Morning, CEO!
Let’s talk about the “40-Year-Old Crisis.”
It’s that specific, creeping terror that hits right after your morning coffee. The one that whispers: If you haven’t Cured Cancer, launched a Unicorn, or at least figured out what “fiduciary” actually means by now, you are officially a Useless Human.
As the CEO of Me, Inc., I hold emergency board meetings about this daily. Usually in the shower.
But I just read Second Act by Henry Oliver, and it turns out my panic might be based on bad data.
I am not broken. I am not a failure.
I might just be... buffering.
1. The Two Types of Brains (Or: Why I Hate Mozart)
The book introduces a concept from an economist named David Galenson that explains why some of us feel like a hot mess while others seem to have life on cheat mode.
He divides creative people into two species.
Type 1: The “Conceptual Artists.”
These are the Mozarts. The Picassos. The 22-year-old tech founders.
They have a precise idea. They execute it perfectly. BOOM. Masterpiece.
They treat their career like a sniper rifle. One shot, one kill.
I hate them. (Not really. But okay, a little bit.)
Type 2: The “Experimental Artists.”
Experimental Artists have no idea what they are doing.
They don’t work with a map; they work by walking into walls until they find a door.
Their process is: “Let’s try this... nope, disaster. Let’s try this... also a disaster, but a fascinating one.”
They figure out their “thing” by trial and error. Mostly error.
Here is the critical update for your CEO mindset:
If you are an Experimental Artist, you cannot force yourself to be a Conceptual one.
You can’t “strategy” your way out of the experimentation phase.
You bloom late because your process requires decades of messing up to accumulate the data you need to succeed.
My life isn’t a series of failures. It’s just really, really avant-garde experimental art.
2. The “Inefficient Preparation Period”
Oliver has a name for that phase where you feel like you’re wasting your life.
He calls it the “Inefficient Preparation Period.”
This is when you’re learning random skills, taking weird jobs, and failing at hobbies.
For reference, my “Inefficient Preparation” apparently involved years of re-watching 30 Rock and perfecting the marinated ramen egg.
But here’s the twist: In the “Agency of One” model, this inefficiency is actually R&D.
The “fast” path learns exactly what is needed for a specific job. The “slow” path learns things just because they are interesting.
To survive this period without quitting, you need three specific tactics:
First: Get in the Loop.
You have to be at the place where things are happening. Even if you’re just the intern getting coffee. Even if you’re just on the bench picking at the grass.
You can’t win the lottery if you don’t buy a ticket. (I use this logic to justify buying snacks. It’s probably not the same thing.)
Second: The Retreat.
This is the opposite. You have to go full hermit to build deep knowledge. Nassim Taleb (the Black Swan guy) spent FIVE YEARS just reading statistics books. Alone.
This is the part I think I’m doing when I’m “researching” on YouTube, but I suspect Taleb wasn’t watching “cat jumps and fails” compilations.
Third: Failure.
There was a study of scientists. Group A barely got their funding (Lucky Winners). Group B barely missed it (Unlucky Losers).
Guess who did better in the long run? The Losers.
Getting punched in the face by reality early on forces you to audit your own code. It makes you stronger.
“What doesn’t kill me makes me... weirdly more qualified.”
3. The Late Bloomer Tech Stack
If you survive the wandering, the hermit mode, and the face-punching, you unlock a specific set of superpowers that the 22-year-old geniuses simply don’t have.
Superpower 1: Persistence.
You are now too stubborn to quit. You’ve already failed, so the fear is gone.
Superpower 2: Earnestness.
You become weirdly intense about your craft. You care about details nobody else sees.
Superpower 3: Quiet.
You have the ability to shut up and do the deep work. (See: The Retreat).
The ultimate case study for this is Katharine Graham.
She was a “housewife” who, at age 45—after her husband’s tragic death—had to take over The Washington Post.
She knew nothing about business. She literally couldn’t tell the difference between “income” and “capital.” She was terrified.
But she had the Late Bloomer stack.
She was quiet enough to listen. She was earnest enough to learn. And she was persistent enough to stand her ground.
She ended up taking on the U.S. government over the Pentagon Papers. And she won.
She didn’t need an MBA. She needed the wisdom she’d accumulated during her “Inefficient Preparation Period.”
So... What Now?
We are living in the era of the 100-year life (yay?).
The old script (Learn -> Work -> Retire) is dead.
As an Agency of One, you have time for multiple careers. You have time to be an Experimental Artist.
So, all my failed experiments? They aren’t failures. They are... uh... strategic capital investments.
Yeah. Let’s go with that.
Now I have some very “inefficient preparation” to do.
(It looks a lot like a nap).
Links:
https://www.henry-oliver.co.uk
https://www.amazon.com/Second-Act-Bloomers-Success-Reinventing/dp/1399813315
