My Story Before Yours

Long before entrepreneurship, I had a much clearer vision for my career: international health and development. I went to graduate school specifically to pursue it and landed what I thought would be my dream job shortly afterward. The reality looked very different. The international work that had attracted me represented only a small portion of the job. Most days were spent on email and spreadsheets in a windowless Baltimore office.

I knew it was a mis-fit immediately. And I spent years trying to make the career fit anyway.

I changed jobs, moved into consulting, and continued pursuing variations of the same path. Walking away meant confronting the graduate degree, money, and years I'd already invested in getting there.

The final breaking point came in 2017. I had recently had my second child and remember sitting in a converted nursing room at work, pumping, looking at my phone, and crying. I was miserable and still determined to prove I could make the situation work.

Looking back, I can see how much fear kept me there. I didn't know what would happen if I let go of the career I'd spent years working toward.

I've now survived enough significant changes to recognize that feeling sooner. My tolerance for staying somewhere simply because leaving scares me has changed considerably.

When Shauna asked what has remained consistent across all of my career changes, I went much further back than my first job. I thought about who I was at 13.

I was loud, curious, adventurous, competitive, and constantly talking. At almost 41, I feel like I'm finding my way back to parts of that person after years spent trying to fit myself into more conventional definitions of valuable work.

Communication is one of the clearest throughlines I can see now.

I'm drawn to conversations. I like helping people understand themselves, hearing what they're actually saying, and helping them communicate it to other people. Those instincts have appeared in different forms across my career, even when the job titles and businesses changed.

For years, I struggled to believe those abilities were substantial enough on their own. In my brand work, for example, helping someone understand themselves more clearly often became attached to a concrete deliverable: a website, marketing pillars, or another visible piece of work that could justify the value of the engagement.

I'm beginning to question how much packaging those strengths actually require.

Another story has followed me through far more than my career.

Growing up, I absorbed a strong expectation to be helpful and attentive to what other people needed. At the same time, I received repeated messages that parts of my personality were too much. I was loud. Direct. Willing to question something I thought was unfair. I remember adults calling me intimidating and, as a teenager, a coach calling me a bitch. I became someone who was naturally inclined to speak directly while also being highly attuned to how other people responded to me.

In adulthood, that has shown up as people pleasing, perfectionism, and attempts to control how other people perceive me.

Shauna and I talk about how much I've been forced to confront that over the past year. I've been having more direct conversations, knowing they won't always land comfortably and becoming more willing to have them when I believe avoiding the issue will prevent everyone involved from moving forward.

Near the end of the episode, Shauna asks what open question I'm living inside right now. My answer surprised even me: Do I have the courage to be disliked?

With a book, podcast, and other work moving further into public view, that's becoming increasingly difficult to avoid. Being visible means asking people to pay attention. It means promoting my own ideas and asking people to spend money on them. It also means accepting that some people may dislike what I make—or dislike me for making it.

I know intellectually that nobody is for everyone. I'm finding out what it feels like to live accordingly.

There’s a reason I asked Shauna to conduct this particular interview. We met in 2019 at a small creative-business gathering in New Mexico. Shauna eventually became my go-to designer, working with me across multiple businesses and creative iterations.

Seven years later, our relationship extends well beyond a typical client and service provider arrangement.

Shauna has enough context to recognize when one of my ideas connects to something I’ve done before, when to rein me in and when to push the idea further. It’s much easier to move when I don’t have to spend hours providing context and filling someone in on the backstory of my journey before introducing where I’m heading.

That relationship has also influenced how I think about friendship and the people I want around me while building. I have a small number of women I could call with almost any piece of news—a divorce, another child, a move to Australia—and trust that their response would essentially be: Okay. What’s next? How can we help? For someone who’s never considered myself much of a “girl’s girl,” experiencing that kind of friendship has been significant.

And it felt fitting that one of those people would be sitting in the interviewer’s chair as I opened the next chapter of this show.