The Wednesday Play: The Hard Choice

Hi Playmakers,

I never imagined I would be writing these words:

I’m going to be a mother.

For most of my adult life, I didn’t think I wanted children. It wasn’t because I didn’t love the idea of family, but because I had seen how motherhood could derail a woman’s career. I watched brilliant, ambitious women face roadblocks the moment they had children.

Promotions disappeared. Assumptions were made. Priorities were questioned.

I didn’t want that to be my story.

So I told myself I would wait. Maybe forever.

But when I turned 30 a few years ago, something in me changed. Or maybe the world around me began to look different. I started paying attention to the women I admire most — founders, CEOs, investors, visionaries. And I noticed that many of them are mothers.

They aren’t hiding it. Instead, they are leading with it.

Motherhood hasn’t softened their ambition. It has sharpened it. They make faster decisions, speak with more clarity, and lead with more empathy. They understand what matters and what doesn’t. They are building companies and powerful careers while raising kids at the same time.

The adage I always used to hear “If you want something done, give it to a busy person” became even more precise over the last few years, as I learned about the intense time management systems the moms around me put in place. Now I think of it as:

“If you want something done, give it to a busy mother.”

Regardless of my choice, however, the system still penalizes mothers. The data is clear, and the reality is frustrating. But I’ve also come to believe something else: being a mother can be a source of power. It can deepen your purpose, refine your leadership, and shift your perspective in all the right ways.

Strangely, even though I’m in my 30s now, many women I know aren’t mothers. Some shared with me that they fear the financial burden will be too much, while others I know simply don’t want to do it. Some just haven’t found the right time or their biological clock has begun to escape them.

Either way, being a mom is a decision every woman gets to make. Being a dad is, too, but the reality is that the burden and monumental life change is largely paid by the woman. There’s no right or wrong answer for what you decide.

For me, I don’t feel smaller stepping into this next chapter. I feel bigger and more whole. More ready.

Motherhood isn’t the end of my ambition. It’s part of the expansion and widens my dreams about my impact on the world.

That’s what I’ve been thinking about this week.

As always, I’d love to hear from you. Which mom changed your life?

Jenny

Before she led a fashion revolution, Jennifer Hyman was a Harvard MBA student with an idea that seemed almost too simple: what if women could rent clothes instead of buying them? That idea became Rent the Runway, one of the most disruptive startups in modern retail — and the company that made history on the Nasdaq.

Read the story now.

Jennifer’s story is about more than fashion. It’s about access, leadership, and the quiet power of challenging the rules that never made sense in the first place.

Jennifer Hyman was born in 1980 and raised in New Rochelle, New York. Her father was a sales executive, and her mother worked in marketing. Their household valued education, creativity, and independence.

After graduating from Harvard University in 2002, Jennifer worked in media and tech at companies like WeddingChannel, IMG, and Starwood Hotels. But it wasn’t until she returned to Harvard Business School that she had her breakthrough.

Read how Jennifer made it happen.

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This week’s challenge: give ME some advice as a first time mom!

I’m talking about “life hack” type of advice. What tips and tricks did you learn? What were things you purchased that you never used? What were the things you wish you had? I want those pro tips that make each moment run a bit smoother.

Call to Action:

1️⃣ Respond to this email with your pro tips.

2️⃣ I’ll share my favorites in the months and years to come!

Every week, I spotlight somebody from the community who is making a big play in their career or industry. This week’s play comes from my friend, Erica Wenger.

I spotlighted Erica as this week’s #Playmaker, because she is quickly building a strong TikTok following as a first-time VC. I particularly loved this week’s video to encourage people to do something “cringey” and get out of their comfort zone.

Try a cringe break and tag @ericawenger and @jennystojkovic to tell us how it went! ;)

Want to be featured next?

Make sure to tag @Jenny Stojkovic on your post for a chance to be featured.

The Wednesday Play isn’t just a newsletter — it’s a community. I’ll be announcing much more in coming weeks and months! For now, let’s connect across social.

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