Adobe-full-color Adobe-white Adobe-black logo-white Adobe-full Adobe Behance arrow-down arrow-right LineCreated with Sketch. close-tablet-03 close-tablet-05 comment dropdown-close dropdown-open facebook instagram linkedin rss search share twitter

Career

The Career Compass: 10 Essential Ideas For Navigating the New Career Landscape

Actionable career insights from luminaries like Debbie Millman, Marissa Mayer, Hunter S. Thompson, and more.


The trajectory of our careers is one of the great manifestations and reflections of our inner potential, desires, and talents.  Our work history can read like the chapters of a book: Each page tells a story about our struggles, moments of luck, growth and change.

However, the changes in our culture and economy are authoring an entirely different kind of book, one that doesn’t follow the traditional storyline that our parents would be familiar with. The paths that we face today have more forks in the road that can lead us to unimaginable destinations. It is essential that we are flexible and adaptive.

Alas, with this flexibility creates more uncertainty, more fear, and more self-doubt. We can dance with this uncertainty by chasing our curiosities and harnessing new skills and knowledge. Indeed, self-education bullet-proofs your career not by making you safe and comfortable, but rather by putting you in a position to readily change your mind and see the world anew.

Below are some of my favorite perspectives and ideas on navigating your career from noted authors, researchers, and creatives. I share them not because these individuals lead flawless careers from beginning to end, but rather because they, like the rest of us, navigated a career path that was imperfect and non-linear. Their obstacles are surely all of our obstacles as we determine the unfolding of our destiny.

1. Know the difference between a job vs career vs calling

In Practical Wisdom by Barry Schwartz and Kenneth Sharpe, they share the work of psychologist Amy Wrzesniewski and her colleagues. For over two decades, her team studied aspects of work. People who viewed their work as a “job” felt minimal meaning, enjoyed the pay only as a necessity of life, and would switch immediately if they had the chance. People who viewed their work as a “career” were more engaged, enjoyed what they did, but at their core they desired promotions, higher salaries, and more responsibilities.

People who viewed their work as a “calling” were most satisfied. Work wasn’t separate from life—it was profoundly a part of their identity as much as their daily activities.

Work wasn’t separate from life—it was profoundly a part of their identity as much as their daily activities.

Schwartz and Sharpe share an observation Wrzesniewski made when she studies administrative assistants working at a college. Each, technically, had the same exact job with the same exact tasks. But some thought of their job as a “calling.” From Practical Wisdom: [emphasis mine]:

“To some degree, the differences are explained by the attitudes these people brought to their work—who they were, not what the work was. But to a large degree, Wrzesniewski found that their attitude toward work depended on how their seemingly similar work was organized and integrated into the mission of the larger units of which they were a part. If the workers had a sense of organizational purpose, and it was a purpose they could be proud to contribute to, if they had a sense of partnership, and if they had a fair degree of discretion and control, they were more likely to view what they did as a calling.

[…]

There’s a virtuous circle here. We are happiest when our work is meaningful and gives us the discretion to use our judgment. The discretion allows us to develop the wisdom to exercise the judgment we need to do that work well. We’re motivated to develop the judgment to do that work well because it enables us to serve others. And it makes us happy to do so.”

This is not only fantastic leadership advice to grant those on your team as much agency as possible, but a chance to reflect where on the job, career, calling axis you’re currently on right now.

2. When lost, methodically define your disposition

I’ve had the great luck of only having four dead-end jobs, and none of them were a waste: each one was an indicator of what I didn’t want to do. Each job made me realize that I didn’t possess a disposition for that field. Why does it matter?

Author Robert Greene calls this trial and error process your “Life’s Task.” In his book Mastery, he studied masters in many kinds of domains and connected the dots on how they lead such remarkable lives. He guides us with a framework of three steps.

The first step is about reconnecting with your inclinations. As artist James Victore says, “The things that made you weird as a kid—make you great today.”

Greene said: “You clear away the other voices that might confuse you—parents and peers. You look for an underlying pattern, a core to your character that you must understand as deeply as possible.”

Once you have self-awareness for those defining traits, the second step is to look at the career path you’re on or about to begin. Does this path champion those traits or hinder them entirely? Does it represent the values that you wish to uphold?

Greene adds: “To help in this stage you will need to enlarge your concept of work itself. Too often we make a separation in our lives—there is work and there is life outside work, where we find real pleasure and fulfillment. Work is often seen as a means for making money so we can enjoy that second life we lead. Even if we derive some satisfaction from our careers we still tend to compartmentalize our lives this way. This is a depressing attitude, because in the end we spend a substantial part of our waking life at work.”

