Before Case Kenny became an acclaimed mindfulness author and influencer, he was just a hardworking young Midwestern man who sought a bit of clarity in his life. Yes, he was a successful regional vice president of a team that sold advertising software. But, from a personal standpoint, Kenny says he felt a bit adrift.
“I was confident in my career because there was a blueprint,” the 36-year-old says. “You do this, you get promoted. You sell this much, and this happens. But I felt like Personal Case, Man Case, Partner Case, Friend Case didn’t really have any clarity about how to be, and as a type-A person that frustrated me. I didn’t want to be different versions of myself.”
Some people might turn to personal development books or gurus to help them work through their existential ennui. Not Kenny, who was at the time a self-described self-help skeptic. In 2018, he launched his podcast, New Mindset, Who Dis?, where he works through the thorny little issues of existence in 15-minute episodes. There are no mindfulness guru guests telling him what to think, and no need for therapy-speak. Kenny just intends to be a dude who logically and vulnerably talks about what is bedeviling him. That was then. Now Kenny has more than a million Instagram followers (@case.kenny), a podcast with at least 30 million downloads, and a flourishing community interested in his books and in-person events.
“I really like staying in this space where I’m learning and I’m reflecting on my experiences,” he says. “Mindfulness is never like, ‘Here’s how to do something.’ It’s more the art of, ‘Why is this a certain way?’ And if there’s any skill that I’ve developed over the years, it’s the art of questioning. It’s the art of your internal dialogue. And for me, it’s a space that I think can help a lot of people.”
Born in Chicago, Kenny and his older brother were raised in Virginia and educated briefly at a Waldorf school, which emphasizes imaginative play in its early instruction. Kenny says his Waldorf education likely played a role in his willingness to play and explore new paths in his life, but his parents also encouraged him to study and pursue his interests.
“Looking back, there was always a sense of encouragement when it came to play, creativity, and arts and crafts,” he says. “I think that was to my benefit.”
In time, Kenny’s interests made him the most unconventional one in his household: his mother was an attorney, his father was a consultant, and his brother became a cardiologist. Kenny, meanwhile, went to Notre Dame and double-majored in Chinese and Arabic, thinking he would either work in international business or for the U.S. government. After graduation, he interned for a law firm in Shanghai for a summer, then went to work for the Notre Dame Alumni Association before finding a Chicago-based job in marketing and advertising.
“Even though that was obviously different from what I got my degree in, it really kind of fit the bill of how I’ve always had an interest in people, cultures, how people think, how people talk, and what moves a person,” he says. “I always say that people should wait tables and do sales at some point in their life. Between those two things, you learn so much about yourself, and so much about other people.”
What Kenny learned about himself was that he needed to learn more about himself. In doing so, he podcasted his way into an entire new life and career. Though some might argue that he lacks the formal credentials to offer mindfulness training, he counters that a lifetime of broad exploration has been just as impactful in shaping his insights that have helped so many people. Still, he remains grounded.
“There’s something powerful about having a breadth of perspective,” he says. “Over the years, I’ve gotten more confident in myself. I feel purposeful in everything I do and who I am, but it’s also come with a huge dose of humility. I think the more that you genuinely throw yourself into mindfulness or the wellness space, it is essential that you become even more humble, because you realize how much you don’t know. The humble people are the ones who are doing the work and practicing these things.”
Part of that humility includes being open to change. Though Kenny defines himself as a Midwesterner, two years ago he and his girlfriend moved to Miami. They both work for themselves (she is a DJ), he says, so they felt it was time for a fresh start in a place with great weather, new people, and plenty of creative energy.
“Miami, and Florida in general, has been so great,” he says. “I’ve met so many amazing people down here—wellness people, heart-driven people, creative people. It has been really inspiring. Frankly, I think the Midwest is fantastic, but down here, it’s just inspiring to be around people who have truly redefined what it means to make a living for yourself and pursue what you’re passionate about.”
Outside of his podcasts, books, journals, and Instagram account, Kenny says he is doing more in-person events. One event he offers is “Mantras and Mindfulness,” which involves journaling in community with other people. He’s worked with NFL teams, corporate groups, and gatherings of all sizes, and says that he likes the events because they force people (himself included) to get offline.
“To me, there’s no work-life balance because it’s one and the same,” he says. “It is a gift and privilege to do this work.”
When he’s not focused on helping others, he and his girlfriend do “the clichéd things” in Miami, like riding their bikes together on the beach. He says he also spends a fair amount of time going to her sets, before pausing to add, “it’s a weird thing to say that I like going to nightclubs, being a wellness person, but I don’t really drink.”
In wellness, Kenny continues, he says it’s easy for people to get obsessive and remove themselves from life—and nightclubs—so they can focus on their goals. He encourages others to experience the full spectrum of life. You can meditate and then go to a nightclub and not drink, and it’ll be okay.
“People come to me to feel seen and to find hope, generally, in that order,” he says. “Even though we’ve never been more connected, there’s still this overwhelming [sense] of feeling alone. So, when I write or when I speak, a lot of it is about grounding and helping people understand the kind of universal condition that they’re going through. And then the rest, really, is engineering hope and optimism for people.”
Kenny wants people to feel capable of making change in their own lives. His new book, The Opposite of Settling, comes out in August 2025, and his hope is that it will help people redefine love and the purpose of a relationship. For him, relationships should not be about settling down, but about leveling up.
“So many people get stuck and static in their lives,” he says. “If I say something or write something that helps someone just try something or invite some sort of goodness into their life, then that’s the mission.”
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