Life of Meaning
"That’s what you’ve got to figure out." —Curly
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Life hides its secrets in plain sight.
In fact, this is so common that my friend Simon and his coauthor Jay have written this secret into the cannon (among many other great minds who have discovered this across the millennia).
Being hidden in plain sight also means it’s hidden to plain sight.
As the 1991 hit City Slickers put it:
Curly: Do you know what the secret of life is?
[points index finger skyward] This.
Mitch: Your finger?
Curly: One thing. Just one thing. You stick to that and the rest don’t mean shit.
Mitch: But, what is the “one thing?”
Curly: [smiles and points his finger at Mitch] That’s what you have to find out.
I remember the first time I watched City Slickers. I was 9.
It was both of my personalities, on the silver screen. The Sierra-Nevada-high-desert-far-west-raised-Oregon-Trail-roots cowgirl and the wannabe urbanite.
I revisited it on the eve of my 40th birthday. Mitch, played by Billy Crystal, was on the eve of his 40th year. Mitch and I have everything in common—and yet, nothing in common—all at once.
I am not the only one turning to this classic in a time where nostalgia is at a premium—arguably, because it “is an emotional experience that unifies” in the words of Dr. Krystine Batcho.
I arrived here, with this movie, because I am looking back at my first 40 years with so much joy and gratitude and liberation—and I cannot wait to keep going. And be a lighthouse for those in need of light; a greenhouse for those in need of nutrients; a turtle shell for those in need of protection; and radical kindness for those in need of salvation.
So, back to a universal City Slicker nostalgia. As one [unfortunately named] publication captured it 30 years since it first aired (circa September 2021):
When Billy Crystal turned 40, he wasn’t happy about it. “I was gripped by a very cloudy mood,” he wrote in his 2013 memoir, Still Foolin’ ’Em. So he did what comedians do when faced with anxiety: He set out to find the humor beneath the heartache.
First would come his hilarious star turn as what the Los Angeles Times called “a reluctantly romantic leading man” in 1989’s When Harry Met Sally. Then he hit on a winning idea for what would become another iconic role.
“City Slickers,” he scribbled. “Three friends go on a fantasy cattle drive” — a metaphor for what was missing in their lives. “My character, like me, in his 40s ... midlife crisis.”
Gonna be honest, Billy: I can relate and don’t relate, in equal parts.
I don’t relate because:
I am not in any way, shape, or form in a ‘midlife crisis’. I am in a midlife Genesis, if anything.
I don’t relate because:
This movie made me curious about what was wrong with people from cities, because my parents were the same age as Billy (!!) when City Slickers was released—and they were at the cusp of moving to Oregon from Lake Tahoe to continue to build their dreams in the Far West. Twenty-nine years after we broke ground and 34 years after they put the first $ in, we now are the dream @ Bradshaw Vineyards. (Maybe this was their midlife Genesis??)
I don’t relate because:
I figured out a long time ago what I wanted to be when I grew up. It’s been building this whole time. I don’t currently have a miserable job or toxic boss or a morally exhausting environment or taker colleagues from whom I would need a break. I am off the grid while I am on it; I know where to find the oxygen, breaks, and renewable energy. I am blessed. I am grateful. I also put up with a lot, navigated a lot, and failed miserably at getting this right a lot, too.
I do relate to Billy because:
I just got back from a hiking / writing / yoga’ing retreat in Peru. This could absolutely be considered my cattle drive with friends.
At times, especially when things were hardest in my 20s, I got lost in the sauce. I saw those playing the finite game of hoarding wealth, objects, status—and like a kid breathing on cold glass as she peers at something too rich for her blood—I couldn’t help but want those things, too. I bought a lot of second hand luxe pieces from Chanel, YSL, Gucci, Prada. After some big wins, I even bought a few firsthand pieces, too. I blend in better. But I prefer to stand out.
For the past 10+ years, I have had the honor of coaching 100+ executives and leaders on the come up. Getting lost in the sauce is #1 thing I find myself treating.
So many of these leaders are struggling to find ‘the one thing’ and looking in all. the. wrong. places.
