The Art of Succession

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Welcome to The Art of Succession Podcast. Host Barrett Young, CPA, talks with Rebekah Olson, CPA, Chief Executive Officer of the Maryland Association of CPAs (MACPA), about her journey from public accounting into leading a long-standing professional organization. Rebekah shares how she discovered her passion for developing people, transitioned into association work, and eventually stepped into the CEO role after years of growth within the organization. She reflects on lessons in leadership, succession, and guiding a 125-year-old organization through change. Today, she focuses on building community, supporting the next generation of CPAs, and helping the profession adapt and thrive in a changing world.

Rebekah shares her journey from public accounting to leading a statewide CPA association after discovering her passion for developing people and supporting the profession. She talks about stepping away from firm work, finding her place within the association, and growing through roles focused on education, membership, and leadership. Rebekah explains how those experiences prepared her to become CEO and guide a long-standing organization through change. She shows how self-awareness, mentorship, and adaptability can shape a path to leadership. Her story highlights the value of community, intentional growth, and helping professionals succeed together.

Join Rebekah Olson, CPA, CEO of the Maryland Association of CPAs, as she shares lessons from stepping into the leadership of a long-standing professional organization. Hear how she grew from public accounting into association leadership, why she focuses on building strong community connections, and how her journey prepared her to guide a 125-year-old organization. Learn how Rebekah now supports CPAs, connects professionals, and helps shape the future of the profession.

Episode Highlights
[00:00] - Teaser
[02:23] - Host Barrett introduces guest Rebekah Olson, CPA
[02:58] - Stepping into a 120-year-old organization
[04:08] - Steering a cruise ship with a fixed North Star
[06:00] - From child entrepreneur to accounting major
[08:36] - Leadership assessment: "spirited vs. systematic."
[10:32] - Career coach suggests trade association work
[15:19] - Rising from membership manager to director
[19:12] - Host: Rebekah earned the CEO role, wasn't handed it
[22:24] - Career path like Lombard Street's switchbacks
[26:59] - What attracted her: the people and community
[29:50] - Two keys to enabling next-gen success
[37:52] - The lost middle generation is hard to engage
[44:57] - Hiring outsiders to challenge her thinking
[49:58] - Leading for the next 125 years, not her own tenure
[53:28] - Blocks Tuesday mornings for big-picture thinking
[56:39] - Visioning happens in community, not alone
[01:00:38] - Her superpower: connecting people to people
[01:03:01] - Lightning round starts
[01:05:45] - Where to find Rebekah and MACPA