Failure is usually treated like a social disease. We hide it, we scrub it from our LinkedIn profiles, and we definitely don't brag about it at dinner parties. But here's the thing: some of the most successful people on the planet didn't just stumble through failure; they used it as a deliberate operating system. It’s kida weird when you think about it. We’re taught that the path to success is a straight line, but if you actually look at the data, it's more like a series of controlled explosions.
Learning how to fail at everything and still win big isn't about being a loser. It's about system design. It’s about moving away from "goals" and moving toward "systems" that pay off even when the specific project goes up in flames.
The Scott Adams Philosophy: Systems Over Goals
Most people set goals. They want to lose 20 pounds or make a million dollars. The problem? You’re in a state of near-constant failure until you reach that goal—if you ever do. Scott Adams, the creator of Dilbert, popularized a completely different framework. He argues that goals are for losers. If you have a goal, you’re waiting for a future moment to be happy. If you have a system, you’re winning every time you apply the system.
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Basically, a system is something you do on a regular basis that increases your odds of happiness or success in the long run. If you start a blog to become a famous writer and it fails, that’s a failed goal. But if you started that blog to practice writing, learn WordPress, and network with experts, you’ve won. You’ve acquired skills that carry over to the next thing. You failed at the "goal" but succeeded at the "system."
Think about it this way. If you spend your time learning a niche skill—let's say video editing—to launch a YouTube channel that eventually flops, you haven't actually lost. You are now a person who knows how to edit video. That skill is a "stackable" asset. You failed at being a YouTuber, but you won at becoming a more valuable human being. That’s the secret sauce.
The Concept of "Skill Stacking"
Most of us aren't going to be the best in the world at one specific thing. Being the top 1% of basketball players or physicists is statistically impossible for almost everyone. But being in the top 20% of three or four different things? That’s totally doable. This is where you start to understand how to fail at everything and still win big.
Success is often just the intersection of mediocre skills.
Take a look at Steve Jobs. He wasn't the best engineer. He wasn't the best designer. He certainly wasn't the easiest guy to work with. But he had a "system" of understanding typography, consumer electronics, and storytelling. Individually, those skills were good. Combined? They changed the world. He dropped out of college—a massive failure by traditional standards—but used that "failed" time to sit in on calligraphy classes. That "waste of time" is why your Mac has beautiful fonts today.
Real-World Examples of Winning Through Failure
- Max Levchin: Before he co-founded PayPal, he had four failed companies. Four. Most people would have quit after the second one, thinking they weren't cut out for business. But Levchin was building a system of understanding digital security and cryptography with every failure.
- Vera Wang: She failed to make the U.S. Olympic figure skating team. Then she failed to become the editor-in-chief at Vogue. She didn't enter the fashion design world until she was 40. Her "failures" in skating and journalism gave her the grit and the visual eye necessary to dominate bridal wear.
- Billion-Dollar Mistakes: In the tech world, failing is almost a rite of passage. Consider Slack. It started as a failed internal communication tool for a gaming company called Tiny Speck. The game, Glitch, was a total disaster and shut down. But the "failed" team realized the chat tool they built to talk to each other was actually the real product. They failed at gaming and won at enterprise software.
Why Your Brain Hates This (and Why You Should Ignore It)
We are biologically wired to avoid the sting of defeat. It’s a survival mechanism. Back in the day, failing to catch a mammoth meant you starved. Today, failing to launch an app just means you have a messy garage and a bruised ego. But our brains don't know the difference. We feel the same level of cortisol.
To win big, you have to rewire that. You have to start looking at every project as a "beta test" for your life. Honestly, if you aren't failing at least some of the time, you probably aren't aiming high enough. You're playing it safe in the middle of the pack.
The Math of Iteration
Let’s talk about "Optionality." This is a term Nassim Taleb talks about a lot in his books like Antifragile. It’s the idea that you want to position yourself so that you have more to gain than to lose.
If you take a job at a stable corporation, your "upside" is capped. You might get a 3% raise. Your "downside" is also capped—you likely won't get fired unless you do something crazy. But if you spend your weekends building small, "failable" projects, you have asymmetric upside. One of those projects might explode and change your life. The cost of failure is just a few hours of your time.
This is how people "win big." They play a lot of small games where the cost of losing is low, but the payoff for winning is massive.
Stop Looking for Passion
Here is a controversial take: Passion is overrated. People tell you to "follow your passion," but that’s actually terrible advice for most. Passion is usually the result of being good at something, not the cause of it.
When you focus on systems and skill stacking, you often find that you become "passionate" about things you never expected. You might fail at a dozen different side hustles, but along the way, you find that you’re really good at managing people or analyzing data. That competency leads to success, and success leads to passion.
Actionable Steps to Fail Upward
Stop worrying about your "permanent record." Nobody is keeping track of your failures except you. To actually start winning big, you need to change your daily inputs.
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- Audit your skill stack. What are three things you are "okay" at? How can you combine them? If you’re okay at accounting and you love heavy metal, maybe you’re the best person to manage finances for touring bands. That’s a niche.
- Kill your goals, build a system. Instead of "I will write a book," try "I will write 500 words every morning." Even if the book is never published, you’ve become a better communicator.
- Choose projects with "Residual Knowledge." If the project fails tomorrow, will you still be smarter? Will you have met interesting people? If the answer is no, don't do it.
- Embrace the "Pivot." When things aren't working, don't just "try harder." Look at the wreckage. Is there a small piece of that failure that actually worked? (Like the Slack chat tool). Double down on that piece.
- Lower the cost of failure. Don't remortgage your house for an unproven idea. Run "micro-experiments." Test things quickly and cheaply.
Winning big isn't about being perfect. It’s about being the person who is still standing after everyone else got tired of losing. It’s about being "antifragile"—getting stronger every time the world tries to break you. If you can handle the ego hit of a few dozen small failures, you’re eventually going to stumble into a win so big it makes all those "losses" look like the best investments you ever made.
The Realistic Next Move
Start by identifying one "low-stakes" project you’ve been avoiding because you’re afraid it won’t work. Commit to doing it for 30 days, not with the goal of succeeding, but with the goal of learning one specific skill (like basic coding, public speaking, or sales). At the end of those 30 days, even if the project is a total bust, document exactly what skill you’ve improved. That is your first win in the system. Use that new skill to inform your next "failure." Repeat this until the market eventually pays you for your unique combination of talents. Success is a lagging indicator of a good system. Focus on the system, and the wins will eventually take care of themselves.