Unfinished Business: Writing the 5 Essential Letters of Your Life

The fact that you found your way to this book might suggest that you have something you’ve been meaning to tell someone. Consider this book your invitation and your guide.

I have been teaching and guiding people in writing letters for over a decade. The first letter that I “midwifed” was with a young mother whose lungs were failing, writing to her two young sons about the importance of kindness. I’ve written with a Lyft driver, sitting together in the front seat of his car as he expressed his gratitude to his mother in Tunisia, and with Otto, an incarcerated man writing to his wife, from whom he had been estranged for twenty-four years.

I met Lou on an airport jitney in Costa Rica. When I told him of my work as a letter midwife helping people write their essential letters, he understood immediately. He and his wife had been in Costa Rica for a spiritual retreat with a rabbi they’d known for years. Lou was battling cancer, so yes, he reflected, he thought he had some letters he might want to write. Two weeks later, he reached out to me. We spoke for over an hour, after which I sent him several pages of notes from our conversation. His intention was to craft his lasting letters to his two daughters in the next two weeks and review them with me for further guidance. As requested, I checked in with him two weeks later and then a month later and then later later, all the while exchanging emails about calendars and tax season and chemo treatments, always with the intention of helping him gather his words onto the page. Lou died fifteen months after we met, his letters unfinished. His wife, Ilene, wrote to me several months later, “Please keep reminding people to write while they can.”

I wrote my first letter to my son before he was born. It was 1991. His father and I were still married and living on a busy street in San Francisco’s Mission District. I was working in an art gallery and had few examples of how to balance my professional life with my parental life and little sense of what lay ahead.

I continued to write to my son with some regular irregularity throughout his first eighteen years. I wrote because he wouldn’t remember anything of those first years and little of the ones that came after. I wrote to him as his father and I navigated a heart-wrenching divorce; I wrote after the World Trade Center came down. I wrote the funny things he said to me when I was driving him to school and when we were negotiating at the toy store; when he was learning to read and when he was learning to drive. I wrote because I wanted him to know me, what I valued, and to know who he was and who I was when he first began. And then I put the pages into a file where he could find them in years to come.

Letter writing is to communication what slow cooking is to fast food; the slow pace is fundamental to the end result. In the process of writing we are thinking, feeling, remembering, wondering, hoping, sharing, caring, worrying, loving, grieving. Simply stated, we are being human.

A letter implies the presence of another person. It is a conversation, whereas a journal is a monologue. Some people think that letters are anachronistic; however, this assessment overlooks the letter’s unique characteristics, the first being the role of time. We know that much of life’s richness is timeless, not timely, so it makes sense that a letter requires time to evoke the words and to recognize ourselves within them. As the words unfurl themselves onto the page, we might think to ourselves, “Oh, right, that’s how I feel” or “Hmmm, I hadn’t quite seen it that way before.”

Emails and texts are efficient messengers serving many purposes, but some messages are too important, too emotional, too nuanced to be relayed by text or email. In a world that is increasingly paperless, a letter stands the test of time. Handwritten or typed, a letter benefits from your touch whether this includes fingerprints, words crossed out in lieu of others, doodles in the margins, or a line from a song or a poem. Written, folded, enveloped, and posted, the letter is sent on its journey from here to there, from now to when.

My friend Angie happened upon a creased and yellowed note from her father wedged into the farthermost corner of a drawer into which she rarely ventured. There in his familiar and awkward scrawl, punctuated with his unique word choices, was her father’s voice on the page years after he’d left this world. On finding it she mused, “It was nice to hear from him again.” Letters don’t change; we do.

In the beginning of my work as a letter midwife, I thought letters were solely for their recipients; however, it quickly became evident that it is the letter writers they serve first. Finding the words we are longing to say—which sometimes takes a very long time—provides a divining rod to our innermost feelings and completes something essential within us. “Putting words to paper is an act of connection,” said the British actor Benedict Cumberbatch, “slow, deliberate, and often more revealing than we expect. . . . Perfection is not required, just honesty. . . . Once it’s written, it lives.”

Imagine if someone who is no longer in your world had sat down some years ago, some distance away, and written a letter in which they described something of great meaning to them and perhaps, in time or in turn, of great meaning to you. Perhaps it is a grandparent writing to your parents about the day you were born or someone sharing a deep sorrow or a deeper love. Letters can be the most unassuming of treasures; they are so light to the touch yet carry so much weight.

There are joyous reasons to write: weddings and births and loves and more. And there are less joyous reasons. No matter how charmed our lives may be, if we are not laid low, if we do not lose someone close to us, if we don’t have a pet die, if we don’t lose a job, if we don’t break up, if we don’t get lost along the way, someone close to us will. All lives are touched with sorrow and loss as well as with love and grace and wonder.

A letter is a reminder that we’re not alone in this adventure called “being human.” We remember when someone reached out to us to acknowledge, to apologize, to express a concern, and others will remember when we reached out to them. “I don’t know quite where to begin” or “You are on my mind” are perfectly fine places to launch. As is “This is awkward, finding the right words is difficult, but I want you to know . . .”

Whether we are reflecting deeply on a relationship, thinking about our legacy, or pondering terrifying what-ifs, we have things we want to say while we can say them, and in saying them, we build better relationships with others as well as with ourselves.

Life gives us prompts: a close call, a terrible accident, a second mammogram, the sudden loss of a dear friend, the arrival of a new baby, an anniversary, a parting. Imagine you are on a plane with severe turbulence. What do you wish you had said? To whom?

The write time is now.

The goal is not a perfect letter. The goal is your letter, a combination of the things you long to say and the things you don’t want to have not said woven with your unique voice, perspective, peccadilloes, and intentions.