The Hard Truth That Almost Cost Me My Company, Career & Life Savings
I became CEO at the worst possible time. Our previous CEO had been seriously unwell but stayed in the role because it was important to him during his treatment. I respected that completely. When I took over, I inherited both his legacy and the reality that the company was hemorrhaging money and running out of cash fast.
I was a techie at heart. I understood systems, problem-solving, and how to build things that worked. What I didn't understand was the revenue and business development side of the business, and that's exactly what needed fixing. So I did what came naturally: I threw myself into learning everything I could about running that side of the operation.
I've always enjoyed learning. Give me a complex topic and I'll happily absorb books, frameworks, and expert advice until I feel like I've mastered it. That approach had served me well throughout my career. But there was a problem I didn't see coming.
The Learning Trap
I found a CEO development group run by Bob Nordlinger. He and the group were incredible, helping me learn much faster than I could have on my own. I was making progress understanding the business, understanding our market position, understanding what needed to change.
But we were still struggling. Despite all the learning, all the analysis, all the understanding I was developing, the company's financial situation kept deteriorating. I borrowed money against our house to inject into the business, and another shareholder did the same. Even with those funds, we were within two months of running out of cash. The stakes couldn't have been higher, but somehow I still wasn't moving fast enough.
During one CEO group session, I was working through some of the issues we were facing when Bob stopped me mid-sentence. What he said next hit harder than any business feedback I'd ever had before:
"Brendan, it seems like you are comfortable with the company failing as long as you understand why."
That sentence landed like a punch to the gut because it was instantly, obviously true.
I had been hiding. Not from work. Not from responsibility. I had been hiding in learning itself, using it as a shield against the discomfort of acting in areas where I still had limited knowledge. I was comfortable analysing the problems, comfortable understanding the theory, comfortable knowing why things weren't working. What I wasn't comfortable with was making decisions and taking action when I didn't feel like I'd thoroughly mastered the subject.
The irony was brutal: my love of learning, the very trait that had made me effective as a technologist, was now putting the entire company at risk. Every day I spent deepening my understanding was a day the company got closer to insolvency.
From Understanding to Action
After that meeting, I consciously changed my approach. Instead of trying to fully understand before acting, I adopted what I now think of as learn-through-action: apply what you've learned so far, see what happens, adjust based on results, and learn more in the process.
It felt uncomfortable. I was making decisions about pricing, sales strategies, and market positioning without the depth of knowledge I wanted. But something shifted. Progress accelerated. We started seeing results.
Within a year, we turned looksoftware from heavy losses to strong profits. We enhanced both our business results and our reputation to the point where we were acquired by Fresche Solutions, a larger international company. The company survived and thrived, not because I finally learned enough, but because I started acting before I felt ready.
The Strategy Execution Gap
I see this pattern everywhere now. Organizations bring in consultants to develop comprehensive strategies. They analyze markets, competitive positions, internal capabilities. They create detailed frameworks and implementation roadmaps. The work is thorough, insightful, well-researched.
And then they struggle to execute.
It's the same trap I fell into. They're comfortable with the strategy work because it feels like progress. Analysis feels productive. Understanding feels safe. Taking action with incomplete information feels risky and uncomfortable.
But here's what I learned the hard way: understanding your strategy isn't enough. Perfect analysis of why you're failing doesn't stop the failure. The real work isn't perfecting the plan, it's moving forward despite uncertainty and adjusting as you go.
Mid-market organizations face this challenge acutely. You don't have the luxury of separate strategy teams who can spend months analyzing. You don't have the resources to perfect every decision. But you also don't have the time to be paralyzed by incomplete knowledge. The companies that thrive are the ones that can shift from analysis to action quickly.
What Changed for Me
Three things made the difference:
First, I redefined what "ready" meant. Ready wasn't having perfect information. Ready was having enough information to take an informed next step, with a plan to gather more data as I went.
Second, I got comfortable with being wrong. Some of my early revenue decisions didn't work. But I learned from them faster than I would have learned from another month of study, and I could adjust quickly.
Third, I changed how I measured progress. Instead of tracking how prepared or even busy we were, I tracked what actions I'd taken and what results I was seeing. Understanding became a tool for action, not a goal in itself.
Moving Forward
If you're leading strategy execution and things feel stuck, ask yourself Bob's question in your own context: Are you comfortable with strategies failing as long as you understand why?
The discomfort you feel about acting without perfect information isn't a sign you're not ready. It's a sign you're at exactly the point where action becomes necessary.
Here's what I'd suggest:
Take whatever strategic initiative you're analyzing right now and identify one concrete action you could take this week based on what you already know. Not a perfect action, just a directionally correct one. Do it. See what happens. Learn from the results.
Set a decision-making standard: if you have enough information to make an informed choice and waiting would only marginally improve that information, act now rather than later.
Create feedback loops that let you learn quickly from action. The goal isn't to avoid mistakes. It's to make them small, learn from them fast, and adjust.
The strategies that succeed aren't the ones that are perfectly analyzed. They're the ones that are implemented, tested, and adapted. Sometimes you need to be comfortable acting while you're still learning why.