Here’s To The Best Of The Rest

Chip Conley, a former advisor to AirBNB is now guiding people through mid life.

I listened to a terrific podcast recently.

It was about middle age.

Midlife is interesting, isn’t it?
It’s the only part of life that is often followed by the word ‘crisis’.

But we try to stay somewhat positive in this space so let’s reframe middle age as a time to blossom.

As Dylan sang: “It’s not dark yet.”

No, Bob it is not. But it’s fall and you can see winter just over the horizon.

Still, there are some things we can do if we wish to live to a ripe old age.

You need three things to live to 100 according to Chip Conley, the founder of the Modern Elder Academy which helps middle-aged people find meaning in the second half of life.




Find those three things, says Conley, and you will add years to your life and life to your years.

Let’s take a closer look.

Purpose—well that’s easy when you’re young. You wake up and you build. You build a career, you raise a family, you find your place in the world. But as you age, things shift. Maybe what you were passionate about at 35 doesn’t float your boat at 55. We must reinvent.

I’ll share what Chip Conley says on this subject. He got this from Carl Jung.

“Imagine that you are standing outside on a sunny day. Think of yourself as a sundial. In the morning, as the sun rises, you cast a long shadow in one direction. As the morning continues, your shadow gets shorter and shorter until, at noon, you cast no shadow at all—with the sun being directly overhead. This implies that by midlife we can lose our sense of identity as we strive to live up to others’ expectations. Yet, there is a profound change in the later stages of our lives.”

Jung continues, “But in the afternoon of life, something new happens. We begin to cast a shadow again.”

As author John Tarnoff infers, “the key difference is that the shadow is lengthening away from us in a new, opposite direction from the one it took during the morning. This metaphor encourages us to redefine ourselves, extending into new territories as we mature, which can be seen as an essential aspect of shaping our legacy.”

That’s a lot to chew on. Hey, it’s Carl Jung!

But basically, what he’s saying is that you can stay young by redefining yourself. You can remain vibrant and purposeful by learning new things. I see a few examples in my life.

My friend Joe in Raleigh, N.C. learned to ride a one-wheel. One wheeling has become Joe’s passion. He races and has found a community with those who share his love of speed (and spills).

My friend Randy learned to play guitar and now he sends his friends videos of songs that actually sound like music. I’m not saying he’s Bruce Springsteen, but he’s good and I don’t have to refinance my house to see him play live.

And of course, there’s my wife who learned Mahjongg, and now basically runs a Mahjongg parlor out of our dining room.

Some people try new businesses, some learn new languages and others travel, volunteer, garden, read, write, or learn how to dance.

It doesn’t matter what you do, as long as you have a purpose other than watching TV, which, sadly. is the avocation of so many in middle age.

Community-–I love this one. Find your tribe, Conley advises. Get involved, join Kiwanis, find a group to run/walk 5K’s. It doesn’t matter. Community is essential to long life and happiness.

Wellness—Illness starts with the letter “I”—which is a metaphor for being alone. Wellness starts with the word “we”—which is another way of saying that purpose and community creates well-being.

My friends and I are well into middle-age, which Conley defines as 35 (kind of young if you ask me) to 70 (that’s encouraging).

As close readers know, I have a set of childhood friends that I visit via Zoom every two weeks. I cherish these friendships, our common history, and the fact that we care about each other like brothers.

We started this Zoom “happy hour” during Covid, to reconnect and stay close during a trying time for everyone.

And we’ve kept it going.

We are all turning 60 in 2024, except for one guy who is a year younger but who is an honorary sexagenarian. That’s the honest to goodness word for people between the ages of 60 and 69. I will resist the obvious joke here because this is a serious and G-rated blog.


Anyway, we’ve decided to get together IRL (in real life) this year to celebrate. The guys will be coming from New York, New Jersey, California, Wisconsin, Virginia, and North Carolina to spend some quality time with each other.

We have decided what we do not want—and that’s anything that could be considered epic—at least in the traditional sense of the word.

No Burning Man.

No Bungee cords.

No jumping out of planes (a few of us did that; it did not work out well for me) and no places where motorcycle gangs might want to hang out (we did that too and lived to tell stories about the experience so why press our luck).

We just want to be together and laugh, talk, and share.

But even the sharing has been redefined. Back in the day, we roomed together. We used to be able to sleep in cars, on beaches, and one time on a cold hard table in a dorm TV room in Buffalo, N.Y. (Don’t ask).

Happily, those days are gone. They are never to return.

As a result, we are designing this trip around snoring and prostates—-everyone gets his own room and restroom.

This reunion will be driven by conversation, shared memories, and aspirations for the future. That sounds epic to this soon to be sexagenarian.







  1. Jeff great blog today and I fit totally into this metric of “where do we go from here” What is important. What brings me joy? what brings me sadness? Do more of the former etc.
    One thing I want to add to your wonderful thoughts here and I would offer up as the fourth item (might be first) is your partner. I find great joy in my wife and our time together. I appreciate all she does for me but I am not in this alone. I am in it with her. We plan our future together excited to do it together. We are both aging. Things are changing but she in my thoughts always as I contemplate my future, our future. Now I have to sign off and got online to the Christies Auction in London to buy a Mark Knopfler guitar original (Mark is the lead guitarist of Dire Straights) and this new hobby is amazing for a guy turning 60. Oh and thanks for telling me about the auction. I hope I don’t need a mortgage as well.

    • Jeff Perlman says

      It’s wonderful to watch you and Lennie blossom further (you were always both very cool). Thanks for being an inspiration to so how many of us sexagenarians. Good luck on the Knopfler auction—I would like to reserve visting rights.

Speak Your Mind


This site uses Akismet to reduce spam. Learn how your comment data is processed.