Forget Making a List
Lists often come from the organized, analytical left side of your brain, and to solve an intractable problem, you want to engage the right, the creative side. Make a mind map instead. Get a big piece of paper and start in the center with a circle that contains the original problem. Write different solutions, and follow paths outward on the page, limb by limb, pushing beyond the obvious. To plan a party, for example, I put "A great dinner party for friends" in the middle, and among the many branches, one went: "Make your own sundaes → mashed potatoes → have dessert first → sit on floor → indoor picnic." Another branch went: "Progressive dinner → go to different restaurant for dessert(s) → show up at friends' houses uninvited → scavenger hunt to find food." A third: "Teach something → learn something → juggling → magic trick → expert invitee on food/wine." Your to-do list will just get you from point A to B.
Hire a Coach
A lot of people tell me, "I'm a smart person; I don't really need help." When I hear that, I point out that Tiger Woods, perhaps the best player in the history of golf, has a coach. My first book came out in 2001, and I was approached by a speakers' bureau that wanted to send me on tour, but I had done zero talks. So I got a coach. I spoke in 16 countries last year. Suddenly, I'm standing onstage with Deepak Chopra! I've got to tell you, for me to discover at age 45 that I could do this? That was a gift. A coach can bring out talents that you haven't fully developed or ones that you might not even admit to yourself that you have.
Keep a Journal But Not Just Any Journal
Good to Great author Jim Collins asked people who felt stuck, "What are you born to do? What are you passionate about?" A lot of them would look at him blankly. So he'd explain: As a kid, he was really into science and jotted down observations in lab notebooks. When he grew up, he worked at Hewlett-Packard—a great company—but he just wasn't happy. While he was trying to figure a way out of his situation, he bought a new lab notebook, wrote his name on the front, and studied himself as if he were a bug, trying to understand what kind of bug was this thing called Jim. Each night he'd write the answer to this question: When during the day did I feel bored; when did I feel engaged? After a while, he noticed that his favorite moments involved teaching people. So he went off to do that and lived happily ever after. When you start paying attention to when you're at your best (it can take a while to find a pattern), the results can open up unexpected new territory.
Blow Open Your Curiosity
Focus on what you love, but don't limit yourself to only things that you love. Subscribe to new magazines, download podcasts on a topic that has nothing to do with your current life, go to lectures by people at the top of their field—even if you've never heard of their field, get books on tape, and follow websites that gather interesting information. (I get Cool News of the Day from Reveries.com and Trend Candy from TrendHunter.com.) If you've been banging your head against an obstacle, this kind of cross-pollination can get you over it.
Let No Idea Escape
Ideas are precious and fragile and tend to show up when we're in the shower, in bed, or stuck in traffic. So we forget them. Try to capture 100 percent of your ideas—on your BlackBerry, in a notebook, on the back of receipts or boarding passes. Go for quantity. Defer judgment until later, when you start to sift through them. You'll probably find that you have a thousand concepts—and most of them are bad. At IDEO, we start a brainstorming session on an empty whiteboard, and in the next 60 minutes we try to fill it with at least a hundred fresh ideas. (By the way, if you number the ideas as you go, no self-respecting brainstorm group would ever want to stop at number 97.) We're happy if we come out with a few leads.
Find a Reverse Mentor
The world is changing at such a rapid rate that most people over 40 and certainly 50 (which is me) find it impossible to stay on top of developments that might contain the perfect solution to your family's digital photos snafu or open you up to a job that would not only put your talents and skills to good use but thrill you. A reverse mentor—someone younger and more plugged in—can get you up to speed on new trends, pop culture, starting a social network account, or more substantial things. I have two reverse mentors. One, Diego, took me under his wing and helps me with blogging. What's in it for the mentors? They're building relationships, for starters. And, as we all know, you learn a subject more completely when you teach it to someone else.