I’m not quite sure when I started to use the term midlife in association with, well, my own life, but I think it was during my late 40s. At the time, it did make me feel older to concede that I had entered this stage. Now, however, having entered the heart of my 60s, I’m wondering how much longer I can claim to be in this relatively youthful category.

Well, my concerns are now somewhat assuaged by entrepreneur and author Chip Conley, who suggests that midlife is a multi-stage journey that “may last from 35 to 75.” This broader chronological framing of midlife is just one interesting piece of his new book, Learning to Love Midlife: 12 Reasons Why Life Gets Better With Age (Little, Brown Spark, 2024). I recommend it heartily, though with a quibble or two.

Conley pulls together a lot of aspects about how we address aging, starting with a look at life expectancy figures and suggesting that at 50 years old, someone could literally be at their midlife point. He encourages us to look at this as a time of growth, purpose, and fulfillment rather than as one marked by steady decline. This includes becoming comfortable in our own skin, redefining our relationship with work, letting go of unhealthy emotional baggage and ties, seeking out meaningful associations and activities, and basically becoming our best selves.

The book mixes the author’s personal anecdotes, summaries of research on aging and lifespan development (he’s done his homework), and a wide variety of other voices. On the latter, if authors such as Brené Brown, Joseph Campbell, Arthur C. Brooks, and Viktor Frankl sound familiar, then you’ll be in comfortable territory. Overall, it’s an easy and thought provoking read.

My quibbles pertain mainly to this genre of writing generally. While Conley has faced his share of personal challenges, he and others who write about life stages and aging from a personal development perspective tend to have financial resources and strong networks. There is, frankly, an upper middle class lean to these introspective looks at life, which makes books such as this more useful to those who have some degree of personal control over their choices and financial flexibility.

That said, Conley isn’t limiting his messaging to those with lots of time and money. His Modern Elder Academy, for example, is offering an online course that includes a copy of Learning to Love Midlife for $49 (link here). 

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By the way, if you’re looking for a more intellectual take on evaluating your life, then I’m happy to recommend the second edition of Leading Lives That Matter: What We Should Do and Who We Should Be (Eerdmans, 2020), edited by Mark R. Schwehn and Dorothy C. Bass of Valparaiso University, where I earned my bachelor’s degree many years ago. It’s an anthology of excerpted texts drawn from literature, public affairs, and philosophy, built around the theme captured by the title. Although written with undergraduate humanities seminars in mind, it’s a great volume for adults engaging in midlife contemplations consistent with Chip Conley’s book above.