The Wednesday Play: Trust & Loyalty

Hi Playmakers!

I cried this week. A lot.

Not because something bad happened, but because I said goodbye to a car.

Now, I know this might sound a bit weird, but this was not just any car. This car was the first thing that my then-newlywed husband Pavle and I ever bought together.

I was 23, had never owned anything new, and we pulled together every dollar we had to buy a $16,500 Mazda3. That car took us across the continent, through 30 states, across the border into Mexico and Canada, and into every new chapter of our lives.

Even when we started to see our careers take off as executives in Silicon Valley and our bank accounts balloon, we kept driving that car. Then, we moved to the foothills of Los Angeles and proudly kept parking our loyal sidekick amongst a sea of Porsches and Range Rovers.

We didn’t care. We started with nothing, and that little car carried us through everything.

The thing is, my car wasn't just transportation. It was trust and commitment. It was a reflection of who we were and what we believed in. And for over a decade, we chose to keep showing up for it, just like it kept showing up for us.

Today, loyalty feels like a fading value.

We’re living in an era where staying power is rare. At this rate, the average Gen Z worker is expected to hold more than 18 jobs in their lifetime. Marriage rates are at historic lows, and divorce rates are highest among younger couples. Many people don’t buy homes, cars, or long-term insurance anymore. Even friendships, communities, and brand relationships have become more fluid, often based on convenience or shared content rather than shared values.

Trust has become transactional. If something stops serving us, we move on.

This mindset isn’t necessarily wrong — it’s simply a product of adaptation. In a fast-moving, unpredictable world, young people are building a new system to survive the future. But, despite that, something gets lost when everything is temporary. When trust is earned for a moment and loyalty is confused with weakness.

Nearly every aspect of my life has relied — and thrived — on enduring loyalty and trust. Whether it is jumping into marriage as a 21 year old college kid or driving a car for 200,000 miles coast to coast, my personal life has been one commitment after another. In many ways, I’ve always felt like I’m a product of a different generation.

But, that loyalty has paid off in ways I could have never imagined in my career, too. Colleagues from my first jobs or even college professors continue to show up for me and open doors. People I have met in the earliest aspects of my career go on to become LPs in my fund. Quiet connections that I nurture and keep warm, year after year, end up changing my career in ways I could never imagine.

Saying goodbye to my car reminded me that trust and loyalty are a rare currency in today’s world, and the more I hold onto the more valuable I become.

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

As always, drop me a line and tell me what you think!

Jenny

Emma’s loyalty to the Kardashians helped her build some of the world’s most iconic brands.

Before she became one of the wealthiest self-made Black women in America, Emma Grede was a kid delivering newspapers in East London, saving money for a future no one around her could yet imagine. Today, she’s the powerhouse behind Good American, a founding partner at SKIMS, and the quiet architect of the Kardashian fashion empire.

Read the story now.

Her story isn’t one of overnight success.

Emma Grede was born in 1982 to a single mother in East London. The second of four daughters, Emma’s childhood was shaped by financial struggle and maternal grit. Her mother, a Jamaican-English woman, worked multiple jobs, including cleaning houses, to keep the family afloat. Emma learned early that success wouldn’t be handed to her — she’d have to work for it.

Read how Emma built her Kardashian empire.

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: thank someone who has always been there for you.

This week’s challenge is an easy one. Think about a person who has always been there for you through thick and thin. Maybe it’s a loved one, an employee who worked for you, or a manager who always had your back.

Call to Action:

1️⃣ Reach out to that person and thank them for being loyal and trustworthy. Make sure they know how much you appreciate them.

2️⃣ Report back and let me know how it went! Drop a comment or share your post below. The best responses may be featured next week.

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 Tyler Chou, the Creator’s Attorney.

I spotlighted Tyler as this week’s #Playmaker, because she is redefining the future of the creator industry… and bringing us along with her for the ride. Her bold post this week invited readers to think bigger — disruptive, even — about their work and how sometimes a negative, like a lawsuit, is a sign of big things to come. Bad ass.

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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