Lastly, it’s helpful to remove the notion that the career path you’re on is a lifelong ride. It’s not to say it’s impossible—Michael Bierut worked at a firm for 20 years (!!)—however, it’s not likely.

It’s helpful to remove the notion that the career path you’re on is a lifelong ride.

Greene said: “You begin by choosing a field or position that roughly corresponds to your inclinations. This initial position offers you room to maneuver and important skills to learn. You don’t want to start with something too lofty, too ambitious—you need to make a living and establish some confidence. Once on this path you discover certain side routes that attract you, while other aspects of this field leave you cold. You adjust and perhaps move to a related field, continuing to learn more about yourself, but always expanding off your skill base.”

We hesitate at the idea that we used to draw or play an instrument or loved numbers. We wave it off as childish and unpromising as a career, never considering how powerful these inclinations are in manifesting our talents and a potentially great life. Often times, when you hear stories of people making drastic career changes, it usually falls into this category of returning to their inclinations and bringing them back to life.

3. Seek enjoyment in the process, not the outcome

Hunter S. Thompson

Hunter S. Thompson

In 1958, 20-year-old Hunter S. Thompson shared similar wisdom with his friend Logan Hume on finding your purpose.

“As I see it then, the formula runs something like this: a man must choose a path which will let his ABILITIES function at maximum efficiency toward the gratification of his DESIRES. In doing this, he is fulfilling a need (giving himself identity by functioning in a set pattern toward a set goal) he avoids frustrating his potential (choosing a path which puts no limit on his self-development), and he avoids the terror of seeing his goal wilt or lose its charm as he draws closer to it (rather than bending himself to meet the demands of that which he seeks, he has bent his goal to conform to his own abilities and desires).

In short, he has not dedicated his life to reaching a pre-defined goal, but he has rather chosen a way of life he KNOWS he will enjoy. The goal is absolutely secondary: it is the functioning toward the goal which is important. And it seems almost ridiculous to say that a man MUST function in a pattern of his own choosing; for to let another man define your own goals is to give up one of the most meaningful aspects of life — the definitive act of will which makes a man an individual.”

(Full letter found in Letters of Note / Brain Pickings)

4. Great careers can be non-linear (and most are)

At the end of undergrad school, Elle Luna applied to nine law schools—and didn’t get accepted to any of them. She then applied to RISD and The Art Institute of Chicago, got accepted to both, and went to Chicago. She started a three-year MFA program in film but halfway through switched to design, earning her degree in conceptual storytelling. 

Weeks after graduating, she searched for jobs. With great timing, she saw an ad from IDEO looking for a storyteller. She applied, was hired, and worked there for five years. She transferred to the San Francisco office and worked there for a few years, until she transitioned again, but this time it would be out of her dream job and into the unknown. 

She enjoyed the idea of empowering startups, so she joined the Mailbox team to redesign email and also had a three-week stint with Uber redesigning their logo, rating system, and app. After Mailbox, she joined Medium to help scale their platform. During all of this, she was also painting. 

Ella Luna shares in this interview with The Great Discontent: “It got to the point where I had one foot in the painting world and one in the startup world, and everyone was losing. I couldn’t fully immerse myself in my paintings to give them what they needed and I couldn’t give my startup work the attention it needed. So I dove into painting full-time. I had no idea what I was doing, but I knew I was on the right path, and that feeling only intensifies with each day.”

Now, she paints full time and just recently published a book called The Crossroads of Should and Must. From a big company like IDEO to joining small startups that became big, to full-time painting and then writing a book, who knows what the next chapter holds. What does hold and remain a constant are her values like creativity and a deep-seated desire to tell a story (see her Do Lectures talk below). 

5. Seek to be indispensable 

Your primary goal—if you have passion, if you desire greatness, if you want to make a difference—is to become indispensable. Being indispensable is about being valuable to an organization or mission. To become valuable is about doing more than the bare minimum; you will never catch an indispensable person saying, “This isn’t part of my job description.”  

Seth Godin said in Linchpin:

“If your organization wanted to replace you with someone far better at your job than you, what would they look for? I think it’s unlikely that they’d seek out someone willing to work more hours, or someone with more industry experience, or someone who could score better on a standardized test. No, the competitive advantage the marketplace demands is someone more human, connected, and mature. Someone with passion and energy, capable of seeing things as they are and negotiating multiple priorities as she makes useful decisions without angst. Flexible in the face of change, resilient in the face of confusion. All of these attributes are choices, not talents, and all of them are available to you.”

