A More Beautiful Question (31 page)

“The things we loved at age six or eight are probably still the things we love,” says Maisel. He suggests drawing up a list of favorite activities and interests from childhood—“and see what still resonates with you today. And then it’s a process of updating those loves. You may have loved something that doesn’t even exist now, or doesn’t make sense in your life now—but you may be able to find a new version of that.”

This needn’t be limited to childhood. Belic looked back at his young-adult years to rediscover the importance of surfing with friends. He was inspired by an even more recent experience when he decided to try to re-create that sense of community he had experienced in his travels for the film.

Jacqueline Novogratz has her own spin
²⁴
on this concept, phrased in the question
What are you doing when you feel most beautiful?
In her travels for the Acumen Fund, she sometimes asks her question in unlikely settings: “I decided to try it out on women living in a slum in Bombay.” At first, it didn’t go over well: “One woman said, ‘There’s nothing in our lives that’s beautiful.’ But finally another woman, who worked as a gardener, said, ‘Well, I can think of one time. All winter long I slog and slog, but when those flowers push through the ground, I feel beautiful.’”

Novogratz maintains, “It’s important to think about that time and place and activity where you shine, where you feel most alive. I get all kinds of different answers—when I’m solving a problem, when I’m creating, when I’m connecting with someone, when I’m traveling.” Whatever it is, Novogratz says, you need to identify it and appreciate it—and if possible, find a way to do more of it.

Sometimes we’re not aware of the things we’re meant to do, the things we’re good at—which is another reason it’s important to step back and look at one’s activities and behaviors from a detached, inquisitive perspective. “Ask yourself,
What do I find myself doing?
” recommends Gretchen Rubin. “What you spend time doing can also tell you what you should do. Because sometimes the things we do without thinking really are things we naturally enjoy or are good at.”

Author Carol Adrienne shares this question, which can be helpful in identifying
²⁵
one’s natural interests:
When you’re in a bookstore, what section are you drawn to?
The things we care about, that we love doing and do well, provide great starting points for questioning. We might, for example, ask the following:

Why do I seem to “shine” when doing certain things?
(What is it about those activities/places that brings out the best in me?)

What if I could find a way to incorporate these interests/activities, or some aspect of them, into my life more? And maybe even into my work?

How might I go about doing that?

Actually doing something about the answers you come up with is harder—though approaching change as a series of modest experiments can help.

What if you made one small change?

The word
experiment
may conjure up images of lab coats and microscopes. Maybe it brings back uncomfortable memories of the dissection of frogs. But experimentation can be thought of as, simply, the ways you act upon questions. You wonder about something new or different; you try it out; you assess the results. That’s an experiment.

The psychologist and computer scientist Roger Schank has written, “In school we learn that experimentation
²⁶
is boring, is something done by scientists and has nothing to do with our daily lives.” But as Schank points out, we’re often experimenting without necessarily thinking of it in those terms—“when we take a new job, or try a new tactic in a game we are playing”—and we should be doing it even more than that because “every aspect of life is an experiment that can be better understood if it is perceived in that way.” If you randomly try things in life, it can lead to haphazard results; but if you bring thought to trying new approaches or experiences—if you take time to consider why they might be worth trying, and what might be the best way to test them out, and then assess whether the trial was a success and worth following up on—it’s a more practical way to bring change into your life.

When I was thinking about this theme of experimenting in life as a way to act on questions, a friend referred me to the writer
²⁷
A.J. Jacobs. “He lives his whole life as one experiment after another,” the friend told me. I was familiar with Jacobs’s humorous first-person essays in
Esquire
magazine, but I didn’t have a full appreciation of the “experimental” nature of his work.

Jacobs is an intensely curious man
²⁸
who often finds himself wondering why some people live their lives in a particular way. He then speculates,
What if I tried that myself?
Then he jumps right into the How stage, as he starts to live the experience. For example, Jacobs found himself wondering about people who say, “I follow everything in the Bible.” “And my question was “Yeah, they say that, but
what if you really lived by everything in the Bible?
” So Jacobs did that, for a year (the experience was chronicled in his book
The Year of Living Biblically
). He grew a large, bushy beard, wore flowing robes, and prayed constantly. Following the Bible’s message about being thankful, Jacobs expressed his thankfulness hundreds of times a day. “When I turned on the lamp,” Jacobs told me, “I was thankful for the light coming on. When I pressed the elevator button, I was thankful that the elevator came, and then thankful it didn’t plummet to the basement and break my collarbone. You realize, doing this, that there are hundreds of things that go right every day and yet we focus on the three or four that go wrong.”

One of Jacobs’s other experiments was
²⁹
reading all thirty-two volumes of the
Encyclopaedia Britannica
from cover to cover (because he wondered what it would be like to “know” everything in there); another came about when he noticed that “outsourcing” was all the rage in business and he wondered,
What if I outsourced my life?
He then hired a team of people in India to do everything from answering his e-mails to reading bedtime stories to his son—“they even argued with my wife for me,” he says.

As a humorist, Jacobs gravitates toward extreme experiences that yield offbeat surprises. But he also conducts small, everyday experiments that offer interesting lessons on taking the first small steps toward change.

