The Dilemma: Do I Stay or Do I Go?

The year was 2005, and Lisa Feuer was at a crossroads. Having built a solid career in the advertising and marketing industry and achieving what most would consider a fair degree of success, she had every reason to feel proud of where she was and what she had accomplished.

And yet, at 38 she couldn’t escape the feeling that her true calling still eluded her. With every passing day the sense that she was missing out on something important grew inside her, until it became too big to ignore.

After watching her husband take the entrepreneurial path by starting his own business, she began to see the stifling constraints she was under in her corporate job as an albatross that was holding her back from pursuing bigger dreams. She knew she was capable of so much more, but at the same time, the risk and uncertainty of the road less traveled frightened her. After all, she was doing well in a job that offered good pay and security, so what was she supposed to do, just throw it all away?

Then, one day, as she pondered the pros and cons of the alternate paths that lay before her, she suddenly came to the fateful decision: she was going to quit and go into business for herself. Far too many people let their dreams whither as they toil away doing jobs they don’t like, she thought, and she was not going to be one of them.

And just like that, she was free from the shackles of the corporate world and living the life of a passionate entrepreneur. With the world at her fingertips, she was ready to attack her pursuits with new zeal.

For Feuer, summoning the courage to jettison corporate life was the hard part. The easy part was deciding what to do instead–as an avid yoga practitioner, she was confident that she could parlay her interests in yoga into a thriving business and help more people become familiar with the practice. She took out a $4,000 loan against the equity in her home to enroll in a yoga instruction class, which put her through two hundred hours of training before she was finally ready to lead classes of her own.

With her shiny new certification in had, she founded Karma Kids Yoga, a practice tailored towards young children and pregnant women. All was going well, and Feuer could finally say she loved what she did for a living.

But, sadly, the good times didn’t last.

Lisa Feuer in a yoga studio. Image courtesy of Michael Chelbin & The New York Times.

In 2008 the Recession hit, which all but decimated Feuer’s fledgling yoga practice. First, one of the gyms where she taught closed down. Then, a local public high school dropped the two classes she taught as the demand for private lessons continued to evaporate. When all was said and done in 2009, Feuer had made less than $15,000 and was forced to go on food stamps just to make ends meet.

And with that, Feuer’s passion-fueled entrepreneurial adventure came to a bitter end.

An Alternate Ending

Around the same time Lisa Feuer’s story began to unfold, another marketing executive found himself grappling with a similar dilemma. Joe Duffy, like Feuer, had built his career in advertising and was itching for a change. “I was tired of the agency business”, Duffy said. “I wanted to simplify my life and focus on the creative side again”. Having been formally trained as an artist, Duffy felt the pull to go back to creating things again, with the complete freedom and flexibility to approach his work on his own terms.

Unlike Feuer, however, Duffy decided to explore another path towards elevating his career to the level he knew it could get to. Rather than quitting his job to pursue his passion for the arts, he instead doubled down on what he was good at that also happened to have a strong artistic foundation: logo design. He became known for his specialty in international logos and brand icons, and as his skills continued to flourish, so did his options.

A few years later he was hired by renowned Minneapolis-based agency Fallon McElligott to run his own logo subsidiary within the firm called Duffy Design. Here he steadily grew his skills and reputation even further, producing logos for the likes of Sony, Coca-Cola, Starbucks, and Toyota. After twenty years he finally decided he was ready to take the leap and start his own company: a fifteen-person shop he named Duffy & Partners.

Joe Duffy in his studio. Image courtesy of the Duffy & Partners website.

At this point, Duffy was widely known as one of the best logo designers on the planet, so when he spun off his own shop, the work poured in. Duffy’s business continued to thrive even through the recession and he was able to afford luxuries typically reserved for the top echelon of wealth and power.

He purchased a 100-acre retreat in the woods of Wisconsin with five miles of private cross-country ski trails so he could pursue an activity he loved in peace. Not wanting to spend all of his winters in the harsh cold and snow of the Midwest, he also bought a winter home in Arizona and keeps an apartment in Manhattan in case he’s craving a dose of big city living.

