2024 Post Mortem: Lessons in Overconfidence and Accountability

As we turn the page to 2025, conversations are abuzz with resolutions, milestones, and goals. Inevitably, someone will ask, “What are your goals for this year?” But one thing often missing from these discussions is reflection on the year that just ended.

In my opinion, there’s immense value in conducting a forensic analysis of the previous year—both the successes and, more importantly, the failures. Reflection offers lessons that can be far more impactful than setting even the most detailed goals for the year ahead.

For me, 2024 brought a particularly painful and personal failure: I missed on a major account. Here’s how I screwed it up.

The Root of the Failure: Overconfidence

For over a decade, the biggest challenge in my business has been convincing customers to give us a chance to prove our technology in their space. Depending on the customer, that convincing could take anywhere from 30 days to 30 months. Once we got that shot, though, our product always delivered.

Well, almost always.

This particular customer presented unique challenges we hadn’t encountered before. Years of successful pilots had fueled not just confidence, but overconfidence—bordering on arrogance. When the initial round of results came back flat, we didn’t flinch. It had happened before, and we were certain the win was just around the corner.

Then the next round of results came back with no improvement. The customer was understandably concerned. Here’s where I personally messed up: I assured the customer that we would overcome the early issues and deliver a measurable gain. Not just confidence—I expressed certainty.

That was dumb.

I hadn’t identified the root cause of the problem; I was merely confident we would figure it out. I’ve always prided myself on being honest with my customers, but in that moment, I let my optimism overshadow my transparency.

When Customers Buy from You, They’re Sticking Their Neck Out

When a customer buys from you, they’re not just purchasing a product or service—they’re placing their trust in you. They’re also putting their own credibility on the line with their internal stakeholders.

In this case, my overconfidence didn’t just cost us the deal; it damaged the professional standing of my client. I set them up for failure by promising outcomes I hadn’t yet ensured. Failure, while painful, is an incredible teacher. It forces you to reevaluate assumptions and long-held beliefs. This particular failure has already led to some of the greatest breakthroughs our company has ever had and will undoubtedly strengthen our product in the long term, that’s not the story here.

The real story is about me failing personally.

The Fallout

We didn’t deliver, and we didn’t get the customer. Worse, I lost a valuable relationship. The client is far too professional and kind to tell me outright, but the shift in our interactions was undeniable. I had hurt them professionally.

Even if I hadn’t lied intentionally—and I hadn’t—they didn’t know that for a fact. For all they knew, I was just another salesperson making empty promises to serve my own interests. That realization hurts, but it’s one I brought upon myself.

I should have been transparent. I should have said something like:

“I’ve never failed in this situation before and don’t expect to now, but I have to admit these results are unexpected so far.”

That honesty would have shown respect for the risk they were taking on me. Instead, I offered an optimistic view based more on hope than on hard-earned insight.

The Hardest Lesson

But that doesn’t erase the personal failure. It doesn’t undo the fact that I let my client down when they needed me most.

I hope one day I’ll write the story of how we turned this failure into a resounding success. But today, I’m writing the story of accountability—acknowledging my mistakes, learning from them, and committing to being better.

We are all planning for our goals and milestones for 2025. We are no doubt planning for success. I encourage you to also evaluate your failures from 2024 because those are the learnings most likely to drive your success in the new year. So my question is not about your goals for 2025. Please tell me about a failure in 2024 in the comments below. It will be uncomfortable and that is where we grow.