Why Failing Increases Your Chance of Success

By Art Harrison • July 5, 2025

Failure isn't the opposite of success—it's the fastest path to it. Learn why entrepreneurs who fail more often actually succeed more often.

Every entrepreneur I know has a failure story they're embarrassed about. A business that didn't work. A product nobody wanted. A strategy that backfired spectacularly.

But here's what I've noticed after 25 years in business: the entrepreneurs with the most failures are also the ones with the most successes.

This isn't coincidence. Failure doesn't just teach you what doesn't work—it fundamentally changes how you approach everything that comes next. And that change is what makes future success not just possible, but probable.

The Counterintuitive Math of Failure

Most people think about failure and success as opposites. You either succeed or you fail. But in entrepreneurship, failure and success are part of the same process.

Here's the math that nobody talks about: if you try 10 things and 9 of them fail, you have one success. If your competitor tries 3 things and 2 of them fail, they have one success too. But you've learned from 9 failures while they've only learned from 2.

Who do you think is better prepared for the next round of challenges?

The entrepreneur who's failed 9 times has developed pattern recognition that the entrepreneur who's only failed twice simply doesn't have. They can spot problems earlier, pivot faster, and avoid mistakes that derail beginners.

What Failure Actually Teaches You

Failure isn't just about learning what doesn't work. It teaches you capabilities you can't develop any other way:

Emotional Resilience

The first time your business fails, it feels devastating. You question your judgment, your abilities, your decision to try entrepreneurship at all.

The second time, it still hurts, but you know you can survive it. The third time, you start focusing on the lessons instead of the loss.

By the fifth failure, you've developed what I call "failure immunity"—the understanding that setbacks are temporary and recoverable. This emotional resilience is what allows successful entrepreneurs to take bigger risks and pursue bigger opportunities.

Problem-Solving Speed

When you've seen a lot of things go wrong, you get really good at diagnosing problems quickly. You develop intuition about what's likely to work and what's probably a waste of time.

Failed entrepreneurs don't stay failed because they can't solve problems—they stay failed because they stop trying. The ones who keep going develop problem-solving capabilities that make future success almost inevitable.

Market Validation Skills

Every failure teaches you something about what customers actually want versus what you think they want. Failed products show you unmet needs. Failed marketing shows you how your audience actually thinks and communicates.

After enough failures, you develop an almost supernatural ability to understand what markets are hungry for. This skill alone can make you wealthy.

The Failure Accelerator Strategy

Instead of trying to avoid failure, smart entrepreneurs try to fail faster and cheaper. They deliberately seek out ways to test their assumptions with minimal investment so they can collect failures (and lessons) quickly.

Here's how to accelerate your failure rate (and therefore your learning rate):

Test Small, Fail Fast

Instead of building the complete business plan, test the core assumption with a minimum viable experiment. Can you sell the idea before you build the product? Can you get three customers to pay for something that doesn't exist yet?

Small failures cost less and teach more than big failures.

Fail in Public

Share your failures openly instead of hiding them. This does three powerful things: it makes failure less emotionally devastating (because you're not carrying shame), it attracts other people who are struggling with similar challenges, and it positions you as someone who learns from experience instead of just theorizing.

Systematize Your Failure Analysis

After each failure, ask three questions:

What assumptions were wrong?
What would I do differently next time?
What opportunities does this create?

Most people ask the first question, few ask the second, almost nobody asks the third. That third question is where the real insights live.

Why Success Without Failure Is Actually Dangerous

I know entrepreneurs who succeeded with their first attempt. You might think they're lucky, but I think they're at a disadvantage.

Early success can create dangerous overconfidence. It can make you think you understand markets better than you do. It can make you risk too much on assumptions that haven't been tested by failure.

The entrepreneurs who built the most sustainable businesses usually have scars from early failures that keep them humble, careful, and realistic about risk.

Failure is entrepreneurial insurance—it protects you from the kind of overconfidence that destroys businesses.

How to Reframe Your Past Failures

If you've tried entrepreneurship before and it didn't work out, you're not behind—you're ahead. Every failure you've experienced is education your competitors paid to give you.

That failed side hustle? It taught you something about market validation that business school couldn't.

That product nobody bought? It taught you something about customer psychology that marketing courses couldn't.

That partnership that fell apart? It taught you something about business relationships that networking events couldn't.

You're not starting over—you're starting with advantages that people who haven't failed yet simply don't have.

The Failure-to-Success Conversion Process

Here's how to turn your past failures into future advantages:

Step 1: Inventory your failures. List every business attempt that didn't work out as planned.