Duffy has built a life for himself and his family that he could have only dreamed of when he started his career as a starving painter, and it’s all because of one fateful decision:

He chose not to pursue his passion and do what he loved.

The Paradox of Passion

Both of these stories started in a similar place: Feuer and Duffy both came from the advertising and marketing world, they both felt the pull to quit their jobs and follow their passions, and they both took the leap to start their own thing at around the same time.

And yet, despite these similarities, one ended up on food stamps and the other ended up a multi-millionaire with properties in several states.

That raises an obvious question: how could two people coming from such similar starting points end up with such different results? How could one experience such abject failure while the other realized such wild success?

The answer can be found in a common idea you’ve likely encountered your entire life: that the key to being happy at work is to figure out what you’re passionate about and then find a job that matches your passion.

You’ve heard the phrase, “do what you love, and the money will follow.”

It turns out that that little piece of advice is a dangerous lie that can lead to potentially disastrous results if heeded. Lisa Feuer is a case in point–when she decided to quit her job in advertising and follow her passion for yoga, she ended up broke and on food stamps. And while following your passion can lead to happiness and career success, in the vast majority of cases this is the exception, not the rule.

Feuer’s decision to quit her job to pursue something she loved was based in what author Cal Newport, who wrote the book on which this article is based, So Good They Can’t Ignore You, came to refer to as the passion mindset. The passion mindset is rooted in the belief that somewhere out there, there’s a magic job just waiting to be discovered and that when you find it, you’ll instantly recognize it as work you were meant to do–your “true calling”.

There’s just one problem: the true calling is a myth.

Let’s take a moment and think about what a true calling might look like if you were one of the few fortunate enough to stumble across it.

We’ll start by painting a picture of the opposite of a true calling: a miserable grind. This is a job you dread getting up for in the morning, one that’s completely disconnected from any meaningful sense of purpose and one that offers few redeeming qualities for self improvement or advancement. In the grind, you may have an overbearing manager, inept leadership, peers you can’t stand or any combination of terrible qualities. You grit your teeth, keep your head down and reluctantly do your work in exchange for a steady paycheck every couple of weeks.

Now let’s look at the flip side: the true calling. In this role, you have complete freedom and autonomy to approach your work the way you believe it should be done. You’re surrounded by people who support and empower you, and you consistently produce amazing work that exceeds most people’s expectations. You feel a close connection between your work and your sense of inner purpose. This is, for all intents and purposes, “living the dream.”

Sound enticing? You’re not alone–it’s probably safe to say that most people would love to find themselves in a dream role where all of the above were true. The problem is, jobs that meet every single piece of this criteria–autonomy over one’s work, a close connection to those around you, and a mastery of the skills you’re applying–are incredibly rare. That, and everybody wants them, which makes them extremely valuable as well.

So how do you obtain something that’s both rare and valuable? Economics 101 tells us that in order to get something that’s rare and valuable, you need to offer something rare and valuable in return. You need to possess something that few others have in order to intersect the supply & demand curve where the supply of great work is low and the demand is high, rather than play at the bottom like most people do throughout their careers.

And that’s where Feuer’s passion-based strategy falls apart. By exiting a field where she had built up a considerable level of skill and experience, she threw it all away to start over at the bottom of the totem pole in the yoga practitioner space. Having only received 200 hours of yoga instruction before striking out on her own put her at the lowest spot on the food chain, where her skills were neither rare nor valuable. As a result, the number of people willing to pay for those limited skills were few and far between, as were her options for leveraging what limited skills she had.

Feuer’s main problem, according to author Cal Newport, was that she lacked what he refers to as career capital, which is the foundation upon which all extraordinary careers are built. Career capital is the accumulation of rare and valuable skills that you acquire over a lifetime of dedication to a craft. Only when you’ve acquired enough career capital can you trade it in for that rare and valuable dream job in return. This can take years, if not decades, to realize. But it’s the price of admission for something that so many people want yet so many aren’t willing or able to obtain.

