This is part of my new series, Letters to Lucy. Lucy was a dear childhood friend who died unexpectedly this past winter, at 72. In these looser, more raw essays, I’m sharing some evolving thoughts with her. 🙏

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Dear Lucy,

I’ve been feeling unreasonably happy recently—truly [b]old; my familiar summer depression, so debilitating and frustrating, has not yet settled over me.

When I began drafting this letter to you a week ago, I used those exact words, and they were accurate.

Read on for family reunions and grief, my mother’s ghost, how to interrupt rumination, the secret of my potted annuals, my experiment with going alcohol-free, and more.

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I first heard about —and her splurge gift to herself on her 70th birthday—after reading her viral essay in ’s Oldster Magazine. And Part II (even more eye opening) a few months later. Then she was interviewed on the New York Times’s Modern Love podcast, and suddenly her late-life sexual adventure was recounted in English-language newspapers around the globe. It was a story you couldn’t ignore.

It started like this: as Gail’s 70th birthday approached, she realized she was terrified of entering the land of the elderly. A practicing psychologist, she wanted to do something scary, something to jolt herself awake… and thus was born the idea of hiring a sex worker to meet her in a hotel room. Less scary, she explained, than jumping out of an airplane.

But it turns out the real draw for Gail was finding her voice, regaining self-confidence, and saying out loud what she really wanted. So many older women can relate to that, myself included. I’ll also admit to a twinge of envy, as someone married for decades to the same man… what would it be like to undress in front of a stranger? Gail’s “sexcapade” (thanks to my editor for that word) sounded scary and, yes, exciting.

What follows is a truly revealing Q&A; we cover what it feels like to become famous, research on loneliness and lack of physical touch, fear of becoming invisible in old age, the challenge of writing a memoir, Gail’s current intimate life, and more.

You won’t want to miss this one! Gail is so open and honest about what it’s been like to become a now 72-year-old celebrity, and how that is affecting her life going forward. Hope you enjoy this Q&A as much as I did.

Debbie Weil: You were living a relatively quiet life in Australia when you suddenly received international publicity about your unusual 70th birthday gift to yourself—how has that been?

Gail Rice: Amazing. It feels like I am living in a parallel universe. I wrote that first essay privately, tentatively. I had never had anything published before…

This [B]old Women Q&A was open to all for 24 hours. After that, it went behind the paywall.

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This LIVE Substack conversation is the new incarnation of the [B]old Women Book Club. It is open to all subscribers until June 25th, publication day for ’s A Creative Compass, so please enjoy! After that, it will go behind the paywall.

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I think you will love this conversation with Substack superstar , a Sunday Times bestselling author and publisher of , read by 82,000 subscribers.

Emma is turning 37, so she is exactly half my age. As puts it, “If you’re British and of a certain age, Emma Gannon will need no introduction.” No matter, you’ll hear that Emma and I have lots in common: too many pairs of glasses, a passion for mint chocolate chip ice cream, a love of stickie notes and bright colors, and the necessity of time alone.

Despite the age discrepancy, Emma is very [b]old; she’s so clear on who she is, what she loves to do (write), and how to nurture her creative self.

The plan was to talk about her new book, The Creative Compass (pub date: June 25, 2026) but our conversation ranged widely.

I asked Emma to talk about authenticity; she spoke candidly about the difference between her public identity as an author (wearing delightful colors and stripes) and her private life as a writer (a more subdued palette). But those are both part of who she is.

We talked about solo travel, writing retreats, and why uninterrupted time alone remains essential to her creative process—another thing I share with her.

The conversation also explored the changing world of publishing. Emma surprised me by saying that if forced to choose today, she might choose Substack over books because of the direct relationship it creates with readers. We discussed self and indie publishing, creative independence, and why authors today have more options than ever before.

We touched on ’s memoir Famesick, with Emma recognizing the themes and stories of Lena’s new book: burnout, illness, and the ways our bodies tell us when we’re living out of alignment with ourselves. Emma’s book, A Year of Nothing, is an account of her deliberate withdrawal from constant visibility and online performance. Solitude, Emma said, isn’t a luxury—it’s a necessity.

