What if the most powerful move you could make at midlife… is to pause?
In this episode of Wisdom Wednesday, Derek sits down with Chip Conley to explore the rise of the midlife sabbatical and why more people over 50 are choosing a reset instead of racing toward retirement.
Chip challenges the old “learn, earn, retire” model and introduces a new idea: the midlife pit stop — a courageous break to refuel before the next chapter.
In this conversation, you’ll learn:
- Why a sabbatical isn’t a vacation. It’s renewal
- How stepping away can strengthen your career and relationships
- What Chip discovered during his own two-year break
- How to design a meaningful month off, even if a year feels impossible
Midlife isn’t about slowing down. It’s about getting intentional.
If this resonates, share it with someone who might need a reset and subscribe for more Wisdom Wednesday insights.
Timestamps:
00:05 Spring Travel Chat & Baja Living
05:34 The Rise of the Midlife Gap Year
11:20 The Midlife Atrium Concept
13:15 Why Employers Should Support Sabbaticals
17:14 Starting Small with a Gap Weekend
18:07 Chip’s Two-Year Sabbatical Experience
23:13 Ego, Curiosity, and Deepened Friendships
24:31 How to Design a One-Month Sabbatical
26:58 Saving for a Midlife Pit Stop
29:19 Escaping One-Dimensional Living
Learn more about MEA at https://www.meawisdom.com/
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