Dark Horse: Achieving Success through the Pursuit of Fulfillment

Dark Horse: Achieving Success through the Pursuit of Fulfillment

Book Notes

How to achieve breakout success and deep fulfillment when you don't fit the traditional mold

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.
  5. they've achieved incredible things, from making music for Prince, to creating floral arrangements for heads of state, to making internationally award winning suits.
  6. They come from an untraditional path, having arrived at their destination through the most unexpected and circuitous routes

The overall premise of the book is that

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.

Mindset 1: Know Your Micro-Motives

What Gets Your Blood Pumping?

The first rule of being a dark horse is understanding what gets you juiced at a very fine-grained level. Not just "I like competing" or "I like making art" but "I like competing in verbal jousts in a team environment" or "I like creating 3d structures out of 2d materials".

If you want to attain fulfillment, it’s essential to know exactly what puts the wind in your sails—not what someone else thinks should get you going. That’s why Know Your Micro-Motives is the first and most crucial element of the dark horse mindset.

Korinne Belock spent a whole decade making a name for herself in professional politics before realizing she wasn’t actually driven by voter research or policy debates. What she really liked was organizing things. She left politics and started a company that helps people organize their lives.

“The only way to ensure that your individuality truly matters is by honoring your most heartfelt yearnings and aspirations. When you engage in activities that are congruent with your true motives, your journey will be compelling and satisfying. If you misjudge or ignore your motives, your progress will be plodding and dreary—or you may abandon the road altogether.”

So how do you know what your micro-motives are?

Get specific about what you like

The first thing to remember is to get really specific about what you like. The book has many examples of people who’ve really niched down. Like a museum curator who feels creative when she works with 3D artifacts like masks and figurines. Two dimensional stuff just doesn’t cut it for her. Or the various field biologists who liked different types of creatures: insects vs birds vs plants, each finding something specific about that type of creature that was uniquely fascinating to them.

Notice what you judge about others

While polite society says to avoid judging others, Ogas and Rose believe our internal judgement of others can help us reveal more about our micromotives.

“Your micro-motives are composed of strong and abiding feelings rooted deep within your unconscious self. They include subtle preferences, frank desires, and private longings. Your goal in playing the game of judgment is to use your instinctive reaction to others to zero in on these live emotional wires and attempt to trace them to their source.”

What do you think is cool about someone else's life? What turns you away in disgust or utter boredom? These insights should help guide your understanding of your micro-motives and what decision you make (coming up).

Having lots of micro-motives

Look for projects and roles that help you leverage multiple micro-motives, which will keep you focused and carry you through tough times.

The key to engineering passion does not lie in following the one motive that burns hottest inside you, but rather in deliberately leveraging as many different motives as possible. The more distinct micro-motives you can identify and harness, the greater your engagement will be with your life.

Saul Shapiro was a hands-on guy who likes working with physical objects. He worked a decent job as an engineer and ended up inventing a piece of technology that helped his employer make a killing. But Saul only got a small bonus.

Miffed, Saul decided to get an MBA to make more money and have more influence in the company, but his two decades as a middle manager are not exactly the most fulfilling. After a mass layoff, Saul decides to take a different tack:

In 2013, at the age of fifty-seven, Saul opened his own Fibrenew Upholstery Repair franchise in Manhattan. If you’ve ever needed to mend the frayed corners of a family-heirloom armchair, remove a stain from a leather sofa, or patch torn vinyl on a car seat, you know how difficult it can be to hide the repair. But Saul quickly developed excellence at these tasks, because he was able to harness an entire platoon of his most fervent motivations.

Finally Saul’s able to combine both his love of hands on problem solving while applying his business acumen refined over years of management experience. And he became wildly successful in the process

“People who know me best would agree that I’m happier now than with anything else I have done with my career,” Saul says. “I enjoy what I do almost every day and I’m financially secure. In the end, I figured out how to align my livelihood to my nature.”

Mindset 2: Know Your Choices

How To Engineer Your Passion By Making Choices

Susan Rogers famously worked with Prince for his legendary album Purple Rain. She’s now a leading faculty member at Berklee College of Music in Boston. But her story begins as a highschool dropout who married an abusive man with a terrible temper. She found solace in music and her dream was to work in the music industry. She loved music and made choices to orient more towards the industry—at one point acquiring a ton of audio engineering guidebooks from the Army from a friend.

“I devoured them. I spent every waking moment reading them. I brought them to work, I brought them to the bathroom, everywhere.” Even though she still did not have access to any studio equipment, she memorized everything she could and visualized how all the devices worked, the same way she used to visualize what was going on inside her toys”

She made the choice to leave her husband. While working as a secretary to support herself, she chose to study hard for a competitive maintenance technician role that she eventually lands, and ultimately makes the leap to move to the middle of nowhere to help Prince record Purple Rain, which worked out big time in the end.

