Meridian Blog

We so rarely provide commentary on books we are reading here on the blog, but I recently read the book Learning to Love Midlife by Chip Conley, and truthfully, I found the insights in the book so profound that I couldn’t wait to share them with you.

I can’t remember how I came to know about the book, but the idea of loving the midlife journey aligned so nicely with the stage of life my husband and I are in that I ordered it right away, and we both read it.

And as the saying goes, when the student is willing, the teacher appears. In reading together, we discovered that the journey into midlife and retirement are essential transitions and how we look at these shifts in our lives matters.

Last summer, I shared about my husband’s preparation for retirement – good news, folks, he has a date set! – and Conley’s book helped us to put language around the idea that retirement isn’t a single decision — it’s part of a much bigger life transition.

And transitions, as it turns out, are exactly what midlife is all about.

Midlife Is a Transition, Not a Crisis

These concepts were the most profound for Dale and me:

• Midlife is a transition, not a crisis. In the book, Conley shares that “Midlife is not a crisis. It’s a chrysalis”— a space between identities. This idea resonated so deeply for both of us. We were able to shift our perspective so that retirement doesn’t feel like the end – but rather a beginning; and for me, midlife became an opportunity for a new journey.
• Growth comes from letting go, not adding more. I doubt this comes as a shock to anyone but letting go of an idea you’re comfortable with is real work, be it an identity shaped around the work you do, or embarking on a life as empty nesters when the last kid leaves for college. In the book, Conley asks us to rethink our definitions of success and the pressure to always be productive and instead shift to what we can remove from our lives to give us more clarity and meaning. And yes, this absolutely means letting go of our old identities to make way for something new, but what a beautiful shift towards choosing meaning over habit.
• Curiosity matters more than certainty. And in choosing meaning over habit, we can really live into the idea that “Aging is an extraordinary process whereby you become the person you always should have been.” Dale and I are taking this time to purposefully design our life around what gives us meaning – specifically, being more present for our family, choosing purpose rather than overwhelming schedules that drain us, and being engaged in our own lives. Being open and flexible and willing to learn is a core part of who we are, and we are leaning into those values as we shift gears.

Retirement as a Beginning, Not an Ending

One thing we didn’t expect was how much our individual transitions would become shared work. Midlife reshapes relationships just as much as it reshapes careers. Roles shift. Schedules change. Expectations need air.

But with this shared understanding that this is a beginning — not a loss — we were able to create room for curiosity instead of fear. For conversation instead of control. For growth instead of comparison.

The book definitely ranks in my top five best non-fiction books of all time – and, in fact, this is one of the books I find myself recommending repeatedly – and it just so happens to be one in a series of books I’ve been reading that speak to perspective shifting and managing change in our own lives (pro tip: read this book along with Reinventing Greatness by Shari Goodwin for maximum impact). Happy Reading!