Throughout the discussion, one theme kept resurfacing: boundaries.

Emma protects her mornings for writing. She has learned to say no, and she believes no one else can protect our creative lives for us.

As someone writing about old age, I was especially struck by her belief in intergenerational friendship. At 74, I’m still learning many of the lessons she has learned at 37.

Thank you, Emma, for this wonderful conversation!

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I want to look under the hood of aging—in real-time. I want to answer the question: what is it really like to grow old in a society that denigrates and devalues old people? - Debbie Weil

Recently, I went back to read the very first post I published on Substack in June of 2023. I was pleasantly surprised (astounded, actually) to see that all the things I promised I would do in my newsletter, I have in fact been writing about, week after week, for close to 150 weeks.

It surprised me because I’ve felt a good bit of doubt, at times, wondering if I had enough to say on the topic of getting old—enough that was worth reading, anyway. That doubt has time and time again been allayed by the many subscribers who have left dozens and dozens of thoughtful comments and contributed meaningfully to the conversation. Your interest in all things [b]old has been the fuel I needed to keep going; my heartfelt thanks.

My aim all along, and still today, as I turn 75, has been to reveal what’s “under the hood” of growing old (and I mean old, not “older”). Three years ago, I identified the big topics that define the journey into old age: health and wellness, retirement, reinvention, money, the new meaning of ambition, love, family and friendships, death and mortality, legacy.

I’ve been steadily addressing these topics in essays like:

I’ve also written about the difficult realities of growing old, including periods of depression and complicated grief:

When I launched this newsletter, I’d been publishing my [B]old Age podcast for four years, talking about reinventing purpose, slowing down, grandparenting, elderly parents, illness and debility, dementia, grief, and more, via interviews with authors and experts. I continued the podcast for one more year; then concluded it in 2024 when I realized I couldn’t do both a podcast and a newsletter.

Writing essays on Substack has enabled me to examine my own experience more deeply, something that began to seem very important after my mother died.

Whether you are a new reader, or have been along for the whole ride (for which I am very grateful), I hope you’ll enjoy this quick trip down memory lane. You’ll also learn why I started this newsletter, and what happened to my podcast.

Moving to Substack + getting old in real time

First post on Substack: notes on a [B]OLDER life at 71

Hello dear reader, old or new,

I’ve been publishing a newsletter for over 20 years but I’m a bit tongue-tied with this debut on Substack. First, a big hello to my longtime subscribers. Some of you have been with me since 2001 as readers of award-winning WordBiz Report, my e-newsletter about online marketing (which led to my book about blogging). A sincere thank you!

Will the [B]OLD AGE podcast continue?

Yes… and NO! Update: my [B]old Age podcast concluded in May 2024 (a year after this first post was published). Find 100+ episodes on Substack or on Apple podcasts.

Growing old in real time with a 71-year-old

But I’ve got a bigger goal for writing on Substack; I want to do more than write notes on [B]old Age podcast episodes—although this particular note, [B]old women are too busy, explains why I want to dive deep and talk about uncomfortable things.

I’m almost 72; I want to look under the hood of aging—in real-time. I want to answer the question: what is it really like to grow old in a society that denigrates and devalues old people? I want to write about complicated family relationships, to understand them better. I’d like to give you an inside glimpse of what it’s like to be married for 50 years.

Because I think we all want to know what aging is like… the good parts, the sad parts, the painful, the unexpected, the wonderful and more.

Old age is a foreign country. In your 30s, 40s, 50s, and even 60s it’s a land somewhere far away. Other people (code for old people) live there, but not you.

What’s it really like to grow old?

Many of us are fascinated by real-time updates written by those living with a terminal cancer diagnosis. Our unspoken question: “What would it be like?” So it goes with old age. It’s a foreign country. In your 30s, 40s, 50s, and even 60s it’s a land somewhere far away. Other people (code for old people) live there, but not you.

What if you could better understand old age before you got there?