Step 2: Extract the lessons. For each failure, identify what you learned about markets, customers, business models, or your own capabilities.

Step 3: Apply the lessons. How can these insights inform your next attempt? What mistakes will you avoid? What approaches will you try differently?

Step 4: Share the insights. Teaching others what you learned from failure often becomes more valuable than the original business you were trying to build.

If you're struggling to see the value in your past failures, read about building confidence through action instead of through perfect track records.

Your Failure Action Plan

This week: Choose one past failure and write down three specific lessons it taught you about business or about yourself.

This month: Apply one of those lessons to a new, small business experiment. Use your failure education to increase the odds of success.

Long-term: Develop a systematic approach to testing ideas quickly and cheaply so you can fail fast and learn faster.

The goal isn't to avoid failure—it's to fail forward. Every setback should make you more capable, not less confident.

If you're ready to stop fearing failure and start using it as a competitive advantage, the FSTEP program provides structured practice taking calculated risks and learning from results.

Remember, failure doesn't decrease your chances of success—it increases them. But only if you keep going long enough to apply what you've learned.

Your failures aren't evidence that you can't succeed. They're evidence that you have the courage to try uncertain things. That courage, combined with the lessons failure teaches, is exactly what entrepreneurship requires.

Stop avoiding failure and start collecting it. Your future success depends on the education that only failure provides.

For more insights on handling setbacks, explore what to do when you're tired of being scared and learn about overcoming analysis paralysis that often follows failed attempts.

