Beyond Retirement: How to Design an Encore Career with Purpose — Jack Calhoun

On Healthy Mind, Healthy Life, host Avik Chakraborty digs into what really happens after you step away from the career you spent decades building. Guest Jack Calhoun, Founder & President of Encore Career Lab, explains why financial freedom alone doesn’t equal fulfillment, how identity loss creeps in post-exit, and how to build an intentional second act that blends purpose, autonomy, and meaningful impact. We cover the pitfalls of the “endless vacation” myth, the value of structure and accountability, and practical steps to map your encore path—so you don’t drift, but design. Optimized for YouTube, Facebook, Instagram, and LinkedIn search: encore career, post-retirement purpose, second act career, identity after work, purposeful retirement, midlife reinvention, career transition coaching.

About the guest

Jack Calhoun grew a wealth-management firm from $50M to $1.5B AUM, exited in his early 50s, and learned firsthand that money planning isn’t life planning. Through Encore Career Lab, he helps high-achieving professionals craft mission-driven “encore” careers that use their unique abilities, wisdom, and autonomy.

Key takeaways

• Retirement as “endless vacation” wears thin; purpose, structure, and community sustain wellbeing.

• Identity loss post-career is common; plan for purpose as intentionally as you plan finances.

• Design your encore around autonomy: what you do, for whom, where, and how.

• Mine your lived experience (“what I know now that I wish I knew then”) into advisory, coaching, or consulting offers.

• Don’t jump into low-fit ventures; pressure-test ideas with a clear framework before committing capital.

• Purposeful work in midlife can be both fulfilling and lucrative—scale is a choice.

• Future-proof now: build skills, relationships, and small pilots before your exit.

How to connect with the guest

• Website: EncoreCareerLab.com

• LinkedIn: Jack Calhoun (search on LinkedIn)

• Email: jack@encorecareerlab.com

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Disclaimer: This video is for educational and informational purposes only. The views expressed are the personal opinions of the guest and do not reflect the views of the host or Healthy Mind By Avik™️. We do not intend to harm, defame, or discredit any person, organization, brand, product, country, or profession mentioned. All third-party media used remain the property of their respective owners and are used under fair use for informational purposes. By watching, you acknowledge and accept this disclaimer.

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