On Being a Female Entrepreneur

Choosing to be an entrepreneur means you are signing up to push yourself not only in your craft but fundamentally as a human being. You are assuming ultimate ownership for the success or failure of your creation which means that your flaws and shortcomings will be thrust into full view. Even your strengths will be tested and pushed and tested some more. 

There is an intensity to the journey of the entrepreneur. Although many of us have great teams, we also bear the ultimate weight of knowing that we are the safety net for everyone else. There’s little room to doubt yourself and no room to give up. This is the essence of the struggle and the euphoria of being an entrepreneur: constantly taking on difficult challenges, testing yourself and your team against them, knowing defeat is possible and yet not an option, and somehow, miraculously, pouring out gratitude as you and the answer find each other just in time. And then doing it all over again.

There is also a solidarity to it: the support of those incredible people you are lucky enough to grow with along the way who take up the cause and invest hard too.Yet there is also a singularity to the journey, an inevitability, an echo chamber of hopes and fears, knowing that you are responsible for everyone and everything, for leading with both heart and mind, and for making sure it all means something in the final reckoning.

To be an entrepreneur is to walk a path littered with the opinions of brilliant people. It means being very credibly told to hire, fire, raise prices, lower them, focus on product, focus on marketing, focus on your people and pivot, pivot, pivot until you are dizzy. It means taking these opinions in knowing that there is a chance that they are sound but also a strong chance that they are flawed. They may equally be the North Star or an errant firefly meandering through the sky on a warm summer night. 

It is a path of extreme ownership because you know you cannot follow someone else’s map to a paradise that has not yet been discovered except in your own mind. And so you must find the silence to hear your own soul’s call amid a riotous jumble of well-meaning wisdom that assaults your ears and your clarity at every turn. And you must do that and nurture the joy, the passion, and the excitement that keeps you going through it all. 

These happen to be my personal experiences, yet I could write these words about any entrepreneur and there is a good chance they would be true. Much of the experience is universal.

And yet, some things are not universal. Some things happen to certain entrepreneurs more than others. 

To me, being a female entrepreneur has also meant being told that the success I have experienced must be because I batted my eyes, or flirted with the right people, or used my femininity to get what I wanted, then laughing it off as though it wasn’t an insult to every ounce of work put in by my team to accomplish what we have.

To me, it has meant being propositioned by clients more than once and walking the delicate line of telling them no ever so gently, without bruising egos or damaging the relationship, while still setting boundaries. It has meant putting their feelings ahead of my own and stuffing down the anger and disgust that welled up inside me.

To me, it has meant being told I’m too emotional, too cold, too assertive, too soft, too nice and that I’m probably just not cut out for the job. It has meant being encouraged to be less feminine, more feminine, sexier, less sexy, more aggressive, softer, louder and quieter all at the same time.

To me it has meant being quietly aware of the unspoken expectation that those who have been allowed to climb up a few rungs of the ladder must never question the foundation on which it sits. It has meant walking the universal tightrope of entrepreneurship in heels, never letting the sweat show, lest someone see the strain and decide it’s proof that I’m just not up to the task. And it has meant striving to do it all with the requisite smile in place, regardless of what I’m feeling inside.

The truth is, every entrepreneur I know has worked very, very hard under their unique circumstances to make it work. I don’t know what this journey would have been like as a man, or as a person of color, or a transgender person, or a person with a disability. Those paths are not mine to walk or tell about.

But I do know what it has meant to be me walking this path. Female: yes. Entrepreneur: yes. Whole, flawed, vibrant person: yes.

To me, being an entrepreneur has meant pushing past where my mind thought we could go. It’s meant long nights and weekends fueled by nothing more than the passion for my creation. It’s meant watching people grow and being dazzled by their talents. It has meant becoming both tougher and more vulnerable. It has meant owning who I am, not who someone wants me to be, whether bossy or quiet, emotional or stoic, flamboyant or demure. It has meant finding that North Star not just externally but internally also. And that comes from remembering what matters: impact.

And that’s why all of the struggles with other people’s opinions, whether helpful or sexist, are just footnotes in the story. Because the impactful moments aren’t victories over people who doubted or underestimated or belittled. They aren’t scoring one up on the people who thought they knew better how to do this or that. In fact, the impact often doesn’t come from victories at all.

The impact is showing up every day, determined to move some cause forward, inch by inch, and the willingness to stick it through as inches become feet which become miles. The impact is creating a wide open space for people to believe that it can be done and it will be done in a way we can be proud of, as long as we keep going. The impact is in the footsteps of those who follow and become their own leaders one day. That is the history I want to be remembered for. For insisting that there is a way, for nurturing the dreamers and the doers and the builders, and for being unafraid to stand up for those who have the audacity to believe that they can make a difference. 

So to the female entrepreneurs I say, take a breath and fill your lungs good and deep with your dreams. Kick the pile of others’ dusty opinions and watch them scatter as dry leaves in the wind. Run until hot tears stream down your face. And keep your eyes fixed on that point on the horizon that only you can see, glimmering a reminder that you are already exactly enough.

A Letter to the Dreamers

A Letter to the Dreamers

I’ve been doing this entrepreneur thing long enough to have lived through two large-scale crises. The first year I launched a custom software development firm, we were in the throes of the Great Recession. I remember the worry of it: crunching numbers in spreadsheets again and again, hoping that somehow this time the number at the bottom wouldn’t be red. I remember the desperate discounting and clawing for business to stay afloat. I remember hearing the whispers of failed businesses and shuddering out silent tears for those who gave it t

This Is 40

This Is 40

It’s a tradition that I write something for my birthday. This year, I’ve been struck with how many people are talking about chaos, uncertainty, hope, and peace. In times of overwhelming unknown such as today, we frantically grasp for what is certain. We are desperate for something to tell us that we are going to be okay.

Because things today are not okay.

The Reality of Illusion

The Reality of Illusion

My dog Lucy was terrified of windshield wipers. She would lunge at the windshield, barking furiously, until she wore herself out and eventually huddled on my lap for comfort. I never did figure out what she thought it was. No amount of soothing or coaxing could convince her that it was going to be okay. And so she lived in fear of those damn wipers her entire life.

Capturing A Cover: Profile of Whitney Warne, Photographer

When it was time to take the cover photos for Soul Uprising, I was already late. I’d been so focused on writing a manuscript and working through edits that I had completely forgotten the part of the book people see first: the cover. I was in total “it will be what it will be” mode when I showed up for the shoot (for those who don’t know me well--this particular mode tends to show up when I’m low on sleep and is not ideal for things that involve attention to detail such as posing for arguably the most important photo of my career to date).

Thankfully, I was working with Whitney Warne.