How I became a boss—and made it my job to bring other women up with me

If you have a business plan sitting on your desktop, just waiting to be put into action (and who doesn’t?), you need to get to know Claire Wasserman. Here, the Well+Good Council member (who’s also a career coach and the founder of Ladies Get Paid) shares her path to becoming a true boss.   

I’m constantly asked about the moment I decided to become an entrepreneur. I always respond, “How much time do you have?” I feel as if I’ve been practicing entrepreneurship my whole life: When I was a child, my grandfather told me that if I loved what I did, I would never work a day in my life. And if I was good at it, the money would come. A little later on, a mentor asked me how I defined success. As I started to respond, he interrupted with “Whose voice is that?” He continually pushed me to identify my values to ensure that I was living life on my terms, and not by the expectations that my parents or society may have put upon me.

Suffice if to say, I’ve always been a self-starter and resisted my bosses. Not to mention the fact that upon graduation from college, I immediately got a tattoo in a visible place so that I would never be hired at a company that wouldn’t let me be myself. I recognized early on that finding the right work environment would help me thrive. (I know, such a millennial.) I also learned how to understand my values as a guiding force in whatever I did. Still, I never intended to own my own business. 

But somehow, I’m missing the fear gene when it comes to taking chances on myself. I’ve always deeply believed that I could achieve whatever I put my mind to. I’ve also jumped without hesitation, rationalizing that whatever happened, I could still get a job. I acknowledge that this fearlessness stems from privilege. While I’ve never received a cent from my parents, I know that if I needed to go home, they could take care of me. I have no children, no health problems, and no massive debt. (Insert praise hands emoji.)

There have been times, however, when I’ve found myself at a career crossroads and made my choice based less on passion but more on identifying the sacrifices I’d have to make. (I should pause here to say that I’m an advocate for therapy and encourage everyone, regardless of whether or not you want to be an entrepreneur, to spend a lot of time getting to know yourself. Understanding what you need to support your well-being is crucial and perhaps the most important thing you can do for yourself. Taking care of myself is taking care of the community.) Doing things that are bigger than yourself, and sometimes stemming from frustration, can be the greatest motivation.

Doing things that are bigger than yourself, and sometimes stemming from frustration, can be the greatest motivation.

In the case of Ladies Get Paid, the decision to venture out on my own was easy when I learned the deep-seated discrimination women face in the workplace. For example, Hispanic women make 55 cents to a white man’s dollar. And black women entrepreneurs generated over $44 billion in revenue last year, yet only 2 percent received venture-capital funding—with an average amount of $36,000.

It wasn’t, “Should I do this?” but rather, “How could I not?” Ladies Get Paid isn’t a labor of love as much as it’s a fire that burns. I’m driven to change the lives of others and must remind myself that if I can positively affect one person’s life, that’s enough. And then I realize: It’s already happened. Mine.

The founder of Ladies Get Paid, Claire Wasserman’s an educator, coach, and podcaster, who helps women navigate their professional options to find fulfilling career paths.

What should Claire write about next? Send your questions and suggestions to [email protected].