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Jack Calhoun is someone who deeply understands the emotional and practical challenges that come with stepping away from a successful career. That understanding led him to create a powerful framework to help others navigate this transition with clarity, confidence, and meaning.

Today we discuss:

The career invested
When you can do anything, how do you define what anything is
The paradox of choice, analysis paralysis
The effect of longer life expectancy
The cultural mindset about retirement
“crystalized” and “fluid” intelligence
“portfolio of small bets”

Jack’s insights allow high achievers – the “career invested” – to forgive themselves for not acing the transition to career divested, and his words ring true for anyone making the transition.

Find Jack at https://www.encorecareerlab.com/

Learn more about Jack and find all his links at The Boomer Woman's Podcast: Jack Calhoun

Want to be a guest on The Boomer Woman’s Podcast? Send Agnes a message on PodMatch, here: Agnes on PodMatch

45:T486,

The Boomer Woman’s Podcast is a conversation-driven show for women who know that life doesn’t stop at midlife—it opens up.
Hosted by Agnes Knowles, the podcast is now in its 7th season and features engaging conversations with guests whose ideas, experiences, and insights are relevant to Boomer women navigating what comes next. Guests may be any age or gender, but their message is always thoughtful, positive, and genuinely useful.
These are not lectures or quick takes. They’re real conversations—curious, open-minded, inclusive, and sometimes unexpected. You might learn something new, rethink an old assumption, or simply feel less alone in the questions you’re asking.
If you’re willing to be curious, tolerant, and open to different perspectives, you’ll feel right at home here.

Follow or su

The Encore Career Blueprint with Jack Calhoun