I am pregnant. I am actually very pregnant — 39 weeks as we speak. I’m also the founder and CEO of an early stage company, and for the first time in my life, I’m wondering if I bit off more than I can chew.
For the last four years, I have poured my whole self into Just Women’s Sports. It’s been a wild, unpredictable ride, one that’s been both incredibly fulfilling and incredibly hard.
When I started JWS, no one wanted to bet on women’s sports, media, or a 26 year old with only one year of actual work experience under her belt. People didn’t think women’s sports could work as sports, and even stakeholders in the space talked about these leagues like they were charities — something nice to have, but not anything that would ever make real money. And that was from the people who "believed" in women’s sports — you don’t want to know what the doubters had to say.
In the early days, it was all heart and hustle. There was no playbook. We had a vision, but that was about it — no real money, connections, or media experience. To keep the lights on and get JWS off the ground, all I did was work. I ran from fundraising meetings to posting on social, to listening to and editing our first podcast with Kelley O’Hara. I designed graphics. I sold to brands. I worked all the time.
At one point, I even hospitalized myself from working too much. But even that wasn’t enough to tell me to chill out — I closed our first big deal sitting in a hospital bed, with a virtual background so they couldn’t tell where I was. For better and for worse, I was willing to sacrifice myself in order to win.
Slowly but surely, we started stacking wins and building some real momentum. But even as we grew and found our footing, I still had the same existential paranoia and grind-it-out mentality that had been there from the beginning. Every win, every new milestone, felt like a reason to push even harder.
But getting pregnant changed that.
I’m fortunate to say this has been a healthy pregnancy, but even then… it’s been tough. I’ve been nauseous the whole time. I can’t sleep. I never knew my back and hips could feel this bad. And in these final stages of my pregnancy, I’ve been more emotional than I’ve ever felt in my life — which is just not ideal when the bulk of your job is to stay level-headed, decisive, and be able to make unemotional decisions.
For the first time in my professional career, I physically cannot just grind it out and push through. Being pregnant has forced me to do something not even a week in the hospital could do: recalibrate my work habits and take time off.
The idea of stepping away for maternity leave is anxiety-inducing. I’ve poured my entire self into getting JWS to this point, women’s sports are taking off like never before, and now I’m supposed to just detach from it for an extended period of time? What will that mean for the company? Will I be able to balance being a CEO and a mom when I come back? Can we keep the momentum we worked so hard to achieve?
I have so many people asking me if I'm ready. And I can say with unequivocal confidence: No, I am absolutely not. My only expectation is that I’m about to get smacked in the face with a brand new version of my life any day now.
But this pregnancy and impending leave have had an unexpected side effect — being forced to "take it easy" and think about not being here has actually improved my leadership.
I’ve had to learn how to get out of the weeds. I’ve had to empower other leaders at the company and build systems where they can step up and take ownership. I’ve also gotten better at saying no and being ruthless about what matters.
Ultimately, I’ve had to learn how to let go a little bit and trust the people around me to a greater degree than I’ve ever felt comfortable doing.
And so far, the wheels haven’t fallen off. In fact, it’s been the opposite — people have stepped up in big ways across the board, traveling for me when I can’t go to events, driving initiatives that I usually would have been leading, and taking things off my plate to help ease the transition. We’re actually growing faster than we ever have before, and the team has collectively taken on a whole new level of ownership.
I’m definitely not the first pregnant CEO, but the fact is, there just aren’t many places where women can lead and grow a family. There isn’t a tried and true blueprint for how to balance being both a mother and a founder. And I won’t lie — that scares me. There’s no way to know what this future will look like. But to be able to build a company and culture where that is possible is, I think, really special.
As we all step into this next chapter, my overwhelming feeling is gratitude. For my family and for a healthy pregnancy, but also for everyone I get to work with everyday building this company and changing women’s sports. For my leadership team, who were the first people I told about my pregnancy after my immediate family. For the whole JWS team that has been unbelievably empathetic, thoughtful, and simply human during this time. And for our investors, advisors, and partners, who never made me feel like I was neglecting the company by starting my family.
We’re all nervous, to some degree. Inevitably, something will happen while I’m away that will be intense. There will be decisions that I would have made differently. Something will slip through the cracks.
But I’m also hopeful — this pregnancy forced us to empower the team to steer the ship and make decisions autonomously, and we’re already seeing the payoff.
There wasn’t a playbook when we started and there isn’t one now. But as has been the story of JWS since day one: We believe in our vision, and we’re taking the leap.
Haley Rosen is the CEO and Founder of Just Women's Sports. Follower her on X @haleyrosen.
