Rob Calvin

Creating the Life You Want


For Rob Calvin, as it was for many, the pandemic wasn't just a global crisis but a personal turning point. As the world paused and introspection set in, Rob found himself questioning his career trajectory in corporate talent acquisition. Despite years of helping others navigate significant life transitions, he felt his career slipping away.

By 2020, as the head of talent at a large, public company, managing over twenty people and working eighty-hour weeks, Rob felt he had drifted far from his initial reason for entering recruiting: to work one-on-one with people, helping them through significant life transitions and setting them up for future success.

This realization hit home during a board meeting when his boss unexpectedly announced Rob as the new director of diversity, equity, and inclusion without previously consulting him. “I like to think that this was [a result of] the company’s confidence in my abilities in a time of real change and unknowns, but it was more of a wake-up call for me to be more intentional in driving my own career decisions,” Rob explains.

Poised at the crossroads of continuing his existing path or embracing a new journey that aligned more closely with his passions, Rob decided to take control of his life and enter real estate in the fall of 2021. Driven by a deep-seated love for architecture, a desire to work more directly with people, and a genuine curiosity about an industry that intersects with many other sectors, Rob found a new way to impact individuals and families at a critical point in their lives: finding a home.

This career shift echoed the bold choices of his parents, who embraced significant life changes later in life. “My parents were the ‘cool kids,’” says Rob. His mother’s side gig during her career as a legal secretary was working as a cocktail server at the Playboy Mansion, and his father was a minor-league tennis pro turned advertising executive turned gallery owner. They didn’t meet until their mid-thirties and chose to start a family in their forties. "They taught me it's never too late to change your path and to do what makes you happy," Rob recalls.

Rob's early years were characterized by intense activity and responsibility. A three-sport, straight-A student in high school, he balanced it all with demanding work hours at Abercrombie & Fitch. At the University of Illinois Urbana–Champaign (1998–2002), where he double-majored in sociology and psychology, he forged deep friendships in his fraternity, a refuge where he first felt accepted as a gay teenager.

In many ways, Rob was compelled to mature quickly. His parents frequently battled cancer. This added pressure on him to graduate on time and secure a stable career to ease his parents' worries, significantly shaping Rob’s work ethic and determination.

Rob's journey was also marked by struggles with imposter syndrome, which began early in his life as he navigated schoolyard bullies. "While I've always worked to shed the anxiety and guilt that comes with feeling like an imposter in everyone else's world, it was easier to just be the person everyone expected me to be," Rob shares. "When someone is uncomfortable with conflict, it unfortunately invites self-doubt and prolongs the evolution of one’s true self. Understanding my fundamentals took me longer, as a result,” he explains.

Entering real estate offered Rob another chance to embrace his true self and live the life he wanted: a life and career largely built on ethics and helping people. In real estate, Rob has found a passion for transparency that guides his interactions with clients and colleagues.

The most rewarding part of his business now lies in collaborating with new brokers, lenders, contractors, attorneys, and clients. The relationships he builds and the direct impact he has on people's lives as they navigate one of the most significant transactions of their lives provide him with profound fulfillment.

To maintain balance outside of real estate, Rob practices yoga almost daily, grounding himself through meditation and physical exercise, and escapes into the pages of history books with his longstanding book club. Engaged to Dan Berliner, a marketing leader in the spirits industry, Rob shares a deeply supportive relationship and home with Dan and their two dogs. Rob’s family ties remain strong too, particularly with his brother, Ryan, and sister-in-law in Fort Myers, whose family became a crucial source of support and connection after the loss of Rob and Ryan’s parents.

As Rob continues living the life he always wanted, he eagerly anticipates a future of continued success and growth in real estate, helping others build their dreams just as he has built his.