To Find Work You Love, Ask Yourself These Four Questions

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firetruck To Find Work You Love, Ask Yourself These Four QuestionsIn my book research, I noticed that introverts often spend so much of their lives conforming to extroverted norms that by the time they choose a career, it feels perfectly normal to ignore their own preferences. So here are four questions to help you find work you love:

1. What or whom do you envy? Jealousy is an ugly emotion, but it tells the truth. You only envy those who have what you desire. Back when I was a Wall Street lawyer, some of my former law school classmates got together one evening, and compared notes on alumni career tracks. They spoke with admiration but also jealousy of a classmate who argued regularly before the Supreme Court. More power to that classmate! I thought, congratulating myself on my magnanimity. Then I realized that my largesse came cheap, because deep down I didn’t aspire to the accolades of lawyering. When I asked myself whom I did envy, the answer came back instantly. My college classmates who’d grown up to be writers, or psychologists.

2. What did you love to do when you were a child? How did you answer the question of what you wanted to be when you grew up? The specific answer you gave may have been off the mark, but the underlying impulse was not. If you wanted to be a fireman, what did a fireman mean to you? A good man who rescued people in distress? A daredevil? Or the simple pleasure of operating a truck? If you wanted to be a dancer, was it because you got to wear a costume, or because you craved applause, or was it the pure joy of twirling around at lightning speed? You may have known more about who you were then than you do now.

3. What work do you gravitate to, even when it’s unpaid or unnecessary? When I was a lawyer, I never once volunteered to take on an extra corporate legal assignment, but I spent a lot of time doing pro bono work for a women’s leadership organization. I also sat on several law firm committees dedicated to mentoring and training young lawyers in the firm. Now I am not the committee type, but the goals of those committees lit me up, so that’s what I did. Today I’m doing a version of this kind of work with my writing and consulting, and I wake up every day excited to get started.

4. What makes you cry? This one comes courtesy of Steve Pavlina, over at Personal Development for Smart People. He advises that you sit down with a blank sheet of paper, ask yourself what your life purpose is, and keep writing down answers until you come to the one that makes you cry.

I experienced a variation of this many years ago. I was having dinner with my good friend Katie Orenstein. I mentioned that I’d always wanted to be a writer but could never find the time to actually write anything. We were having a casual conversation, but I saw the depth of my emotions reflected back in Katie’s face. And burst into tears.

Now here I am, with my first book coming out in January.

(Check out Katie’s inspiring Op-Ed project here; she may change your life too.)

This last question conflates work with life purpose, of course. In an ideal world they will be one and the same, or at least work will be a subset of a larger life purpose. For many people, however, it’s not an ideal world. In that case, try to earn your income from work that doesn’t take too much time and energy. Then you can spend the rest of the time doing your thing.

Do you find these questions helpful? Have any of your own to add?

(Longtime readers of this blog may recognize this post. We have so many new readers all the time that occasionally I re-post old favorites.)


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  1. Christy on 13.09.2011 at 17:08 (Reply)

    I love the question about what we wanted to be as children, particularly what we loved. I loved historical fiction, and one of my first great ambitions was to be an archaeologist and dig up Ancient Greece. Particularly the Parthenon. Never mind that it didn’t want digging. But now, twenty years later, I’m in love with history, want to teach it and to teach how it impacts us now, not just what happened then. I’m always working little historical details into my science fiction writing.
    My second great ambition was to be a heart surgeon. Thank God I never tried to go into that field, but I can see that my attraction to it was an attraction to the fine details of the work and to making things come out right. I can see the same attraction in my love for languages and grammar and my current occupation as a web developer/programmer.
    Aside from what I wanted to *be*, what I loved to do as a child is still what I love to do and more and more impacts what I want to do and be. I loved reading and writing, and here I am with a science fiction series almost ready to approach an agent with; I loved church and the Bible, and now I have Bachelor’s and Master’s degrees in theology and biblical languages.
    I never have strayed very far from my first loves.

    1. Susan Cain on 13.09.2011 at 19:56 (Reply)

      That is probably why you always seem so centered in your opinions and outlook. Or maybe it’s the other way around — you never strayed BECAUSE you are so centered. Either way, good for you. I look forward to reading your science fiction, and love that you work historical details into it — that is my favorite way to learn history. So great that you’re almost ready to approach an agent! Almost means what? Like, next week? Next year?

      Also, I don’t know whether you were planning to participate in this month’s Book Club, but the protagonist of People of the Book is a book conservator and seems, like you, very motivated by the fine details of her work and making things come out right. I think you’d find it (and her) interesting.

      1. Christy on 13.09.2011 at 21:47 (Reply)

        Almost as in I have to completely rewrite one book and thoroughly edit another, and I keep putting it off and writing new books. Plus the thought of approaching agents rather scares me.
        I hadn’t actually planned on taking part in the reading, but the book does sound most interesting.

      2. Christy on 13.09.2011 at 21:53 (Reply)

        I also love learning history from fiction. I gained my sense of the sweep and flow of history from reading all kinds of books about it. I learned about the French Revolution from “The Scarlet Pimpernel” and “A Tale of Two Cities,” about women’s dress styles in the 1800s from Jane Austen and “Anne of Green Gables,” about the fall of Jerusalem in 70 A.D. from a fictional series about Christian martyrs, about Tiberius and Caligula from “The Robe”… So long as it’s accurate, fiction is a wonderful teacher.

        1. Susan Cain on 14.09.2011 at 08:57 (Reply)

          One of my favorites along these lines is “The Poisonwood Bible,” set in the Belgian Congo. Have you read that one?

