The Wednesday Play: Why Not Me?

Hi Playmakers,

Here’s something I’ve learned the hard way: the first person who tells you “no” is usually you.

Before the world has a chance to shut our dreams down, we shrink them ourselves. We tell ourselves it’s too ambitious, too risky, too soon. We lower the bar just a little and decide not to shoot for the stars.

For me, this happened when I was 17 years old. I was in 11th grade and earning the top grades in my high school in my small farm town. The only problem? My mum was a cashier and my dad was blind. As two high school dropouts, they did the best they could, but a college fund was never in the cards for me.

Most people in my town had very different ambitions than I did. While I was watching Shark Tank and dreaming of moving to Silicon Valley to work at Google, most folks were eying up a union job at the local Honda Plant. It worked for them — and I’m glad it did — but it wasn’t for me.

So, I started researching how I could get to college. It was then that I found an opportunity from a man named Ted Rogers. I knew the name but didn’t realize at the time that he was the CEO of Rogers and one of Canada’s most wealthy billionaires. I’m glad I didn’t realize this then, because I sat down that afternoon and wrote a letter to Ted, explaining why I wanted him to pay for my university tuition. If I had known who he was, I probably would have doubted myself and never sent off that letter.

Months passed and my university acceptance letters rolled in. While acceptance letters are a cause for celebration for many kids (sparking an entire Instagram trend these days), they’re not much celebration for kids like me. Finding out you got into every school you picked — but not having the money to go — is bittersweet, at best.

Then, one day, a letter appeared. It was already April and I had been patiently trying to figure out if I’d get to college that fall. I opened it up and there it was: congratulations, you’ve been selected.

I couldn’t believe it. After all those years of wondering if I’d get to go, I was finally in.

The day the check arrived in the mail, I held it in my hands for nearly 10 minutes. I stared at it, bewildered. I had never seen a five-figure check in my life.

A few months later, I was invited to receive the award in a ceremony at the Rogers HQ. Then, Ted hosted me and a few others in his boxed seats to see the Yankees play the Blue Jays. I’d never been to a boxed suite.

Though I met him for only a brief few seconds, Ted’s impact was immeasurable. I was so nervous at the time that I could barely say hi. He sadly passed away a few months later, before I got a chance to thank him properly.

Ted’s life motto was: the best is yet to come.

Because of this opportunity, I did finally get to Silicon Valley. I did finally work for Google. I did finally become one of the venture capitalists I grew up watching on TV.

Then, in a poetic twist, I received a call last year and found that I was getting the Alumni Achievement Award from my university — becoming one of the youngest recipients in history. An achievement that would have never been made possible without the belief that Ted had in me.

That’s why this week’s newsletter is your reminder to dream bigger. Don’t sell yourself short. Don’t pre-negotiate your own limits. Shoot for the stars.

Always ask yourself: why not me?

Let’s get into it.

Jenny

Nearly everybody is talking about the flashpoint moment of this week’s “Space Girls”. Most of the press coverage and criticism has centered around the idea of billionaires or celebrities in rockets going to space. Rarely do we think of survivors, activists, or children of refugees making that journey.

That was until Amanda Nguyen launched.

Read her story now.

Born to Vietnamese refugees in San Diego, Amanda grew up dreaming of the stars. But before she ever stepped into a space capsule, she rewrote U.S. law, built a global civil rights movement, and became one of the most recognized voices for justice in the world.

Her path to space wasn’t paved with privilege or power. It was built through pain, persistence, and the belief that dreams — no matter how improbable — still belong to everyone. She is the true embodiment of the mantra, “why not me?”

Read the full story of how Amanda Nguyen took her fight from the courtroom to shoot for the stars.

Today is Selena Day, a day held in honor of the birthday of the late Mexican-American singer. In her short life, Selena shot for the stars and never settled for less. In her honor, let’s go big this week.

This week’s challenge: add 20% to one of your existing goals.

One piece of advice I give young leaders is to never negotiate against yourself. Never sell yourself short. The world will constantly look for ways to drive down your self worth. You are the only person that can truly advocate for yourself.

Negotiating a salary? Ask for 20% more. Running a 5K? Run a 6K instead. Push yourself beyond the goals you’ve set, and you’ll realize that you’ve been negotiating against yourself.

Call to Action:

1️⃣ Take one of your existing goals and push yourself 20% harder. Reflect on the outcome. Were you successful?

2️⃣ Report back! Post about it on LinkedIn and tag me and add the hashtag #Playmaker.

Every week, I spotlight somebody from the community who is making a big play in their career or industry. This week’s play is my friend Simran Kaur, Founder of GirlsThatInvest.

I spotlighted Sim this week because she’s a true master of educating her audience while doing it with flair. She demonstrated exactly what it takes to make a post viral and relatable: timely, action-oriented, easy to understand, and, most importantly, helpful.

Plus, let’s be honest — it’s just a fun way to break down complicated content.

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 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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