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Book Club: Learning to Love Midlife

For Book Club in September, Rachael helped select our book, and Chip Conley’s Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age was the winner.

Chip Conley is the founder of The Modern Elder Academy, and at times the book feels a bit like lead gen for that organization, but generally he manages to maintain a call to action and not devolve into an ad campaign. Mr. Conley was early at AirBnB where he was considered their “wise elder” since before that he had been a boutique hoteliere. The book starts with his personal midlife crisis, and evolves into a treatise on why midlife is a time to savor wisdom, self-knowledge, and joy. 

The midlife crisis is the butt of so many jokes because the stastics are real: suicide, mental health crises, illness, loss of friends, spouses, jobs, parents, financial stress, and so much more often hits in the 40s, 50s, and 60s. The book tries to 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, where we shed our skin, spread our wings, and pollinate our wisdom to the world.”

Of the 12 reasons he lists for why life gets better with age, two really resonated with me:

  1. My appearance doesn’t define me

I grew up performing (dancing and singing), and appearance was critical to landing a part (often more important than my skill). Then when I entered engineering, my appearance was also defining and not in a good way. I didn’t “look” the part, and I got to experience all the cliche moments one might predict: being propositioned, asked if I could get folks coffee when I was actually teaching the class, etc.

As I get older, appearance matters less to me: how others perceive me and how I judge myself. I am just grateful to be able to move, dance, run, sing, and HOW I do it matters so much less than the fact that I still can. Whether I match someone’s mental model of an engineer or not is their problem. What matters to me now is helping other people who aren’t the norm find their place in this profession because ultimately that will lead to better solutions and systems. Getting through the shock of being an outlier requires a mental and emotional energy beyond just the day-to-day effort of investing in one’s real work: I want to help people who are experiencing that weather the challenges and reassure them that people care a whole lot less than they think they do.

2. Letting go of our emotional baggage, mindsets, and obligations that no longer serve us

Much like the above, there are modes of operation that get you to a certain point in your career and life journey, but if you are not willing to find your reason and seek a greater purpose than your own success, you likely won’t be very happy. Whether that is music, family, religion, or community, much of the joy of being in this life phase is saying “I have enough” and “I am enough.” We push so hard to prove ourselves through school, landing a job, getting the next promotion, finding our partners, building our families, etc. At some point we have to transition to a place of enjoyment in what we have, and not just the next mountain we are seeking to climb: this is your life! It is a gift to not need someone else to validate you. To see feedback as a signal of how people are perceiving you, and choose to adapt your behavior if they are important to you, but not to take it personally. Being able to step back from that baggage is absolutely a gift of experience, self-assurance, and wisdom.

There are definitely some good nuggets in this book, and getting to share it at Book Club with so many of my former colleagues making major life changes (retirement, entrepreneurship, empty-nesting, managing health and wellness scares, etc.) led to deeply meaningful conversations. If you are going through a transition and feeling like you are the only one: you aren’t alone, and maybe this is a good book to pick up. Happy reading!  

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