Hi Playmakers,

This week is a very personal update from the Stojkovic family.

I missed seeing you last week, and you probably have an idea of why…

On Friday morning, I woke up in what would appear to be a rather comical scene from a movie — as I stood up to get out of bed, my water broke. Just like that.

Now, unlike the movies, this is not a typical way for labor to begin. In fact, only 10% of women have their water break before going into labor, I learned. So, as I tend to be on the more unusual side of the statistic, I promptly found out from my doctor that the next step in the process was… wait.

Yep, go home. Have a shower. Wait for the party to start.

At 39 weeks pregnant and a first-time mom, I was a bit taken aback that this is really it.

By that evening, we were at the hospital, and that’s when things began to get real. The beginning of a 15-hour journey was on its way, complete with all kinds of bumps, twists, and turns. I’ll spare you the details, but all I can say is, after unintentionally experiencing unmedicated full-on active labor contractions, y’all better call your moms and tell her you love her. She’s a god damn hero.

By the time dinner rolled around, our baby was well on his journey out. Along with our doctor, we were fortunate to have a fantastic team of nurses and our wonderful doula with us, who set up our favorite playlist and helped cheer the birth along.

At 5:24pm, Edge of Seventeen by Stevie Nicks played across the speakers, as Roman Eddy Stojkovic was born. Delivered by his father’s bare hands at 7lbs 14 oz and 20.5 inches long in Los Angeles, Roman entered this world as the first American in our bloodline.

He has no idea how far his parents came to get him here or how lucky he has it.

I don’t know what the world will be like as Roman grows up. We’re on the brink of a total transformation of how we live and work on this planet. What will things look like for Gen Beta — the newest generation to begin in 2025?

Should we ban smartphones? Will he go to college? Is social media healthy for him? Will he bring home an AI girlfriend for us to meet? Will we still be using the American dollar when he graduates high school?

It’s been blissful to be away for a few days and not care about the price of gold or the new Sora app. It’s been nice to shut off my phone and focus entirely on giving new life to a human being.

There are so many challenges I’ve undertaken in my life, but this is, by far, the biggest yet.

Feel free to drop us well wishes, as Pav and I enjoy some well-needed time away as a new family of 3 (plus, our 3 dogs, too!)

Jenny

At 32, Rea Ann Silva was a single mom working as a makeup artist on TV sets in Los Angeles.

By 42, she had invented the Beautyblender — a teardrop sponge that changed the way the world does makeup. Today, her company is valued at over $1 billion.

Meet Rea Ann Silva, founder and CEO of Beautyblender.

Software was supposed to make work easier. Instead, most teams are buried under it.

That’s SaaD – Software as a Disservice. Dozens of disconnected tools waste time, duplicate work, and inflate costs.

Rippling changes the story. By unifying HR, IT, and Finance on one platform, Rippling eliminates silos and manual busywork.

Companies like Cursor, Clay, and Sierra have already left outdated ways of working behind – gaining clarity, speed, and control.

Don’t get SaaD. Get Rippling.

Is SaaD hurting you?

This week, I’ve been thinking a lot about reinvention.

Motherhood, like entrepreneurship, has a way of stripping away everything you thought you knew about control. It forces you to adapt, improvise, and find new ways to move forward — even when things get messy.

Rea Ann Silva didn’t set out to build a billion-dollar company. She set out to solve a small, personal problem. But that act of creativity — of daring to try something new — changed her entire life.

This week’s challenge: Reinvent one small part of your routine.

This week’s spotlight features Mrs. Gontjes, a choir teacher who recently went viral for letting her students replace the lyrics to her songs with Gen Alpha slang. As anyone with Gen Alpha kids knows, the slang is — well — pretty weird these days.

I’ve been thinking a lot about the future of education and how important skills-based learning is. I’m glad there are so many amazing teachers like Mrs. Gontjes out there in our school system, building our future generation.

Want to be featured next?

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

I’d love your help spreading the word about The Wednesday Play. Refer other people to the newsletter and get free time with me for a video call.

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.

Join 130,000+ followers on LinkedIn!