Knowing Your Choices is powerful. You get to choose the opportunities that use your micro-motives. You may find things nobody else has even thought of (PG also has a framework for this!).

Evaluating risk

According to Ogas and Rose, as dark horses, we should evaluate risk in terms of “fit” instead of "risk".

In the standardization mindset, risk is determined by odds. But in the dark horse mindset, risk is determined by fit. Dark horses evaluate how well their personal pattern of micro-motives matches up with the features of an opportunity. Thus, fit is a multidimensional interaction between the individual and the opportunity.

The “fit” and risk have an inverse relationship — good fit = low risk; bad fit = high risk. This flies in the face of the idea that we should opt for the "safe job" and a "steady paycheck". If you're neurodivergent like me or just not interested in fitting into the mold, picking the straight path can actually be riskier because you'll end up acting out, making mistakes, or just phoning it in because you're not engaged with the work (as it doesn't fit your micro-motives). Which makes you more likely to get fired or quit.

Perhaps the greatest illusion perpetrated by the Standardization Covenant is the presumption that the straight path is the safest route to professional excellence. In reality, it’s only safe if you are one of the lucky few who naturally fit the institutional mold. But for everyone else, when you must passively pick instead of actively choose, the gap between your individuality and the institutional mold represents pure, unadulterated risk.

Decisions after success

Rose and Ogas warn that as dark horses start becoming more successful, it becomes tempting to take the "safe" or "easy" path. The pressure to maintain your level of success

We’ve spent our lives in a standardized culture that forces us to operate without a safety net. We are taught to avoid bold moves that could threaten the stability and comfort of what we’ve already acquired. You worked so hard to get here—why risk your gains by pursuing a new and uncertain opportunity? Suddenly, playing the odds starts to look appealing again. You might even begin to experience grave doubts about the wisdom of fit. Don’t fall for it.

Megan Stanley was an IT manager at a home automation company in Canada when her employer offered her a contract that guaranteed job stability—but she'd have to commit for 10 years. Her family urged her to take it, but she knew the job lacked something she desparately sought: dogs.

Megan had always loved dogs and dreamed of a job where she could work with them regularly—and decided to quit the IT gig, became a dog trainer to learn the ropes, and eventually opened an award-winning humane dog training facility and eventually a second one. She earns more than twice what she would have had she stayed in the IT role.

The same assumptions still hold, the same math is still in effect, and the same mindset that got you here has not come close to reaching its limit. Keep evaluating opportunities the same way you always have: if a new opportunity provides a better fit than your present one and you can live with the worst-case scenario, then no matter how seemingly stable and satisfactory your current opportunity appears, you should still choose the more fulfilling option. The reason is simple. Seemingly small differences in fit can lead to very large differences in fulfillment and excellence.

Mindset 3: Know Your Strategies

How You Can Keep Getting Better

By age thirteen, T.V. Raman had lost his eyesight. Raman had always excelled at math in school. But the facilities for blind kids in his home country of India in the 80's weren’t particularly accessible—he had to find a way to keep up by himself.

He developed his own Braille shorthand to take down notes quickly. When traditional studying techniques like hammering flash cards didn't work, Raman chose to lean into his strenghts: writing papers. He forced himself to write academic-style papers for every tricky subject (this might sound horrible to you, but it came much easier to Raman which is why he chose it).

Know Your Strategies is about letting your strenghts guide you to the right study method, training regime, or learning system, instead of passively following strategies handed down to you from on high. When you do, you might very well come up with ideas that appear strange to others, even though they seem entire natural to you.

Raman got a PhD in computer science from Cornell, and is now a senior research scientist at Google. Obviously Raman was a smart dude. But his intelligence was not enough—he needed to find strategies that fit his strengths and micro-motives.

Find the method that’s right for YOU

As you master this element of the dark horse mindset, remember that knowing your strategy is not an endgame in itself. It is a process.

In the dark horse mindset, a strategy is a method for getting better. Thus, every strategy involves improving yourself over time. You need a strategy for learning how to hit curve-balls, a strategy for increasing your sales, a strategy for becoming a more efficient leader. Identifying the right strategy for you is the key to attaining excellence.

Failure is part of the process

An important part of Knowing Your Strategies involves finding out what you are good at i.e. your strengths—which is often harder than figuring out our micro-motives. Our yearnings are more obvious, while our strengths can only be revealed when compared to others and used in real-world situations.

Our brains are designed to know—to experience—our motives very directly. Indeed, desires often elbow their way into our consciousness entirely unbidden...

Our brains are not designed to intuit our strengths. It’s no mystery why. Almost everything we label as a personal strength is an artificial construct imposed on you from outside yourself rather than something that emerges naturally from within yourself.

