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Why “Failing Forward” is the Best Strategy for Success

And How to Laugh at Yourself While Doing It

By Oren Yehuda CohenPublished about a year ago 5 min read
Why “Failing Forward” is the Best Strategy for Success
Photo by Razvan Chisu on Unsplash

We’ve all been there: you set a goal, make a plan, and then reality comes crashing in like an uninvited relative at Thanksgiving dinner. Whether it’s that new diet you abandoned after two days or the business idea that sounded great until you realized you had no idea what you were doing, failure is an inevitable part of life. But here’s the secret that nobody tells you — failing is actually the best way to succeed.

Before you roll your eyes, hear me out. Failure isn’t just something you endure; it’s something you can embrace, learn from, and — most importantly — laugh at. Because if there’s one thing that makes failure easier to stomach, it’s knowing that it’s just part of the process. Let’s dive into why failing forward might be the most powerful tool you’ve got, and why you should start celebrating those missteps instead of avoiding them.

1. Failure is Just a Detour, Not a Dead End

Imagine you’re driving to a destination, and suddenly, your GPS says, “Recalculating.” That’s failure in a nutshell. It's not the end of the road; it’s simply a change in direction.

Take Mark, who started a tech company in his mid-30s. His first attempt was a spectacular failure. He spent months developing an app that he was sure would change the world, only to have it flop harder than a bad audition for a reality show. But instead of packing it in, he asked himself: “What did I learn from this?” What he discovered was that the market he was targeting wasn’t as ripe for his product as he thought. He pivoted, made adjustments, and tried again with a different approach. Today, his company is thriving.

The key takeaway here? Failure isn’t a full stop; it’s a chance to figure out a better route. Instead of getting discouraged by the wrong turns, embrace them as learning opportunities.

2. You Have to Fail to Find Your “Aha” Moment

If you’re constantly playing it safe, you might never discover your true potential. Think about all the great inventions and ideas that came out of failed experiments. Post-it notes, chocolate chip cookies, and even the microwave oven — all born from mistakes, accidents, and unexpected discoveries.

Take Rachel, for example. She had a dream of opening a boutique fashion store. Her first attempt was a disaster. Her chosen location was a ghost town, and her inventory was too niche. But instead of shutting up shop and sulking, Rachel figured out what worked and what didn’t. She started offering online sales, focused more on social media, and revamped her inventory. Fast forward a year, and Rachel’s boutique is booming.

Failure is like the messy room you have to sift through to find the treasure. It’s the chaos that leads you to your “Aha!” moment, where everything suddenly clicks. Without those mistakes, you might never know what truly works.

3. Learn to Love the “Messy Middle”

We’ve all seen those inspirational posts on Instagram: “Success doesn’t come easy,” followed by a photo of someone sipping a green smoothie while meditating in a yoga pose. It’s all sunshine and rainbows, but in reality, the middle of the journey is more like navigating a jungle gym blindfolded. That’s where failure lives — in the “messy middle.”

James, a freelance photographer, had his fair share of failures. From missed deadlines to botched shots, he felt like a walking disaster. But the messy middle is where you learn the most. After each failed shoot, he fine-tuned his skills and found creative solutions to his problems. Eventually, he became a sought-after photographer in his city, with clients lining up for his services. The failures weren’t the problem — they were part of his evolution as an artist.

Failure is messy, chaotic, and frustrating, but it’s also where the magic happens. It’s like a messy kitchen before the five-star meal. You can’t skip it, and you shouldn’t.

4. Failure Helps You Get Comfortable with Risk

Risk and failure go hand in hand. If you’re going to do something big, you’ve got to get comfortable with both. No one ever changed the world by playing it safe, and no one ever achieved success by avoiding the possibility of failure.

Take Olivia, a graphic designer who wanted to switch careers and become a UX/UI designer. She took several online courses and got a part-time internship, but despite all her preparation, her first few design mockups were less “visionary” and more “who approved this?” But she kept putting herself out there, taking bigger risks. Eventually, those “failed” designs led her to find her own unique style and approach. Today, Olivia is working with top tech companies and living her dream.

The takeaway? Every risk you take might come with failure, but each failure also brings you closer to the kind of success you want. If you’re afraid of failing, you’re probably also afraid of succeeding.

5. Failing Makes You Resilient (And Humble)

Success is great, but let’s be real — it’s the failures that build character. No one wants to hear a success story from someone who hasn’t failed. Think about the greats: Oprah, Steve Jobs, Elon Musk — all of them faced major setbacks before they became household names. And each time they got knocked down, they came back stronger, more determined, and (perhaps most importantly) less likely to let their egos get in the way.

Alex had a dream of becoming a professional writer, but after getting rejected by multiple publishers, she was starting to think her dream was just that — a dream. But she kept sending her work out, revising, and improving. Today, Alex’s books are bestsellers. She credits her failures for teaching her humility and resilience. Failure didn’t knock her down; it built her back up.

The road to success is full of detours, potholes, and the occasional faceplant. But those failures teach you how to bounce back — and that’s the real key to long-term success.

6. Laugh at Yourself

If there’s one thing failure has taught me, it’s the importance of not taking myself too seriously. Laughing at your mistakes doesn’t just make you feel better — it makes the journey a whole lot more enjoyable. Remember, it’s not the failure that matters; it’s how you react to it.

Timothy was determined to launch his own podcast. The first few episodes? Let’s just say he was a little too excited about his own voice, and the audio quality was… let’s call it “vintage.” His first review? “Sounds like you’re recording from the inside of a tin can.” Instead of getting upset, Timothy laughed it off and learned from the feedback. Now, his podcast has a loyal following, and he’s become a guest on major shows. Those “disastrous” first episodes? They were a badge of honor. They were also a reminder that everyone starts somewhere.

7. Failing Forward Makes the Victory Sweeter

In the end, failing forward is about perspective. It’s about seeing setbacks as stepping stones rather than roadblocks. Every mistake you make is a chance to learn and grow. And when you do finally reach your goal, the victory feels that much sweeter because you know the effort it took to get there.

Think of failure as your personal cheerleader — loud, obnoxious, and always there to remind you that you can do better. But at least it’s helping you improve. So next time you fail, laugh a little, learn a lot, and keep pushing forward. The success you’re chasing is just around the corner, and it’s waiting for you to enjoy it with a smile on your face and a story to tell.

advicepersonal financecareer

About the Creator

Oren Yehuda Cohen

Spurts on Personal Finance, Humor, and more!

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