There is a lot of talk about decluttering these days. I am in full support of this movement. I am ready and willing to toss, say, the bank statement from 1976 or the baby bonnet knitted by an elderly aunt that shrunk to thimble size in the dryer. Stuff is stuff, and though it may represent memories, though we may cling, clutch and even smell these objects in order to keep these memories fresh and real to us—they are still stuff. They are not the actual memories.

This is why dealing with the past itself—especially the not-so-happy past—is so much more difficult. You can't throw it out. You can't give it away. You can't even buy an elegant leather storage container, dump it inside and slap on a sticker that reads in tasteful, graceful cursive: My Lack-of-Self-Esteem Years, 1982–1999.

I wish we could. But the sad truth is, boxing up and refusing to live with any part of your life takes as much energy as gripping it tightly or wishing it could have happened differently. Both approaches take too much work. Think about it: You've either got to keep that feral cat in the bag or live with it loose in the house.

I need a more reasonable, forgiving stance, one that lets me lose some of that less-than-joyful history, and keep some of it too. I don't speak symbolically either. I made an honest-to-God list for all of us out of there struggling with our former selves of what to keep and what to gently, firmly let go of...

To Keep: The Horrifying Photo
Mine dates back to age 24, an uncertain and not particularly flattering period of my life. I am a little heavier than plump, a little blonder than even acceptably fake blond and terrifically misguided in my fashion choices. (Was I the only one who believed that big, gauzy, ruffled pirate shirts brought out the best in a short, round woman? Was I the only one who believed in big, gauzy, ruffled pirate shirts at all?)

Should a friend look at me objectively in this photo, she would not gasp in horror and toss it out to protect my ego and love life. I look bad, but not mutant-ish (examples of which do exist, unfortunately). The horror here belongs to me and me alone.

This is, of course, the horror of regret and embarrassment. Over the years, I internally writhe each time that image floats to mind or shows up in some ill-fated family scrapbook viewing—as if the whole discouraging period is about to come back to life: the first job, the first loss of a job, the men who not only didn't love me but didn't notice that I was alive, the solace found in triple crème Brie.

Recently, however, I stumbled onto the photo while cleaning out my mother's house and realized that I am not only smiling like no tomorrow (eyes, mouth, cheeks, teeth), but further, my arms are flung clumsily but with great affection around a friend—a woman who remains my friend to this day. These were details I hadn't remembered. These were details I needed a lot of years to finally see.

If you look at a picture with this particular kind of horror, unique to you, that's a signal to keep it. Forever. True, the person in this sort of picture is a clunkier version of your adult self. But there are things this former you can teach the present one. First of all, nothing is as dreadful or miserable as we imagine it. There might have been great big gobs of forgotten fun (in my photo, for instance, I am smiling and hugging someone). Secondly, that imperfect you had to first try something in order to fail at it—something it might behoove you to try again. In my case, this doesn't mean wearing pirate shirts again but rather going all the way again, experimenting with full commitment, with no thought of what is unattractive or just plain foolhardy. Courage, after all, is something that must be continually learned.

Next: Two more things you absolutely have to keep

To Keep: The Inappropriate Laugh
You have been there, haven't you? In the picturesque meadow or on the mountaintop or at the beach where somebody is about to throw a box of ashes into the flowers/valleys/waves. There have been months of decisions and caretaking that have led to this moment, not to mention the end of the daily making of ice chips and the return of the rented walker. People you detest have lectured you on the importance of an official urn. People you love have gotten into fights over the sale of the house or a pair of tacky candlesticks. The person you have lost is not coming back, and the place where they used to live (your heart) feels like a TV with the screen kicked out of it.

This is when your uncle (who may or may not be a little tipsy) sits down heavily on the boulder beside you on the beach, just before the scattering of the ashes, and splits his ancient wool pants up the derriere. You will laugh and laugh and laugh and laugh. So will he. So will everyone. You will know that the laughter was a little uncontrolled and a little wacko. But you may not dismantle it as fake or cheesy, or some kind of nervous reaction to sadness, and dismiss it hastily. That laugh you have to keep forever. It was real laughter. It was a choice by you and whoever laughed with you—to celebrate instead of judge—while sitting side by side.

To Keep: The Random Person
For the most part, we turn to family or close friends for advice and encouragement. These are the people who know us, after all, and, more importantly, are the people who have to help us (another way to think about this: the people who can't hang up).

It's true that occasionally a taxi driver or waiter will toss off the most insightful, most absolutely needed comment at just the right time. The odds of your hanging out with this waiter or taxi driver for the rest of your days are pretty low, though, if only because taxi drivers and waiters help a lot of strangers though rough times. They can't buddy up long term to us all.

This is why another group of accidental sages exists. These are the people you run into, say, right before a job interview or during a marital separation or during a nerve-wracking trip to the emergency room. They do not belong in the ambulance or at the rehearsal dinner or at the book club meeting, but they are the ones who look at you and say, out of nowhere, with no authority or information, "This too shall pass." Or, "You're making the right decision. It might not feel like it, but I can tell." These people have displayed—in the quickest flash—a strength of character and compassion that you will admire for the rest of your life. These people you must make real, lasting, forever friends with. These people will show you how to live (and how to listen) for the rest of your life.

To Leave Behind: The Wince-Provoking Letter
We all make mistakes. Some of them are more horrid that others. Some of them are actually cruel. We slept with a friend's boyfriend. We hit a co-worker's car. We left the door open to a neighbor's house and caused it to be ransacked by a passing band of robbers. I have done something along those lines. I am loath to think about it, and yet I do think about it. I also think about how I apologized to the friend and about how I tried to make amends by inviting her on vacation and paying for everything she ate or drank (plus hotel) for three weeks. I think about the odd little apology presents I made with my own inept hands, like soap and the weird waxy muddle in a crafty tin that I referred to as "orange-scented lip gloss."

I think about how none of this worked.

When I open my jewelry box, right there next to the ladybug necklace from my grandmother lies a folded-up piece of notebook paper on which the friend explained—in intricate detail—why we had to end our friendship. I tried. She had seen how I had tried. She understood. And she tried too.

But she just couldn't get over it.

For a few years, you may keep this letter. (You really should have it around in case you receive a second one—just to make sure that you don't "forget" the first.) Assuming that no additional missives arrive, however, there is only one reason to keep such a letter: to beat yourself up. Burn it. Flush it. Rip it up. You have changed, and you're still changing, with luck, because shame isn't the lesson here. Forgiving yourself (finally) is.

To Leave Behind: The Story You Tell Yourself
You're a complete disaster when it comes to dancing or eating or even talking in general. You're too loud or too quiet or too tall or too old or too blunt. You're not smart enough or not sexy enough or not risky enough or not fast enough. You never catch on like other people. You ruined the family holiday. You bungled your own marriage. You never loved him in the first place. You'll never love again. You'll never be loved again because love is for other people with smaller hips and larger hearts and a better sense of when to stay and when to leave and who to trust. You're alone. You deserve it. It's all your fault.

These are stories we tell ourselves. In most cases, they are also the stories that were told to us—by our families, by boys, by other girls, by exes and by teachers. Or even by the TV shows we watched, thinking that we would grow up to be TV humans who have jobs where nobody works, who give presents that come perfectly wrapped, and who had boyfriends.

These stories are listed, by title, in a thick, moldy dictionary that we drop on our own heads. They have to go. Now.

Are You Ready to Move On?

• The joys of letting go
• What Oprah knows for sure about getting unstuck
• Making your goodbyes good: 5 ways to come to terms with change