Hi Playmakers,
The first time I applied for a job I wasn’t “qualified” for, I nearly backed out.
It was a Silicon Valley tech role asking for an Ivy League degree, years of experience, and technical skills I didn’t have. The majority of people in the industry with similar roles were lawyers or people with Masters degrees.
But I applied anyway.
I figured: “Why not me?”
Much to my surprise, I got the job — not because I checked every box, but because I showed I could figure it out. Months later, I was leading executive meetings and solving problems with the very people who I had been intimidated by because of fancy resumes and designer degrees.
That moment changed everything.
Here’s what I’ve learned:
Reframe your story. Don’t list what you lack — show how you learn fast, solve problems, and deliver value. Never point out what you are missing.
Do the homework. Learn the company’s language and needs. Speak like someone already inside. AI can help by analyzing the company’s materials.
Focus on the 20% that matters. Every job hinges on a few core things. Identify them and lead with how you’ll deliver.
Don’t just apply — pitch. Make your application a proposal. Share what you’d do in your first 30–60–90 days.
Ask yourself, “Why not me?” Then back it up with action. The number one reason you are not getting an opportunity is not because you’ll be rejected, but because you never applied.
Most people think they need to tick every box before they go for it — but the truth is, most men apply for jobs when they meet just 60% of the qualifications. Most women wait until they meet 100%. That stat has stuck with me for years.
That’s why this week, I want you to go for it. Don’t be the first person to count yourself out.
Because success doesn’t go to the most qualified.
It goes to the ones who show up anyway.
How are you going to show up this week?
Jenny
P.S. Liked this note? Forward this email to a friend who needs some motivation.
The Play of the Week: Anastasia Soare, CEO of Anastasia Beauty
Anastasia Soare came to the U.S. as a single mom with $200 and no English.
Today, she is worth almost a billion dollars with her iconic Anastasia Beauty brand.
Anastasia started by offering her services for free. Soon, her unique approach to eyebrows caught the attention of supermodels like Cindy Crawford and Naomi Campbell — and later, Oprah. In 1997, she opened her Beverly Hills salon. A year later, she launched her now-iconic brand.
Today, Anastasia Beverly Hills is one of the most beloved brands in the industry, with millions of loyal fans and products in thousands of stores.
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: nominate someone who doesn’t realize how ready they already are.
We all know someone holding back — waiting until they feel “qualified” enough to go for the job, award, panel, or press opportunity. But sometimes, all it takes is a little nudge from someone who sees their potential.
This week, be that person. Be the person Dolly thinks you are.
Call to Action:
1️⃣ Nominate someone for something they might be too afraid to go after — a job, a speaking gig, an award, a board seat. Or just send them a message and tell them, “You’re more than ready.”
2️⃣ Report back and tag me in the post. I’ll feature a few of your responses next week.
Sometimes, the best way to silence self-doubt is to borrow someone else’s belief in you.
This week, be that belief for someone else.
Playmaker’s Spotlight: Real People, Real Wins
This week’s #Playmaker is Jean Kang with this viral post below on how to combat imposter syndrome. In line with my letter this week, Jean shares techniques on how to combat that nagging feeling that you’re not quite qualified enough.
Repeat after me:
“You miss 100% of the shots you don’t take.”
Bonus points: who knows who said the quote above? My Canadian is showing… :)
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
🐰 An end for animal testing. FDA plans to phase out animal testing in drug studies.
🐣 Do you say please to ChatGPT? Science leaders believe AI consciousness is coming.
🥲 New federal guidelines recommend pain medication for IUD insertion. Finally.
🎥 Google just unveiled their new AI filmmaker Veo 3. RIP Hollywood.
This iconic woman, widely believed to be the greatest poet in American history, passed away on this day in 2014.
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.
