141: How to Be a Dark Horse

141: How to Be a Dark Horse


Cultivating Resilience is a weekly newsletter about rebounding from setbacks and reinventing the future—by 3x founder and executive coach Jason Shen.

Once you pass 35 you really start to rethink the idea of redeyes.

On a recent West ✈️ East flight, I tried my best to get comfortable in a middle seat, with my boots on (to save space in luggage), padded eye mask, bite guard, and Airpods nestled in my ear canals.

I think I caught 3 hours of ZZ's which wasn't bad all things considered. Rest and rejuvenation becoming my clarion calls as I prepare to enter my late thirties. What I lose in raw horsepower, I hope to make up in wisdom.

Speaking of horsepower—let's talk about being a dark horse.


🤔 Announcements

  • 📆 THESIS is an IRL and virtual conference featuring some of your favorite internet writers and thinkers from Every and Interintellect. I'll be hosting a conversation with ex-Wall Street MD turned creator & productivity expert Khe Hy on "What Productivity Can Reveal About Our Inner Desires" (Feb 25 in NYC & online)
  • 📝 I sat down for an interview about tech layoffs with Rachel from Merit (read it here)

🧠 Book Notes on Dark Horse

Most of us grew up understanding there was a basic formula for success:

  • Do well in school, get into a highly ranked college, major in something "useful".
  • Land the highest paying job you can at the most prestigious employer
  • Go to grad school after a few years then focus on grinding your way to the top.

Even if you decide to pursue a non-corporate route, the idea is that the right credentials (e.g. Forbes 30 under 30, Y Combinator, Guggenheim Fellowship) will open the doors to future success.

In Dark Horse: Achieving Success through the Pursuit of Fulfillment: authors Todd Rose and Ogi Ogas call this the "Standardization Covenant" where we trade personal fulfillment in pursuit of a ladder of professional excellence.

"If you can follow the straight path to its destination, you will be granted employment, social status, and financial security. This promise eventually became so firmly entrenched in American society (and calcified into an even more rigid form in Europe, and petrified into an utterly inflexible form in Asia) that it assumed the form of a fundamental social contract"

— All quotes are from Dark Horse / Todd Rose & Ogi Ogas unless specified. Thanks to my writing assistant Rhea for helping me on the 1st draft here.

The book is part stories, part strategy, and part call to transform society to support a world where more people can be successful without having to force themselves into the Standardization Covenant. My book notes will focus on the first two parts and leave the important policy advocacy to policymakers and education leaders.

What is a Dark Horse?

Rose and Ogas both see themselves as not well suited to the Standardization Covenant. Rose was a high school dropout who eventually made his way to becoming the director of the Mind, Brain, and Education program at Harvard University. Meanwhile Ogi dropped out of 4 different colleges and struggled to hold down a 9-5 job before becoming a neuroscientist and a $500k winner of Who Wants to be a Millionaire.

Rose and Ogas wanted to explore the idea of the Dark Horse, someone who becomes wildly successful without following the traditional path. They interview a bunch of fascinating people who achieved this and developed a framework for how to succeed using a different approach—the Dark Horse Covenant.

Maybe most dark horses would turn out to be mavericks with outsized personalities, like Richard Branson—rebels driven by a fierce ambition to make their mark and prove the world wrong. That’s not what we found at all. Instead, we discovered that the personalities of dark horses are just as diverse and unpredictable as you would find in any random sampling of human beings. Some are bold and aggressive; others are shy and deferential. Some enjoy being disruptive; others prefer being conciliatory.

Dark horses are not defined by their character. Nor are they defined by a particular motive, socioeconomic background, or approach to training, study, or practice. There is a common thread that binds them all together, however, and it was hard to miss. Dark horses are fulfilled.

They open with the amazing stories of astronomer Jennie McCormick and tailor Alan Rouleau—this book is chock full of inspiring stories and is worth the price of the book alone.

Alan’s and Jennie’s journeys break the mold for how we think about the development of talent. To become a successful astronomer, the prescribed sequence is to obtain your PhD, complete a postdoc at a respectable university, and settle into a tenure-track professorship—not drop out of school, then teach yourself astronomy in your backyard.

To become a successful bespoke tailor, the conventional route is to follow a youthful passion for fashion and slowly and steadily hone your skills over many years of apprenticeship at the feet of a master—not perform a midlife swivel from an entirely unrelated profession.

Jennie and Alan seemed to come out of nowhere, bursting onto the scene with their own signature version of excellence. There is a term for those who triumph against the odds—for winners nobody saw coming. They are called dark horses.

These “Dark Horses” leaned into their own individuality and went after work that actually fulfilled them.

People often believe that when it comes to earning a living, you must choose between doing what you like and doing what you must. Dark horses teach us that this is a false choice. By harnessing their individuality, dark horses attained both prowess and joy.

By choosing situations that seemed to offer the best fit for their authentic self, dark horses secured the most effective circumstances for developing excellence at their craft, since engaging in fulfilling work maximizes your ability to learn, grow, and perform.

Thus, dark horses provide a new definition of success suited for the Age of Personalization, one that recognizes that individuality truly matters: Personalized success is living a life of fulfillment and excellence

If you're anything like me, this line gives me a deep sense of hope and possibility, mixed with a tinge of fear and angst (it sounds too good to be true!).

The four dark horse mindsets Ogas and Rose identified are:

  1. Know Your Micro-Motives—figure out what uniquely makes you tick. What gets you juiced, keeps you interested, drives you to stick with something for a long time. These motivations are crucial to drive your fullfillment and longterm success.
  2. Know Your Choices—rather than just accept what the world hands you as options, make your own choices. Find a path that lets you pursue and express your micro-motives as its the only way you'll be fulfilled enough to stick with something to get good and innovate.
  3. Know Your Strategies—unlike micro-motives, strengths are discovered through real-world application. You have to go out and try things and be willing to give up on the "one best way" in order to find "your best way" to do things.
  4. Ignore Destinations—rather than get fixated on some far off achievement or outcome, dark horses succeed by following their fulfillment and acheiving success in the short-to-medium term, shifting focus as their interests and the world changes.

To avoid clogging your inboxes, I've included the full write up (4k words) in the Book Notes section.

Dark Horse: Achieving Success through the Pursuit of Fulfillment
How to achieve breakout success and deep fulfillment when you don’t fit the traditional mold

👉 Links

  • Courage / Risk ⚡️My friend Cedric took a leap and returned to Judo in his mid-thirties in an attempt to study deliberate practice and make the Singaporean national team (An Expertise Acceleration Experiment in Judo)
  • Relatable 🏋  My writing assistant Rhea on discovering the joys of working out in her twenties (Twitter)
  • ADHD 🧠  A helpful thread for getting going when you're paralyzed with life (Reddit)
  • Systematic ⚙️ How to structure your threads so people get maximum value (from one of my favorite truly no BS experts Erica Schneider)
  • Generative 🤖 A deep explanation for how large language models (LLM's) work, with examples, from Stephen Wolfram. Some parts are fairly technical but there are nice pictures and you can skip straight to "The Training of ChatGPT" if you want.
  • Togetherness 🫶 Kareem Abdul Jabbar penned a beautiful piece when Lebron James broke his scoring record. "There are no “yeah, buts,” just praise where it is rightfully and righteously due."
  • Creative 👁️ Using AI to turn low-fi musical input (a 8 button "keyboard") into high-fidelity music in real-time! (Twitter)

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