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.
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]:
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.
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
In 1958, 20-year-old Hunter S. Thompson shared similar wisdom with his friend Logan Hume on finding your purpose.
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.”
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:
6. Remove external validation; focus on your curiosities
Jane Smiley, in Why We Write, shares why curiosity is essential for our careers, and why external validations must be recognized and removed:
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:
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]:
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:
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
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.
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):
How about you?
What career advice have you received that has helped you?