Find Your Passion With These 8 Thought-Provoking Questions by Warren Berger via @FastCoDesign
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Find Your Passion With These 8 Thought-Provoking Questions

Warren Berger, author of A More Beautiful Question, collected the provocative questions top designers, tech innovators, and entrepreneurs ask themselves to spark creativity.

In a previous post, I shared questions that can help in overcoming fear of failure. But sometimes, there’s an even more basic problem that can stop us from pursuing bold challenges and ambitious goals: not knowing which challenges or goals to pursue. These days, you're urged to "follow your passions" and "lean in"—but what if you’re not sure where your particular passion lies? What if you don’t know which way to lean?

This can be an issue not only for those starting out in a career, but also for some who are established, even highly-successful, yet unfulfilled. It’s easy to find oneself on a path determined by others, or by circumstance (i.e., the job offer or project that comes along unexpectedly and is too good to turn down, then becomes a career).

Whether you’re starting out or considering a possible change in direction, asking yourself the right questions is critical. The following eight—shared by a noteworthy lineup of entrepreneurs, innovators, consultants, and creative thinkers—can help you figure out where your heart lies and what you really ought to be doing.

What is your tennis ball?

This question, derived from a terrific commencement speech given at MIT last year by Dropbox founder Drew Houston, is a good place to start because it cuts to the chase. As Houston explained, "The most successful people are obsessed with solving an important problem, something that matters to them. They remind me of a dog chasing a tennis ball." To increase your chances of happiness and success, Houston said, you must "find your tennis ball—the thing that pulls you."

Sometimes, we may not be aware of what truly engages us until we examine our own activities and behaviors from a detached, inquisitive perspective. "You almost have to ask yourself, What do I find myself doing?," explains the author and happiness guru 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."

So pay attention to what pulls you. For instance, "when you’re in a bookstore," says author Carol Adrienne, "what section of the store are you drawn to?" That will not only tell you what books you love—it may point to where your tennis ball can be found.

For a slightly different spin on the "tennis ball" concept, ask: What am I doing when I feel most beautiful? This is about identifying not only what draws you in, but also what makes you shine. Jacqueline Novogratz, founder of The Acumen Fund, told me that in her globe-spanning travels she often asks people this question, sometimes in unlikely settings. She once posed the question to women living in a slum in Bombay. At first, "one woman said, ‘There’s nothing in our lives that’s beautiful,’" Novogratz says. "But eventually, a woman who worked as a gardener said, ‘All winter long I slog and slog, but when those flowers push through the ground, I feel beautiful.’"

Novogratz says it’s important to think about "that time and place where you feel most alive—whether it’s when you’re solving a problem, creating, connecting with someone, traveling." Whatever it is, Novogratz says, identify it—and if possible, find a way to do more of it. (A different version of Novogratz’s "beautiful" question is suggested by consultant Keith Yamashita of SY Partners: "Who have you been, when you’ve been at your best?")

What is something you believe that almost nobody agrees with you on? This question, which PayPal co-founder and Thiel Foundation chief Peter Thiel has shared publicly in interviews and lectures, is designed to do two things: help you figure out what you care about and also determine whether it’s worth pursuing, based on uniqueness. Thiel concedes that it’s a challenging question because it can be tough to find an idea or belief that isn’t shared by many others. "Originality is deceptively hard," he told Pandodaily.

But if you can find a problem or challenge no one else is tackling, you can carve your own niche and create value. "You don’t want to be interchangeably competing with people," Thiel says. Though we’re taught to do what others are doing and try to succeed by out-competing, this, in Thiel’s view, amounts to "beating your head against the wall—rather than going through the open door that no one is looking at."

What are your superpowers? The idea behind this question from Yamashita is to "unpack the combination of personality traits and aptitudes you bring effortlessly to any situation." The filmmaker Tiffany Shlain of The Moxie Institute also explores strengths and natural "superpowers" in her new web film "The Science of Character," which suggests that if we can identify our inherent character strengths and build on them, we can lead happier, more successful lives. Having trouble listing your powers and strengths? Check out the "Periodic Table of Character Strengths" in Shlain’s film, or refer to Gallup executive Tom Rath’s popular "StrengthsFinder 2.0" program, with its menu of 34 traits. Once you’ve identified your own strengths, you’ll be in a better position to make the most of what you already have going for you.