Rose and Ogas tell us that our strengths are "inaccessible, contextual, and dynamic" aka "fuzzy". The only way to find out what your strengths are is to get out there and try different things.

Failure is an essential component—perhaps the defining component—of the process of developing excellence. Failure is the only way you can unearth the hidden contours of your fuzzy strengths. Every attempted strategy is a personal experiment. Does this approach suit me? Is it helping me make progress? If so, what might that say about my strengths?

Mindset 4: Ignore Destinations

Most professions already have standardized tracks through which individuals can scale the echelons of success. These well-established career paths — aka the “One Best Way” to success — end up robbing people of the chance to develop their own strategies. But Rose and Ogas say it's better to focus on the ways that work best for you.

The world's best wine drinkers

Being awarded the title of master sommelier is a huge honor that is very selectively bestowed. There are just 157 master sommeliers in the western hemisphere. For context, that’s less than the number of people who have visited outer space.

Rose and Ogas reveal how different sommeliers trained for the tasting portion of the master sommelier exam differently. Many use the "brute force" technique of simply trying thousands upon thousands of wines. Others focus on combining their knowledge of geology and geography to connect the wines to their grape varietals and vineyard regions.

Still others focused on the visual hue and used "calibration wines" to track acidity more accurately. And one master sommelier failed the test 5 times trying many techniques and studying 20-40 hours a week before landing on a "physiological" strategy that allowed him to reduce his study hours to only 5-10 hours a week and pass the test on his 6th try.

When you learn to Know Your Micro-Motives, you can engineer your own passion, which endows you with energy and authenticity. When you learn to Know Your Choices, you can engineer your own purpose, which provides you with meaning and direction. And when you learn to Know Your Strategies, you can engineer your own achievement. When you do, you will experience a deep sense of pride and self-worth because you will have accomplished meaningful feats while remaining true to your authentic self.

Rose and Ogas also point out that the Standarization Convenant really emphasizes time. Time in role. Time to get a degree. Years of experience.

The single most important finding of the Dark Horse Project might be the spectacular variety of individual expertise. In every field in which we interviewed multiple experts, we discovered meaningful differences in the way they approached their craft that were traceable to the individuality of the person.

Yet, as we noted, when you find the right strategy, you can spend less time and get better results. And if you bang your head against the wall, you can spend time but make little progress.

Most researchers investigating excellence treat time as an independent variable rather than a dependent variable—which is to say, they view time as a cause of expertise. This leads scientists to pose the innocent-seeming question “How much time is necessary to develop excellence?”

Sure, 10,000 hours might the average time to reach expertise in some fields, but again, it depends on the person and the job.

In each case, the most important temporal factor was not the inherent difficulty of the task they were trying to master or their general capacity for learning, but rather each man's ability to find the right strategy for his own patter of strengths.
Crucially, each aspiring master sommelier had to surmount a private mental hurdle that prevented him from recognizing that he needed a strategy (or suite of strategies) customized for his own individuality, and the time it required to come to that realization and find a strategy suited for his fuzzy strengths was far more impactful than the time necessary to develop competence once the right strategies were chosen

Goals > Destinations

Attaining excellence requires that you engineer purpose. Engineering purpose requires that you maximize the fit between your micro-motives and the opportunity you choose to pursue. Thus, there are two obvious problems with pursuing a professional opportunity that lies somewhere in the far-off future. Number one, by the time you finally get there, your understanding of your micro-motives may have changed. And number two, the opportunity itself may have changed.

This is the danger of focusing on far out destinations. You are going to change and the world is going to change prior to you getting close it. It's like deciding where you're going to eat for lunch on the 4th leg of your round-the-world journey. It just doesn't make sense.

Instead, the authors say to focus on goals. What's the difference?

Dark horses may ignore destinations, but they don’t ignore goals. In the dark horse mindset, there is a clear distinction between the two. A goal always emerges out of your individuality. More pointedly, a goal is born out of an active choice you have made. In contrast, a destination is someone else’s idea of an objective that you have acceded to. More often than not, a destination is defined by a standardized institution of opportunity.

The authors go on to clarify that a goal is immediately actionable, you can put in effort and implement strategies that will help you get there in the immediate future—finishing a novel, winning the next soccer game, beating next quarter's sales quota.

Meanwhile destinations are longer term and depend on many factors outside of your control—winning a major award for your book, becoming a Nike-sponsored athlete, and becoming the #1 product in your market by sales volume are destinations that dark horses would do best to avoid overly focusing on because they offer less consistent and immediate fulfillment.

You need the energy of self-engineered passion and the direction of self-engineered purpose to scale the mountain of excellence, and you need the pride, self-worth, and sense of meaningful accomplishment from self-engineered achievement to experience the full flush of fulfillment.