6. Remove external validation; focus on your curiosities

 

Jane Smiley

Jane Smiley

Jane Smiley, in Why We Write, shares why curiosity is essential for our careers, and why external validations must be recognized and removed:

“I’ve had some rewards. Rewards are fantasies. You can’t wish for an award. You cannot say, ‘My career will finally be worth it if I win the Nobel Prize.’ That’s false consciousness. If your career wasn’t worth it while you were writing those books, then what a sad life you’ve led. For me, it goes back to curiosity. I suppose my career will be over when I look around and say, ‘This is all boring; there’s nothing more that interests me.’ You want your interests to outrun your actual days on earth.”

We want people to acknowledge our hard work and efforts. After all, it’s easy to say that we shouldn’t chase awards or money. But without this affirmation, how do we know if we’re heading in the right direction?

Maria Popova, editor and creator of Brain Pickings, shared her approach when writing about the 7 lessons learned in 7 years of reading, writing, and living for Brain Pickings:

“Do nothing for prestige or status or money or approval alone. As Paul Graham observed, “prestige is like a powerful magnet that warps even your beliefs about what you enjoy. It causes you to work not on what you like, but what you’d like to like.” Those extrinsic motivators are fine and can feel life-affirming in the moment, but they ultimately don’t make it thrilling to get up in the morning and gratifying to go to sleep at night—and, in fact, they can often distract and detract from the things that do offer those deeper rewards.”

7. Work hard to be lucky

It would be incomplete to talk about careers and not talk about luck. As the pioneering psychologist Mihaly Csikszentmihalyi said in his timeless book, Creativity: The Psychology of Discovery and Invention, where he interviewed 91 eminent artists, scientists, and writers, he concludes, “Entering a career requires a great deal of determination and a good dose of luck. In fact, the majority of the people we interviewed mentioned luck most frequently as the reason they had been successful.”

What about our persistence and hard work?

Debbie Millman, in How To Think Like a Great Graphic Designer, interviewed Carin Goldberg on her illustrious career. Goldberg shares a story about how she used to go fishing with her father. Sometimes there would be big pockets of flounder, and sometimes there weren’t. She compares this moment to her career [emphasis mine]:

“And that’s how I think of my career. I hit some flounder holes. I hit the record business at a time when flounders were there for me. I hit the book business at a time when flounders were there for me.

[…]

I was very lucky to find these flounder holes, these moments of utter fertility. I was lucky. Lucky to be there, while it was all happening. But after the luck, there was all the hard work. That’s the part that makes me just absolutely livid, when I hear men talking about women and their careers. In my own career, I had to be as tenacious as a dog with a bone.

I made sure I was observing and watching and looking over the shoulders of the right people and learning from them and killing myself to learn everything I could. So my career has been about luck and hard work.”

8. Seek perspectives outside of your normal circle

Cognitive scientist and author Alexandra Horowitz recorded her walks with different experts around her neighborhood. From artists to geologists to her dog, she realized how much of the world she was missing, and by embracing the lens of the experts she walked with, the familiar soon became unfamiliar.

She says about expertise in On Looking: 11 Walks With Expert Eyes:

“There is a certain bias in everyone’s perspective that has been named, by the French, déformation professionnelle: the tendency to look at every context from the point of view of one’s profession. The psychiatrist sees symptoms of diagnosable conditions in everyone from the grocery checkout cashier to his spouse; the economist views the simple buying of a cup of coffee as an example of a macroeconomic phenomenon.”

In order to truly refine our craft, to expand and stretch it beyond its confinements, we must learn and try a new skill. As a writer, you can start painting; or as a painter, you can start writing. Learning new skills and seeing the world through the lens of an architect or biologist or scientist enriches our senses and ignites new ideas and points of view.

9. If given the opportunity, play with varsity

Marissa Mayer

Marissa Mayer

According to Business Insider, in her last year at Stanford, Yahoo CEO Marissa Mayer sat at her computer reading emails. She had 12 job offers and didn’t seek any more. When a recruiter’s email fell into her inbox, she meant to hit delete, but accidentally hit the spacebar instead. The subject line read, “Work at Google?”

She read the email and remembered a conversation she had with her mentor Eric Roberts. Based on her talk about a recommendation engine that she had built, Roberts recommend Mayer to pair up with two Ph.D. students who were working on something similar. Guess who they were: Sergey Brin and Larry Page.

Mayer knew that Google was their startup, so she asked her mentor for an interview. She got one and met with engineer Craig Silverstein and realized that he was a varsity player. Google offered her a job.

Mayer crunched the data and realized that Google only had a two percent chance of succeeding. When people asked her about the decision to join Google, she tells the “Laura Beckman” story about the daughter of her middle school piano teacher.

Mayer said:

“Laura tried out for the volleyball team her junior year at high school. At the end of the tryouts, she was given a hard choice: bench on varsity, or start on JV.

Most people, when they’re faced with this choice, would choose to play — and they’ll pick JV. Laura did the opposite. She chose varsity, and she benched the whole season.

