Middle age shouldn’t be a drag. How a ‘chrysalis’ mind-set can help.

Midlife desperately needs a makeover. Too few of us dream of glory and glamour in our second half. But best-selling author Chip Conley, a hospitality entrepreneur who co-founded the Modern Elder Academy, thinks differently.

In his book “Learning to Love Midlife: 12 Reasons Why Life Gets Better With Age,” Conley, 63, asks: “What if we could reframe our thinking about the natural transition of midlife not as a crisis, but as a chrysalis – a time when something profound awakens in us, as we shed our skin, spread our wings, and pollinate our wisdom to the world?”

With the American population rapidly aging, there’s a new urgency for reframing midlife as a promising time of positive transformation. Conley shared his thoughts on how to achieve this.

The following conversation with Conley – which was conducted via email – has been edited for brevity and clarity.

Q: Who was your role model for midlife transformation?

A: My father. He is a bit of a rebel but took the safe path in corporate America. Both his father and my mom’s dad only worked for one company in their 40-year careers.

At a time when my parents had two kids at Stanford and another one about to go to [the University of California at Berkeley], Dad decided to start his own business in his late 40s. His perspective on both society and politics started to soften and he sprouted a newfound curiosity about purpose and meaning. … He’s a great example of someone [whose] life – as he now knows it at 86 – began at 50.

Q: You wrote, “When we resist a transition, we are actually resisting one or more of its three phases.” Can you offer pro tips on navigating the transitions of midlife?

A: There are typically three stages to a transition: the ending, the messy middle and the beginning. If I were to summarize what people with high TQ (transitional intelligence) do in each phase, they tend to ritualize the ending of something, they seek social support and look for the through-line or thread when going through the messy middle, and they apply a growth mind-set to becoming a beginner, no matter how silly they look.

Q: To blossom after retirement, do we need to be part of a community?

A: We need to retire “to” something, not just “from” something.

We are so well prepared to plan and curate our career early in adulthood that it’s rather surprising that most retirees don’t develop an engagement plan that will distract them from the 47 hours per week that the typical American retiree watches TV. Dr. Phil Pizzo, who used to run Stanford medical [school], has shown that the three foundational parts of a healthy retirement are finding community, cultivating purpose and investing in one’s wellness.

And, I believe that wellness isn’t just personal wellness, but it’s also “social wellness,” as Harvard’s Robert Waldinger [a psychiatrist and the director of the Harvard Study of Adult Development] has shown that the most common variable of healthy, happy 80- and 90-year-olds is being invested in their social relationships in their 50s.

Q: Would you share a bit about your personal experiences with cancer? [Conley, 63, has had prostate cancer for six years and has faced multiple recurrences.]

A: I’ve learned four lessons:

1. Emotional: I’ve realized that willpower alone – which has served me so well in my career – can’t beat this. I’ve read Rumi’s “The Guest House” poem once a week for the past year to remind myself that all these emotions that are coming through me are just visitors who will “check out” as long as I don’t dwell on them (an apt metaphor for a hotelier).

2. Physical: Nausea. Incontinence. Fatigue. Body aches. Weight gain. Brain fog. No libido. This experience has been more inconvenient than impossible. I’ve come to realize my body is a rental vehicle I was issued at birth and, as I’ve put on more and more miles, I need to maintain this vehicle even more, not for short-term vanity, but for long-term health.

3. Relational: What a gift to be able to spend quality time with my parents late in their lives. I’ve also had to ask for extra love from my partner, Oren, which has tested my non-neediness ethos.

4. Spiritual: In this time that has felt somewhat existential for me, rather than fearing the mystery, I’ve been trying to embrace it with faith that I’m going to become a better human as a result of this experience.

Q: As a cancer patient, I can relate to hearing unhelpful war stories from well-meaning folks. What question should people ask themselves before speaking when trying to offer wisdom?

A: Before trying to show how smart and empathetic you are with your advice, try to understand the state of mind and heart of the person who you’re trying to help. Context and timing are everything.

Q: Does the need to be adored fade away naturally in midlife or must it be chiseled out of us with hard work and intentionality?

A: This depends upon the person. … By the second half of our lives, we’ve learned not to personalize everything and to care less about what other people think of us (because they’re not thinking about us nearly as much as we think they are).

Q: What is your message to anyone who might be feeling stuck, lost or alone?

A: [As Conley wrote in “Learning to Love Midlife”] Albert Schweitzer wrote, “In everyone’s life, at some time, our inner fire goes out. It is then burst into flame by an encounter with another human being. We should all be thankful for those people who rekindle the inner spirit.”

UC-Berkeley professor Dacher Keltner (on our MEA faculty) wrote in his book “Awe” that the two most common ways we feel awe are through experiencing collective effervescence and witnessing moral beauty – courage, kindness, equanimity – the best that humans have to offer. So, at the time when you most want to hide under the covers, that’s when you’re supposed to seek out people to become your “emotional insurance.”