In one of Jacobs’s more practical projects, which began as an
Esquire
article called “The Rationality Project,”
³⁰
he set out to catalog everything he did during his days and ask himself why he made each decision, no matter how small.
Why did he use Crest toothpaste?
Thinking about it, he realized, “It was because I had some friends at camp when I was twelve years old who used to tell me it was a cool toothpaste. That’s literally why I’ve used it for thirty years.” Such was the case with many of his daily activities and choices: “You discover that we do so many things by rote.”

Jacobs believes every now and then one should go through one’s day, from waking up until bedtime, questioning and reexamining everything. “One of my thoughts is that all of this is like when you’re skiing and the skis create ruts and it becomes easier to just follow those,” he says. But if you keep changing things up, “it keeps you from staying in these ruts and allows you to see the world in different ways.”

The small changes could be in the route you take to work. It could be something done around the house, such as the way you make the bed. Cooking is a great opportunity for experimentation; the chef Chris Young told me that he tries to remind people, “You have a wonderful lab in
³¹
your home that’s ideal for experimenting—it’s called the kitchen.” The small change could be in the way you dress, the way you fix your hair:
Why do it the same old way? What if you tried something different?
Jacobs told me about an Orthodox Jewish woman he interviewed who said that on the Shabbat she always tries to find small things she could do in a slightly different way—“so instead of putting her lipstick on clockwise, she would put it on counterclockwise. Just being more aware of what you’re doing, more mindful—there’s something wonderful about that.” When you change one small thing
³²
and it works, it can help breed the confidence to change other things—including bigger ones.

Jacobs offers another tip on small changes: If necessary, fake it until you make it. Or, to put it another way, Jacobs quotes Habitat for Humanity founder Millard Fuller, who said, “It’s easier to act your way
³³
into a new way of thinking than to think your way into a new way of acting.”

Jacobs has found this to be true in his own small-change experiments: “If you just go ahead and do something differently, and you do it enough times, it will change your mind. If you force yourself to smile, you trick your brain and then you start to become happier.” Jacobs has tried this “act as if” approach with everything from changing his posture to behaving as if he were more confident than he is. When he finds that he’s doubting himself on a project, Jacobs asks,
What would an optimistic, confident person do?
That person would probably cast aside those doubts and forge ahead, so Jacobs tries to do likewise.

Experimentation can and should be applied to big shifts as well as small changes. Career change is a good example: According to Herminia Ibarra, a professor of organizational
³⁴
behavior at INSEAD in Fontainebleau, France, and author of
Working Identity: Unconventional Strategies for Reinventing Your Career
, the best way to find a new career is to keep asking, and quickly acting upon, the question
What if I try this?

This is somewhat counterintuitive, Ibarra points out; most people assume that you should devote extensive time, research, and planning to figuring out the perfect new career before taking any action. The typical career change, she notes, often involves poring over self-help books, talking to people who can offer advice, and waiting for the epiphany that shows you your “true self”—at which point you can strike out confidently in a new direction. That’s all wrong, says Ibarra; “We need to act.” Through her research, Ibarra learned that most real-life career transitions take about three years, and they rarely happen in a linear path. It’s a series of trials and errors, and where we end up often surprises us. But the main thing is to get the testing and learning under way as soon as possible.

A key first step to a successful career change, according to Ibarra, is crafting experiments. She advises looking for temporary assignments, outside contracts, advisory work, and moonlighting to get experience or build skills in new industries; executive programs, sabbaticals, and extended vacations can be valuable in providing opportunities to experiment. She concludes, “We learn who we are—in practice, not in theory—by testing reality.”

Eric Ries of the Lean Startup has led a rapidly growing movement encouraging companies to do exactly what Ibarra is talking about for individuals—i.e., to experiment as a business, try lots of new ideas to see what works, and introduce new products and services quickly in order to “test and learn.”

Ries feels the Lean Startup approach and philosophy can be applied to one’s life, as well. The basic principles hold up; if you’re starting a new career or even just embarking on a creative project or some other type of initiative, you’re in “start-up” mode—and the “lean” rules apply. Ask yourself a lot of What If questions to come up with new possibilities that you can try out; give form to those ideas quickly and put them out into the world; get feedback on what works and what doesn’t. In a word, experiment.

What if you could not fail?

One of the hallmarks of a powerful question is that it gets passed around, and that has certainly been the case with the question above. It was popularized a couple of decades
³⁵
ago by the American pastor Robert Schuller. The full version of his question was
What would you attempt to do if you knew you could not fail?

In the past few years, the question has had another surge in popularity that seems to have been jump-started by the former DARPA director Regina Dugan, who used it in a widely circulated TED speech.
³⁶
The question has also been picked up and championed by the influential Google X founder Sebastian Thrun, who has quoted it on Reddit and elsewhere.

What if a TV drama could inspire real-life change?
³⁷

When the gritty television series
The Wire
ended in 2008, lead actress Sonja Sohn wasn’t ready to say good-bye to urban Baltimore, where the show was set. Sohn’s own hard-knock upbringing had given her empathy for the troubled lives depicted in
The Wire
; she wanted to help in some way. So she asked:
What if we took
The Wire
into schools, dissected how characters negotiated their environment—and got kids to talk about how they did the same in their lives?
Could that help them step outside themselves and see how they were making decisions and what they might do differently?
Sohn founded the community-based nonprofit ReWired for Change in 2009, and was gratified to find that episodes of
The Wire
(along with other exercises and life skills lessons) did indeed prompt hard-case kids to open up about their lives, while teaching them critical thinking about morality, cause and effect, decisions, and consequences.