A few years ago, I met someone who was a partner in a business that sold for a significant amount. We connected not long after the deal had closed, and I asked him what he planned to do next. He told me he was going to start consulting, helping other business owners grow, and eventually exit their companies.
I was skeptical (quietly!). This was the first time he had been involved in a business that had been sold, and that doesn’t always translate into repeatable success. Over the years, I’ve met several people who have grown and sold businesses. A few have been able to do it multiple times, but many struggle the second time around. Without saying it out loud, I had already formed a conclusion. His plan seemed to be based on experience, but looking back, it might have been an assumption.
Experience is one of the most valuable things we have. It helps us recognize patterns, avoid mistakes, and move faster than we otherwise could. It builds credibility and becomes something people rely on. But there’s a subtle shift that can happen over time. The more experience we gain, the easier it is to assume we’ve seen it all before. A situation feels familiar, so we assume we understand it. A person reminds us of someone else, so we expect the same outcome. A problem looks similar, so we apply the same solution. And sometimes we’re right. But sometimes we miss what’s different.
What experience needs is curiosity. Not all the time, but often enough to ask one more question, listen a little more closely, and consider that this situation may not be exactly like the last one. Because the risk isn’t that experience is wrong, it’s that reliance on it becomes automatic.
When that happens, we stop exploring and start concluding. We think we’re drawing on wisdom. Sometimes we’re just pattern-matching on incomplete information. That conversation stayed with me, not because I was right or wrong, but because it made me realize how easily experience can create a false sense of certainty. Not just in that moment, but in so many others.
It shows up more often than we think. In how we evaluate people, how we approach decisions, and how quickly we decide, we already understand what’s happening.
That’s the thing about assumptions. They don’t feel like shortcuts. They feel like knowledge. The goal isn’t to distrust experience. It’s to recognize when it quietly turns into an assumption, and to stay curious long enough to see what might be different this time.
“It ain’t what you don’t know that gets you into trouble. It’s what you know for sure that just ain’t so.” – Mark Twain
Where have you seen experience turn into assumption, either in yourself or in others? I’d be curious to hear your perspective.
Have a great weekend.
-Vijay