
Hi Playmakers!
Perhaps unsurprisingly, I’ve been spending a lot of time thinking about those rare moments in life when everything changes. The ones you can only count on one hand. Being 36 weeks pregnant will do that to a woman. It’s making me get philosophical.
I’ve talked about those rare moments in my life many times in the past: moving to America, meeting my husband, and losing two of our closest friends. They’re the moments in life that shape us in profound ways, and today I want to celebrate them. The good, the bad, and the ugly.
It’s not really about any one moment in particular, but it’s the concept I’m fascinated by. I generally categorize them into two buckets: the ones you see coming, and the ones you don’t.
The ones we see coming are relatively straightforward. I knew my life would change dramatically by moving to the US and eventually to California to try to build a name for myself in tech. They were a leap of faith that guaranteed a radically different life on the other side.
Life has a way of solidifying around one path if you’re not careful, and I’m a firm believer that creating radical moments of change in your life suddenly shakes you loose, allowing for multiple paths to branch out before you. Success is, in part, due to your ability to create options for yourself. Sometimes, that requires change.
The other category requires a little less intentional thought. These are the Black Swans. (If you haven’t read economics leader Nassim Taleb’s The Black Swan, now is a perfect time.) These are the moments — no matter how hard you try — you can never see coming. They can be good or bad, but no matter what, they lead to radical change.
Perhaps the most profound example of a Black Swan event in recent years is the COVID-19 pandemic, which completely uprooted global society and business. For some, it was devastating, but for others, it represented a massive windfall.
In this changing moment in time, there are talks of other major Black Swan events coming soon. What are they? How can you prepare? Are there ways you can benefit?
Nobody wants radical change thrust upon them, but the winners in these moments are the ones that lean into — and take advantage of — the change. If you fight and resist, you waste valuable energy longing for a world that is no longer available to you.
To put it simply, the only path you have is forward.
What Black Swan event are you preparing for?
Jenny

The Play of the Week: Clara Shih, Former CEO of Salesforce AI

She grew up as an immigrant kid that pushed herself to excel in school.
Then, at just 27 years old, Clara Shih maxed out her credit cards to build a startup that most investors dismissed.
A few years later, she was on the board of Starbucks, and today she’s leading AI at Meta.
The Execution Plan: Your Play for the Week

Right now, I’m focused on having a loose grip on my path in life. I have a wishlist of things I want to see happen, and I’m putting things in place to make them so, but I’m not expecting them to happen. I’m allowing my life to unfold, and I’ll accept the changes as they come my way.
I want you to think about an area of your life where you have a tight grip.
This week’s challenge: Let. Go.
Radical change comes when we least expect it. Find an area of your life where you can loosen the reigns and see what happens!
Call to Action:
1️⃣ Identify an area of your life where you can allow for things to unfold organically.
2️⃣ Report back and let me know how it went! Drop a comment or share your post below.
Playmaker’s Spotlight: Real People, Real Wins
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 Bemi Orojuogun, aka “Bus Aunty”.
Bemi has been going viral on TikTok for the last half year for her love of London city buses. Her enthusiasm has helped bring joy to public transit in the megacity, and helped create appreciation for London’s bus drivers.
Try to watch without a smile on your face. :)
@bbcnews Bemi Orojuogun, known as "Bus Aunty", has gained nearly 300,000 followers thanks to her selfie videos with London's red buses. #BusAunty #... See more
Want to be featured next?
Make sure to tag @Jenny Stojkovic on your post for a chance to be featured.
The Extra Edge: Industry & Success Trends
👁️ I’m obsessed with this Chella eyebrow pencil. They’re 100% vegan and some of the most dedicated founders I know.
☄️ A house with a ball pit? You know you’ve thought about it…
🐬 This town in Nova Scotia rallied to rescue 16 dolphins. Every life counts.
☕️ Want to have virtual coffee with me?
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.
How to Get Involved:
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.


