Success and Why Women (And I) Struggle To Own It

Success She Can & She Did


Success is something I've spent the majority of this past year trying to define. I'm the crazy person on first dates who asks a dude how they define success. Or the person sitting next to me on the subway. Or my seatmate on a cross-country flight.

I've literally asked everyone and anyone who found themselves next to me for more than five minutes not only how they define success, but how their perception of it has changed over the years.

And the answers I got were eye-opening.  

  • "Success is fulfilling your life's purpose."
  • "Consistently stepping outside of your comfort zone."
  • "Leaving the world a better place than you found it." (If you only could have been a fly on the wall during that dinner.)
  • "Making enough money to retire before I'm 40."
  • "Being the best."
  • "Never having another drink again."
  • "Dying as much in love as I was the day I said it the first time." (Again, if only you could have been a fly on the wall during that dinner.)
  • "Feeling proud of who I am."
  • "Finding someone to share my life with that I trust fully."
  • "Living my purpose."

But those are just the tip of the iceberg. The answers were sometimes long and winded while someone tried to figure out their answer or they were dripped in confidence during a short, sentence-long definition. Sometimes people backpedaled when they saw their answer was judged by their significant other and sometimes people told me that all they cared about was money. 

At times, it was frustrating to hear so many different explanations. How could something so fundamental be so different for so many people? The more I asked, the more muddled my own answer became.  

Which is probably normal. I might be one of the few 28-year-olds who is as reflexive and introspective as I am. Most people my age are trying to figure out where their next paycheck is coming from, how to climb a corporate ladder, or if they should get married. I lie awake at night pondering my purpose, what success means, and if I'm happy. 

A few weeks ago, I had the honor of traveling out to San Diego to speak as a keynote during the Fellow Flowers retreat. We talked about everything from staying vulnerable after getting crucified online to how the #SportsBraSquad came to be when Mel asked me a question that stopped me in my tracks. She brought up my Women's Running magazine cover, my sponsorship with Oiselle, Global #SportsBraSquadDay, and how I felt about my success. 

I froze. 

I turned to face her and in that pause, tried to figure out if I should laugh it off or pivot completely so that I wouldn't have to talk about "success". Then, I realized that my mouth was moving and I was actually saying out loud what I thought I was thinking in my head.

I realized that I'm terrified to acknowledge, celebrate, or feel anything other than grateful for what I've accomplished in front of anyone who isn't a close friend or family member.

I didn't give myself permission to celebrate my sponsorship with Oiselle because, if I'm being totally honest, I was terrified that they were going to realize they'd made a mistake by bringing on a blogger and end our partnership.  

I didn't stop to celebrate the success of the Run, Selfie, Repeat podcast because apple throwing it on the "Hot and New" list and then Squarespace's sponsorship legitimized my passion project and intimidated the hell out of me. 

I never stopped to take in how successful and life-changing Global Sports Bra Squad day was because when Oiselle suggested it, I told them that I was afraid to put myself out there. What if no one showed up? What if people thought I was doing it for the wrong reasons?  

Without Oiselle's support, I never would have had the courage to make Global Sports Bra Squad Day a thing. And after seeing the number of women who hosted meetups and who showed up for themselves, Global Sports Bra Squad day will forever be one of my proudest moments in my life.

Kelly Roberts Women's Running Magazine

And finally, that little thing that was getting to be on the cover of the body issue of Women's Running Magazine. I still don't know how to explain what it means to me to have been given the chance to be on the cover of Women's Running Magazine. It's still surreal. 

I realize now that I spent most of this year overloaded with projects so that I wouldn't have to slow down and process what was happening. And it worked! At least, it worked until Mel hit me with that gift that was a question about my success and gave me a chance to step back and rumble with why I'm so uncomfortable talking about my accomplishments publicly.

Because here's the thing, I'm beyond grateful for the opportunities I've had. And as these things were happening, I took the time to dance around my apartment or grab my journal and write down how grateful, proud and scared I was with each new opportunity or achievement. 

But I never stopped to wrestle with the idea of success or give myself a chance to unpack why I was struggling to acknowledge my success or achievements.

