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Boardroom Guests Reflect on Key Moments of Clarity

Last Updated: September 5, 2023
In partnership with Cierto, Boardroom’s Rich Kleiman asks his ‘Out of Office’ guests about the key moments on their journey that helped them to clarify the path forward.

Every successful individual can point to one or two key moments in their lives that changed their trajectory forever.

On recent episodes of Boardroom’s Out of Office show, in a segment sponsored by Cierto, Rich Kleiman asked his guests about what they labeled as their own moments of clarity. These are the pivotal “lightbulb” moments they had about their career which defined everything that happened in their pathway thereafter.

Let’s break them down.

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Terence Crawford

The undisputed welterweight champ reflected on how it took him unpacking the convoluted contracts to learn that he needed to ask questions in order to truly understand what was possible as a fighter. He breaks down that moment and how it impacted his relationship with his then-promoter and how he approaches new deals moving forward.

David Adelman

“I have this unique mix of ADD and OCD … I needed an environment to be able to float in that,” Adelman reflected.

When the serial entrepreneur and the minority owner of the Philadelphia 76ers and the New Jersey Devils realized that he was, in his words, “unemployable,” he realized he was unable to work in a traditional environment and had to take his future in his own hands.

Rich Kleiman

In 1999, Rich was figuring out what was next. It wasn’t until he linked with Mark Ronson, who was one of New York’s hottest DJs at the time, that he could see a pathway where he could blend his skills to help someone else and to build his own business. As Ronson’s manager, he got a peek into a world in which he’s been building ever since.

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About The Author
Bernadette Doykos
Bernadette Doykos
Bernadette Doykos is the Senior Director of Editorial Strategy at Boardroom. Before joining the team, her work appeared in ELLE. She previously served as the head of evaluation for a nonprofit where she became obsessed with systems and strategy and served as the curator of vibes and extinguisher of fires for the design thinking firm Stoked. She is constantly plotting a perfect tunnel ‘fit and a playlist for all occasions.