· Chapter One ·

DEFINE YOUR SUCCESS

This is the beginning of anything you want . . .

—ANONYMOUS

Our earliest ideas of success come from others. It starts at home with what our parents and family think and then continues at school and work with what behaviors our teachers and bosses reward. We respond to these early influences by internalizing the versions of success we see around us. If we let them, these external versions of success can overwhelm our own visions, causing us to follow the well-worn path to a life that we might not want to live.

Brenna was leading a typical life of an MBA student. She was in her third year working at a Fortune 500 company in a job that made her feel trapped. She enrolled in the MBA program even though she preferred on-the-job learning to the classroom. And she was living at home with her parents in the suburbs, which she found dull, in order to pay down her student loans. She was pursuing a path based on external markers of success rather than her own vision and goals.

Brenna was my student, and after finishing my course (which was the first in her MBA program), she quit her job, dropped out of the MBA program, and moved into the city. When I caught up with her about a year later, she was working for a well-funded startup in a challenging role that aligned with her long-term interests, she was enjoying the convenience and ease of urban living, and she was engaged to be married. She still had not re-enrolled in the MBA program and wasn’t sure if she ever would. Brenna had stopped living the life others expected her to and started following her own interests and desires. She created her own vision of her success.

If we don’t take the time to reflect on what success means to us and what our version of it is, we can all too easily fall into living a life based on the priorities of others: how much time our boss thinks we should spend in the office, what our parents want us to study, and what career will impress our friends. If we haven’t taken the time to reflect and be intentional about our priorities, we risk making decisions that deviate from what we truly want. We end up taking that lucrative job that requires a ton of travel when what we really want is time to connect and contribute to our family and friends at home. We work too much and too long, even though we say we want to prioritize raising our kids, training for the marathon, or hanging out with our aging parents.

To define success for ourselves, we must turn away from the external and cultural versions of success around us. Only when we quiet the peer, parental, academic, corporate, and social voices telling us what we “should” want and what we’re “supposed” to do can we listen for our own internal desires and dreams. And only by listening carefully can we start to see what our version of success looks like.

Jessica Fox, a former storyteller at NASA and author of Three Things You Need to Know About Rockets, recommends a process that she uses to tap into her own thoughts and dreams called “playtime” (she reveals the interesting outcomes of this process in her book).¹ She describes playtime like this:

There should be a time of day, every day, when you’re alone, when you put your phone down and, to quote my favorite author, Joseph Campbell, “simply experience and bring forth what you are and what you might be.”² How you do that doesn’t matter. You can just sit there and stare out a window, you can sketch, or you can see what images or words come up, and write them down. The point is simply to get in touch with your own thoughts. Something within that mire of ideas that comes out will be a seed or a germ that’s incredibly important to you, that you wouldn’t have had time to listen to unless you did this kind of exercise. Or something will come forth that’s been in you but you’re not listening to it. Sometimes you’ll notice a pattern, something coming up over and over again. Pay attention to that. There’s no need to create anything out of this, this is a time of creative incubation. You just see what happens.

Try taking some playtime, and then completing the exercise below.

The New American Dream

Our American version of success has historically been tied to our vision of the American Dream: the house, the car, the 2.3 kids, and the leisurely retirement at the end. Yet there’s some evidence that this image is changing. MetLife conducted 1,000 interviews for its Study of the American Dream and concluded, “Americans are less concerned with material issues, and that life’s traditional markers of success—getting married, buying a house, having a family, building wealth—do not matter as much today. Rather, achieving a sense of personal fulfillment is more important toward realizing the American Dream than accumulating material wealth.”³

The Center for a New American Dream survey of nearly 2,000 Americans reached a similar conclusion.⁴ Their respondents named personal freedom, security, achieving personal potential, and having free time to enjoy life as their top answers to the question of what their particular version of the American Dream looked like. We’re seeing a new version of success taking hold that is more focused on personal priorities. It’s less about square feet in our home(s), the car(s) in the driveway, and dollar(s) in the bank and more about experiences, relationships, and personal fulfillment.

