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How to Win Even When You Fail

winner-success-jumpWhat do the premier designer Vera Wang, the famous 1800s scientist and author of “On the Origin of Species” Charles Darwin, and NPR radio icon Terry Gross have in common? They all failed. And it wasn’t just the trial-and-error, have-to-pay-your-dues kind of failures that most anyone has to endure in order to succeed in any given field. These talented people actually failed to reach their initial dreams, aspirations that were based on entirely different professions than what they are so famously known for!

Vera Wang dreamed of becoming an ice-skater but failed to make the 1968 U.S. Olympic figure-skating team. Then, she became an editor at Vogue but was later passed over for a much coveted editor-in-chief position. It wasn’t till the age of 40 that she started to design wedding gowns and is now one of the top designers in the fashion industry.

Charles Darwin had wanted to be a doctor, but eventually gave up his career in medicine to become a parson. Yet, due to the encouragement of a mentor, Darwin finally discovered his lifework when he traveled as a naturalist on a five-year journey around the world to uncover nature’s mysteries.

After graduating as an English major, Terry Gross set out to be a teacher. She landed a teaching position in a tough inner city junior high school and admitted that she couldn’t keep any order in the classroom — much less teach a lesson plan. She only lasted six weeks at the job. After a year, Gross discovered radio and now hosts “Fresh Air,” a popular show that reaches over five million listeners on 450 stations.    

Although it’s a rare to become as professionally successful as the above innovators, most anyone can still learn how to live a happier, more productive life from these stories. Why? Because we all have dreams, dreams that don’t always come true — no matter how hard we try to make them happen. Knowing that even the most determined, hard-working, and talented people had failed to create what they first thought was their life’s work — only to find something even more meaningful — reminds us that we can create a different path, even if the one we happen to be on right now is making us feel as if we’re failing, that what we held onto as our only way to “be” can change with time and experience, and that flexibility may be one of our biggest allies.

So what are some positive ways we can rise above the frustration and disappointment when our dreams aren’t coming true? Below are three coping skills that may help:

1. Challenge What You’ve Been Taught.

From our earliest years, we’ve been bombarded with the well meaning and sometimes-logical message that we hold the power to make our dreams materialize, that if we work hard enough, sacrifice enough, and keep at it, we can make the even the most unattainable goals, attainable.

This mindset may be true for many occupations — but doesn’t always work when someone is trying to break into the most advanced, competitive, and/or artistic professions. For instance, what if you want to be an actor, artist, musician, or writer — and actually make a living? I’ve met some wildly talented people who have received degrees in their given medium, continued to hone their craft, sacrificed time with friends and family in order to pursue their passion, while promoting their work — and years later are still are struggling to make ends meet and/or get the one big break they’re so relentlessly striving toward.   

What then? Does it make sense to still follow the belief that no matter how big the dream, we can always make it happen? Unfortunately: no. This doesn’t mean you should give up on your life’s passion, though. But what it does say is that you may want to also find another avenue that gives you meaning, whether that is through a regular job, volunteer work, or even taking more time off for friends and family. In doing this, you’re creating a better balance in your life that may help you feel less disappointed in your perceived failures, remind you that “success” isn’t always about money or fame, and maybe even give you more joy and energy when you set the time aside to work on your craft.

2. Don’t Bank All Your Happiness on the “Pot of Gold at the End of the Rainbow.”

As a struggling writer, I often daydream about my own big break. I’ve done this so often that I sometimes forget to enjoy the writing process itself, the very thing that “keeps me going.” I finally realized that, yes, I do have to continue to work hard in order to achieve my goals — yet at the same time, I also have to come to terms with the harsh reality of the publishing world. Keeping my dreams alive, while also keeping myself grounded, reminds me that I better not wait for happiness to appear at that elusive pot of gold at the end of the rainbow. Rather, my happiness is right here, right now. Whether it’s my cup of coffee in the morning, connecting with family and friends, walking my dog, reading a great book, and, yes, writing, too, my happiness doesn’t need to wait for the future.

No matter what your personal dream may be (and no matter how big of a daydreamer you are), remember that if you bank all your happiness on some perceived success in the future, you’re missing out on your current “joy standard.” Remind yourself that the more you acknowledge all of your current accomplishments (being a thoughtful neighbor, loving parent, kind friend, for example) and the small, everyday joys of life, the better prepared you’ll be to actually enjoy whatever gifts await you in the future.

3. Remember that Neither “Success” Nor “Failure” Defines Who You Are.

We all have known, or at least heard about amazingly successful people, who have clawed their way to the top of their field, made a boatload of money, people who seemingly “have it all.” Yet some of these very same individuals are some of the most unhappy and stressed-out people you’ll ever meet. Perhaps it’s because monetary and professional success are the main things they feel define them; that even though they attained their dreams, there’s an emptiness that cannot be filled.

Regardless of the reasons why some of the most successful people are still unhappy, it’s important that whether you attain your own dreams or not, you remind yourself that you are still you. You do not have to label yourself as a “failure” just because you failed to achieve something you set out to do. Rather, look at failure as a teacher and motivator. And…mark your successes not as some future-end-all dream — that may or may not materialize — but in the grounded happiness of everyday work and life.  

How to Win Even When You Fail

Tracy Shawn, MA

Author and speaker Tracy Shawn lives and writes on the Central Coast of California. Her debut novel, The Grace of Crows (Cherokee McGhee, 2013), won awards for Indie fiction, including the 2013 Jack Eadon Award for Best Book in Contemporary Drama and Second Place for General Fiction from Reader Views. She’s written numerous articles for print and online publications. Ms. Shawn has currently finished her second novel and is now working on her third. You can visit her website at:

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APA Reference
Shawn, T. (2018). How to Win Even When You Fail. Psych Central. Retrieved on October 24, 2020, from
Scientifically Reviewed
Last updated: 8 Jul 2018 (Originally: 21 Nov 2017)
Last reviewed: By a member of our scientific advisory board on 8 Jul 2018
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