Would you live your present life differently? Can old age be lived differently — defying all the ageist stereotypes that still define old people? Can we do it better? And I don’t necessarily mean longer. And the burning question: would you be less afraid of dying?

Life expectancy

My husband for 50 years, , is a physician author. In his book, AT PEACE: Choosing a Good Death After a Long Life, he writes that, on average, if you reach the age of 65 in good health (I did), you have 19 years and six months left of life. Let’s round up to 20 years. Add that to 65 and you get to the ripe-sounding age of 85. Not to put too fine a point on it, but 85 is only 14 years from where I am now. I could live longer, of course, but these are the average numbers.

The big topics related to aging

So I’ve got a front row seat to aging. And I’m feeling a sense of urgency.

As Sam likes to remind me and everyone else: you could die at any time! My plan is to examine the big topics that define the journey into old age: health and wellness, retirement, reinvention, money, the new meaning of ambition, love, family and friendships, death and mortality, legacy—from a wider perspective but especially as an individual [b]old woman.

BTW, these are all topics I’ve explored on the [B]OLDER (since renamed [B]OLD AGE) podcast over the past four years. But never with an eye specifically focussed on how they affect me personally. I was a mere 67 when I started the podcast in 2019. Old age seemed very far away at that point. Now, it doesn’t.

Who is Debbie, anyway?

I’m a podcaster, writer, editor, storytelling director, former reporter, Web pioneer, nonprofit volunteer, wife, mother, and grandmother. More here. Not necessarily in that order. It’s complicated. Or maybe it isn’t. Let’s get started.

Published June 7, 2023

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Questions for readers

• 🎂 🎉 How should I mark three years of publishing [B]old Age?? I do love cake (and especially thick, buttery icing).

• 🤓 🙏 What topic am I not covering that you’d like to hear more about?

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🔥 🔥 Let’s celebrate!

Please become a paid subscriber for access to my most revealing Personal Essays, plus membership in the [B]old Women Book Club.

Our next guest is bestselling author and Substack superstar Emma Gannon.

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First, I’m going to write in a more informal style, at least for these summer months, because… why not. I’ve discovered a sense of freedom in writing Notes on Substack where I often disregard proper punctuation, use swear words when it feels right, and sometimes post on [b]old age-adjacent topics, like the stack of books I’m reading. I want to bring some of that [b]oldness, and informality, over to this newsletter.

Second, and in line with the above, I am going to publish some shorter, looser, more raw essays; you might remember I gave myself radical permission to do this a while back.

Third, I’m starting a new essay series I’m calling Letters to Lucy.

Lucy is my childhood friend who died this winter, unexpectedly, in her early 70s. She was that rare person who is utterly authentic, utterly honest, direct to the point of being rude—and yet you accepted and believed her no matter what. She was so warm and embracing (she was literally a hugger), and the best way I know to honor her memory, is to be more honest, to be less afraid.

So here goes, my first Letter to Lucy…

As always, there are Questions for readers at the end. I hope you’ll join in for the conversation.

I deliberately keep my annual fee as low as possible; if you absolutely cannot afford to pay, email me at debbieweil@substack.com and I will comp you.

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Dear Lucy,

I’m turning 75 this year and I’m excited about it but dang how I wish you were getting to this milestone with me. I know, I know. I can hear you laugh, what’s the big deal? It’s something about the roundness of the number, something about a resounding entry into old age, that just feels good. Still, I look at my hands and am startled to see that they look as gnarled as my mother’s did when she was 90.

I wish I could change them back to a smoother, straighter, more youthful appearance. Ugh.

It’s going to be a busy summer; we’ll be driving back and forth, up and down the East Coast, between Maine and Connecticut. I can’t fill you in on exactly why, at least not here, with others reading, but I promise to catch you up on that later. Suffice it to say it has to do with family, and it’ll break up our normal rhythm of settling in for the summer on the Maine coast. For the moment we are relaxing; the weather is sunny and the sky is a perfect blue. We love it here.

