“In the future, there will be no female leaders. There will just be leaders.” 
― Sheryl Sandberg

Why I Plan to Fail More in 2019

Why I Plan to Fail More in 2019

Written by Hillary Kirtland


Over time, I’ve become more and more comfortable with what our society considers failure. I’ve come to realize your first (or second, or third) taste of failure doesn’t have to be the final answer. I’ve failed to get many jobs I wanted, but I accepted the role of my dreams. I’ve failed to earn top grades in classes in which I worked diligently, but I earned three degrees. I’ve failed to win big games, but I trained harder and became a stronger competitor. I’ve failed to lose weight more times than I’d like to admit, but I learned how to be a healthier person overall.

No one likes it when they come across a reminder that whatever they’re striving for is still out of reach. But what’s out of reach now will not be out of reach forever. What I try to give myself credit for, and permission to continue in these moments, is failure. You cannot fail if you never try anything new, and what you’ll find if you fail enough times at something, is that you learn and improve enough that you also eventually succeed. That’s the agreement I have with myself—to fail enough that I eventually succeed, and why I plan to fail more this year.

J.K. Rowling: Reportedly, the only person to be taken off the Forbes billionaire list for the $160 million she donated to charity in 2012 (she has since more than made her way back on). Before her success, Rowling was a struggling, divorced single mom living on government benefits. Harry Potter was rejected 12 times by various publishers, before one finally agreed to take her on.

In 2019, I plan to risk failure by preparing myself to complete a full marathon in 2020. This will be something that pushes me to my limits and may literally make me fall flat on my face (more than once), but I plan to keep trying and failing as much as necessary to achieve it. Think of something you’ve always wanted to do—something that scares you, intimidates you or just something you’ve put off for too long. Write it down and hang it somewhere you can see it on a regular basis. Make 2019 the year you risk failure to work towards that goal.

After “failing” in my career for a few years, because I’d been endlessly floating around trying to find my niche, I immediately recognized the right role as soon as I stepped into it. In 2019, I plan to keep chasing that feeling. I will fail in areas that make me the most uncomfortable and become a better professional as a result. I will ask for feedback, even if that feedback makes me feel like a failure, so I can take action to keep moving forward. I will take on responsibilities I’ve previously never tried, and I will learn from the mistakes I make along the way. Failure will be an inevitable part of this pursuit of professional development, but each step will make me better than I was the day before. You can probably think of at least one goal you’ve failed at again and again, that gave you the perspective you needed to finally succeed. Keep chasing that success and don’t be afraid to fail at the next step. It may be exactly what you need to learn from to eventually succeed and reach your goal.

Oprah Winfrey: Oprah has had her fair share of setbacks to overcome along the way. After being fired from a television anchor role in Baltimore for "getting too emotionally invested in her stories," she picked herself up and persevered to become one of the most recognized and beloved TV personalities. She created a media empire and, according to Forbes, is worth approximately $4 billion to-date.

My personal life will always be the most vulnerable when it comes to goal-setting. Putting things that matter to me out in the open puts those things at risk. Regardless, in my personal life this year I plan to fail as much as I need to, to make moving in with my (previously) long-distance partner a success. I plan to fail at enough article pitches and rough drafts that I can deliver even better contributions to Babes Who Hustle. Think of a goal you’re afraid to put out in the open—whatever is so personal you feel vulnerable saying it out loud—and then give yourself permission to fail at it until you achieve it. I want to try and fail at enough things in my personal life, that success becomes the result.

Lucille Ball: Our favorite “I Love Lucy” star couldn’t get off the B-list for years. She was affectionately known as the “Queen of B Movies.” She not only went on to become the star of the classic comedy show we know and love, she was the first woman to run a major television studio, Desilu Productions. Her studio went on to produce shows including “Mission: Impossible” and “Star Trek.”

I can’t say every setback in 2018 was easy, or every obstacle didn’t feel like a failure at the time. There were times I didn’t hit my savings goals, or days when I was too lazy to get to the gym when I should have, but every time I’ve picked myself up from those “failures” I’ve come back even stronger and more empowered for it. I hope you all plan to fail more in 2019, to try something that scares you, discover something deep within yourself or pursue a passion you’ve put off longer than you maybe you should have.

I hope you all risk falling flat on your face and learn to pick yourself back up every time you think you’ve “failed.” True failure isn’t a lack of ability, but rather a lack of perseverance. If you have something you care about, go after it and put yourself out there for it. Never let fear or failure tell you when to quit. Let’s all make failure our goal for 2019, so our success will be inevitable and unstoppable.


Hillary works as a Senior Strategy Consultant at IBM. She found her passion for her new job in the two years she took off work to pursue a full-time, Global MBA degree at George Washington University in Washington DC. She is driven by her constant curiosity and her truest love is for travel and adventure. Outside work you can find her playing in two of the local DC kickball leagues, taking Jiu Jitsu, boxing, and yoga classes at her gym, reading a book, or binge watching a new show (Currently obsessing over Outlander, because Jamie). Find her other contributing pieces 
here and here.

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