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Video Transcript

all right I know I probably shouldn't say this but I kind of hope you fail and not just a little I hope you fail a lot and that you fail often because I know that failure is where real growth happens every single success that I've ever had no matter how big it was no matter how small it was it all came from failing first all the lessons that I learned and all the opportunities that I had the privilege of being part of they all started as some sort of a failure so today today I'm going to share with you why I love failure and why I think you should learn to love it too and I hope that by the end of this video you're less afraid to try less afraid of failure and that you can see failure in a new light because I'm a massive failure and I'm still a success I have failed so many times I am failing at so many things right now and I hope that I have the opportunity to fail more in the future and to prove it to you I'll share with you one of the more painful failures that I had just so you know that I've really been through it the I live to talk about it when I was in my 20s the thing that I wanted more than anything else was to become a stand-up comedian it was my biggest dream I adored The Comedians like Chris Rock and Bill Hicks and Richard prior so when I was old enough I signed up for an amateur night and I drove myself into the City and I got up on stage but the problem is I hadn't actually prepared anything somehow in my mind I believed that I had so much charm and so much Charisma that it would just carry me through that everybody would love me instantly and that I'd probably be signed to a deal and that my career would take off from that night but obviously that didn't happen I failed I bombed spectacularly I remember how flush my face was it was burning I remember that I almost threw up on stage and I remember that not a single person in the crowd laughed not even one time and basically that dream that I had the thing I wanted more than anything else died in a matter of just a few minutes that night if I want to I can still relive the negative part of that I can still remember the MC getting up on stage after me and saying something like give it up for bravery because well my set wasn't funny or entertaining I guess it was Brave I I tried something there was something to that what I also remember is that as painful as it was I went home and I told every one of my friends and all of my family about it in excruciating detail I told them about the bright lights I told them how hot it was and how silent the room was and I told them that I cried on the way home and I don't normally cry and I definitely don't talk about it very often but whenever I told that story ended by saying that I knew something good was going to come from it I was proud that I had at least tried and I had gone after my dreams and that I knew somehow in some way I was going to learn a valuable lesson from that night and over time the more I told the story the less painful it became I can still go back to that moment if I want to but most of the time what I'm talking about it's just an anecdote I don't feel the same feelings I had then because when I tell the story now I'm telling it to share a lesson that I learned learned the lessons about resilience and preparation because ever since that night I didn't want to feel that experience again so no matter what I'm doing if I'm doing something new I make sure that I'm actually ready for it because I tell the story so often and because I identified what I learned from it it's changed who I am and it turned something that was an absolute failure something that felt like an ending into a beginning something that made me who I am today and that's the trick that all of you should use every single day you're going to tell your stories right we're all going to tell stories about good times and bad times so you might as well learn to enjoy them to be honest about them and to recognize that you're never alone everybody every single person has their own failures as well so you got to turn your stories your failures into stories of growth for example let's just say that you applied for a job and you didn't get it yeah that hurts but it's okay because if you had gotten that job you wouldn't have been looking or available for the better J job that came along 3 months later you don't always know that in the moment but if you keep telling the story if you keep searching for the meaning in the failure eventually you recognize how that failure LED you to the place you ultimately needed to be since you're going to be telling your stories anyway just like I am you might as well have fun with them seriously failures are funny think about when you're sitting around with any of your friends the best stories and the best times that you have are likely when you're laughing about something that went wrong nobody really cares about about the time you scored the goal or won the big game but if you tell your friends the stories about when you flopped when you basically threw up on stage or the embarrassing thing you did at work or on a date well then they get excited they start getting engaged they laugh with you not at you and if they're like my friends maybe my friends are different they probably jump in and try to oneup you they say you think that's bad here's what I did and they tell you that they've done even bigger failures than you failures are familiar and Universal they bond us together they're funny so don't ever shy away from talking about your failures it's not something to be ashamed of it's part of who you are it's part of where got you where you are today just make sure when you're telling them that you identify how or what you're going to learn from it the funny thing about failure is that it also kind of rewires our brains it opens us up to a different way of thinking and I think that's important if you want to be creative and more Innovative then you have to build up a tolerance to failure because if you don't you end up avoiding things that can make you fail you do things the safe way you take the conventional path through things and you never try new ideas or new approaches but real Brilliance comes when you step outside of that comfort zone and most people are only willing to do that if they've experienced failure if they've learned to embrace it that's where creativity and Innovation come from when you go outside of your comfort zone you have the opportunity to actually differentiate yourself to do something amazing to achieve things that seemed impossible to you and to all the people around you I think about it all the time because I come from the startup world and in the startup world there's a mantra that people know you probably know it it's fail fast every startup tries to live by this they are all trying to do something big impressive and new so they have to fail fast they have to experiment and try new ideas and usually like 99.9% of the time they fail but they do it quickly and they learn from it they learn what works and what doesn't work and their goal is not to just fail but it's to ultimately find the thing that works because that's where their business is that's where real change happens even though it's a startup idea it's not just for startups it's an idea that you can apply to any area of life even something as random as Pottery now you may have heard this story before it's a famous story but there's a pottery teacher and they tried an experiment where they took their class and they split them into two groups one group was told that they should just make as many pots as possible and the other group was told that should try to make the perfect pot and the goal was that after a month the teacher would review everything they made and they would try to identify who had come closest to building a perfect pot the funny thing is when they looked at all of the pots the best ones the ones that were closest to Perfection were all from the group that focused on quantity over quality and the reason for that is that group the ones who weren't focused on Perfection they just kept experimenting they tried new things they learned from every mistake they made and they ultimately kept improving they got better with each and every attempt but the second group they had this idea of perfection in their minds and they didn't want to do anything wrong so they overthought every step and they avoided taking risks they didn't want to ruin their one perfect pot but ultimately it limited how good they could get and so the lesson there is kind of universal the more you do the more you experiment the more you fail the better you actually get at whatever it is you're trying to do so failing is part of the journey it's an important part it's not limited to startups and pottery it's anything whether you're learning a new skill or you're starting a project or you're pursuing your dream if you Embrace failure and you learn from it then you're actually on your way to succeeding hopefully I'm convincing you that failure can be fun and that it's important and you see the value in doing it so let's do something different together something that might push you out of your comfort zone but as we talked about before that's a good thing usually in a video like this someone like me would tell you that you should start journaling you should write down your most recent failure and maybe try sharing it with a friend and see what happens but we're different here I'm Different I think you're different too so let's be different let's use the comments under this video and here's what I want you to do I want you to go to the comments and I want you to share a failure that you've had something that you don't normally talk about talk about it in detail see how many other people have failed just like you and comment on them treat them like you would your friends try to one up them talk to them about what's funny about their failure or what they might be able to learn from it even if it's scary sharing failures builds community and trust and when you hear about other people's failures it makes you realize that you're not alone and it gives you an opportunity just like it gave them to actually learn what does and doesn't work you don't have to fail at everything to learn but you do have to listen to other people's stories and other failures because you'll know what not to do or you'll know how to do it a little bit better when you have the opportunity so go forward enjoy your failures share them laugh at them know that every failure you have is actually helping you get one step closer to achieving something remarkable if you want to see how you can turn a failure into a fun story then watch this video about how I was so close to becoming a billionaire it's one of my biggest failures and I documented it because I think that it's funny and because I know that in that story are lessons that led me to where I am today so go at it Go fail at something and if you found this video valuable then share it with somebody else that needs to hear this message or share it with someone that you want to fail but that you want to fail for the right reasons not because you're being mean or vindictive