The Wednesday Play: Redefine Success

Hi Playmakers,

When I was growing up, success looked pretty straightforward.

You got a stable job, bought a modest home, drove a reliable car, and saved for a two-week vacation once a year. If you were really lucky, maybe you got a boat, paid off your mortgage early, and had enough leftover for a college fund for the kids.

In my head, the secret number to achieve that was a crisp $100,000.

“If I could just grow and make $100,000 one day, I’d have it made,” I used to think to myself.

It wasn’t glamorous, but it was safe and achievable.

That version of the “good life” is dying.

This week, I saw a headline that stopped me in my tracks: “$80,000 is now considered low income in Los Angeles.”

Eighty. Thousand. Dollars.

Once the benchmark of middle-class success and now it’s barely scraping by.

And LA isn’t an outlier. Across the U.S., housing prices have soared. Childcare costs have doubled. Groceries, insurance, and even basic healthcare now feel like luxury items. Meanwhile, wages have barely moved. Owning a home feels out of reach. Renting feels unstable and most of my Millennial and Gen Z counterparts have already bid the dream goodbye.

We are watching the death of the mid-tier life in real time.

And what’s wild is: for so long, that was the life we were told to stay loyal to.

Go to school. Work hard. Don’t be too risky. Get good benefits. Buy used, save often. Play it safe, and you’ll be rewarded.

But the goalposts moved and the rules changed. And playing it safe doesn’t feel so safe anymore.

So what do we do?

We start redefining success on our own terms.

For me, that has looked like walking away from the safety of Big Tech and building something on my own, after I quietly packed lunches and spent my 20s socking away thousands a month to invest in an aggressive plan to reach financial freedom (any FIRE friends here?)

It also meant driving the same car for over a decade, even while raising a $23 million dollar VC fund. It’s meant staying scrappy, creative, and sometimes a little uncomfortable — because I’m no longer chasing stability.

I’m building sustainability. On my terms, especially as a soon-to-be parent.

The system wasn’t built for us. But that doesn’t mean we can’t build something better.

That’s what I’ve been thinking about this week.

Jenny

P.S. I’d love to know: What does “success” look like to you now?

Today, Aicha Evans is one of Silicon Valley’s most powerful Black CEOs.

But before she led one of the world’s most innovative transportation startups, Aicha was born thousands and thousands of miles away in a small West African nation.

Today, she’s the CEO of Zoox, the Amazon-owned company building fully autonomous vehicles from the ground up.

Her rise didn’t follow the traditional playbook.

As one of the few Black women to run a billion-dollar tech company, Aicha is breaking barriers while building the future.

Read how she became one of the most powerful CEOs in Silicon Valley.

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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: redefine your version of success.

The “good life” used to mean a steady paycheck, a house with a yard, and maybe a couple of weeks off each year. But for many of us, that version doesn’t feel possible — or even desirable — anymore.

So let’s rewrite it.

Call to Action:

1️⃣ Take 5 minutes this week to write down your new definition of success. What does security, happiness, or “making it” look like to you now — in this season of your life?

2️⃣ Share it. Post it publicly or send it to me privately.

Because when the rules change, so must the dreams.

Every week, I spotlight somebody from the community who is making a big play in their career or industry. This week, however, I decided to focus on little Brielle Bird.

Brielle is currently suffering from terminal cancer and, in her final wish, created a TikTok dance she had hoped would go viral. Now, celebrities and supporters around the world are recreating Brielle’s dance to bring joy and comfort in her final days. Though her time might be limited, I couldn’t think of someone who more embodies the definition of a playmake than Brielle.

Want to be featured next?

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

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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