The Secret-Keeper's Dilemma
The Secret-Keeper's Dilemma
Should we hoard secrets for private gain, or spread the wealth? • Leadership Land reader check-in #3
Adventures in Leadership Land is a little over a year old! We launched last September when the Leadership Land gimmick metaphor was still incomplete. In our very first article, we covered topics from all over the surface and underground of Leadership Land, but we didn’t have names for those locations. Now we do.
Let’s celebrate!
Fun Birthdays vs. Effective Birthdays
Most people celebrate fun birthdays by throwing a party and distracting everyone from the fact that we’re all one year closer to death. We celebrate effective birthdays in the most anti-fun way possible: by soberly conducting a year-end review of our lives. A typical review involves:
Evaluating what we accomplished in the past year
Counting the days we have left in our actuarial life expectancies1
Mapping out what we hope to accomplish in the ever-decreasing time we have left
As you can imagine, we’re horribad at birthday parties. In our defense, we’ve gotten better at keeping our killjoy tendencies to ourselves, so we no longer ruin other people’s birthday parties 😅
In our last post about following conventional wisdom vs. thinking like a contrarian, we advocated for following “best practices” in non-competitive environments. We practice what we preach; our morbid birthday ritual falls into the category where “best practices” are widely known, but rarely followed.
“Wait!” you say. “Since when has it been a ‘best practice’ to spend a birthday wrestling with existential questions and contemplating mortality?”
…okay, fine. You don’t have to do it on a birthday. We do it because birthdays are an appropriate (and convenient!) time to apply the conventional wisdom from:
Leadership development programs: These teach you to formulate a vision, mission, and strategic plan. You already do this in your organization. Why wouldn’t you have one for your life?
Self-help books: The 7 Habits of Highly Effective People advises you to “begin with the end in mind.” The book walks you through a thought experiment where you attend your own funeral and decide what you want the eulogy to say about you.
The ancients: The practice of memento mori has been around since the days of ancient Greece, featuring prominently in the writings of Stoic philosophers like Seneca, Epictetus, and Marcus Aurelius.
“Beginning with the end in mind” is simple, but it isn’t easy to think about death – and that’s why most people don’t do it. If you’ve never engaged the Grim Reaper in a staring contest, fear not! You can benefit from our fun-free labors without ruining your birthday party, or anyone else’s.
The Secret → Conventional Wisdom Treadmill
Consider the following hypothetical scenarios:
A famous CEO retires and starts the Super-Duper Leadership Academy to teach everyone the Super-Duper Proprietary Process. Other CEOs attend the Academy to learn the Process that made the founder famous, but these CEOs lock themselves in a war of attrition because they’re all competing for the same customers by using the same Process.
A YouTuber releases a video titled How I Earned $10 Million Dollars by Working 10 Minutes a Day. Her millions of subscribers all emulate her and, predictably, fail to replicate her success. “Too good to be true?” Never heard of it.
A pick-up artist writes a book called 10 Easy Strategies to Seduce any Woman, which becomes a New York Times bestseller. In every bar across the country, single men begin reciting the book’s pick-up lines and using its “negging” tactics. These pick-up techniques soon become so cliché that their practitioners gain an unsexy reputation for being desperate losers.
The three examples above involve people following conventional wisdom in a competitive, dynamic environment. They all follow a predictable pattern we call the secret → conventional wisdom treadmill:
Someone extracts Cerebrium in the Secret Grottos and becomes a secret-keeper. In the darkness of the Contrarian Caves, they use the secret in unorthodox ways to gain an edge over competitors (who are too busy fighting a war of attrition to think differently).
The secret-keeper becomes successful, which attracts unwanted attention. Other people eventually reverse-engineer the secret by careful observation, or via independent development. The Cerebrium’s glow fades as more people become aware of the secret. The secret-keeper’s rivals begin catching up.
The secret-keeper capitalizes on the Cerebrium’s declining potency by divulging the secret far and wide…for a price. The secret-keeper’s reputation serves as a powerful marketing tool for their book, lecture circuit, and training workshops. The Cerebrium’s dying light enters a terminal decline as public awareness transforms the secret → conventional wisdom.
