Self-development

Blessings in Disguise: 7 Lessons on How to Fail Well

by Kinga Lewandowska — 7 min read

Blessings in Disguise: 7 Lessons on How to Fail Well

When kids learn to walk, they fall down constantly. Never, for a split second, does a child think walking might not be worth trying harder next time. Then, at some point later in life, we start magnifying the tiniest failures to be the end of the world. When we go to school, we learn that failure in the form of bad grades is invariably frowned upon, which only promotes risk-averse behavior and hinders creativity. Add overprotective parents, social media, self-limiting beliefs, and the unnecessary burden of comparison. How many dreams perished this way? Too many.

As we grow up, some of us manage to unlearn this early conditioning and redefine failure, turning it into a necessary step towards success. As bitter as defeat might feel in the moment, it is always a lesson in disguise. But don’t take just our word for it – many incredibly successful people we all know and admire praise the benefits of failing because they lived through it time and again in order to get where they are now.

We’ve chosen seven success stories to prove that defeat can lead to victory. Do any of the names below ring a bell?

Marie Forleo

“Stay on your game and keep going for your dreams because the world needs that special gift that only you have”. This is how Marie Forleo, writer and entrepreneur, finishes every episode of her show Marie TV. She’s the founder of B-School, an online business training program, and the author of the New York Times bestseller Everything Is Figureoutable. As an advocate for multi-passionate entrepreneurship, she teaches how to build a business and life you love without squeezing your soul into a labelled box.

Marie has helped thousands of people reclaim their courage after setbacks because she never allowed fear to calcify in her bones. On vacation in Italy she had a scooter accident and was faced with a choice: follow fear back into the comfort zone, or learn and try riding again. “The decisions you make when you’re down determine how high you’ll eventually fly”, says Marie. Once, when asked about her failures during an interview, her mind went blank. Of course she stumbled in her various endeavors more times than she could count, yet treating missteps and flops as such an integral part of the game made her redefine them as success. If failure is guaranteed, you can never BE a failure, but you can befriend it.

“Failure is a given if you're in the game. But here's what's important to remember — a fall isn't final unless you stay on the ground.” – Marie Forleo

Lesson:

Failure is inevitable. Find something you’ll love more than you fear failure.

Yara Shahidi

Before we grow into adulthood, we search for our identities, definitions for our feelings and dreams, we navigate the waters of early life with little to no experience, and we learn what it means to fail. Yara Shahidi, actress and activist, went to Harvard with a letter of recommendation from Michelle Obama. Her resume consists of movies starring Angelina Jolie and Eddie Murphy. She founded WeVoteNext, a platform encouraging young people to vote. Net-a-Porter ranked her one of the best dressed women and in 2019 she appeared on the cover of the September issue of British Vogue curated by Meghan, Duchess of Sussex.

What is Yara’s secret to so much success at age 21? Embracing failure as part of the natural process of growing. She remembers how, being a straight A student, her first C in English almost defined her as a person. Instead, she reforged failure into motivation for improvement, bid farewell to perfectionism, and focused on progress. It doesn’t take a fortune teller to predict more success to come in Yara’s future.

“I allowed myself to realize that one, there’s no need to be perfect and two, failure is the essence of improvement and the essence of growth. Sometimes our growth isn’t linear or as clean as we want it to be, but these moments that we may consider failure are extremely important.” – Yara Shahidi

Lesson:

You define failure but failure never defines you. Let it lead you through growth to success.

Seth Godin

The world knows him as a writer and marketing guru who mentions failure in most of his seminars, interviews, and books (24 of those and counting, including 20 worldwide bestsellers in 36 languages). Here’s Seth’s bit of success: his book Free Prize Inside was a Forbes Business Book of the Year in 2004, Purple Cow sold over 150,000 copies in the first two years, and Linchpin is one of "20 of the best books by the most influential thinkers in business" according to Business Week. Seth has been inducted into the American Marketing Association's Marketing Hall of Fame, his blog was among 25 best blogs of 2009 according to Time magazine, and his podcast Akimbo was one of the top 1% of all podcasts of 2018.

Yet, Seth was also close to bankruptcy for 8 years and received 800 rejection letters in a row in the first year of his career in publishing. Still, he founded businesses, sold businesses, and never took failure personally. Seth Godin’s risk-taking puts a dent in the universe. It takes a true artist, leader, and innovator to constantly challenge the status quo and invent new paths. Paraphrasing Seth himself, he wins because he is willing to be the person who fails the most.

“If failure is not an option, then neither is success.” – Seth Godin

Lesson:

To change the world – create and fail. Invent and fail again. Innovate and keep failing.

Barbara Corcoran

The queen of real estate, founder of The Corcoran Group, fierce businesswoman who sued Donald Trump to collect due commission – Barbara Corcoran believes failure and success are linked. Unable to read until she was in seventh grade, she was labelled “stupid”. Having worked twenty jobs before the age of 23, she met her first life and business partner while waitressing in a diner. He offered her $1000 to start a real estate business. The powerful rich men in the industry’s high places had little respect for her until she became their number one rival. When Barbara’s partner left her, convinced she was never going to succeed without him, she turned $1000 into $66 million (the value of her empire when she sold it).