Sometimes by looking back into the past, says Rubin, you can get a glimpse of who you really are and what you loved doing before others started telling you what you should do. So what did you enjoy doing at age 10?

Eric Maisel, a psychotherapist and author, agrees, adding: "The things we loved as a child are probably still the things we love." 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."

What are you willing to try now? One of the best ways to find your purpose and passion is through experimentation. For many people, this is counter-intuitive. Herminia Ibarra, a professor at INSEAD and author of Working Identity: Unconventional Strategies for Reinventing Your Career, points out that there is a tendency to devote extensive time, research, and planning to figuring out the ideal path before taking any action. This may involve poring over self-help books, soliciting advice, and waiting for the epiphany that shows you your "true self"—at which point you can strike out confidently in a new direction.

But that’s all wrong, according to Ibarra. "To launch ourselves anew, we need to get out of our heads," she says. "We need to act." That means devising a series of trials and errors: Ibarra 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 also can be valuable in providing opportunities to experiment. She concludes, "We learn who we are—in practice, not in theory—by testing reality."

Looking back on your career, 20 or 30 years from now, what do you want to say you’ve accomplished? In an interview, LinkedIn CEO Jeff Weiner said that he often asks prospective employees the above question. "You’d be amazed how many people I meet who don’t have the answer to the question," Weiner said. So here’s your chance to answer it (without the pressure of having Weiner across the table, awaiting your response). Think of this exercise as a less-gloomy version of write-your-own-obit. What would you include on your list of hoped-for achievements? Or, even better than compiling a laundry list, why not figure out…

In the end, simplicity is best. What is your sentence? is a question designed to help you distill purpose and passion to its essence by formulating a single sentence that sums up who you are and what, above all, you aim to achieve. It’s a favorite question of To Sell is Human author Daniel Pink, who acknowledges in his book Drive that it can be traced back to the journalist and pioneering Congresswoman Clare Booth Luce. While visiting John F. Kennedy early in his presidency, Luce expressed concern that Kennedy might be in danger of trying to do too much, thereby losing focus. She told him "a great man is a sentence"—meaning that a leader with a clear and strong purpose could be summed up in a single line (e.g., "Abraham Lincoln preserved the union and freed the slaves.").

Pink believes this concept can be useful to anyone, not just presidents. Your sentence might be, "He raised four kids who became happy, healthy adults," or "She invented a device that made people’s lives easier." If your sentence is a goal not yet achieved, then you also must ask: How might I begin to live up to my own sentence?

[Images: Multi colored sands and sand art via Shutterstock]

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  • Fantastic article..<any feelings that concur with. my thoughts and things I must try out. As 48% of most creative minds I am a willing ADHD creative powerhouse making choices is always an issue. Having worked for "Conran Design London" of "Sir Terence Conran" provided me with a huge uplift under my wings to go solo since the early 90s. European educated, YSL Paris trained in Hong Kong since 83 with an international Interior and Fashion Designer career spanning over 30 years for Visual Senses Design, I can't hide that I knew for many years that I am a frustrated Architect. Since then as I love computer and owned several of the early toys in the 80s I taught myself 3D Architectural drawing. Lucky I actually have built for others two homes over 5000sq feet. My big dream finding a developer who would show interest in my very edgy high rise concept. Anyone?

  • Nicholas Bramwell

    Bad isn't it when you look at an article like this and you see it as history being written by the exceptional case. I would proffer that 99% of people are in a situation where they cannot afford to take any kind of risk like this. Following your dream is a thing of the past. Paying your bills is the aspiration of the present for at least half of the population with the remaining part maintaining their position to create a scenario of sustainable affluence (ie. retiring at some point)

  • mo128

    All my life I have asked the question, "What do want to do. What is your true passion."

    I am now 60 with a host of successes in computer systems most of your will never see. Perhaps, one you use every day, is using your ATM card to buy gas or groceries. I was part of that 3 person team in 1984. Others transfer trillions on a daily basis between major banks, etc.

