Hi Playmakers,
Last week, I did something ambitious that I never imagined I’d be able to pull off (more on that soon). As I took a step back from the adrenaline, it got me thinking: when is the last time I took a big swing at something?
Big swings are the moments in life that make your heart race and your stomach drop a little. You know the kind: the bold career pivot, the long-shot pitch, the new chapter you’re not “ready” for (but are doing anyway).
The truth is, no one ever feels fully ready. I’ve felt that way every time I’ve started something new — including this newsletter. But big plays don’t come from waiting. They come from leaping.
If you’re standing at the edge of something right now, consider this week’s newsletter your sign: swing big.
Let’s get into it.
Jenny
The Play of the Week: Thasunda Brown Duckett, CEO @ TIAA
When you build a life of intention, taking risks and betting on yourself becomes less… well, risky.
That’s just one of the reasons I admire Thasunda Brown Duckett.
What makes Thasunda’s story remarkable isn’t just her impressive title, it’s how she got there. Yes, she’s got the grit and determination to charge ahead, but it’s her lifelong commitment to service, equity, and building a career with intention that inspires me.
Taking big swings in life doesn’t mean going in without a plan. It means trusting in your convictions in the face of adversity. Thasunda focuses on lifting others as she progresses in her career, giving herself and those around her the confidence to take big swings in both their personal and professional lives.
The Execution Plan: Your Play for the Week
Insights are only valuable if they’re acted on. Let’s turn this knowledge into impact with small but powerful action steps.
This week’s challenge: Take a risk by betting on yourself. Accept that you might fail.
Let’s get out of your comfort zone this week by taking a risk to go after that personal or professional goal that might seem just out of reach. Apply for a job that’s a step-up from your experience, email a CEO to ask how you can join the team, or say ‘yes’ to an event that you would typically skip.
Call to Action:
1️⃣ Get out of your comfort zone and make yourself visible to a person or company that wouldn’t have heard about you otherwise.
2️⃣ Let me know how it went! Post about it and tag me at @jennystojkovic on LinkedIn, X, Instagram or TikTok for a chance to be shared.
Check out one of last week’s posts here.
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 is Andrea Hernández, who is an endless source of consumer memes and insights through her LinkedIn.
I spotlighted this post because Andrea is a one-woman show who continuously amuses and delights with her insights on consumer spending. She hits the nail right on the head with what we’re all thinking right now.
Plus, you know your girl Jenny loves a good Barbie meme any day of the week.
Want to be featured next?
Make sure to tag @jennystojkovic on your posts across LinkedIn, X, Instagram, or TikTok, and use the hashtag #Playmaker.
The Extra Edge: Industry & Success Trends
🧬 23andMe filed for bankruptcy. Can you delete your data? Check out the story.
📷 Google Gemini can now “see” through your phone camera. Read the story.
🤖 The Bot Company raises another $150 million to build robots for household chores. Read now.
🐬 Dolphins greeting the astronauts as their capsule lands in the ocean is the best end to this story. Check out the video.
Which famous popstar is turning 80 years old today and was once dubbed by Guinness Book of Records as "the most successful female artist in history"?
How to Get Involved:
The Wednesday Play isn’t just a newsletter — it’s a community. I’ll be announcing much more in the coming weeks! For now, let’s connect across social.
