The Wednesday Play: Tackling Imposter Syndrome

Hi everyone!

You’re officially reading the very first edition of The Wednesday Play! I am thrilled to have you here for today’s launch.

This newsletter has been a goal of mine for the past while — ever since I started writing my long-form content on LinkedIn last year. Like most creators, when I first started writing, I didn’t think anybody would be interested in my content. Though I had already built thriving careers in tech, entrepreneurship, and venture capital, I thought to myself, “People already know everything I’m going to share, so who will be interested in what I have to say?”

Turns out, tens of millions of you were interested. The lessons and experiences that I thought were obvious? Not so obvious.

So, what was that nagging feeling? The one that told me to quit before I even started? It was just imposter syndrome, rearing its ugly head once again. Because, as we know, imposter syndrome never truly goes away. Even when you reach the highest rungs of the career ladder, major Fortune 500 CEOs doubt themselves, too (I’ll get into this more below).

Still, I pushed forward, and now that tiny idea has turned into today’s launch, The Wednesday Play. Each week, I’m excited to take you on a deeper dive into “the big plays” that will help you succeed in your life and career, with everything from the iconic women’s leadership stories you love to the productivity gains and strategies that build better, wealthier careers. Here’s what each newsletter will look like:

I hope you enjoy this first edition and I hope you’ll reshare with your network!

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

Jenny

P.S. If this looks familiar, this email is a re-send. Some folks didn’t receive it last week. Expect new content next week.

When it comes to truly redefining an entire industry, there are few industries more resistant to change than Wall Street. With hundreds of years of entrenched history and culture, banking rarely shows a glimmer of modernization. Its leadership, particularly in the United States, tends to be a homogenous group of white, male leaders that persist year after year. Seldom do outsiders of different backgrounds break into this space.

That was until Jane Fraser arrived.

Read the story now.

Born in a small village in Scotland, you’d be hard-pressed to believe that Jane’s story would ever lead to her becoming the first woman in history to lead a major bank on Wall Street. And how she did it is even more impressive.

While everyone else began grueling 80-hour work weeks, Jane focused on motherhood and started her career started her career part-time.

Each time she climbed farther up the ladder, it felt more and more like a mom like her didn’t belong. Imposter syndrome was rife.

Then, when the century’s worst financial collapse in history started, Jane made a very, very big play. That play would solidify the future of her career and make her an icon of banking.

Read the entire story on Jane’s iconic rise to fame as the first female CEO on Wall Street.

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: overcoming imposter syndrome

Let’s get out of your comfort zone this week and share a story about a job you had early in your career and what lessons you still use today. By thinking back on where you were then, you’ll realize just how far you’ve come in your career today.

Call to Action:

1️⃣ Post on LinkedIn or your platform of choice about one of your earliest jobs. Share what it taught you and what lessons you still use today.

2️⃣ Take action and report back! 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 Carly Williams, whose post on a funny job offer experience is going viral across social media.

I spotlighted Carly as this week’s #Playmaker because she is bringing levity and optimism to the job search experience at a time when the job market is horrible. It can be easy for job seekers to feel they’re doing everything wrong, but Carly is breaking through the narrative to show that good recruiters are still there to support talent.

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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