Introducing The Craftsman Mindset

The key to acquiring the career capital you need to buy yourself into the fulfilling job at the top of the food chain that you’ve always dreamed of is by applying what’s known as the craftsman mindset to your work.

The term craftsman conjures the image of a weathered and experienced master of his craft, like an expert sword maker in Imperial Japan. This is someone who’s dedicated a lifetime of learning and practice to his craft to get to a point where he’s widely regarded as one of the best in the world at what he does–so much so that the Emperor himself commissions his work for his own personal collection.

When you read Joe Duffy’s story again, it’s immediately obvious that this is a clear-cut case of the craftsman mindset in action–only instead of making swords for the Emperor, he was crafting logos for the heavyweights of the business world. At every step along the way, Duffy focused on continuing to hone his skills and improving just a little bit every day until those improvements compounded into something massive over time. Eventually, he acquired enough career capital to buy his way into the life he wanted–running his own shop, making boatloads of money, and being recognized as one of the most respected and talented logo designers in the world.

Duffy recognized something important about the exchange of career capital for fulfilling work that perhaps Feuer did not: that on its own, simply summoning the courage to quit your job and follow your passion is neither rare nor valuable. While it’s true that many people dream about jettisoning their corporate handcuffs for the freedom of entrepreneurship yet most never do, that doesn’t make the act itself valuable for the simple reason that anyone could do it without much effort or skill.

Think about it: how much work and skill does it really take to put in your two weeks’ notice and leave your job? Not a whole lot. Contrast that with the level of skill and effort required to become the world’s best logo designer, a leading public speaker, a New York Times Bestselling author, etc. The former anyone could do; any of the latter would take years, if not decades, to accomplish.

(There is a right way and a wrong way to go about quitting your job, however. If you’re considering a similar move, don’t miss my post on how to put in your two weeks notice the right way).

So if you’ve been beating yourself up over the fact that you haven’t yet had the courage to take the leap that you’ve been wanting to, stop right there and ask yourself: Is this the right move you should be making? Have you acquired enough career capital to realistically exchange it for more rewarding work? If not, then you need to rethink your strategy for getting to where you want to go, because enthusiasm and courage alone won’t be enough to get you there.

Here’s What to Do Instead

I’ve got some good news and some bad news.

First, the good news: Practically anyone (yes, that means you!) can realistically obtain the level of career fulfillment and success that Joe Duffy did in his career.

Now, the bad news: Doing so is hard, and it takes time.

Ira Glass, host of the widely acclaimed podcast This American Life, strongly emphasizes how difficult it is to get to a place of notoriety. He didn’t just stumble into his spot as one of the leading podcast hosts in the country; it took years and years of effort and struggle. “The key thing is to force yourself through the work,” he says, “force the skills to come, that’s the hardest phase.”

Force the skills to come. Doesn’t sound very fun, does it?

Well, it’s not. It’s hard–really hard. And that’s what makes it rare and valuable. Most people aren’t willing to put themselves through the years of constant practice and dedication it takes to get to an elite level of performance, which is why those who are ultimately get rewarded for it. By separating themselves from the pack and refining their skills to a level where most are unwilling to go, they naturally find themselves on an elite playing field with few competitors–where the supply is low and the demand is high. And once you’re there, you can pretty much name your own price.

There’s a reason why most of the people who are considered the best in the world at what they do–Fortune 500 CEOs, chess grandmasters, concert pianists, logo designers–more often than not have years of experience behind them that they can point to as the catalyst for their place in the pecking order. Even those who are widely regarded as prodigies–thought to possess natural, even superhuman abilities at whatever it is they do well–are most often nothing more than the product of intense and dedicated practice.

