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updated 12/4/2008 7:03:35 PM ET 2008-12-05T00:03:35

When I had just graduated from college and was struggling to pay for my rent and groceries with the money I saved by swiping spare rolls of toilet paper from the office, my life list looked something like this:

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1. Lose 5 pounds.

2. Find boyfriend who isn’t a total jerk but isn’t a cling-on either (not in a band).

3. Drop a few pounds.

4. Get my own place; no more roommates!

5. Lose weight.

6. Find a job that pays more than $20K.

I also believed that if I lost weight, number two would be more likely to happen, and that number six would help bring number four into being. It all seemed so simple.

It wasn’t, mostly because I was 22 and had no idea what would make me happy. It was only through trial and error that I discovered a few things on my list were steps in the right direction (having a home that afforded me privacy and a job that let me pay for it would both build my confidence). Others were red herrings, like losing 5 pounds, which would have been nice but wouldn’t rid my life of anxiety — which is what I sorely desired.

What makes you happy?
Nowadays, life lists seem to be newly popular, as evidenced by a slew of list-manic books and Web sites — “1,000 Places to See Before You Die” (Workman Publishing) and 43Things.com, to name two. Ellen DeGeneres has had fans share their life lists, and “The Bucket List,” a movie in which terminal cancer patients have a few last adventures, was a hit despite terrible reviews.

We live in a to do–oriented culture, which is perhaps why so many of us, alongside our “Pick up dry cleaning” jottings, also have a dream-centered list or two that reflect our longings and even frustrations. Yet whether they are conventional (i.e., go to law school; exercise more) or focused on emotional goals (make peace with a sibling), life lists typically have one thing in common: They’re meant to help us clarify our values so we can get the life we want. That, or they’ll make us miserable trying.

I’ve always suspected that for me, keeping a life list would do the latter. I tend to be hard on myself; if I didn’t get to each item, I worried I’d feel like a failure. Of course, that misses the point. “If you can release yourself from a sense of duty to your list, it can take the pressure off,” says Kate Ebner, founder and CEO of The Nebo Company, a leadership coaching firm in Washington, D.C. “The trick is to see your list as a chance to examine what matters to you, without self-criticism or self-imposed deadlines. Think of it as a way of taking a small stand for what you truly want.”

I’m skeptical. After all, we’ve all known someone who makes a list, follows it slavishly, then wonders why she’s so unhappy, like the serial dater with such specific criteria for her “perfect guy” that she’s certain to be alone until she has a man bioengineered in a lab. “Having a list can blind you to the possibilities in your day-to-day,” says Susan Piver, author of “How Not to Be Afraid of Your Own Life” (St. Martin’s Press). “If someone calls you and you have a nice talk, but he doesn’t have certain traits, you might not meet him,” Piver says. And that person might have brought you untold joy, albeit not in the ways you anticipated.

I’m all for unexpected sources of joy, so I decided to get help from experts and see if I could come up with a list-generating system that would help me focus on what I care about most and make me feel like an eagle soaring rather than a caged bird banging my tiny head against the bars. Below is a list (a list!) of things to think about should you decide to make one for yourself.

1. Know the purpose of your list. A grocery list specifies the foods you need to buy so you won’t starve before the week’s out, but a life list can be harder to categorize. It might contain the things you’d like to experience before you settle down with a partner; it might simply be a tally of 100 different beaches you’re dying to go to, or it could contain ideas for having more fun at work. Whatever ends up on your list, whether pie-in-the-sky dreams or more mundane concerns, “being clear about its purpose will help prevent you from losing sight of why you’re pursuing your goals in the first place,” says Karen Reivich, Ph.D., co-author of “The Resilience Factor” (Broadway Books). That’s especially true if the steps you have to take to hit your targets aren’t always enjoyable: Say that one item is to spend a year traveling and that entails earning extra money; it can help you stay motivated when you’re working overtime on a weekend if you envision yourself on the beach in Fiji in six months. If the purpose of your list isn’t immediately obvious to you, Ebner recommends reshaping it by asking yourself these questions: (1) What do I want to be known for? (2) What kind of person would I like to be? (3) How do I want to live my life? Then create a list — or even multiple lists — that represents those core values.

2. Consider what already makes you happy. “List making can stem from anxiety, but when you’re able to consider what’s already working for you, you’ll have an easier time coming up with a focused, short list that reflects where you want to go next,” Reivich says. She suggests I think about my strengths before I begin writing. I’d have to say that I’m a kick-ass mom who also feels lucky to be paid to do something I enjoy (writing). I still think I could lose 5 pounds, but I look pretty darn good, considering I have 5-year-old twin girls. Which means there’s no need to address career or parenting on my list; I already have those covered. I can also nix “lose 5 pounds,” although letting go of a 25-year-old goal is admittedly tough. “The self-help world is built on the deficit model — you’re not good enough, so you need to improve,” Reivich says. “But constantly giving yourself the ‘better, faster, slimmer’ message can be more toxic than helpful because you can always be better, faster, slimmer than you are at the current moment.”

