Chapter 1

Start Jumping Lily Pads

"Not all those who wander are lost."

-J. R. R. TOLKIEN

Taped above my desk is an article from the Onion with the headline "24-Year-Old Receives Sage Counsel from Venerable 27-Year-Old," and a picture of two twentysomethings in plaid shirts in deep existential conversation over pints of beer at a bar.

When I told my dad I was writing a career advice book, he looked at me like I was crazy and asked, "What qualifies you to be writing a book about careers? You've changed what you wanted to do with your life every other year since you were a kid."

My dad is absolutely right. I've never been able to focus on any one thing for very long, and I still have trouble answering the question "What do you want to be when you grow up?" At first, I wanted to be Big Bird, road-tripping around the country in Follow That Bird. Then I wanted to be Mister Rogers. Once, my family was staying at a hotel, and Fred Rogers was there having breakfast. I ran right up to him and exclaimed, "Excuse me, Mister Rogers, Mister Rogers! How did you get out of the TV?!"

When I was in fourth grade, I wanted to be a play-by-play announcer for the Olympics. In eighth grade, I wanted to be Adam Sandler. In high school, I wanted to be a sports writer. Then I went to a liberal arts college, which is to say I majored in film studies, studied abroad in Cuba, and took intro to dance senior year. Making career choices has proved difficult ever since.

After graduation, I could write a fifteen-page shot-by-shot analysis of David Lynch's Mulholland Drive and tell you the difference between cage-free, free-range, and pasture-raised eggs. But I realized that college had not prepared me for the job-finding process in the slightest. Since I had no idea which "career ladder" to climb, I moved to the city where all my friends were moving (Brooklyn), and got a job that matched my college major (film), which is what I thought I was supposed to do at the time.

In the ten years since graduation, I've had ten drastically different jobs, lived in six cities, and gone down four career paths. I've never once seen this elusive "career ladder" everyone talks about. But I do know that whoever invented the ladder has been freaking twentysomethings out for a long time.

Where do you get on the ladder? Is there one in each city in the world? If you hop off for a detour, do you have to start back from the bottom, or do you get to keep your place in line? Is there music along the way? Is it like Pandora-can I choose my station?

As insufferable as this ladder mind-set can be, twentysomethings are still unfailingly being told to maintain a linear career trajectory. Even my father, who was born in the 1950s, hasn't followed any sort of career path. He has worked in stage management and lighting design for off-off-Broadway shows, then for a rock 'n' roll theater start-up in London, dropped out of NYU's theater school, sailed across the Atlantic, joined Pink Floyd as a roadie doing lighting on their international tours, became disenchanted with life on the road and enrolled in architecture school, worked as an architect, raised kids, spent time in corporate real estate, got his MBA at the age of fifty-three, built dialysis clinics, and managed projects and workplace innovation for a large electronics company. Yet even he was skeptical when I told him I wasn't pursuing a "traditional" career path after college, and instead was headed to New York to freelance on film sets.

If you've struggled with picking a career path, or focusing on one interest or calling, then you're not alone. Only 27 percent of college graduates have a job related to their college major.

In high school and during college, I scooped ice cream at Ben & Jerry's, had a few stints as a barista, and among other things, worked at a garden shop, helping customers pick out shade perennials (pretending that I actually knew what a shade perennial was). To list all of my high school and college jobs would be overwhelming. Here's the eclectic array of jobs I've held since graduating from college.

My Wandering Journey

Age Job + Motivation

18 Student at Wesleyan University (Middletown, CT)

Make friends, protest George W. Bush, gain liberal arts education

22 Move back home with parents (Cambridge, MA)

Unemployed and broke

22 Freelance film location scout (Brooklyn, NY)

Live with best friends in Brooklyn, major in film, love movies

25 Film festival assistant (Buenos Aires, Argentina)

Live in Argentina, learn Spanish, travel

26 Obama 2008 campaign field organizer (Anderson, IN)

Join change movement, support gay marriage, keep John McCain from destroying the world

