- “Ten years from now, what will you regret if you don’t learn it or do it now?” Anticipated regret is a form of wisdom and can be a catalyst for action. Many people in midlife feel stuck, bored, and bewildered, and it’s often because they haven’t broken out of their comfort zone. This question helps you to see – as I did – that even though I had a fixed mindset about learning a foreign language or putting myself at physical risk at 56, I could learn Spanish or how to surf in my mid-50s because it wasn’t going to be any easier in my mid-60s. This question addresses two of the most correlated variables to living a longer, happier life: curiosity and an openness to new experiences.
- “What are three pieces of advice or wisdom you might offer someone younger and your origin story for each that illuminate your ‘wisdom fingerprints’?” Our painful life lessons are the raw material for our future wisdom so metabolizing our experiences is essential for us to cultivate and harvest our wisdom. Wisdom is a social good so it’s meant to be shared, but first you have to make sense of what you’ve learned along the way. This question is well-suited to preparing you to be a “modern elder,” someone as curious as they are wise. This question will help you to have the confidence to do an archeological dig to find the wisdom nuggets of your life.
- “How might you curate your relational life if you recognized that friendship is a practice?” Poet David Whyte recently toured our MEA Santa Fe campus and has written that “Friendship is not improvement, neither of the self nor of the other. The ultimate touchstone is witness, the privilege of having been seen by someone and the equal privilege of being granted the sight of the essence of another, to have walked with them and to have believed in them, and sometimes just to have accompanied them for however brief a span, on a journey impossible to accomplish alone.” The most common variable of those who live longer, happier lives is how invested they are in their social relationships in midlife and beyond, often having seen some atrophy in these relationships during the busy decades of our 20s through 40s. Thinking of friendship as a practice that you can constantly improve will help your “social wellness.”
- “How are you complicit in creating the conditions I say I don’t want in my life?” MEA faculty member Jerry Colonna created this provocative question as one of the world’s leading coaches. We are often complicit in unconsciously operating our lives in ways that are at odds with what we would consider ideal. This is an important question in our 50s because we have time to change our habits or mindsets to live a better life in the second half of our adulthood. A couple of corollary questions are “What are you not saying that you need to say?” and “What are you pretending not to know?”
- “If the first half of my life I was building my resume, what would it mean to approach the second half of my life as if I was creating my eulogy?” What do I want said at my funeral? This isn’t a morose question as death is an exquisite organizing principle for life. What if you created an annual New Year’s ritual of writing your eulogy as sort of a living obituary? How do you want to be remembered and what kind of ROI (Ripples of Impact) have you had on others? Imagine three to five positive adjectives that you’d like sprinkled in your eulogy – what habits or practices do you currently have in your life to make you more “encouraging,” “reliable,” “inspiring,” “adventurous,” or “wise”? Think of this exercise as being a gentle, aspirational annual accounting of who you are as a human being, not a human doing. It seems dreadfully unfair that we wait until after our deaths to let someone else do an accounting of our lives.
-Chip