Megan Hellerer is a career coach and founder of Coaching for Underfulfilled Overachievers. She has worked with hundreds of women, including Representative Alexandria Ocasio-Cortez, to transform their careers by challenging traditional boxes of success. Her work has been featured in New York, Vogue, The Wall Street Journal, CNBC, and The Times.
Below, Megan shares five key insights from her new book, Directional Living: A Transformational Guide to Fulfillment in Work and Life. Listen to the audio version—read by Megan herself—in the Next Big Idea App.
1. The traditional career approach is failing.
Work isn’t working. Recent studies show that engagement at work is at an 11-year low. Only 30 percent of U.S. workers feel engaged with their jobs, and only about 17 percent find their work to be a source of meaning. This is half of the reported rate from just four years earlier. On top of that, 84 percent report symptoms of burnout, and almost 50 percent of millennials report symptoms of depression or anxiety disorders. These are not metrics of success by anyone’s definition.
The result is an entire generation of people I call Underfulfilled Overachievers (UFOAs). UFOAs are people who checked all the boxes, did all the “right” things, often have resumes chock full of impressive accomplishments, and yet still find themselves unhappy, wondering, “is this really all there is?” UFOAs have great lives on paper but feel far from great inside. They’re living great lives; they’re not their lives.
I know because I was one. I graduated from Stanford at the top of my class, landed a dream job at Google, and dutifully climbed the corporate ladder, all with the expectation that if I worked hard enough, I’d be happy and fulfilled. Instead, I found myself miserable, clinically depressed, experiencing almost daily panic attacks, and totally at a loss about why I was feeling this way or what to do about it. So, I quit my job with no plan and made it my mission to figure out what I was doing wrong, convinced that there must be another way to build a career. The more I started sharing my story, the more I realized how widespread this problem is. Many of the smartest, most accomplished, creative, and talented people I knew had accumulated all the accomplishment and none of the fulfillment. This is a systemic problem.
2. Focus on the direction, not the destination.
We are all deeply unfulfilled because we were taught that achievement is the path to fulfillment. We were told that if we worked hard and made the “right” choices, we would be successful and have happy, secure lives. But most of us learned the hard way that this is a lie. Achievement does not inherently lead to fulfillment.
The Achievement Lie orients our entire lives to reaching destinations—the finish lines, the outcomes—regardless of what we must sacrifice to get there. We privilege results over all else, and our primary purpose becomes acquiring as many achievements as possible as quickly as possible. The degrees, awards, titles, and promotions matter more than our experience or the impact of the work. The thinking goes, “Who cares if the trip is miserable? It’ll all be worth it once I’ve arrived.” But when we arrive, we’re often shocked to find that we have no desire to be ‘there.’
This outcome-oriented, Destinational approach has been the dominant cultural paradigm for navigating life. But to live meaningful, fulfilling, purposeful lives, it’s time to divest from the belief that our “best life” is a destination waiting at the end of a sacred ten-year plan. Instead, we want to start living Directionally, where the focus is on moving iteratively, in our own personal right direction, without needing to know the precise destination. We’ve been trained to believe that we need a perfectly plotted life itinerary and a fully baked master plan to be happy, when all we truly need is a direction.
“Achievement does not inherently lead to fulfillment.”
A perfect analogy for this Directional approach comes from the late novelist, E. L. Doctorow: “[It’s] like driving a car at night. You can see only as far as your headlights, but you can make the whole trip that way.”
Focusing on your direction—just the headlights—would be deciding to take a constitutional law class because it feels interesting, without knowing exactly where it will lead. Taking a Destinational approach would be starting law school with a definition of “success”—say, being appointed to the Supreme Court one day—and then dedicating every decision thereafter to that sole pursuit. Living Directionally means that instead of trying, right out of college, to lock in the company and career from which you’d like to retire at sixty-five (destination), you simply select the next job role you’d like to experience right now (direction). Instead of trying to determine whether your date is The One (destination), you focus only on whether you want to go on a second date with them (direction). In fact, you stop trying to decide whether anything is The One—the house, the career, the crush, the business, the best friend. You instead decide only on your single next directionally right step. Focus on the headlights, knowing you can make the whole trip that way.
3. Forget your purpose; follow your curiosity.
One of the latest incarnations of the Destinational paradigm is the focus on finding “purpose,” but purpose isn’t some static, immutable destination that you need to predetermine before you begin living. Treating life purpose like a Destination freezes us. We stay stuck. We do nothing, while we stare at the wall, or a spreadsheet, trying to “figure it out.” This attempt to “find your purpose” holds a person back.