I've read enough books about women in the workplace to know that my reaction to Mel's question about success is common for women. First, I put myself down through a self-depreciating joke because that's what women do. We put ourselves down because we think we can beat others to the punch. Because the truth of the matter is, women have a hard time publicly owning their success because doing so makes them less likable. 

And I'm terrified of not being liked! My career, in a sick way, gets measured by the amount of "likes" I get on Instagram. (Literally likes and engagement is how companies and brands I work with measure my success.) 

But I'm always walking this fine line between wanting to be heard and wanting to be liked. It's a hard balance to maintain because I'm human. And even though I know better, sometimes I can't help but misstep when I'm feeling insecure. I've gotten a lot better at stepping back when I feel unsure of myself but I firmly believe that doing anything because you want to be liked is a recipe for disaster. 

A lot of what I've discovered through sharing my story on my blog goes hand in hand with what Brene Brown talks about in her latest book, Braving the Wilderness. As a teenager and young adult, I tried really hard to either fit in or ostracize myself. When I finally found my voice, I opened up because I saw how liberating it was to forgive myself for all the shame and fear I'd attached to what I'd been through. I realized that the only person who really needed to like and love me was me. And when I did that, I opened myself up and made it possible for other people to love me as well.

I'm a storyteller because discovering that I wasn't alone saved my life.

From my grief to my struggles with my weight, a lot of the shame that I tied to my past came from a desire and a paralyzing fear to be loved, heard, and understood. I used to live my life terrified that the people I cared about would find out what I was or what I had gone through. I was afraid they'd judge me because my life was so chaotic and difficult. So I constantly tried to hurt myself before anyone else could hurt me because I felt like I needed to beat people to the punch.

Which couldn't have been further from the truth. 

Now I know the power of truth and vulnerability. I understand how liberating it feels to not feel compelled to hide parts of myself that I'm ashamed of because they make me unlikeable. It's so much easier to be who I am instead of trying to pretend to be someone I think I need to be.

And ironically enough, success is something I feel insecure about because I know it makes me unlikable.

We live in a time where elevating and empowering women is at the forefront of the zeitgeist. But we need to remember that until we can start to do something about the fact that success and likeability are positively correlated for men and negatively correlated for women, we're going to go in circles. We can march around wearing our "nasty woman" shirts, reminding one another to write down our successes or personal and professional achievements all day long. But until ambition, confidence, and a competitive drive in women are universally accepted as likable traits, seeing women own their success is going to be an uphill battle. 

So while on a cognitive level, I know that in order for that change to occur, I need to lean into how uncomfortable I feel when I acknowledge my achievements, I also know how f*cking hard it is. I spend so much time talking about how important it is to celebrate our own accomplishments while I'm over here downplaying what I've worked for because I don't want to seem like an a-hole. I use running as an example because celebrating an accomplishment in running is a hell of a lot less threatening than celebrating your professional achievements is. 

But we have to do it. It's not easy to say that we've fought for our accomplishments or that we deserve them. It's easier to give that power to luck or happenstance. "I was just at the right place at the right time." Sure, maybe that's a piece of your story. I ABSOLUTELY had luck on my side. My foot in the door came during a slow news week when I took selfies with hot guys behind me.

But good things don't happen to lucky people. Good things happen when you go out and work for them. I've worked my ass off in the four years since I went viral and I've had to make a lot of sacrifices to try to live in New York and make it work. I've embarrassed myself in front of more people than I can count because I didn't know what I was doing. I've made mistakes and I've been crucified for them online. It's been hard. It's been really, really hard but I love what I do.

One thing I've learned this year after asking what feels like a million people what success means is that success is different to all of us. For some, success is only attained through status and power and for others, we just want to make the world a braver, happier, and more loving place.

Here's where I'm at with it: I think success is consistently stepping outside of my comfort zone and using my voice along with my purpose, gifts, and talents to help other women do the same. 

Will it change over the years? Absolutely. I think as long as you're staying true to who you are and what you want out of yourself, your loved ones, and your life, that's all that matters.

It's never too late to be the person you already are. Success is in the eye of the beholder. But ladies, we have to start acknowledging ambition, drive, strength, and power as beautiful things.