26 Waiter at Eatonville restaurant (Washington, DC)

Make money to pay rent, love food and people

27 Move back home with parents (Cambridge, MA)

Unemployed and broke

27 Special assistant at US Peace Corps (Washington, DC)

Believe in Peace Corps' mission to promote world peace and friendship

30 Freelance writer & Bold Academy director (San Francisco, CA)

Live in San Francisco, love to write, support social entrepreneurs

32 Author, speaker, and Hive Global Leaders Program facilitator (San Francisco, CA)

Empower millennials to have breakthroughs and find meaningful work

There are two mind-sets through which one could analyze my "career" up to this point. The first is what I'll call the career ladder mind-set, the one we've been taught to follow most of our lives. This mind-set tells us that the more AP classes we take, the better we do on our SATs, the better college we go to, the more money we make, the higher on the ladder we rise, the more successful we are.

Someone with this mind-set would look at my career and say, "This kid Smiley is a hot mess; he lived at his parents' house at the age of twenty-seven! He can't make up his mind. He won't stay in a job for more than two years. He'll never be successful because he's not on a specific career ladder. Think of where he could have been if he had spent the last eight years in film."

Although recent college graduates are often encouraged to adopt a career ladder mind-set, these career ladders have several essential flaws:

Career ladders limit new opportunities, experimentation, and risk taking. What happens if an amazing opportunity presents itself-say, to join the 2008 Obama campaign-and I want to get off the ladder, but I've already spent two years on a different career? Ladders encourage people to avoid new challenges in exchange for safety and "moving up." Avoiding these risks may mean avoiding the very opportunities that provide us the greatest satisfaction in life. If there isn't only one answer, there probably isn't one "top of the ladder," either.

Career ladders define success on someone else's terms. Career ladders lead to promotion potential and higher salary. The theory is, "Pay your dues early, and you'll reap the benefits later." I'm not a huge fan of delayed gratification in general-not many millennials are-but it's especially annoying when I don't even get to define what my gratification is or what success means to me. What happens if I'm not in it for a fancy job title or a big salary? What happens if success for me is not my retirement package at sixty-five, but one person realizing their life potential from a book I write?

Career ladders make me stress about the future, which inhibits me from taking action now. When I was thinking about leaving my job at the Peace Corps, one of the things I was interested in pursuing next was writing. Whenever I brought up the possibility of becoming a freelance writer, all I heard from people was, "Well, it's a hard career ladder to climb. You can't get a staff writing position at a major newspaper anymore. Newspapers don't even exist. The New Yorker receives one hundred thousand submissions an hour."

To some degree, the people warning me not to go into freelance writing at the age of twenty-eight were right: writing is extremely competitive, and it's the opposite of financially lucrative. But stressing about my future career as a writer and about where I'd end up ten or twenty years down the road nearly stopped me from even trying. I hadn't even written a blog post yet, and I was thinking about writing for The New Yorker. I was stressing about the future, instead of taking action now.

The best advice I got about starting a writing career was from my friend Ryan Goldberg, a freelance journalist who lives in Brooklyn and has numerous bylines in The New York Times. At the time we talked, Ryan was also refereeing dodgeball to supplement his income. He told me, "Smiley, if you want to be a writer, write. Start writing today."

Stop Climbing Ladders, Start Jumping Lily Pads

The other way of looking at my career is through what I'll call the lily pad career mind-set. My friend and career strategist Nathaniel Koloc sometimes describes careers as a series of lily pads, extending in all directions. Each lily pad is a job or opportunity that's available, and you can jump in any direction that makes sense for you, given your purpose (how you want to help the world). Nathaniel founded ReWork, a talent firm that places purpose-seeking professionals in social impact jobs, and then served as director of talent for Hillary Clinton's 2016 presidential campaign. He has made it his job to study how people build careers worth having.

Nathaniel says, "There is no clear way 'up' anymore-it's just a series of projects or jobs, one after another. You can move in any direction; the only question is how you're devising your strategy of where to move and where you can 'land,' i.e., what you're competitive for."

Leaping to another lily...