Purpose is a direction, not a destination. You don’t achieve purpose once and for all; you move toward it. The best proxy for our purpose is curiosity. Our curiosity is the equivalent of “just the headlights.” It’s not a distraction; it’s showing the path forward. Think of curiosity like hunger. As hunger is meant to tell you where the nourishment is, curiosity is meant to tell you where the fulfillment is.
When I worked with Congresswoman Alexandria Ocasio-Cortez when she was a bartender looking for purpose, we identified that her curiosity was leading her toward public service. We didn’t need to know exactly what role, or title, or even type of public service, we only needed to be able to identify the single next directionally right action in the overall direction of public service. Her curiosity led her to take a road trip to Flint, Michigan and to Standing Rock, fundraising and live-streaming along the way, “just because.”
This course of action didn’t fit neatly into some larger strategic career plan. There was no destinational life goal in mind. This is just what her headlights were showing her. It was on the very day that she returned home from this trip—which had demonstrated her advocacy and aptitude for communicating and connecting with people on political issues—that she got a call from the organization that would eventually sponsor her run for Congress.
4. Seek aligned ambition, not blind ambition.
Many UFOAs initially mistake their under-fulfillment problem for over-ambition but ambition itself is not the problem. Ambition is simply a desire to make an impact; it means placing a high value on contributing to the world. In fact, this is one of the greatest strengths of UFOAs.
Rather than get rid of ambition, trade the classic blind ambition for what I call aligned ambition. The problem with blind ambition is the lack of alignment—being divorced from our authentic needs and wants—on our path to achieving. Ambition without alignment feels empty. It doesn’t matter how amazing the accomplishment is; winning an Olympic gold medal will feel empty if it was driven by blind ambition instead of aligned ambition.
With blind ambition, we select destinations according to what has been deemed impressive and valuable by the collective. In other words, we’re outsourcing our trajectories and turning a blind eye to what matters to us personally. It takes the you-ness out of the equation and results in a success that is arbitrary and generic. This is how we end up with lives that don’t feel like ours. Being, or appearing, successful is a very different experience than feeling successful—that is, from achieving according to what is aligned for you.
“Where ambition comes from and why you are ambitious matters.”
Aligned ambition is inner-directed ambition versus externally-dictated ambition, that incorporates your personal, authentic preferences, talents, joys, curiosities and experiences to create a career and a life that is particular to you and no one else. Where ambition comes from and why you are ambitious matters. Did you inherit or absorb that aspiration, or did you generate it yourself? We want to be ambitious for the achievements and the success that are uniquely well-suited to us, because that’s where fulfillment lives, not to mention where we can have the greatest impact and contribution.
Working at Google was a version of success, but it did not feel like success for me. It didn’t matter how many promotions or bonuses or awards I got. For me, it was blind, generic success and was not aligned for me. Publishing a book and having a thriving coaching practice would be considered by many to be another version of success. However, my experience of these two versions of success is vastly different, where the latter is deeply fulfilling because it is aligned—it’s the work that I’m uniquely well-suited to do in the world.
5. Life is a game of “Warmer-Colder.”
Directional Living is like playing the children’s game of “Warmer-Colder” where one player hides an item and directs another player to find it by calling out “Warmer!” when they are getting closer to the hidden object or “Colder!” when they are headed farther away from the hidden object. At each juncture, you simply ask, “Is this warmer?” or “Is this colder?”—by which we mean more aligned and directionally right, or less? In other words, you move iteratively in the “warmer,” most aligned direction, without knowing exactly where you’re going to end up. So long as you’re getting “warmer” with each step, you’re doing it right.
The key component of this game, as in life, is moving iteratively. To navigate effectively, take an experimental approach of testing, learning, and acquiring new information to refine along the way. Don’t just sit in one spot and arbitrarily guess the game-winning destination. That would not only be less fun, but also a lot less efficient. The goal is to evolve and fine-tune over time by being alert and responsive to new inputs. The only way to fail is to refuse to iterate and adjust. When in doubt, take action, any action.
In the real world, this launch-and-iterate strategy becomes even more important because of constant change. It’s as if the original hidden object is constantly moving. What is “warmer” for you at age 25 is going to be different than at 35, 45, and 75. And what the world looks like and what’s possible and salient and impactful is going to be different 10, 20, and 50 years from now. The world is not static and fixed, and neither are we. We want to be able to evolve in response to our inner and outer world.
So long as we’re focusing on the direction, the destination—no matter how much it moves—is irrelevant. This is the paradox at the center of Directional Living: the less focus you give to the outcome, the more fulfilling the process and result will be. When we stop needing to predict exactly where we are going, opportunities emerge. When we interact with the world as it is, as opposed to how we expect it will be, new options that were once inconceivable to us present themselves. We can make the whole trip that way, individually and collectively.
To listen to the audio version read by author Megan Hellerer, download the Next Big Idea App today:
