Owning Your Bravery as a Leader

I need to admit something: I haven’t been honest. Well, maybe that’s not entirely true. But I haven’t been forthright. People in my circle might know me as someone who is “fearless” or “direct,” but throughout my career, there have been times when it felt easier or safer to hold my cards close to my chest (which I also do very well in a card game).?

But as I’ve reflected on the ups and downs of my job experiences, I’ve realized that to be truly bold, to be truly brave, I have to be honest. And the truth of the matter is, I’ve failed. Quite a bit. I’ve been fired, I’ve let myself down, and I’ve let other women down. But, I have to think another part of bravery is owning these mistakes and moving forward.?

I haven’t always shied away from uncomfortable or uncertain situations. In fact, early in my career, I was sometimes the only openly out person in the office. I was also the first of my LGBTQIA+ friends to get married (before it was legal), the first to have children, and the first to start their own business (during a terrible recession in 2007).?

In these moments of boldness, in these moments of saying “screw it” and taking a risk, my bravery paid off. I was able to see the fruits of my labor flourish quickly. But bravery often only feels good when success follows. So, what does it mean when you decide to be brave, but you fail? What does it mean when your bravery isn’t enough? How do you move forward? How do you find your bravery again?

When I started my own business, Marbles: the Brain Store, I received the coveted 2% of venture capital that is awarded to women. My bravery paid off–I found success with something I created, growing it into a $40+ million brand with a fanatical following and national presence. (My time as Marbles’ CEO also led to my Crain’s 40 Under 40 recognition and a full front-page feature in the Tribune’s Business section.)

This all seems great, right? I was brave, tried something risky, and it all worked out! But while I’ve shared this story many times, I have left out a very important detail–I was fired. Three times. From my own company!?

At that moment of being fired, it seemed that my bravery failed me. That my bravery wasn’t enough to keep the success I had found. But instead of being deterred, I showed up. I put on a brave face because I realized that while being brave for myself had offered me plenty of opportunities, I needed to be brave for my employees. I needed to be brave for others. A year after I was let go for the final time, the company went bankrupt and disbanded.?

Naturally, I looked back on this experience and reflected on what I could have done better or differently as a leader. With the benefit of hindsight, I now realize that I failed to be brave in the most important way–demanding equity, representation, and fairness. Here are some examples:

• I let sexual harassment and gender bias surround me–my Board, for many years, consisted mostly of men and there were countless times when members of my team and I were treated unfairly, harassed, and demeaned because of our gender. (A solution: we need? boards of female-led startups with 50%+ women)
• I didn’t take (two separate) maternity leaves because I couldn’t show any “weakness.” (A solution: maternity and paternity leave should be required)??
• I didn’t properly negotiate my equity, my salary, or my eventual severance in a way that I feel proud of. I was painfully underpaid, and my equity position always left me embarrassed at the negotiating table. (A solution: Founders/CEO should retain 50%+ equity for as long as they can and they should never start below that level)

What kind of example was I setting for my team, for other female entrepreneurs? I was perceived as a risk taker, but was I really taking the right risks??

When I am honest with myself and how I’ve failed, I can more clearly see how I could have been stronger, more direct, and more representative of what I wanted for others. What would have been the outcome if I had been more brave??

Experiencing and reliving the effects of my failures could have led to me retreating into myself, never taking a risk again. But instead, I leaned back in, and this time harder and more clearly. This led me to lead a new venture–BREAKTHRU Brands– women-owned, women-led, no outside investors, our rules, our time.?

At BREAKTHRU, we are bravely and boldly looking to change the archaic patriarchal system that isn’t working for all of us by empowering women to lead us into the future.

I used to think I was being brave by showing up. But by being honest about my setbacks and owning my shortcomings, I now know it is much more about standing up and speaking out. I think I have found my bravery once again–and I can help you find yours, too. Together.