I have lived in Manhattan since 2014 (SoHo and Alphabet City); Miami before that (2013-2014); LA / DC before that (2005-2012); and Chicago before that (2001-2004). In each of these cities, there are so many souls who think that if they pray to the altar of TED-celeb sightings and The Hamptons and Tesla, they’ll find redemption. I wish them well with these reliquaries of the bourgeoisie.
Prompts for Thought
What is the right ‘one thing’? what’s the wrong one? which are you chasing? which gets your best time?
Are you playing a finite game? or an infinite one?
Discernments for Thought
Whose game are you playing—are you winning? are you losing? what are you trading off? [See TRTL Archive: The Score]
To whom are you listening? do they have your best interests in mind? or theirs? can they ever be the same? [See TRTL Archive: The Chosen]
Are you inadvertently discouraging someone else’s journey by giving all the answers? what would trading answers with questions look like? [See TRTL Archive: False Prophets]
40th Bonus Birthday Sagacity
Going from 30 to 40: Top 10 Learnings & Next Steps
She loves a good recap. Born in 1982, she has a few things to share with yew:
Go on the adventure. Stay late. Stay up all night, even. Ask meaningful questions of those whom others ignore—listen, really, truly listen, when they answer. Befriend everyone behind the scenes. Go. Deep. Get lost in your mind. Confuse yourself to make sense. Explore like your life depends on it.
You’re not a #2, you’re a #1. But you also love a good assist / teamwork moment, so you can also not even have a number. Privacy and much more discernment around what I publicly post / who is in my inner circles has been liberating AF.
You have abundant creativity and ability. You are magnificent. Even when the myopic can’t see the forest when they stare at single-gravity trees. You operate in multiple gravities, zero gravity, and other dimensions.
Deep roots, protected shoots. Build community, support networks, and mutually beneficial, non-transactional relationships. Be sincere, keep it real. And anyone who comes in trying to monetize you before the second date, don’t let them go past first.
Beware of late stage Capitalists (and Takerists, as coined by Scott Galloway). They will use the language of the zeitgeist to lure you into their oppressive systems, built to vulture your culture and exploit your labor. And while going entirely off grid sounds appealing in the face of this noise, I must also call up the words from my coach Nitzan: we must all negotiate with reality. So when it comes to their Matrixed organizations: know what you are getting into; rent your labor; sell big; get royalties; and get out. Let them play checkers and chess in their finite games. We, Turtles, are playing the infinite game. We fight to play another day and find abundance through what we give (not what we take).
It must check the big box. As one of my wisest collaborators Joe Chernov once told me on a walk around Boston in 2013: he can check all the small boxes, but if the one big box isn’t checked, it doesn’t matter. I get that now. Especially because this isn’t just a meme, it’s my life. It’s also not just applicable to romantic love—it’s life.
Choose consciously your words & your timing. To go further and make bigger impacts, it takes longer to refine your evidence and build coalitions. It’s also totally OK to be direct in the moment if something / someone violates your core beliefs, principles, ethics, and values. If you are ready for the consequences, then full steam ahead. Even if it means losing your job (a privilege I had in 2020 because of savings, which I realize is a privilege enjoyed by some and missed by many).
Don’t debug your features. You’ll be a bug in systems that don’t understand how to interact with your features. Don’t let this discourage or diminish your greatness. It’s also for the best—save your energy for the real ones.
You stay young by doing these things. You age by ignoring them. You also age faster if you act as a False Prophet in someone else’s universe. Tread carefully, for you tread on Turtles.
Not everyone can handle the uncertain, emergent spices of life. For those who are ready to take the next step with me, join the paid TRTL here. Not for the nominal money exchange, but because I am using the paid service to indicate your interest in hearing what will be hard to share—and, sometimes, hard to hear.
More About Spicy TRTL
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What: Monthly-ish deep dives that will humorously and honestly share things such as…
How I really feel about [x], where x = something I’ve kept quiet about for 40 years.
Behind the scenes of my Valleywag experience in 2014.
Behind the scenes of a proposal for meaningful wealth building / exchange that was too soon for conservative audiences in 2020.
Research process behind TRTL’s investment thesis and growth portfolio.
Generative, life-affirming opportunities to be a part of the logarithmic growth at TRTL Ventures and TRTL Academy.
If you’ve made it this far, you’re a real one. Thank you.
ps: I believe it was Fate that I was born on the day known as International Workers' Day. I receive this responsibility.