Your experience is making you dumber
I was 21, sitting across from my first investor. He wrote the check, then told me why: "I invest in young people because you don't have baggage yet. No walls of strong assumptions. No sourness from failures. I can help build fresh walls with you."
I nodded like I got it. But what I heard was: You're investable because you're too naive to know this is hard.
I'm in my thirties now. I finally understand. The walls are real.
How walls show up
I started my first company at 19 back in college. Sold DIY science kits door-to-door to schools. Had no idea what I was doing. Thought you just needed a good product and people would buy it. I was wrong about so many things. But I tried everything. Cold called schools. Showed up unannounced. Wrote terrible emails. Gave awkward demos. Failed in every possible way you can fail.
By my second startup in my late twenties, I'd learned what worked. I had frameworks. I knew the "right way" to do sales. I'd done 1000+ sales meetings by then. I could spot red flags in the first five minutes. I knew which leads to pursue and which to ignore. This felt like progress. It was progress. But it was also the beginning of something else.
I started seeing patterns everywhere. A founder would describe their problem and before they finished, I'd think "this is just like that company I worked with in 2019." A potential hire would say something in an interview and I'd think "this person reminds me of X, who didn't work out."
The pattern recognition was useful. It saved time. It prevented mistakes. But it also made me less curious. Less open. Less willing to be surprised.
The younger version of me wouldn't have made that mistake. Not because she was smarter. Because she didn't have enough opinions yet to get in her own way.
The identity trap
There's another kind that builds slowly. It's about who you think you are. At 21, when someone asked me to do something I'd never done, I'd just do it. I wasn't good at these things. But I hadn't decided yet what kind of person I was.
By 32, I'd figured it out. "I'm a GTM person" "I can only do B2B" These felt like self-knowledge.Like I'd finally understood my strengths and could lean into them. But they were actually limits.
The most painful wall is built from actual knowledge. I have learned the frameworks, read books, managed teams, built stuff. I know the right way to do things. I have earned this sophistication. But sometimes sophistication becomes a cage.
What I'm Trying
I'm trying to notice when I'm building walls. It's hard. The walls don't announce themselves. They feel like wisdom.
1. Question one "truth" once in a while: Every few months, I write down something I'm confident is true about our market or product. Then I spend the week looking for evidence that proves me wrong. Most weeks I'm right. But every few weeks, I find something that changes everything.
2. Do something badly: In the last few years, I have tried learning many new skills like American accent, swimming, consistent with writing, building marketing flywheels and more. I was terrible at most of them initially. But that feeling of being genuinely bad at something, it reminds me being a beginner isn't end of the world. Not knowing is the starting point for learning, not a problem to hide.
3. Listen to people who suggest things that sound wrong: This is harder than it sounds. When someone suggests something that contradicts my experience, my instinct is to explain why it won't work. Now I'm trying a different thing: I ask "What made you think of that?" And then I shut up and actually listen. Not to find holes in their logic. Just to understand how they're seeing the problem. Sometimes their logic is flawed. But sometimes they're seeing something I've trained myself not to see. The angle I've dismissed without noticing I've dismissed it.
The unfair advantage
Young builders have real advantages, no walls, willingness to try anything, not-knowing-what-you-don't-know. But sometimes it waste enormous amounts of time like chasing wrong markets, wrong hires and more.
But a founder in 30s/40s who's learned to keep beginner's mind, that's different. That person has judgment about which walls matter and which don't. They can see the pattern but choose to ignore it when the situation demands it. They know which conventions exist for good reasons and which exist because nobody questioned them.
They have the patience to ship things in real world, communication skills to get buy-in, the wisdom to know when to push and when to wait.
That's an unfair advantage. But only if you're willing to do the work of keeping the walls down.
What that investor did not tell me?
That investor was right about young people, we had no walls yet. But he missed something: You don't have to be young to have fresh walls.
You just have to be willing to tear down the old ones. Over and over. Even when they've served you well. Even when it feels like giving up hard-won wisdom. The walls aren't inevitable. They're choices repeated until they feel like fate.
The test I give myself:
When was the last time I tried something I wasn't already good at? When was the last time I was wrong about something I was sure about? When was the last time someone younger than me changed my mind? If I'm struggling to answer these, the walls are back. Time to start tearing them down again.
Note: Written from my own experience, with Claude helping me structure my rambling thoughts into something readable