Why Success Makes You Stupid
The most dangerous thing that can happen to a founder isn't failure.
It's success.
Because success breeds the kind of confidence that stops you from questioning your decisions, challenging your assumptions, or listening to uncomfortable feedback.
Success makes you believe your own press releases. And that's where things get dangerous.
The Success Drug
I watched a founder make the same mistake three times in a row last month. When I pointed it out, his response was immediate: "But this approach worked before."
That phrase—"it worked before"—is the beginning of every founder's downfall.
Success is intoxicating. It whispers that your instincts are flawless, your judgment is superior, and your methods are proven. The more successful you become, the louder that voice gets.
You start believing that the things that got you here will automatically get you there. You stop questioning whether "there" is even the right destination.
How Success Rewires Your Brain
Confirmation Bias on Steroids
When you're successful, you start seeing evidence of your brilliance everywhere. That risky decision that paid off? Pure genius. That market timing that worked perfectly? Strategic mastery.
You forget about the luck, the circumstances, the help you received. You forget about the decisions that almost backfired or the timing that was nearly disastrous.
Success makes you cherry-pick your own history.
The Expertise Trap
Success convinces you that you're an expert in areas where you simply got lucky. You nailed one marketing campaign, so you're a marketing genius. You hired one great person, so you're a talent scout.
The dangerous part? You start making decisions in these areas based on confidence rather than competence.
Feedback Immunity
The more successful you become, the fewer people tell you when you're wrong. Your team starts agreeing with ideas they privately think are terrible. Advisors become less willing to challenge your thinking.
You develop immunity to the feedback that could save you from your next big mistake.
The Success Paradox in Action
BlackBerry's Keyboard Addiction
BlackBerry dominated the smartphone market in the early 2000s. Their secure email and physical keyboard made them essential for business professionals. But when Apple introduced the iPhone in 2007, BlackBerry dismissed the idea of a phone without a keyboard.
They believed their customers needed tactile buttons to be productive. Even as the market rapidly shifted toward touchscreens and app ecosystems, BlackBerry doubled down on what had made them successful in the past.
Their past wins became their prison. Clinging to the keyboard cost them the future.
Toys "R" Us and the Amazon Deal
In the early 2000s, Toys "R" Us made a deal with Amazon: Amazon would run their online store so Toys "R" Us could focus on their very successful in-store experience. But Amazon didn't just fulfill orders—they built relationships with customers, gathered data, and grew their own toy sales.
By the time Toys "R" Us realized what was happening, it was too late. They had outsourced their future to a company that was eating their lunch.
They underestimated the importance of owning the customer relationship—because their traditional retail model had always worked before.
The Personal Example
I nearly made this mistake myself. My Australian business was successful using a particular approach for years. When I came to the US, I assumed the same methods would work.
They didn't. The market was different. The customers were different. The competition was different.
But because that approach had made me successful before, I kept pushing it longer than I should have. Success had made me stupid about adapting to new realities.
The Warning Signs
You Stop Asking Questions
When you catch yourself saying "I know this market" or "I understand what customers want" without having recent data to back it up, that's success talking.
You Dismiss New Information
When market research contradicts your instincts, and you trust your instincts over the data, that's success making you overconfident.
You Avoid Experiments
When trying something new feels like a waste of time because you already know what works, that's success limiting your learning.
You Surround Yourself with Agreers
When your inner circle consists of people who rarely challenge your thinking, that's success insulating you from reality.
The Antidote to Success Stupidity
Question Your Greatest Hits
Your most successful strategies might be your biggest liabilities. Ask: What assumptions are these built on? What would happen if those assumptions changed?
Seek Disconfirming Evidence
Instead of looking for proof that you're right, actively search for evidence that you might be wrong. What data would change your mind about your current strategy?
Hire People Who Disagree with You
Build a team that includes people who think differently than you do. Give them explicit permission—and incentives—to challenge your thinking.
Set Learning Goals, Not Just Performance Goals
Measure what you're learning about your market, your customers, and your business, not just what you're achieving.
Embrace Beginner's Mind
Approach new challenges as if you're starting fresh, not as if you're applying proven formulas. What would you do if you had no successful playbook to fall back on?
The Success Recovery Program
Weekly Reality Checks
Schedule regular sessions to examine your assumptions. What did you believe this week that might not be true?
Customer Immersion
Stay connected to your customers directly, not just through reports. Your success might be creating distance from the people you serve.
Failure Analysis
Study your failures as intensively as you celebrate your successes. What patterns do you see? What assumptions led you astray?
External Perspectives
Join groups where your success doesn't insulate you from honest feedback. Find peers who will tell you when you're being stupid.
The Bottom Line
Your past success isn't a reliable predictor of future results, no matter how much you want it to be.
The market doesn't care about your track record. Customers don't owe you continued loyalty because you did something brilliant five years ago.
The most successful founders aren't the ones who never make mistakes. They're the ones who stay curious enough to recognize when their success is making them stupid.
Because in business, yesterday's breakthrough can become tomorrow's blind spot faster than you think.
The question isn't whether your success will try to make you stupid. It will.
The question is whether you'll be smart enough to notice.