Aspirants pay the secret-keeper for a lump of inert Cerebrium. The aspirants expect that the dark Cerebrium will bestow riches and glory just like the radiant Cerebrium did for the secret-keeper. By the time aspirants figure out that the Cerebrium is useless, their money is jingling merrily in the pocket of the secret-keeper, who is long gone. Or, in the case of the retired CEO, long dead.
This is like selling rotten fruit by packaging it with the credibility of past triumphs. If you tell your customers that this magic fruit made you successful (technically the truth), most of them will assume the fruit is still fresh and nourishing. But you’re also telling a lie of omission: that the only reason you started selling the fruit in the first place is because it started rotting.
How gullible are you? Take this test for $99.99 to find out!
There’s a sucker born every minute, and they are the most likely to get on the secret → conventional wisdom treadmill. They buy into fads. They fall for “get rich quick” and “10 easy steps to win at life” schemes. They might even occupy high positions in organizations, but they are not true leaders – they are authoritative followers.
Being recovering suckers ourselves2, we know how tempting it is to jump on the bandwagon of social proof. We sometimes toy with the idea of becoming secret-keepers and parting the gullible from their money. The little devil on our shoulder keeps whispering “it would be so easy…”
This is the secret-keeper’s dilemma:
Should we hoard secrets and enrich ourselves in the gloom of the Contrarian Caves? Once the golden goose starts dying, we could squeeze out one final golden egg by creating a secret → conventional wisdom treadmill.
Should we divulge our secrets now to spread the wealth? By exhibiting our Cerebrium on the internet, the potency of the secrets will decline with increasing public awareness. We risk becoming victims of our own success.
A Trail of Breadcrumbs up the Mountainside
We tried to resolve the secret-keeper’s dilemma when we conducted our year-end review. We “began with the end in mind,” thinking about the legacy we want Adventures in Leadership Land to have on your life. Using the via negativa approach from our About page, we decided first on what we do not want:
To sell rotten fruit. It’s immoral.
For Adventures in Leadership Land to have a short shelf life.
To compete with our readers, or for readers to compete against each other.
Do-Not-Want #1 means we would not intentionally create secret → conventional wisdom treadmills to enrich ourselves. However, the secret-keeper’s dilemma remained unresolved. Should we shut down Adventures in Leadership Land and return to obscurity in the Contrarian Caves? Or do we keep writing and watch our Cerebrium lose its luminosity?
The answer came to us when we revisited a conversation we had years ago with a mentor. This person is wildly successful; his rags-to-riches story would inspire the skeleton of Horatio Alger to bootstrap himself out of the grave and tap-dance.
Our mentor used to write a blog. After he stopped writing regularly, he told us:
I felt like I was climbing a huge mountain when I built my business. I knew a bit of what I was doing, but had to figure the rest as I went along. The blog was my way of scribbling notes and tossing them over my shoulder as I climbed toward the peak.
A few years go by, and I’m halfway up this mountain. I turn around, and I see a bunch of people reading my blog. It was like they were following a trail of breadcrumbs I left behind!
The memory of this conversation inspired us to resolve the secret-keeper’s dilemma in favor of continuing to write. We were one of those readers following the trail of breadcrumbs up the mountainside. We owe much of our progress to our mentor, who generously shared his insights and wisdom with internet strangers.
There’s only one way we can thank our mentor: by paying his legacy forward to readers like you. As we travel throughout Leadership Land, we want to leave a trail of Cerebrium breadcrumbs for anyone willing to follow along. When we finally put down the proverbial pen, we want you to eulogize us by saying that we walked the deserts, shoals, caves, and mountains of Leadership Land together.
Keeping the Cerebrium Bright
With Do-Not-Want #1, we decided that we won’t intentionally create a secret → conventional wisdom treadmill for private enrichment. However, as awareness of Adventures in Leadership Land increases, the potency of our Cerebrium will naturally decrease. This is not unique to our blog – anytime you share a secret, you’re slowly converting it into conventional wisdom. In competitive environments, sharing secrets is self-sabotage.
During our year-end review, we concluded that this problem couldn’t be avoided, but it can be mitigated. Here’s what we decided.
Do-Not-Want #2: Short shelf life
If we treat Substack newsletters as a medium for disseminating the news, then we guarantee that Adventures in Leadership Land will have a short shelf life. What’s trendy will certainly attract more eyeballs, but it will rapidly become stale as rigor mortis sets in. What do we write about, if not snarky commentary on the latest scandal that Elon Musk instigated on Twitter X?
