How to Handle Fear and Failure Like a Boss

UPDATED: December 2, 2016
PUBLISHED: December 2, 2016

“If you don’t risk anything, you risk even more.” —Erica Jong


We can’t talk about being in business for ourselves without talking about fear, right? Because when we learn to move forward despite our fears, we become unstoppable.

One of the first things I ask my clients is, “Why do you feel stuck?” And 99 percent of the time the answer is because they are afraid—afraid of failing, afraid of being judged, afraid of not being good enough, afraid of not having enough money, afraid of not making enough money, afraid of not getting enough clients, afraid of being happy, afraid of finally having their dreams come true. Fear wears many different outfits and none of them are cute. Many times we don’t even realize fear is the culprit behind why we have not been able to move forward.

Related: How to Confront Your Fear-Based Thoughts

In my book Fearless & Fabulous, I write about how fear would not exist if failure didn’t. So many of us are so terrified of failing in some way that we never even begin. We never take that first step and prove to ourselves how courageous and fabulous we can be.

But what if we reframed failure? What if we learned to see every situation as a chance to grow? I bet if you looked at every single woman in business whom you admire, you’d be blown away by how many times she has “failed.”

J.K. Rowling is one of the most famous failures out there, and it’s a badge she wears proudly. Although she is now a self-made billionaire, she has experienced failure many, many times and strongly believes those failures shaped her into the woman she is today. She admits that at one point, she was the biggest failure she knew. She was in a broken marriage, poor and unemployed. And although she eventually found massive success with the Harry Potter series, the manuscript was rejected 12 times before eventually getting published.

Rowling publicly talks about fear and failure often. In fact, she gave the commencement speech at Harvard University to the class of 2008. The entire speech was profoundly inspiring, but here is the part that truly resonated with me:

“Failure meant a stripping away of the inessential. I stopped pretending to myself that I was anything other than what I was, and began to direct all my energy into finishing the only work that mattered to me. Had I really succeeded at anything else, I might never have found the determination to succeed in the one arena I believed I truly belonged. I was set free, because my greatest fear had been realized, and I was still alive, and I still had a daughter whom I adored, and I had an old typewriter and a big idea. And so rock bottom became the solid foundation on which I rebuilt my life.

“You might never fail on the scale I did, but some failure in life is inevitable. 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.

“Failure gave me an inner security that I had never attained by passing examinations. Failure taught me things about myself that I could have learned no other way. I discovered that I had a strong will, and more discipline than I had suspected; I also found out that I had friends whose value was truly above the price of rubies.

“The knowledge that you have emerged wiser and stronger from setbacks means that you are, ever after, secure in your ability to survive. You will never truly know yourself, or the strength of your relationships, until both have been tested by adversity. Such knowledge is a true gift, for all that it is painfully won, and it has been worth more than any qualification I ever earned.”

And Rowling isn’t the only famous failure out there. Did you know that Anna Wintour was fired from her position as a junior fashion editor at Harper’s Bazaar after just nine months because they felt her photos were too edgy? Oprah was let go from her position as an evening news reporter at Baltimore’s WJZ-TV because they felt she wasn’t good on TV. When Lady Gaga was finally signed to her first record label, she was dropped three months later. These women are icons to me. And you should view yourself as no different than them. Can you imagine if they had allowed those failures to stop them from living out their dreams?

Related: 31 Things That Happen When You Finally Decide to Live Your Dreams

When you have passion, you cannot fail. The world simply cannot reject anyone or anything that comes from a place of passion. Just because something doesn’t work out one way doesn’t mean it can’t work out another way. Take a deep breath, regroup and keep moving forward. And when in doubt, channel Oprah or Rowling. I’m happy to call myself a failure if I’m in their company.



“The difference between successful people and others is how long they spend time feeling sorry for themselves.” —Barbara Corcoran


Failure is a part of the path to success. In fact, if you’re not failing, you’re really not doing much of anything. The biggest mistake I see female entrepreneurs make is giving up after a failure. I get it; it sucks. It’s not fun to have an idea that we thought was so brilliant not pan out. It hurts to get knocked off of our pretty pink cloud. But you have got to pick yourself up by the stilettos, dust yourself off and keep going.

The next time you feel like you’re about to throw a pity party for yourself and invite all of those nasty little voices in your head (and their plus ones), take a moment to feel the sadness and frustration. Set a time limit for feeling bad. Tell yourself, I can feel this emotion, but in 15 minutes, I’m getting up and stepping into action again. The best way to pull yourself out of self-pity is to go do something positive for yourself or your business. Idea rejected? Go treat yourself to a glass of champagne, bring a pretty notebook with you and start coming up with new ones. Lost your dream client? Put on your favorite outfit, go book a manicure or a blowout, and chat up the women in the salon. And don’t forget your business cards, because you never know where your next dream client will be.

They don’t serve champagne at pity parties. So take your moment, then smack on some lip gloss and get moving.