Barbara’s fear of public speaking muted her in front of 300 investors, so she took a teaching opportunity at NYU to turn that failure around and met her top sales employee as a result. She lost $77 000 on video tapes of apartments which led her to discovering the Internet ahead of her competitors. When she was first offered and then denied a seat at the table on ABC’s Shark Tank, she rejected the rejection and claimed her spot. Barbara is great at failure and this is why she succeeded.

“All of my singular, phenomenal successes that helped me build my business happened on the heels of failure.” – Barbara Corcoran

Lesson:

Your strengths can turn failure into an opportunity. Pivot, change your plan, but never the goal.

Michael Jordan

Considered the greatest basketball player of all time, Michael Jordan is no stranger to failure. In fact, he’s a fierce advocate for it. Before he could score an average of 30.1 points and become the NBA's most valuable player in the 80s and 90s, he stumbled many times. Beginning in high school when he did not make the varsity team because he was too short at the time, he learned that talent simply isn’t enough, you need to add hard work and dedication to the equation of success.

Michael’s intrinsic motivation pushed him to work himself to the limits and relentlessly double the effort every time a setback occurred. His drive helped him break numerous records and become the most decorated player in the history of the NBA. And then the most famous basketball player failed again when he made an attempt to become a professional baseball player – to no avail. But if you never try, you’ll never know.

“I’ve missed more than 9000 shots in my career. I’ve lost almost 300 games. 26 times, I’ve been trusted to take the game winning shot and missed. I’ve failed over and over and over again in my life. And that is why I succeed.” – Michael Jordan

Lesson:

Failure is something to strive for. Fail often to learn how to succeed.

Sophia Amoruso

Entrepreneurs like Sophia Amoruso eat failure for breakfast. When she got a hernia and had to accept a security job in an art school to earn her health insurance, Sophia realized she’d never be happy working for somebody else. She then started an eBay store called Nasty Gal selling vintage clothes. Knowing very little about business, she managed to scale her project into $100 million in revenue. When her eBay account got suspended, Sophia opened another online store and over the years switched her office from an ’87 Volvo to a fifty-thousand-square-foot space in Los Angeles. Her book #Girlboss became The New York Times Bestseller, she appeared on the cover of Forbes magazine and her journey was adapted by Netflix (not without another failure of getting cancelled after one season).

When Nasty Gal filed for bankruptcy in 2016 Sophia founded another Girlboss business, a community for ambitious women (and then she sold it). Today you can find her teaching and mentoring the next generation of rebel entrepreneurs.

“There are secret opportunities hidden inside every failure.” ― Sophia Amoruso

Lesson:

Be unapologetically you and swim against the current. Use failure to reinvent yourself.

Steven Pressfield

He helped us understand and conquer the power of resistance. As a writer he knows it very well. However, before Steven Pressfield could reach a wider audience with The War Of Art, or with any of his other outstanding fiction and non-fiction books, he had to persevere through years of failure. In his lifetime, he worked as a schoolteacher, driver, bartender, oilfield roustabout, attendant in a mental hospital, and fruit-picker. Steven Pressfield worked 21 different jobs in 11 states (let that really sink in) before he could earn a living from what he loved doing most – writing. He was also homeless for a period of time and lived in the back of his car.

It took him 17 years before he earned his first penny from writing, 27 years to get his first novel published and it wasn’t until he was in his early 50s that he could finally make a living as a writer.

“When a pro hits adversity, they simply rally in the face of it and use it in their own way.” – Steven Pressfield

Lesson:

Adversity might test your resilience to the limits. If you want to succeed, fail and persevere.


You Only Fail When You Stop Trying

Steve Jobs began his tech career by hacking landlines to make free long-distance calls. Arianna Huffington’s writing was rejected by 36 publishers. Walt Disney got fired from a newspaper for his “lack of creativity” and Steven Spielberg didn’t get accepted to film school twice. Who would all of these remarkable people be today if they weren’t willing to fail?

Not every failure leads to success, yet success is hardly possible without failure. The more we fail, the more likely we are to succeed. We have the power to redesign our circumstances and live life on our terms only if we’re willing to lose a few battles to win the war. When failure stands in the way, it becomes the way.

Let’s recap 7 lessons on how to fail well:

  1. Failure is inevitable. Find something you’ll love more than you fear failure.
  2. You define failure but failure never defines you. Let it lead you through growth to success.
  3. To change the world – create and fail. Invent and fail again. Innovate and keep failing.
  4. Your strengths can turn failure into an opportunity. Pivot, change your plan, but never the goal.
  5. Failure is something to strive for. Fail often to learn how to succeed.
  6. Be unapologetically you and swim against the current. Use failure to reinvent yourself.
  7. Adversity might test your resilience to the limits. If you want to succeed, fail and persevere.

“It is impossible to live without failing at something, unless you live so cautiously that you might as well not have lived at all – in which case, you fail by default.” – J. K. Rowling

Self-development

Toxic Positivity: In Defense of Negative Emotions

Toxic positivity is forced happiness. It’s the assumption that despite your difficulties and challenges you should be cheerful. But life is a package deal, it comes with both light and darkness and we need an array of emotions to accept and deal with both.

Read more
Self-development

Dealing With Grief and Loss

In this article, we’ll explain what grief actually is, share some common myths and facts, and, most importantly, share tips on how to deal with it in as healthy way as possible.

Read more
Self-development

Gratitude Letter to My Former Self

The process of thanking ourselves puts into perspective how much we’ve grown over a certain period and helps us highlight the most important qualities and milestones we’ve reached along the way.

Read more