Champion chess player Bobby Fisher trained for ten to twelve hours a day, six days a week. Kobe Bryant’s off season workouts consist of two hours of running, two hours of ball skills, and two hours of weightlifting. Oh, and he wakes up at 4 am every day. Famous composer Frederic Chopin would lock himself in a room with Johann Sebastian Bach for two weeks straight before a performance to attain his desired level of perfection.

The necessary ingredients for honing a world-class skill set that can be parlayed into a fulfilling and passionate career at the top of one’s field are universal and span the generations throughout human history. They were just as relevant hundreds of years ago when composers were producing master works as they will be hundreds of years from now, when a yet-to-be-born individual arrives at the top of a yet-to-be-formed area of expertise. Regardless of the era, the equation remains the same:

Deliberate practice + persistence + time = Success + passion

Notice that passion only comes after the addition of deliberate practice, persistence, and time, which brings up an important point: Passion for a particular area isn’t something you naturally have, it’s something that comes as a byproduct of mastery over that area and a well-defined personal mission that develops over time. The fact that it’s impossible to predict in advance what you’ll grow to love completely shatters the notion of “finding” your passion entirely.

In a world where you have infinite choice over what to pursue, the odds of finding that one thing you were naturally meant to do are infinitesimally small. And yet, there are millions of people around the world who are not only great at what they do, but who also love doing it.

Why? Because passion isn’t found, it’s earned–through the dedication to mastery and the relentless application of the equation outlined above.

Where the Craftsman Mindset Falls Short

While it’s true that you’ll eventually need to pick a field in which to accumulate your expertise, that doesn’t mean that you need to double down on something that clearly isn’t a fit for you. Continuing at plug away at something you hate isn’t a recipe for success, regardless of how good you become at it.

According to Cal Newport, there are three circumstances that should disqualify you from applying the craftsman mindset in order to accrue the career capital you need to build a career you love:

1- The job presents few opportunities to distinguish yourself by developing relevant skills that are rare and valuable

Examine your field for evidence of an elite level of mastery. Who’s at the top, and is that somewhere you’d like to get to? If there are few examples of standout successes, that may be an indication of a field where it’s simply not possible to grow one’s skills enough to warrant the type of career you’re likely hoping to grow into. In that case, you may want to pivot into something with a more clearly defined path.

2- The job focuses on something you think is useless or even actively bad for the world

Sure, you could gun for the spot of a top tobacco company executive, but is that something you really want to dedicate your life to? Think about the good you’re adding to the world–if you can’t get excited about your contribution to the well-being of society, then there’s probably something else you should be directing your attention towards.

3- The job forces you to work with people you really dislike

If you’re required to work with people you dislike, then you probably won’t stick around long enough to acquire the career capital you need to get to where you want to go. Successfully applying the craftsman mindset requires a positive environment in which to nurture it, and that won’t be true if you can’t stand the people surrounding you.

The key difference between the craftsman mindset and the passion mindset is that the craftsman mindset focuses on what you can offer the world, while the passion mindset focuses on what the world can offer you. The former forces you to become really darn good at what you do in order to produce something the world finds valuable. The latter seeks nirvana while having few things to offer in return–and this something for nothing exchange more often than not leads to big problems when applied in the real world, as Lisa Feuer found out the hard way.

If you remember one thing from this post, make it the fact that working right trumps finding the right work. People don’t necessarily come to love what they do, but how and why they do it. Intense dedication to a craft over a long period of time allows you to acquire the autonomy and control that naturally accompanies great work along with a life-transforming mission that can only transpire after years of honing your craft. So pick the what, and you’ll eventually fall in love with the how and why as you progress through the various stages of mastery.

And, eventually, you’ll get to a point that comedian Steve Martin describes as being “so good they can’t ignore you.” That’s when people start to take notice and when all your efforts begin paying off. But even then, you can’t take your foot off the gas because mastery is a lifelong effort. When you commit to something, commit to it over the long haul.

Stay focused, be patient, and one day you’ll wake up with all the passion you’ve ever hoped for.