To answer that, let’s turn to another one of our role models, Nassim Nicholas Taleb. In a Medium post, he wrote:
The common fallacy is that if you want people to read you in the future, you must project something related to the future, focused on the contemporary and be as different from the past as possible –say by populating your work with space machines, high technology, and revolutionary ideas.
[…]
No, no; it’s the exact opposite […] If you want to be read in the future, make sure you would have been read in the past. We have no idea of what’s in the future, but we have some knowledge of what was in the past. So I make sure I would have been read both in the past and in the present time, that is by both the comtemporaries [sic] and the dead.
In other words: if we want Adventures in Leadership Land to be relevant 50 years from now, then our writing must have been as relevant 50 years ago as it is today. We must create timeless content, like the books that are still relevant centuries after their authors stopped breathing.
Do-Not-Want #3: Competition with readers
What good would it do to hand our readers Cerebrium if it were weaponized for a war of attrition? We thought of several ways to reduce competition between us vs. readers, and between readers vs. other readers:
Compared to traditional mentoring or coaching within an organization, writing online results in less competition in the real world. Adventures in Leadership Land readers are spread out both geographically and across different industries: military, academia, tech, and government. The risk of any of us using the same secrets against each other is negligible - at least while we remain a small outfit.
For competitive environments, we’ll focus on teaching you how to think differently, not what to do. Instead of handing you Cerebrium that becomes dimmer the more it’s shared, we’ll hand you a pickaxe so that you can mine your own Cerebrium. We can be secret-keepers together!
For non-competitive environments, we can hand out Cerebrium like candy. The only person you’ll be competing against is your past self; if you don’t win, you’re not improving.
Together, we hope these strategies will discourage secret-hoarding. If you can gain more by sharing a secret than by hoarding it, then the result is a win-win-win: you gain social currency, your confidant gains valuable information, and we gain another reader.
Slowing down the secret → conventional wisdom treadmill
The attorneys reading this are probably wondering why we’re taking such a philosophical approach. We can hear their thoughts through the computer screen:
Trade secrets and non-disclosure agreements already exist, you moron! Why aren’t you using them?
Because that’s like summoning the fun police to arrest everyone at a birthday party. Even we aren’t that anti-fun.
Instead, we’re going to:
Turn Adventures in Leadership Land into a paid publication at some point. Not all essays will be withdrawn behind the paywall, but the ones that contain secrets probably will.
Continue writing long, rambling posts about difficult topics. Like this one, where the first thing you see is a cute birthday cake, but by the second paragraph you’re reading about death and funerals.
Writing about topics in the Taboo Tunnels and Contrarian Caves, which will naturally stir controversy. People who can’t handle the discomfort will stop reading.
These will make Adventures in Leadership Land less palatable to many people, raising the barriers to entry. That also means you can benefit from potent Cerebrium for longer before it completes its one-way transformation into conventional wisdom.
Secret-Seeker → Secret-Keeper
What’s the biggest difference between those who gain 20 years of experience and those who gain 1 year of experience 20 times?
Our answer is that those in the first category are secret-seekers. Instead of waiting for the mysteries of the universe to reveal themselves, secret-seekers actively probe the unknown. By mining Cerebrium in the Secret Grottos, secret-seekers eventually become secret-keepers.
That’s a roundabout way of saying: thank you for reading Adventures in Leadership Land. Thank you for taking this secret-seeking journey with us.
Our current assumptions for people living in developed (OECD) countries:
Capacity for high-intensity physical feats: peaks in early 20s
Capacity for low-intensity feats of dexterity: peaks in ages 30-40
Fluid intelligence: peaks in 30s and disappears by the 60s
Crystallized intelligence: matures like a fine wine between ages 0-60, and its quality can be preserved by staying mentally active until the very end of life
Expected age of death: 80 (male) and 85 (female). We evaluate our exposure to life-ending events (accidents, natural disasters, terminal illnesses, etc.) separately from our year-end reviews. We use the static 80/85 number for simplicity even though life expectancy increases with time. For example, if you’re an 88-year-old-man, your life expectancy is not negative 8 years; healthy 88-year-olds can expect to live another 5 years on average.
If the facts change, we’ll change our assumptions.
It’s possible we’re current suckers for something else, but we won’t find out until the consequences smack us in the face later.