Clocking Out with Raymond Lee

In this episode of Clocking Out, we meet Rachel Humphrey — a former trial attorney who once believed she'd spend her entire life arguing cases in court. But after two decades in law and a major cross-country move, Rachel found herself at a crossroads: unfulfilled and reevaluating her life’s direction. When her longtime nanny unexpectedly resigned, Rachel made a bold decision — she quit her job without a backup plan, determined to rediscover what truly fueled her.

That leap led her somewhere she never expected: the hospitality industry. Through a serendipitous conversation, Rachel discovered that the skills she honed in the courtroom — advocacy, negotiation, and leadership — could translate far beyond the law. She soon joined AAHOA, the largest hotel owners association in the country, and ultimately rose to interim CEO.

Throughout her career, Rachel quietly carried a lifelong battle with self-doubt — often feeling the need to prove she belonged. But time and again, others saw something in her before she did. Their faith, combined with her relentless curiosity and drive, helped her rise to heights she never imagined for herself.

From that experience, a new mission emerged: Fueled by a passion for equity, Rachel went on to found the Women in Hospitality Leadership Alliance, a consortium dedicated to amplifying women’s voices across the industry. Today, she mentors rising leaders, co-hosts a podcast spotlighting the human side of leadership, and speaks openly about reinvention, resilience, and learning to bet on yourself.

Rachel’s story is a powerful reminder that we’re often more capable than we think — and that the most fulfilling chapters begin the moment we step outside the story we thought we had to live.

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