The first thing we should value in midlife and beyond is Time and the question to consider is:
Ten years from now, what will you regret if you don’t learn it or do it now?
Time is the one asset we keep underestimating. This question cuts through procrastination and fantasy and asks us to get honest. Not someday. Now. While we have fewer days ahead of us than we used to have, we always have the ever-present Now, which can feel timeless.
The second focuses on Relationships:
How would your relationships improve if you thought of friendship as a practice?
We don’t “have” friendships—we invest in them. They’re not a possession. They’re an action. In my speeches, I often invite people to text a friend they haven’t talked to in ages in that very moment. It’s amazing how this intentional act helps them to see that “practicing relationship” could be the most valuable investment you make in your longevity.
The third is about Wisdom:
If someone younger asked you for three bumper-sticker truths you’ve learned in life—and the origin story for each—what would you say?
Midlife isn’t just about acquiring experience; it’s about metabolizing it. Wisdom unshared is wisdom unfinished. Mindfully sharing our wisdom is a core part of our later life.
And then there’s the fourth question—the one that opens the deepest doorway. It’s about valuing Life itself:
If you could only choose three people to spread your ashes, who would you choose, where would they separately spread your ashes, and what’s one thing each one of them would say about you? (play along with me, even if you don’t plan to be cremated)
This is where résumé values quietly step aside and eulogy values take center stage. It’s no longer about what you achieved, but how you made others feel. Seen. Calmer. Braver. Less alone.
Taken together, these four questions invite a shift—from success to significance, from doing to being, from ego to essence. They don’t demand immediate answers. They ask for attention, courage, and practice.
And if we’re willing to live into them, they just might change not only how we spend our days—but how we’re remembered for a lifetime.
If I were to recap these things we ought to value in midlife and beyond, it would read like this:
Time → What would I regret delaying?
Relationships → How do I practice showing up?
Wisdom → What have I learned that matters?
Life → Who matters most to me and how am I experienced while I’m here?
-Chip