Research on what leads to a happy and meaningful life suggests that modifying the traditional American Dream to focus more internally and on personal fulfillment is a step in the right direction. Tim Kasser, a professor and the author of The High Price of Materialism, analyzed a decade of empirical data on materialism and its effect on our well-being. His research shows that focusing our lives on material pursuits breeds anxiety, isolation, and alienation. He found that placing a high value on material goods is associated with insecurity and lower levels of social and empathetic behavior. His research results suggest that organizing a life around our intrinsic values is the best way to increase our sense of well-being.⁵

The emergence of “digital nomads” is one example of this new, less-materialistic version of success. Digital nomads use technology to work, live, play, and travel when they want, from where they want. Freed from commuting, cubicles, the suburbs, and the status quo, they build geographically flexible lives around the places they want to be. It’s the antithesis of the traditional life centered on an office building, a mortgage, and a commute between the two. Unconcerned with what “everyone” thinks they “should” do, digital nomads are creating lives defined by their own version of success and working according to their own rules.

Harness the Power of Hindsight

Hindsight is a useful tool for reflecting on our life choices and how we might make them differently going forward. The Harvard Study of Adult Development, started 75 years ago, has been following a group of 724 men throughout their lives. The study uses hindsight to help us understand what has mattered over the course of its subjects’ lives. Its biggest finding was:

. . . many of our men, when they were starting out as young adults really believed that fame and wealth and high achievement were what they needed to go after to have a good life. But over and over, over these 75 years, our study has shown that the people who fared the best were the people who leaned in to relationships, with family, with friends, with community.⁶

In the end, money and career success didn’t correlate to greater happiness or meaning—only relationships mattered.

With similar results, hospice nurse Bronnie Ware summarized the regrets she heard most frequently from people at the ends of their lives. She found that people were most disappointed about their failure to prioritize internal priorities over external markers of success: “I wish I’d had the courage to live a life that was true to myself, not what others expected of me” was the most common regret.⁷

If only we had the foresight of our hindsight, we could make better decisions. In the absence of that, these three thought experiments attempt to harness the power of hindsight to home in on our internal vision of success.

Defining our vision of success is not a one-time exercise. It’s one we should revisit routinely throughout our lives. We’re usually in our teens and early 20s when our first vision of our adult life starts to form. It’s then that we start building a life around what success looks like and map out a plan for our future: Law school! A 10-year slog to partner at the firm! A big house! A family and a dog! Then, 20 years later, we’ve made partner, hold the title and the degree, and live in a five-bedroom house with our family and the requisite dog but feel dissatisfied, unhappy, and unfulfilled. “Is this all there is?” we wonder. We’re in our 40s and on the verge of a midlife crisis because we’re living with decisions we made two decades ago, when we had different values and experiences to draw upon. We never stopped along the way to check in, reflect, reconsider our choices, and make changes to our vision.

How do we avoid this trap and, hopefully, the crisis? Richard Shell, a professor at the Wharton School of Business at the University of Pennsylvania, advocates that we take “pit stops” along the way to accomplishing our goals in order to evaluate our priorities and our varying definitions of success.¹¹ This means that we need to check in, reflect, and recalibrate regularly. We should—both on our own and then together with a partner or close friend—stop to reflect and update our definition and go back through this chapter to review and respond to the list of questions again. Our answers are likely to have changed, and, if so, we’ll need to course correct.

These “pit stops” should be frequent because research shows that we are very poor predictors of what our future selves will enjoy, be happy about, and find meaningful. Daniel Gilbert, a professor of psychology at Harvard University, has found through his research that we are poor predictors of how our future selves will feel in any given situation.¹² When we imagine what might make us happy or fulfilled or how we might feel in different circumstances, we’re mostly wrong. Gilbert found that one of the best ways to figure out what we like, what we enjoy, and what makes us happy is to observe and ask others who are already doing it.