Instead, focus on who you are when you’re at your absolute best, then build on that. I like to think I’m at the top of my game when people are laughing at my jokes. While I’m not planning on bumping Joy Behar from “The View” any time soon, I’d love to do more humor writing, which could mean starting a blog where I can let my quips fly. In fact, when I think about it, I’ve been itching to do that for the past few years. Time to make it a priority.

3. Be sure your goals are things you’re pursuing for yourself. “When the items on your list are intrinsically motivated and mesh with your values, that can be truly liberating,” says Sonja Lyubomirsky, Ph.D., professor of psychology at the University of California at Riverside and author of “The How of Happiness” (Penguin). So if getting a Ph.D. is on your list, make sure it’s your dream and not a dream of your mother’s, who always wanted to be an academic but wasn’t able to afford college.

4. Concentrate on doing, not having. Studies show, over and over again, that money and material objects are no guarantee of happiness. “When we look back on life, we tend to value experiences over things,” says Timothy D. Wilson, professor of psychology at the University of Virginia in Charlottesville. That means it’s smart to focus on strolling the winding streets and sipping the perfect cup of cappuccino in Rome, which will provide you with lasting memories, rather than spending all your time scoring a pricey Italian handbag. “Of course, if you want to be a writer and a windfall allows you to quit your dull job and write full-time, that money can make you happy,” Lyubomirsky qualifies. “But a bigger car or TV — we tend to adapt to those once we have them. And then we inevitably want more or newer or bigger versions of them.”

“It’s simple,” Reivich agrees. “Happiness is about the quality of the moments in your life. People matter more than things.”

5. Include enjoyable goals on your list when possible. Let’s say your aim is to exercise more so you can feel healthier and look toned. The StairMaster may get you fit faster than a round of golf, but if you despise cardiovascular machines and love to be on the greens, you’ll be happier at the ninth hole than climbing to nowhere. You’ll also be more successful if you pick goals that are ongoing and offer the chance for variety and social contact (join a book club; exercise with a partner), rather than tactics that call for you to change your habits all on your own (read more books; work out daily).

6. Phrase your list in a way that elates and excites you. People are less apt to succeed when they try to avoid something (“Stop biting nails!”) as opposed to pursuing something. “In terms of motivation, it makes sense to state your goals in the affirmative,” Lyubomirsky stresses. Instead of “Quit dating jerks,” try “Make a point of dating only kind men.”

7. Break down your goals. Head off panic by focusing first on what you can do to achieve your dream in the short term, then tackle the longer term. You may want to save enough to buy a home, but you’ll feel less overwhelmed if you start by getting referrals for a good financial planner. Next, you might decide on a percentage of each paycheck to squirrel away. And so on. “As you tackle each aim, your confidence and knowledge will grow, taking you closer to your dream,” Lyubomirsky says.

8. Reread your list and notice how it makes you feel. If any item brings up a sense of dread, rewrite it until it sounds enticing or at least like something that feels worth doing. If you still can’t stomach it, cross it off. You can always add it back later. “Whether or not you do something should depend only on how much you want to do it, rather than a feeling that it is something you should do,” Ebner says. The same goes for revising — you’re always free to make new lists or add items even if they’re relatively improbable (“fly to the moon before I turn 40”) simply because you want to.

9. Be prepared to ball up your list and flush it. “The items on your list should be flexible so you can respond to various life circumstances as they unfold. That means thinking of your tally as a guide, as opposed to a hard-and-fast contract,” Piver says. Plus, by taking a loose, almost playful approach to list making, you’ll be less likely to hold back. So include your wildest dreams. You’re free to go after them — or not.

After talking to the experts, the number-one thing on my own list? Write a list! Which still makes me want to do 700 other things first. Perhaps that’s because life lists are not for everyone. For some people, “meaning is something that is discovered as your life is lived, not in advance,” Piver notes.

So rather than jotting down things I ultimately want to achieve, I decided to catalog what I was already managing to do well or, at least, trying to do well, sort of like a best-practices roundup. The result is kind of random, but I’m planning to use it to reflect on what works for me and follow it as often as I’m able:

  1. Set aside some time to do nothing each day.
  2. Assume I’m doing a good job unless told otherwise.
  3. Don’t do anything I’d be horribly ashamed to explain to my kids if they found out about it.
  4. Tell myself how grateful I am for the life I’ve built.

In fact, that last item may be the very next list I want to make: “It’s smart to have a ‘How lucky I am to have what I have’ list, to remind yourself of what you’re thankful for,” Wilson says. Happily, for me, these days that list is too long to write down here.

Copyright © 2012 CondéNet. All rights reserved.

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