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Cass Cooper | The Chaos Whisperer

Executive Coach | Keynote Speaker | Author | Podcaster

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Work-Life Balance Is the Wrong Goal: A 3-Question Rhythm Check

CASS COOPER THE CHAOS WHISPERER Hi Reader, Turns out I wasn't bad at balance. I was living a life that only worked if I disappeared. Story time: five years ago, on paper, I was winning. Corporate leader. Teams to manage. Shattering goals. But behind the scenes, every morning was an event of Olympian size: up before my daughter, a short walk or yoga (maybe), breakfast (for her, yes; for me, another maybe), school drop-off in an obscenely short window of 8:15 to 8:30 am, then across town to...

CHAOS INTERPRETED Cass the Chaos Whisperer™ In my first management role, another woman was promoted over me. It was widely known inside the organization that she and the owner were in a sexually intimate relationship. Sensing my disappointment about being passed over, a colleague encouraged me (or at least tried to) by saying, “Well Cass, you might have to accept that some women just want to sleep with the boss to get ahead.” YUCK. The question we could have been asking was: why does the...

Know Better Studio · Episode 21 You Already Know: Trust Your Intuition & Inner Wisdom What if the answer you've been searching for is something you already know? We spend so much of our lives looking outside ourselves for answers. We follow the rules, check the boxes, make the choices that look good on paper, and sometimes ignore the quiet voice inside telling us something different. In this episode of Right There With You, Cass Cooper sits down with Lisa Caruso to explore the different ways...

Know Better Studio · Episode 20 Stop Bringing Folding Chairs. Build Your Own Table. In Episode 20, a solo conversation with me, we look at the cancellation of the Grace Hopper Celebration and what it reveals about spaces that depend on institutional funding. What if the room you've spent years trying to get into disappears overnight? "Sometimes the next step isn't bringing another folding chair. It's building a different table." — Cass Cooper A room that depends on someone else's funding was...

Me and my dad in 2019

CHAOS INTERPRETED Cass the Chaos Whisperer™ This is Bob... After my keynote in Maine, Bob walked up to me, and I haven't stopped thinking about him. Bob is about to go through a big transition. He told me he's spent his life teaching others how to set boundaries. His kids, the people around him. He's worked hard to share the importance of mental health and work-life balance. But for himself? Not so much. And I stood there thinking, oh. I know this one. Because I've been Bob. For years I held...

Know Better Studio · Double Dose Double Dose: Two Episodes, One Email Two weeks, two conversations I can't stop thinking about. This week you're getting both: Jess Wass on why you can't have it all (and why that's the point), and Mai Nguyen on why we don't need more content, we need more connection. Dose 1 · Episode 18 You Can't Have It All—And That's the Point Reworkit founder and CEO Jess Wass on letting go of the "have it all" promise and building a life around intentional tradeoffs that...

CHAOS INTERPRETED Cass the Chaos Whisperer™ The Cornell Seven Could Be Your Boss A note before you read: this essay touches on sexual harassment and assault. I didn't know where to start with this essay, but I have to get something on the page. I cannot sit back and watch us disconnect the different parts of our culture, including rape culture, from the way we live and the way we work. I could go on about how intersectional the ways we live are, not just through race, gender, and class, but...

CASS COOPER THE CHAOS WHISPERER Hey Reader, September moved fast. Here's the recap, in case life happened and you missed a piece of it. 👇🏾 On the Podcast 🎙️ Three new episodes of Right There With You this month: Jonathan Sims — "It Doesn't Make Cents: Measuring Value Beyond Money": mutual aid, real value, and why community currency beats capitalism. Miri Rodriguez — "Success, AI, & the Power of Becoming Yourself": rewriting your story, redefining success, and what AI actually means for human...

CASS COOPER THE CHAOS WHISPERER Death to imposter syndrome. I was on a panel last week with a woman who runs the office of a very senior executive at a company you'd recognize. Right before we went on, she told me she was nervous. Then she said the thing. "It's just imposter syndrome." I stopped her. Not gently. Imposter syndrome is not real. It is not a condition you have. It is a story you were handed about who gets to be in the room, and you have been carrying it so long it feels like your...

CASS COOPER THE CHAOS WHISPERER I used to think a full calendar meant I was doing too much. Last week I was in New York to speak at Out in Tech for the second year. I was excited. It's a great room to be in. But before I left, I had orthodontist appointments, a piano to tune, laundry to do, bags to pack, and house and dog sitters to coordinate. It was a lot. And old me would have called it overwhelming. New me knows better. Because the chaos I'm living in right now was created by a version of...