But then an amazing thing happened. Senior year she tried out and she made varsity as a starter, and all the JV starters from the previous year benched their whole senior year.

I remember asking her: ‘How did you know to choose varsity?’ And she said, ‘I just knew that if I got to practice with the better players every day, I would become a much better player, even if I didn’t get to play in any of the games.’”

If given the opportunity, learn directly from experienced peers who are playing at the level that you want to someday play. It’s the equivalent of “dressing for the role you want, not the role you have.” Put yourself in a position to observe the rules, the environment, and people. You, in turn, will be challenged to learn and grow at a rate that would be incomparable elsewhere. You’ll also get all the chance collisions that eventually make for opportunity.

10. Cultivate patience, and enjoy the ride

One of the truest, if not most difficult, pieces of advice worthy of embracing is that anything worthwhile will take a long time. Five years, ten years—Who knows how long it’ll take for you to find your center, your tribe, your voice? There will be moments where you question if you’re on the right path, and then there will be moments where you cannot look back because the new views are better than before.

One piece of wisdom that I constantly return to is from Debbie Millman’s commencement speech to the graduating class of San Jose State University in 2013 (audio below):

“I recommend the following course of action for those, like you, who are just starting out, or who, like me, may be re-configuring midway through. Heed the words of Robert Frost. Start with a big fat lump in your throat. Start with a profound sense of wrong, a deep homesickness, a crazy lovesickness, and run with it. If you imagine less, less will be what you undoubtedly deserve. Do what you love. And don’t stop until you get what you love. Work as hard as you can. Imagine immensities. Don’t compromise and don’t waste time. In order to strive for a remarkable life, you have to decide that you want one. Start now. Not twenty years from now. Not thirty years from now. Not two weeks from now. Now.”

— 

How about you?

What career advice have you received that has helped you?

Paul Jun

Paul Jun is a writer and author. His latest book, Connect the Dots: Strategies and Meditations on Self-education, is available. His blog, Motivated Mastery, is where he connects the dots between subjects like mastery, philosophy, psychology, culture, self-awareness, and more.

Comments (11)
  • MierD. Luffy

    Great piece. I have also dropped out of college to do a totally different course. Looking forward to what’s coming

  • JJ Wong

    Amazing article Paul thank you for your insights and for conveying such valuable to-the-punch dopeness. Respect and best of luck on your endeavours!

    -JJ

  • Angelica Sereda

    Love #3.

  • Nobuko Aiso

    I have read some of your other articles but this one was particularly insightful and inspiring! So insightful that I am introducing this on a Japanese site (I have already requested permission from 99U, so no worries) that I write for. Please do keep on posting more inspirational articles!

    • Paul Jun

      Great to hear!

  • tseib

    Good article once again. However, on point #9 I think it’s fair to ask “Is varsity where I really want to play?” before just jumping on the court with them when the opportunity arises. I noticed early on that varsity often dominates in the office but fails in the realms of relationships, health, and integrity. There’s no doubt you can learn a lot about a profession or field from the best of the best, but make sure you examine and accept the tradeoffs they often make in the personal realm of their lives, because emulating them will likely lead to many of the same outcomes.

  • http://blog.theadamthomas.com Adam Thomas

    Thanks Paul,

    2 Things that struck me –

    You have to enjoy the ride – you don’t last long enough, or are curious enough, to become a true master if you don’t learn to sit back and work without the crowd.

    Work with the best – Working with the best will make you better. Big fish in small ponds are stuck. Small fish in big ponds find a bunch of opportunity.

  • http://www.skyboxcreative.com/ Angelina Sereno

    Wow, wow, wow… that video! I’m blown away. Thank you for this amazing article! 🙂

    • hansy

      Ethan►✈☃☛❖

      < Lots of good stuff here. People especially need to understand controlling fat is good

      but when you eat a fat free item alone your brain gets zero signals that you ate

      anything so you remain ravenous and either eat too much of the item or go on to eat

      something else. Get this absolutely FREE now http://••►► See more info here/2…

      ✔❖☃☛❖✌✔❖☃☛❖✌✔✔✔❖

    • accua

      COOK✔❖☃☛❖

      < Most over eating is due to STRESS. People will eat when they are nervous, worried, sad, depressed, anxious,

      scared, etc.This is a very common problem facing our society and there is a simple solution. Manage your

      stress. One easy way to lose weight quickly without actually doing ANYTHING physical or to your diet,

      decrease your stress levels. It's really FREE for all http://••►►SEE MORE INFO HREE ••►►/new…

      ???????????????????????

blog comments powered by Disqus

More articles on Career

illustration by eron hare design awards
Farai Chideya