This process of observing and asking people who are already in the situation we’re contemplating is called surrogation. It sounds incredibly simple, but Gilbert’s research shows that just asking other people about their experiences doing the thing we want to do improves our ability to predict our future experiences by 30 to 60 percent over our own reflection, research, and contemplation. The reason surrogation works is because we all share a common and broad base of likes, preferences, and reactions to events. As Gilbert notes, “Everybody prefers a weekend in Paris to being hit over the head with a two-by-four.”

Surrogation can help us define and refine a vision of success that is most likely to be fulfilling. By identifying people who have achieved our version of success, we also give ourselves role models and a possible path we can follow to achieve our vision. We likely already know or are aware of people who we think are successful. Consider who they are and what they’ve done that makes them successful in your mind.

Success Is Contagious

While we’re looking in our networks for successful people, it’s a good time to also take stock of the people closest to us and who we spend the most time with. Nicholas Christakis and James Fowler, professors at Harvard, spent significant time mapping the social connections of the 50-year-long Framingham Heart Study, which has followed more than 15,000 people over the course of their lives. The study offers evidence that behaviors and attitudes spread socially among groups of friends and even friends of friends. They called this phenomenon “social contagion” and found that smoking, drinking, obesity, happiness, and even loneliness appeared to spread socially. They also document how creativity, wealth, political views, violent tendencies, and happiness spread through social networks.¹³ The authors concluded that we’re influenced not just by the attitudes, feelings, and behaviors of our immediate circle of friends but also by people within three degrees of separation from us (i.e., our friends’ friends’ friends).

Jim Rohn, a personal development expert, famously noted that we become the average of the five people we spend the most time with.¹⁴ Stop and consider for a moment who your five people are. Do they reflect your vision of who you want to become?

Rohn’s theory also reflects the idea that we’re heavily influenced, whether we realize it or not, by the behaviors, thinking, and attitudes of the people closest to us. The lesson is, if we want to achieve our vision of success, it helps to surround ourselves with people whose priorities and vision are aligned with ours (we’ll talk more about how to intentionally connect with others in chapter 4). We might define our version of success, but the people closest to us play an important role in helping us achieve it.

The Timeline of Success

The time frame we set to realize our goals influences whether we achieve our vision of success. We might not be able to start our own small business and write our debut novel next year, but we can probably accomplish one, or even both, during the next five years. Nigel Marsh illustrated this concept best during his popular TED talk “How to Make Work-Life Balance Work.”¹⁵ He emphasized the importance of selecting the right time horizon for evaluating whether we achieve work/life balance. He noted that “a day is too short; ‘after I retire’ is too long. There’s got to be a middle way.”

Marsh’s point is that the time frame we pick to accomplish our goals can impact whether we achieve them or not. In his example, we might not be able to achieve work/life balance on a particular day, but if we extend the time frame to a month or to a year, we’re more likely to be successful. The same concept applies to achieving our version of success.

Time horizons can help us better allocate all of our resources—our time, energy, attention, and money—to achieve our goals. We have to beware of our natural tendency to over-allocate our resources to short-term activities that offer immediate rewards instead of to our long-term goals and priorities. Clayton Christensen offers the most compelling illustration of the consequences of overinvesting in the short term. In his Harvard Business Review article “How Will You Measure Your Life?” he describes how, more than 30 years after graduation, many of his classmates have ended up “unhappy, divorced, and alienated from their children” even though none of them set out to do so. Too many of them spent too much time on short-term wins in the workplace and not enough time investing in the longer-term, harder-to-measure rewards on the home front. Christensen asserts that our overinvestment and over-allocation of time and energy to short-term goals puts our longer-term goals at risk. To overcome this tendency, we need to keep our long-term goals “front and center” and consciously allocate our resources to them.¹⁶

Why Is It Either/Or?