    Now, homeless, broke, and dying inside, I will say that because I had no goal or dream in life, I went with the flow. Getting money, expensive Silicon Valley homes, cars, women that were after only money, is the worst scenario you can follow.

    Had I joined the Air Force at a young age in my passion for flying a fighter jet, I may have died in Afghanistan or even Viet Nam, but I would have died following my dream. What better way to have lived and ended a life, doing what you love. Now, what worse way to end a career.

    To our congress and executive branch -- you have destroyed the once great USA. May you rot in hell

  • We are same age. I LOVE computers and always put my trust in them. When other fashion designer were drawing pretty pictures with markers and pencils I made top income selling 4 colour way prints that took me one afternoon. I have been Art Director for a 2mill$ Hollywood movie. I have lived in 13 countries and a super condo in Hong Kong, a mansion in South Africa. Lost 800K in seven minutes know the feeling and am still standing up. We live in Vancouver Canada it's not a mansion but a nice home. I understand your feeling of dying inside. All creative do that when not working in the right field. I allow that sort of thought only a tiny bit to live within me everyday. But I beat it back every day.Yes this world is often made of "what we had and don't anymore". Can you work with data bases like dating sites? Get in touch lets talk. I have concept content own the right matching ".com". Has been does not have to last for ever. If you have access to the Net you can't be that broke.

  • motionformat

    Sad to hear your forsaken dream, and very true what you said. but the good thing about passion is that it can change over time, and although you're in your 60s, you still have the choice to choose what you love to do, although there might be some seeking going on, but it's definitely worth looking for it, and it may sounds a little bit weird, you may eventually die for your dream. It's never too old to dream, just keep looking and don't settle.

  • Great article Warren! I love that you take it to another level. You read the basics on finding your passion on other sites but I like your perspective and taking it to another level. Thank you for sharing!

  • This is a really fantastic article. I am going to play with some of these questions and test them on others too. My favourite is 'What is something you believe that almost nobody agrees with you on?' That's a lovely expression of, 'What in my uniqueness can I offer to the world?'

  • Frank Daley

    This is good stuff, Warren. Complex, fascinating and important.

    In order to find your passion, you have to know yourself.

    If you don't know yourself, three bad things will happen to you: you will not be with the right person (if that is a desire); you will not be in the right line of work; and you will not be happy.

    It comes down to four crucial questions, all of which have to be answered rigorously, not superficially:

    1. What do you want?
    2. What do you need?
    3. What are you willing to do to get it (that is, what you say you want and need)?
    4. What are you afraid of?

    The first three answers are different for everyone in the world. The fourth question's answer is the same for everyone.

    You can get these questions in detail free from my site, Self-Knowledge College


  • jgrandits

    How can we all be afraid of the same thing? Some people are terrified of public speaking while it's exhilaring for others, one fear might be raising alcoholic or drug dependent kids while some don't even want to have offspring.

    So what is the commonality we're all afraid of, dying?

  • jgrandits

    How can we all be afraid of the same thing? Some people are terrified of public speaking while it's exhilirating for others, one fear might be raising alcoholic or drug dependent kids while some don't even want to have offspring.

    So what is the commonality we're all afraid of, dying?

  • PJ Hammer

    I believe he's implying that everyone is afraid of failure thus why most people don't take that leap to follow their passion and are filled with regret. Then again I might have just revealed more about my own fears than people in general.

  • Great article! As Happyologist & a positive psychology practitioner I've been researching passion for over a year now and have found very similar things. I especially love Hermiania's approach to learning through action. If you want to bring out your passion, you've got to be proactive! I recently did a TEDx talk on my passion research findings which reveals 5 principles you can follow to unlock the passion within wherever you are. Have a glimpse of it if you're curious ;)

  • er025

    and what if all of the above does not work and you are still stuck? then what?

  • Try all the above. Make a note of your progress or lack of progress along the way. If you are still stuck then come back here and I will try to answer your question.

  • er025

    Where my heart lies....? what is pulling me. I am not feeling anything sticking