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What does good leadership look like?

What are you like when you are called into a role of leadership? And what does it feel like to work or live with a bad leader?

I’ve been thinking a lot about leadership this week since spending Tuesday with Michal Oshman, TikTok’s Global head of culture. Michal joined our Jewish organization of entrepreneurs in Chicago (JWE) to inspire us by lessons from her experience as a working woman in the cut-throat tech world, as a sergeant in the Israeli army and as an observant Jewish mother of four.

Michal Oshman with JWE
Michal Oshman speaking in Chicago for a packed rooftop of Chicago Jewish entrepreneurs and professionals

If you had to guess what a woman in a senior position at the fastest-growing social media channel (who was also a sergeant) is like as a leader, you’d likely imagine she’s tough. Michal exudes warmth and wisdom. As author of her new book, What Would You Do If You Weren’t Afraid?, Michal shares her vulnerability of growing up with anxiety and her journey to finding strength in Jewish wisdom.

She’s brought that wisdom into both her home and workplace culture.

The message that stood out to me most from Michal’s book and talk is that of the Kabbalistic concept of tzimtzum–making space for others. She writes, “We might think we are being helpful, but when we impose too much of ourselves – whether by talking over someone, offering too many ideas or solutions, or not listening humbly to how others feel or think – we are taking up too much space.”

This is one of my biggest weaknesses. I’m the queen of ideas, which helps when you need a marketing consultant to brainstorm for a project. It’s a disaster when you need to just listen to your teen vent.

In a team setting, taking up too much of the air in the room leaves little space for others’ creativity.

Michal too had to learn to integrate this lesson into her marriage. And then she brought it to the culture at TikTok, where she says everyone there knows about tzimtzum.

5 more lessons on leadership and life from Michal:

  1. The day you were born was the day the world was missing you. Each of us is still here because we matter.

  2. When people see you respect yourself, people around you respect you.

  3. It’s such a waste of time to put energy into trying to be like someone else. But we all do it anyway.

  4. How do you make a hard decision? Look at it like a bridge you have to cross. Do you feel you belong on this side of the bridge, or do you think you belong on the other side? Fear is normal, but we can overcome our fears and cross bridges.

  5. If you channel your energy into helping someone else, you always feel better about yourself.

Our world today can feel like we’re living in a vacuum of positive leadership. But opportunities for good leaders are everywhere. Politics and the world economy affect the macro elements of our lives. But our homes, businesses, places of worship, communities, social circles and even workout classes all have a bigger impact on the microlevel.

These are the spaces where each of us has the opportunity to be a leader for good. And to create spaces where people are welcome, feel heard and feel supported.

According to Michal, culture is everywhere. It's the rules of engagement in every situation. Either you define it, or it defines you.

Each of us has the opportunity to direct that culture in ways that bring out the best in everyone – in our homes, in our businesses, our practices and in our communities.

Here's to living a life that matters, Wendy

P.S. I'd love to hear from you, what does it look like to work and live in a culture run by good leaders? Let me know on LinkedIn


Sparking your interest

💥 The American Academy of Pediatrics released updated recommendations on breastfeeding until 2. I can't agree with this article enough on how tone deaf this is in its timing and in its total disregard for women's realities.

💥 I felt this article on our culture's association with guns as a symbol of masculinity in real life this week. A high school classmate of mine offered on Facebook to organize a reunion. Instead of grabbing our attention with a throwback photo to 1996 or a pic of his cute kids/dog, he used a photo of the three (!) tables of guns he laid out in his yard at his 4th of July celebration. Talk about misguided leadership!

💥 This This American Life episode on whether most people are basically good or bad was delightful. The opossum story had me guffawing on my run. This episode from the week before, The Pink House at the Center of the World, is one of the most important podcasts I've ever heard.

Sparks of Marketing for healthcare podcast

This week's episode of the podcast features my conversation with my guest and cardiothoracic surgery PA, Sabrina Runbeck, as we cover productivity in your practice or healthcare company. Contrary to how we sometimes think of productivity, Sabrina sees it as a way to avoid burnout, focus on the work you enjoy and take more breaks. Listen here

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