Time horizons are also powerful because they can help us avoid false dichotomies—choices that look like either/or decisions in the short term but are really and decisions within a more generous time frame. For example, if I’m a self-employed consultant, I might find myself deciding whether I want to either spend the summer off with my kids or work during the summer to achieve my financial goals for the year. In the short term, the choice is either/or. But if I extend the time horizon and plan to spend next summer off at the beach, I can use the year in between to save money, take on additional clients to generate more revenue, and give advance notice to existing clients that I’ll be taking off next summer. By allowing myself the additional time to plan and execute those three steps, I can do both—spend the summer on the beach and achieve my financial targets for the year. We can accomplish more of our biggest and most meaningful goals if we give ourselves the right amount of time.

This question of either/or versus and isn’t a concept that applies only to time horizons. It’s a framework that is useful to challenge our assumption anytime we’re faced with any choice. It forces us to examine more closely if any given choice is real or false. Let’s consider the most common dichotomy: Should I do what I’m passionate about or what makes me money? Rather than operate within this limited choice, why not consider doing what you’re passionate about during the day, as your primary activity, and take on a side gig that makes you money? Or vice versa: Work during the day and find your passion during non-work hours. By questioning why it is an either/or decision, we can challenge our assumptions and, in many cases, find a better and more satisfying and option.

Adopt an Opportunity Mindset

Succeeding in the Gig Economy requires us to work in different ways—not always as full-time employees—and to think about work differently by shifting from an Employee Mindset to an Opportunity Mindset.

The worker with the Employee Mindset seeks to answer: What job can I get?

The worker with the Opportunity Mindset seeks to answer: What work can I do, and what value can I bring?

A worker with an Employee Mindset wants, or even expects, an employer to organize, structure, and present a preconstructed job with a ladder to climb, and a predefined version of success at the top: the corner office, the title, the big salary. Workers with Employee Mindsets largely delegate their sense of security, financial stability, and professional development to their employers. They rely on their employer to help them realize success and achieve financial security. The Employee Mindset is relatively passive in nature and counts on an employer to organize and provide a predefined job with prepackaged benefits.

This mindset has persisted in part because companies were once willing lifetime stewards of an employee’s career trajectory and financial security. Companies used to offer long-term secure jobs, regular promotions, raises, and benefit increases tied to seniority. They also rewarded workers with guaranteed pensions and healthcare benefits during their retirement. It was reasonable to rely on employers because they were reliable. Now that companies make no promises or guarantees, offer no sense of security, and increasingly avoid hiring full-time employees, maintaining the Employee Mindset is unrealistic and highly risky.

A less-risky approach to succeeding in the Gig Economy is to transition to the more proactive Opportunity Mindset. Workers with Opportunity Mindsets see themselves as active creators, builders, and architects of their own career trajectories, not the recipients of them. They accept and expect to generate their own customized version of security, stability, and identity that is separate from any one company or organization. They create their own visions of success and work to achieve it.

An Opportunity-Minded worker actively connects with others, learns new skills, and seeks out new experiences. Even when working as full-time employees, those with Opportunity Mindsets think more strategically about what skills, experiences, networks, references, and knowledge their current job can offer to position them for a better future. They try to determine what they can achieve and learn in their current role that is transferable for their next one. The Opportunity Mindset requires more effort than the Employee Mindset but is a much less risky one to adopt.

YOUR DEFINITION OF SUCCESS IS
THE NEW AMERICAN DREAM

Greater flexibility in the way that people can work, as a contractor or freelancer or in traditional full-time jobs, is increasing our options and augmenting our choices about what success looks like and how to achieve it, allowing us to dream and creatively build our lives around our priorities and values. There are many versions of the new American Dream and what success looks like. In the Gig Economy, we are each more free to pursue our own.

As you think about defining your own version of success, consider:

How can I better define and refine my own version of success?

Do I surround myself with people whose vision of success is aligned with mine?

Have I selected the right time horizon for achieving success?

Have I adopted an Opportunity Mindset?