn’t notice the transition.
The key is recognizing when context has changed. What works at $100K in revenue doesn’t necessarily work at $500K. The scrappy improvisation that launched your business can become the chaotic approach that stunts its growth.
Step back and assess: Which of your natural tendencies served you in startup mode but might be holding you back in scale mode? Then create systems that harness the positive aspects while containing the negative ones.
Building your early warning system
I pride myself on my “spidey-sense.” I have a nose for trouble. My brain often tells me something before my conscious self has processed what’s happening. Maybe you feel the same. But I also know that radar sensibility can’t be the lone mistake detector. I need systems.
The best entrepreneurs don’t make fewer mistakes, but they catch them faster. They’ve learned to recognize early warning signs before small problems become expensive disasters. This means building feedback loops into everything: customer satisfaction, cash flow, team morale and operational efficiency.
The more connected you are to what matters, the greater your warning system will be. That’s why it’s great to schedule regular check-ins with your primary stakeholders. Meet with your best customers. Hold weekly team temperature checks. Review financials weekly, not monthly. These habits feel like extra work when things are going well, but they’re your insurance policy against blind spots.
Train yourself and your team to speak up when something feels off, even if you can’t articulate exactly what’s wrong. That vague sense of unease often precedes major issues. Honor those gut feelings by investigating them.
Recognize when everyone else’s playbook doesn’t fit your game
You’ve read the business books, attended the webinars and followed the “proven formulas.” But sometimes the biggest mistake is trying to force your square-peg business into someone else’s round-hole strategy. What worked for that entrepreneur you admire might be completely wrong for your market, your personality or your stage of growth. And good business is all about building unique value.
I’ve watched owners twist themselves into pretzels trying to implement systems that conflict with their natural strengths or their customers’ actual needs. They’re so busy following someone else’s blueprint that they miss obvious opportunities right in front of them.
The breakthrough comes when you realize your “failure” to follow conventional wisdom might actually be your competitive advantage. For example, maybe everyone says you need to scale fast, but steady growth serves your life goals better.
Learn from others, but don’t let their playbook override your instincts. Sometimes the smartest move is to throw out the “best practices” and trust what you’re seeing in your own business.
The view keeps changing
My husband and I still quote our “cost of a seminar” line, but something’s changed. These days we say it faster, with less sting. Sometimes we even laugh before the words come out because we both know what’s coming. The sting wore off somewhere along the way, replaced by something that feels more like curiosity.
That competency cliff isn’t going anywhere. You’ll keep scrambling up different versions of it for as long as you’re in business. But you don’t need to see the top to take the next step. You just need to trust that each stumble teaches you how to stumble better. Eventually, you realize you’re not really stumbling anymore. You’re just climbing. And the view is beautiful.
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Anne Lackey is the co-founder of HireSmart Virtual Employees, hiresmartvirtualemployees.com, a full-service HR firm helping others recruit, hire and train top global talent. She has coached and trained hundreds in creating successful businesses to be more profitable and to create the lifestyle they desire. She can be reached at anne@hiresmartvirtualemployees.com or at meetwithanne.com.
