The Wednesday Play: Rewear the Runway

Hi Playmakers,

Here’s a stat that stopped me in my tracks: women don’t wear 55% of the clothes they buy.

I posted about this on LinkedIn last week.

Even more interesting? A ton of men replied to the post that they felt the same way, too.

Where does it come from? 1 in 3 women feel they can’t publicly wear the same outfit more than once or twice.

Think about that for a second.

An average clothing budget of $2,500 a year means more than $1,300 sits unworn in the closet every year. That’s a mortgage payment or a plane ticket. A chunk of retirement savings. All tied up in clothes we don’t feel “allowed” to wear more than once — which pollute the planet, too.

The unspoken pressure to always look “new” is really just the fear of being seen in the same thing twice. The closets stuffed with unworn pieces are more about managing other people’s opinions than dressing for ourselves.

In an era of constant “personal branding experts” and the need to sell ourselves over and over again, we’re all constantly trying to figure out how to stay relevant and fresh.

Constant pressure to stay ahead of the curve in a shrinking job market. Trying to figure out the next AI tool, so we don’t fall behind. Feeling the need to craft a “professional persona” when you’d rather not be on social media at all.

So here’s my take: enough of that. Seriously. You’re fine the way you are.

Rewear the outfit. Wear it three times. Wear it ten times. If you love it, keep wearing it.

It’s not really about the outfit — it’s about pushing back against the fear of judgment and the opinions of others.

So, I’m pledging to rewear mine. Who’s with me?

She transformed a struggling video platform into a multi-billion dollar company and became one of the youngest women to take a startup public.

Read the full story now.

Before she became a two-time tech CEO, Anjali Sud was a teenager from Flint, Michigan, trying not to fail out of boarding school. Her parents had immigrated from India and made education their highest priority, even when money was tight.

At just 14, she earned admission to Phillips Andover Academy, one of the top private schools in the country. But once she arrived, she struggled to keep up. The coursework was rigorous, and for the first time, she began failing her classes.

That early setback could have broken her confidence. Instead, it became a turning point. Anjali went on to graduate from the University of Pennsylvania’s Wharton School, then earned her MBA from Harvard. When she started applying for jobs in investment banking, she assumed the hard work would pay off. But every major firm turned her down. No one was interested in giving her a shot.

Read how Anjali climbed her way to the top.

Insights are only valuable if they’re acted on. Let’s turn this knowledge into impact with small but powerful action steps.

This week, I put my husband to work. (Yes, my husband did most of the work. I’m seven months pregnant, after all.) Our family room was dark, and the fireplace was begging to be updated. So we (he) got to work painting the walls. With some leftover tile we had in the garage, we started updating our fireplace. It’s like a completely new home!

This week’s challenge: revisit something old, and see how you can make it new.

I’m not talking clothes here. I want you to find a new way to love something that has grown stale in your life. Got an old, reliable car you’re taking for granted? Do a deep clean and pop on a new steering wheel cover. Living room feels boring? This is a great time to paint the walls. Is there a relationship you’ve been letting grow distant? Pick up the phone and give that person a call. Yes, a call. Not a text.

Call to Action:

1️⃣ Reflect on one area in your life that you can revitalize.

2️⃣ Report back and let me know how it went! Drop a comment or share your post below.

This week’s play comes from legendary VC Nichole Wischoff. She’s here to remind us of the most important part of life:

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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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