Once a reliability engineer in the high-pressure world of mining and oil pipelines, Kalwarowsky is now a sought-after executive coach, TEDx speaker, and the provocative voice behind Antidote for the A$$hole Boss—a book reshaping how we think about leadership from the inside out.
Rob’s journey from a toxic workplace and mental health crisis to coaching Fortune 500 executives and Olympic gold medalists is not just a career pivot—it’s a radical reinvention.
And he’s doing it all from the sun-soaked coasts of Costa Rica.
“I Thought I Was Doing Everything Right”
Kalwarowsky’s early life was built around a familiar script. “My parents always told me—get A’s, go to a good college, get a stable job, and you’ll be happy,” he reflects. And on paper, he nailed it: MIT graduate, three-time NCAA Academic All-American in water polo, and a decade-long engineering career in some of the most demanding industries.
But beneath the accolades, Rob was unraveling. His first job exposed him to toxic leadership—bullying, credit theft, and egocentric management—that drove him into a spiral of depression. “In 2013, I hit rock bottom. I tried to take my own life,” he shares. “And yet, I still believed I had to follow that traditional path to be a ‘real’ person.”
For the next six years, he bounced from job to job, city to city, chasing novelty to mask the pain. It wasn’t working.
The Moment Everything Changed
A turning point came during a visit to an old college friend in Knoxville, Tennessee. A casual conversation about Warren Buffet’s lifelong learning habits sparked something inside Kalwarowsky. “I realized I’d stopped growing. I was stuck in survival mode.”
That moment catalyzed a period of deep self-work. He devoured entrepreneurship podcasts and launched his own show focused on engineering—his first taste of creative autonomy. A few months later, he hired a coach with the aim of launching a solo consultancy.
What he didn’t expect? That decision would unearth years of unprocessed trauma and crack open a door he didn’t know existed: coaching.
From Trauma to TEDx
Rob committed fully to the inner work—therapy up to three times a week, coaching, and eventually finding the right psychiatrist and medication. Two months after starting treatment, he quit his job. The floodgates opened.
From 2020 onward, Kalwarowsky’s life transformed at warp speed. He got married, moved to Costa Rica with four suitcases and his dog—without ever visiting beforehand—and dove headfirst into executive coaching. In just a few years, he delivered a TEDx talk titled How to Handle That Boss, coached Olympic athletes and high-level executives, and published his debut book.
“People say change takes forever. It doesn’t have to,” he says. “Once I aligned with who I really am, things started happening—fast.”
Craft Your Life—Don’t Quit It
One of Kalwarowsky’s key teachings is “job crafting”—the idea that you don’t have to make dramatic life changes overnight. “You can make tweaks to your current job. Lean into what energizes you and step back from what drains you.”
He encourages clients to start by listing the activities and people that give them energy versus those that take it away. “Even small shifts can create huge momentum.”
For those feeling stuck or unhappy, his advice is simple: start moving. “You don’t need perfect clarity. I didn’t plan to become an executive coach. I just took one step—hiring a coach—and it all unfolded.”
Why “A$$hole Boss” Hits Home
Kalwarowsky’s book isn’t your typical leadership manual. Rooted in the psychological model of Internal Family Systems, it reframes destructive leadership behaviors as parts of ourselves we can understand and manage—not just in others, but in ourselves.
“The title is provocative for a reason,” he explains. “When I said ‘asshole boss’ in Japan while preparing for my TEDx talk, people lit up. Everyone has one. The term resonates in a way ‘destructive leadership’ doesn’t.”
Through the lens of self-leadership, Kalwarowsky argues that better teams, better businesses—and better lives—start with confronting our own inner dynamics.
Success, Redefined
Kalwarowsky is not interested in hustle culture or chasing numbers for the sake of them. His clients—many scaling businesses from $3M to $15M annually—know that success without fulfillment is a hollow victory.
For him, living an unconventional life means being true to yourself. “You don’t need to move to Costa Rica or start a business. You need to find what you love—and make that your life.”
His story proves that the biggest breakthroughs often come after our lowest moments—and that with the right mindset, strategy, and support, transformation isn’t just possible, it can be wildly fulfilling.
Visualize your Future
Rob’s giving away a 15-minute guided meditation to help you tap into your subconscious, gain clarity, and start creating the life you actually want.
Connect with Rob:
- Website: robkalwarowsky.com
- LinkedIn: Rob Kalwarowsky
- Check out Rob’s Book: robkalwarowsky.com/book
