What if the reason you feel like a stranger to yourself isn’t that you’re lost, but because you’ve been performing for so long, you forgot what authenticity looks like? From childhood, so many of us learned that success meant following the script: get the degree, climb the ladder, earn the title, achieve the milestones. But somewhere along the way, that external validation became internal disconnection.
In this powerful episode, bestselling author and mindfulness expert Case Kenny reveals the truth about modern identity: it’s not about finding yourself once and being done. It’s about constant reinvention through reflection. He explains why “just being yourself” might be the worst advice you’ve ever received, and how the traits you think make you too much are actually what attract the right people to you.
This is a conversation for anyone who’s tired of feeling like one person at work and a stranger at home, for anyone questioning whether the life that looks good on paper actually feels good in reality. Because real fulfilment doesn’t come from collecting achievements. It begins the moment you become the same person inside the conference room and outside.
The Man Who Walked Away
Case Kenny didn’t just study personal development; he lived the crisis that demanded it. At 28, he was the Regional Vice President of Sales at an advertising agency, crushing quotas and living what looked like the professional dream. He knew exactly who he was supposed to be in the office: confident, successful, the man with all the answers.
Then he’d go home.
“I would go to my job and feel like one person, and then I leave and I don’t know who I am,” Case recalls. “I’m like, I don’t know who I am on a human level, or a boyfriend level, or a partner level, or a son level, or a brother level. And I was like, that’s problematic for me.”
This acute disconnect sparked a radical experiment. In 2018, he launched a podcast not to build an audience, but to force himself into self-reflection. Each episode became a laboratory where he’d unpack an emotion, desire, or expectation and “beat it up with mindfulness and logic.” Eight years later, he’s left corporate life entirely and built a career around what he jokingly calls “sharing my feelings for a living.”
Why “Just Be Yourself” Is Terrible Advice
“I’m really not a big fan of advice that’s like, just be yourself,” Case explains, “because if you decide that when you’re 20, you should not be the same person at 25, 30, 35, 40.”
The popular wisdom tells us to discover ourselves and commit to that identity. But Case argues this is a dangerous fallacy. Real wisdom doesn’t come from experience alone; it comes from reflecting on experience. Without constant reflection, we risk living according to outdated beliefs and values that no longer serve us.
“We don’t get wisdom from life experience. We get wisdom from reflecting on life experience,” he says, paraphrasing John Dewey. The things that happen to you shape who you are, but it’s reflecting on those experiences that should have the final say in who you become.
His background in languages (he double majored in Chinese and Arabic at Notre Dame) resurfaces in his work. Case views personal development through a linguistic lens, believing that the words we use to describe our experiences fundamentally shape our reality.
Out-of-Town Confidence: The Framework That Changes Everything
One of Case’s most powerful concepts is “out-of-town confidence,” a mental model that reframes how we approach relationships and life goals.
Imagine you’re visiting Miami for the first time. You’d probably be more extroverted, more confident, more open to new experiences. Why? Because you’re not fixated on any single person or outcome. The focus is on the experience itself, and if you happen to meet someone amazing along the way, that’s a bonus.
“Get the most out of life as possible, not in a crazy, selfish, narcissistic way, but just as the human endeavour,” Case explains. “And then you use that as the lens to say, is this person right for me?”
This philosophy challenges the traditional narrative that finding “the one” is life’s ultimate mission. Instead, he argues we should extract maximum value from being human rather than outsourcing our happiness to external validators.
The Liking Gap and Your Weird Wealth
Research proves something counterintuitive: you’re more likable than you think you are. It’s called the “liking gap,” and it operates across cultures and languages. After interactions, we consistently underestimate how much the other person enjoyed our company.
“You and I interact. I leave the conversation thinking, I don’t think she really liked me that much,” Case describes. “Overwhelmingly so, you are more likely to say, no, I liked Case. He seemed like a cool guy.”
Even more powerful: the traits you consider “too much,” weird, or outside normal are actually nonconforming traits that research shows are more attractive than conventional ones.
“Double down on the things that you think make you weird,” Case advises. “Your passion is a magnet for the right people and a filter for the wrong people.”
Having It All Together Means Nothing
When asked about “having it all together,” Case reframes the entire concept. We imagine perfection as possessing everything simultaneously: the career, partner, body, happiness, and friendships all at once. That’s fantasy.
“I’ve had the career but not the partner, the partner but not the career, the career but not the money,” he explains. Reality is transitional, and the binary thinking of “everything or nothing” sets us up for perpetual disappointment.
His alternative is simple: ask yourself one question as often as possible. “In this moment, with what I’m doing, with my habits, with my partner, with my diet, with my friends, with my city, do I feel like my most honest self?” Then adjust, pivot, and move accordingly.
About Case Kenny
Case Kenny is a bestselling author, podcast host, and creator who left his role as Regional VP of Sales in advertising to pursue full-time work in mindfulness, language, and personal development. With a background in Chinese and Arabic from the University of Notre Dame, he brings a unique linguistic lens to self-discovery. He’s been podcasting twice a week for eight years, helping people find clarity, kindness, and optimism in their lives.
Key Takeaway
You are not destined to remain the person you were at 20, 25, or even last year. The identity crisis you experience isn’t a problem to solve but an invitation to evolve. When you stop performing and start reflecting, when you bring out-of-town confidence to everyday life, and when you embrace the transitional nature of having it all, you become the same person inside the conference room and outside. Coming home to yourself means releasing the belief that there’s one right way to live and claiming your right to constant reinvention.
Watch the full conversation on YouTube
Find Out More About Case Kenny
Website: https://casekenny.com
Follow on Instagram: @case.kenny