“It’s very important to take risks. I think that research is very important, but in the end you have to work from your instinct and feeling and take those risks and be fearless.” —Anna Wintour


Charting your path as a female entrepreneur requires many things, and leaving your comfort zone sits high on the list. Sometimes a comfort zone feels really damn good. It’s easy, it’s harmless and it’s, well, comforting. But do you know what feels even better? Proving to yourself just how amazing you can be when you step outside of that comfort zone and push your limits. When you start making things happen that you never imagined you once could. When you start living beyond your fears and learn to get excited rather than afraid. When you reframe scary situations into fabulous opportunities for growth and learning. When you finally let your passion trump your fear.

One of the scariest, most out-of-my-comfort-zone things I’ve done in my career is pursuing my dream of doing live TV. Are you sweating just thinking about it? I was too.

So much went into the process of becoming camera ready. From admitting out loud that I was ready to chase this dream, which is sometimes the hardest first step, to hiring my broadcast coach, to booking all my own travel, to actually walking on to a live TV set and praying for the best. Did I mention I used to be terrified of flying? I am exhausted just thinking about it.

But I wouldn’t change a thing. The sleepless nights, the exhaustion of flying in and out of a city in under 24 hours, the feeling of facing my fears head on. It’s all worth it. When you know how hard you have worked for something, it just makes success that much sweeter. And when you are grateful that you have those opportunities in the first place, somehow fear falls to the wayside.

Related: Why You Should Look Your Fears in the Eye and Smile

How can you enjoy the process (even when the process is kind of terrifying)? How can you embrace all the highs, lows and in-betweens? How can you channel your inner badass boss woman and kick your fears in the face? How can you truly live your dream life personally and professionally?

You’ve got to interrupt your fear with gratitude.

Research shows that we can literally shift our energy, increase our happiness and become physically healthier when we change our attitude to gratitude. We give ourselves the biggest gift possible when we focus on all the things we’re thankful for. And we immediately take ourselves out of the stressful, anxious state that happens when fear takes the wheel.


Around the time I was getting ready to quit my full-time job at MTV, I kept hearing the song “Bittersweet Symphony” by The Verve come on the radio. You might remember the song—it came out in 1997, but for some reason, in 2014, it was in my face more than ever. Music is my second language. I live for song lyrics and the first chords of certain songs can bring tears to my eyes. So when “Bittersweet Symphony” started popping up, I started really listening to it. And I started relating it to my life and my current situation.

It was a punch in the gut. The lyrics describe living a life where you feel powerless, trapped and chained to an existence that does not feel like your own. They talk about the struggle between desperately wanting to blaze your own trail, but feeling stuck and following the path you feel you “should” be on. It’s about feeling trapped and powerless to change your behavior or your life due to circumstances beyond your control. It is about the sense of desperation you feel as your life passes before your eyes and you struggle unsuccessfully to control and shape it. It is about the perpetual conflict between the path you want to follow and the path you are compelled to follow.”

That was my life. Every single day.

As depressing as one interpretation of the song can be, the sound of it is uplifting and powerful, much like a symphony, which I think is what drew me to it in the first place. And I’m no songwriter, but my guess is that it was done on purpose to evoke that dichotomy of emotions, to make you notice something.

After realizing how much the song resonated with me, I downloaded it. I would play it each morning on my way to work and sing along in my mind. It became my own little fearless anthem and I would imagine myself hearing it on full blast the day I walked out of my day job forever, as if I were in the final scene of a movie.

Fast-forward to Oct. 10, 2014, and that exact scene played out (except unfortunately I had to use my iPod instead of loudspeakers, but it certainly did the trick). As I walked into the 48th floor elevators at 1515 Broadway, I hit play on the song. I cranked it up in my ears, walked downstairs, hailed a cab and drove off with my own little empowering soundtrack on full blast.

Isn’t it time you faced your fears and started living your most empowered life?

Related: Face Your Fears


Excerpted with permission from Girl Code: Unlocking the Secrets to Success, Sanity, and Happiness for the Female Entrepreneur by Cara Alwill Leyba, author and master life coach.

Cara Alwill Leyba

As a best-selling author, speaker and master life coach, Cara Alwill Leyba empowers women to live their most effervescent lives, celebrate themselves every day and make their happiness a priority.

As a social influencer, Cara reaches her following of more than 80,000 fans across all her social media platforms and inspires them daily with lifestyle tips, mindset advice, #girlboss strategies, and does it all with a chic and fashionable flair. Cara has done collaborations with Macy’s, Kate Spade, SoulCycle and others, and is an influencer for fashion powerhouse network rewardStyle/

Prior to taking her brand full time, Cara spent eight years at MTV Networks as a digital advertising director where she oversaw a 20-person sales team that managed multimillion-dollar ad campaigns for brands like CoverGirl, Pepsi and others. Her unique background gives her an in-depth understanding of sales and marketing and makes her a strong influencer with her own brand in the online space.

For more, please visit