So why do so many people fill with dread when they’re asked? My opinion: it’s nearly impossible to answer. It’s not as impossible as the utopian “What do you see yourself doing in 20 years?” but it’s well on its way.

For many, the question they hear is: “What’s the one thing you want to do?” or “What do you want to do with your life?” You mean, the rest of my life? It’s an awkward position to be put in. You either need to skirt around the truth by stating there’s only one conceivable thing you want to do for the next 70 years which may put a big dent in your credibility, or if you don’t know, then you look shallow, unprepared, or even weak by not having a genuine answer to such an important personal question.

Awkward. It’s possible the person is trying to test you, but most often it’s someone trying to be friendly, someone who really wants to see you find it, whatever it is. In fact that someone may be you, asking yourself for the umpteenth time.

Ask a different question. The direction is right, but the framing is wrong. Instead of going for certainty, lower the bar a bit.

What do you think you want to do?

This seemingly small change acknowledges you’re a warm-blooded person with multiple (if not disparate and conflicting) interests, and gives you space to be intrigued by something, but not wed to it.

Then put the drop on the forever thing. Move the horizon to something much closer that you can actually picture and act on. Two years out is about as far as I can picture, and truthfully it’s already pretty blurry by that point. Continuing to re-frame, it looks like:

Over the next two years, what do you think you want to do?

For getting stuff done, two weeks is a much better period to have a clear line-of-sight. The problem with two weeks though is it’s hard to do anything that really stretches you; it’s a tactical block of time. If you’re thinking about a full-time role as the next step in your work life, a two year horizon gives you enough room to start to think big and has the benefit of being a period of time that hiring firms know how to speak.

Sometimes though, even this question is still too open-ended to be able to answer. The canvas can feel too blank. The implied question can still often be “What job do you want to do?” You and I both know life is so much bigger than a job. I find It’s easier to answer a question about an idea, an interest, a way of doing things, or a result. In other words, think about what else you’d like to include in your growing reputation.

Over the next two years, what do you want to be better known for?

Now that’s a question you can sink your teeth into. For example:

• I’d like to be better known for my real estate deal analysis prowess
• I’d like to be better known for my open source code
• I’d like to be better known for my growing microfinance expertise
• I’d like to be better known for closing big sales
• I’d like to be better known for describing our cleantech future
• I’d like to be better known for enabling local eyewitness reporting to flourish

This form of the question is not a 100% solution; it’s simply one step along the way. Nonetheless, I’ve found working with folks that it’s a good way to break the logjam of beginning to think about what next. What do you think?

Today Mark Hurst’s Good Experience newsletter arrived with a great pull-quote from David Byrne on this very topic. From Mark’s column:

Finally, for more listening: throughout the month of March, David Byrne streams old school gospel. He writes (and I agree):

Byrne…

With the economy and people’s finances in free fall, this is a time when many of us pause to reassess our values — what is important to us, what really matters and how we might restructure our lives to reflect those values. …

Whether you believe in the geezer upstairs or not, you might enjoy these tunes. They’re also the structural foundation upon which a lot of popular music was built — a strong foundation, I might add.

http://www.davidbyrne.com/radio/index.php

It’s the line in the middle that I hear people asking more and more:

what is important to us, what really matters and how we might restructure our lives to reflect those values….

The opportunity cost has never been lower to explore what might be right for you. It’s great to see people doing it.

Kate Winslet has been getting traction for a while now. Peer recognition, in the form of nominations and actual awards, has been active for her at the highest levels for over ten years.

Sometimes you can spot when people truly are doing something they love — they enjoy their craft visibly, they excel in ways that no one else seems to be doing, they attract people who want to work with them. And sometimes, in addition to these, they just plain come out and say it, like Kate Winslet did at the Oscars this week:

And I am so lucky to have a wonderful husband and two beautiful children who let me do what I love and who love me just the way that I am.

Place Kate Winslet in the group of people who discovered her way into doing what she loves, and has had the support required to get there.

Jessica Jackley Flannery’s story is an impressive illustration of someone sharp pursuing their own path, even when all the steps were not visible.

In the Stanford Social Innovation Review article “How I Became a Social Entrepreneur”, we learn Jessica co-founded Kiva, the first peer-to-peer microlending Web site, and believes that microfinance, relationships, and stories are powerful tools for change. She’s right.

Because she did a great job of looking back on her path, we can also see some of the moments that led up to her making the leap:

I remember first hearing the term “social entrepreneurship” in a lecture…I was instantly intrigued. I wanted to be a social entrepreneur!..But doing what, exactly? I had no idea. The motivation, values, and energy were all there, but the specific context was missing. This was a problem…I felt like someone who…dreamt of going to the Olympics but hadn’t chosen a sport…So my task became choosing a context, and finding my one, specific mission.

She goes on to provide some really solid advice that’s worth following:

Learn: Read, research, write, etc. Go to lectures. Absorb whatever you can on the topics that interest you. Get an idea of what the issues are. Take a class or just make up your own little reading lists and assignments if you love structure.

Listen: Reach out to a real, specific, human being who could be your “customer” (someone whose problems you want to understand, and who you’d like to serve by addressing those problems). Listen very carefully. Learn as much as you can. Then, reach out to another person, then another, then another. (Read Paul Polak’s amazing book, Out of Poverty, for much more on this concept!)

Ask: As you start to amass questions and can’t find the answers yourself, reach out to people who might. Get their opinions, their insight, their advice. Learn how their organizations work, what problems they face, what challenges and successes they’ve had. A special note: There are many ways to be entrepreneurial and create significant social change without starting your own organization. Sometimes you can be more effective at doing the specific thing you want to do in the world by joining an existing group or project, and revolutionizing from within.

Jump: At a certain point, you just need to start pursuing what resonates with you. Follow it as best you can, wherever it leads. It’s OK if you don’t know what the next five steps are. It’s enough to take one step in the direction of your interest. Sometimes you can only find the second step after you’ve taken the first one.

Keep Dreaming: Kiva represents my wildest dream of what I wanted to do in the world. And it’s happening! I couldn’t be more thankful for this. But something else is happening too: The faster Kiva goes, the more it grows, and the more I’m convinced that other great changes are possible in the world. I hope never to stop dreaming, preparing, and being ready to see what’s next.

Place Jessica Jackley Flannery in the group of people who discovered her way into doing what she loves.

Nevertheless, there are some strides that people hit where looking forward is an expectation of doing something that truly turns you on. This is not dissimilar to Mihály Csíkszentmihályi’s work on flow.

As I was reading Daily Routines‘ posts, the one on Ernest Hemingway struck me as an illustration of exactly this feeling.

You write until you come to a place where you still have your juice and you know what will happen next and you stop and try to live through until the next day when you hit it again…nothing means anything until the next day when you do it again. It is the wait until the next day that is hard to get through.

Put Hemingway in the group of people who discovered his way into doing what he loved.