Well-th Blog

Reframing Midlife Transitions

By Hightower Advisors / June 15, 2023

Midlife comes in the blink of an eye, with time seeming to accelerate in our 20s and 30s as we pursue education, careers, family and other life goals. Then, suddenly, we’re not only adulting — we’re older adults. This tends to cause anxiety, uncertainty and the feeling of being in a rut. Questions like, “Is this it?” and “What is my true purpose?” commonly weigh on those in their 40s through 60s.  

Chip Conley, hotelier, hospitality entrepreneur, author and speaker, can attest to this. Even after achieving great success as founder of the second largest operator of boutique hotels in the world, he still hit a midlife wall, as unhappiness and a near-death experience left him seeking something more meaningful.  

In the years that followed — while he was leading a worldwide revolution in travel as Airbnb’s Head of Global Hospitality and Strategy and co-founding the Modern Elder Academy — Conley discovered his purpose: helping others reframe the concept of aging.

To learn how, we recently hosted Conley on our Well-thy Conversations series. Here are some themes he discussed:

  • Longer careers and lifespans extending the midlife phase
  • Anticipatory regret — proactively imagining what you may regret later as a strategy to avoid inertia   
  • Shifting from a fixed mindset to a growth mindset
  • Exchanging fear for curiosity as a means to open up new possibilities
  • The growing importance of different age groups learning from each other as the workforce transitions (most Americans will soon have a younger boss)

To learn more, watch this replay of our conversation with Conley. Also, please know we are here for you during your midlife transition. We recognize that wealth and well-being are inextricably intertwined and are here to support you on your journey toward achieving both.


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