          People of the Book is also a historical novel! Parts of it are set in WW2 Sarajevo.

          Re: agents — not scary, truly. When you find the right one, it changes your life. I think of mine as a partner in my career, not just the salesperson for this particular book.

  2. Grace on 13.09.2011 at 18:49 (Reply)

    I find it interesting that my answers for all four questions are the same. The people I envy are those who write for a living, those whose writing I love, those who I think write better than me. When I was little, my craft time consisted of creating “books” that weren’t really stories, but still looked like it. When I played pretend games, I would play the same game over and over until it sounded right. Now I realize that I was basically orally writing stories. Unpaid? Unnecessary? Ha! I challenge someone, anyone, to keep me from writing. It can’t be done. Finally, after going through a really challenging period of creative exhaustion, I discussed the possibility of not seeking writing as a career. That single idea made me sob. I know that writing for a living is challenging, but I am determined to enjoy every step of that journey. Hey, at least I know I’m going to college for the right reason!

    1. Susan Cain on 13.09.2011 at 20:00 (Reply)

      If you want it that much, it will no doubt happen, in one form or another. Keep us posted!

      1. Grace on 13.09.2011 at 20:06 (Reply)

        Thanks! I will.

  3. elledee on 13.09.2011 at 20:36 (Reply)

    Fantastic post and so totally true. I did find work I loved without this list, but it took longer than it should have (and in retrospect, I could have found it easily going through these points). I was that girl who ordered the GREAT UNSOLVED CRIMES paperback from the book order in 3rd grade. There was a rusty ax on the cover because one of the stories was about Lizzie Borden. All through elementary school, high school, and college, I watched Unsolved Mysteries, The Practice, and lots of documentary-style shows on Court TV about various cases. NEVER ONCE did I think about a career in criminal justice, until I found myself in a position among law enforcement people and wished I was them. Fast forward a few years, and I have found myself doing work I love, and feeling so passionate about it that I do sometimes cry.

    1. Susan Cain on 14.09.2011 at 08:52 (Reply)

      What a great story, Elldee. How old were you when you found yourself wishing you were a law enforcement person? In my case I was already into my thirties, but I think these things can happen very young and also when quite old.

  4. elledee on 13.09.2011 at 20:40 (Reply)

    As a P.S., I looked back on when you posted this the first time, with a fifth item on the list: “You may think I’m conflating work with life purpose here. I am. In an ideal world they will be one and the same.” I live in this ideal world, which is not always appreciated or understood by everyone. There’s so much encouragement to get a life or stop working so much, so I’m heartened to see I could be considered lucky (at least by this standard), not just over invested.

    1. elledee on 15.09.2011 at 09:13 (Reply)

      I figured it out at age 25, and it took me 4 years to reach the goal I set then. Not incredibly late by most standards, but law enforcement has a limited age range (you can’t make it a second career in most cases, because many agencies force retirements somewhere in the 50s), and most of my colleagues started a criminal justice track in their first semester of college.

  5. Darren on 14.09.2011 at 07:20 (Reply)

    I was lucky enough to find work in science, just as I wanted to do as a child. Now I look back and realise that I fell into an all-too-common trap – I was good at what I did because I liked it. This led to promotions and further responsibilities which have simply taken me away from the lab and stuck me in an office. I am increasingly resentful of it.

    Be careful what you wish for ;)

    1. Susan Cain on 14.09.2011 at 08:53 (Reply)

      Is there a way to get back to labwork, even now?

      1. Darren on 15.09.2011 at 02:07 (Reply)

        I’m working on it Susan!
        I really do like this post though, and it certainly made me think.

        The answer to two of the other questions:

        What or whom do I envy? Friends of mine who make their living growing and selling plants (plants and my garden are my great passion in life).
        What do I gravitate towards even when unpaid – gardening again.

        So I guess that tells me what I should be doing. Ironically my wife just started a degree in Horticulture this week after being made redundant from her job in science. As you can imagine this is making me evaluate my priorities even more. Our eventual dream is to set up a gardening/nursery business and work for ourselves – which sounds ideal for two introverts!

  6. Doing Work You Love on 14.09.2011 at 10:54

    […] I simply would not be able, on a daily basis, to approach strangers and ask them questions!) In today’s post, she posed four questions to help introverts (and others) figure out what career path might be best […]

  7. James on 14.09.2011 at 17:20 (Reply)

    I haven’t found my life purpose by crying yet, though I’m only 16 and only did 11/2 sides of paper…

    I guess it’s too much to expect me to have found out by 16.

    Which leads me to t

    1. Grace on 14.09.2011 at 18:40 (Reply)

      I think you’re ahead of the game just by reading something like this at 16. Good for you!

    2. Darren on 15.09.2011 at 02:09 (Reply)

      I agree with Grace – well done for even thinking about it!

  8. […] having trouble figuring out what it is that you really want to do with your life, here are four tips for determining your dream job, courtesy of Susan Cain over on Quiet: The Power of Introve…. I’d seen some variation on the first three ideas before. But I’d never seen the last […]

  9. […] Susan Cain’s  4 questions to help you find work you love doing (The Power of Introverts) […]

  10. Heidi on 21.01.2014 at 00:51 (Reply)

    Given the link between stress, cortisol levels and an introvert forced into an extrovert role, is there any evidence of either weight gain when in the extrovert job or weight loss when the introvert changes jobs to something more suitable for their personality? Note I am not sure this belongs in this section but since it relates to careers somewhat, I put it here.

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