The Wednesday Play: Embrace Failure

Hi Playmakers,

Last week, I talked about taking big swings. But here’s the thing no one tells you about big swings: sometimes, you miss.

This week, I stumbled. Something I really cared about didn’t go the way I hoped. And while my instinct was to brush it off and keep moving, I paused instead — because failure, as uncomfortable as it is, is also where the magic happens.

Failure teaches. It humbles. It sharpens. It reminds us that we’re in the arena, trying. And honestly? I’ll take a thousand stumbles over standing still.

So if you’ve recently fallen short, fumbled, or flopped — good. It means you’re in motion. It means you’re brave enough to care about the outcome.

Let this week’s newsletter be your permission slip to fail forward.

Let’s dive in.

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

Jenny

When you’re born in Kolhapur, India and grow up to become the Global CEO of Chanel, you’re bound to make mistakes and learn along the way.

Leena Nair is the perfect example of taking life’s challenges head on to pursue your dreams.

Read the story now.

Her ambitions were not typical for girls growing up in India at the time. In the late 1980s and early 1990s, it was still relatively rare for women to pursue higher education—especially in male-dominated fields like engineering and business. Cultural expectations often steered women toward domestic roles, not corporate careers. Leena, however, had different plans.

Leena went on to earn her MBA and start her career as a management trainee at Unilever in 1992. She became Unilever India’s first female factory manager, but there were many more firsts to come.

Read Leena’s entire story of her rise to global leadership.

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: celebrate a failure, publicly.

Anyone that has ever been successful at anything, whether that’s raising a family or growing a business, will tell you there were dozens if not hundreds of failures along the way— sometimes in spectacular fashion. It’s only with the benefit of hindsight do we realize that our greatest failures often enable our biggest successes.

Call to Action:

1️⃣ Post on LinkedIn or your platform of choice about a personal or professional failure. Share with others what you learned (or are in the process of learning) from that experience.

2️⃣ Report back! How was your post received? Did anyone else benefit from your wisdom or share in your experiences? Drop a comment to share your post below. The best responses will 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 is Colleen Slagen aka @namingbebe, whose TikTok on “female CEO” names recently went viral.

Colleen is a former nurse-turned professional baby naming consultant. She shares a wide variety of unique baby naming trends, including the new trend of “hot female CEO'“ names. You know I’m all about it.

What’s your favorite hot female CEO name?

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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