My always-wise editor, , suggested I write a follow-up to my very popular post of several months ago, Three realities of aging hit me last week—the one where I told readers about your sudden death. I think you’d appreciate a list like this, so here goes.

Three more realities of aging

1. Physical disability sucks.

I had more strabismus eye surgery last week. My eye surgeon is a woman about the age of one of my physician daughters; she’s engaging and warm and says things like, “Let’s just go for it!” meaning let’s do the eye muscle-tightening surgery and see what happens. (She’s less cavalier than she sounds; she pretty much promised she could fix my double vision.). Eye surgery involves total anesthesia, with a kick of fentanyl to put you under. I’m not a fan of medical procedures, having had very few, so it was scary.

Well, here I am a week out, squinting in normal lighting, feeling a bit dizzy, having trouble reading up close, wanting to get back in bed several times a day just to close my eyes… And yet, I’m not seeing double! In fact, things are looking sharp and colorful at a distance.

But Lucy, this might not surprise you… I feel emotional and weepy, like a wailing toddler. I hate this feeling of disability. I want to ignore it, hide it, I don’t want people to know. I’m wondering if you felt the same way your last few years. And I’m kicking myself for not having checked in with you more often, and more closely, to find out how things were going. I don’t think I really understood, then. I still don’t, probably, but this is my way of saying that even as I approach 75 and feel good about getting old, I’m keenly aware of how distressing physical disability is, and of how much effort it takes to put up with it. Really, it’s about loss of control. No matter how much I want to wish away wonky eyesight, I can’t. I know I’ll never see normally.

For the moment it’s hard to read (which drives me crazy); I have no depth perception (the surgeon can’t fix that) and it makes me feel (and look?) off balance when I walk. I look straight ahead and down, scanning for any bumps or irregularities, so that I often miss what’s going on around me. I walk right past people I know, including Sam.

But enough complaining! (I learned that from you.)

2. Relationships with adult daughters don’t magically get better.

I know this will resonate with you. I’m not going into any specifics except to say that, when I step back, I begin to see this as another issue of control. Why doesn’t an adult daughter say this or that, do this or that? I want her to! When she doesn’t, it feels so painful; I feel unloved. Or maybe I’m just a bad mother (there’s always that question).

As another dear friend put it, I need to start saying, “I’m not on that committee.” If you’ve ever been on a nonprofit board, you know exactly what she means: it’s not your business and you’re not responsible; stay out of it.

Both of my daughters sweetly called me on Mother’s Day, as they were riding in a car together. “What’s challenging about being a mother?” one asked. I laughed. “I have so many questions I can’t ask.”

Lucy, I expect you understand (although in your case I suspect you did ask the questions).

Will my daughters read this? I want them to, I think, and it’s okay if they do; no secrets have been divulged. (You may remember that I’ve written about a bruising incident with my daughters.) How best to relate to one’s adult children is an ongoing discussion. Can we come back to this later?

3. It’s still hard to plan ahead, dammit, but I’m trying.

Your premature hard stop precluded any need for this kind of planning, but I’d really like your input. Lately I’ve been having a discussion with Sam about looking into assisted living, or more specifically CCRC’s (Continuing Care Retirement Communities). Even a few years ago, this would’ve been an absurd topic. Never, I would’ve said, never will I move into a retirement community filled with old people. I never got to ask you: did you ever consider this?

But my perspective is slowly changing. Or at least altering enough that I’m willing to consider doing a bit of research. We’re going to tour one such “community” in Connecticut this summer. I have my eye on a handful of others in Portland, Boston, and New York City. I’m not ready to commit to anything, but I hear there are years-long waiting lists at the most desirable CCRC’s.

What’s changed for me is witnessing my parents’ final decline in their early 90s. They never considered such a move; thus their end-of-life years, requiring round-the-clock care, were the responsibility of their children, and specifically, my younger brother. It was a huge burden for him, although he was very cheerful about it. “They never expected to get really old,” he kept explaining, as if that was an excuse for the situation they put us in.

But I don’t want to do this to my children; I don’t want them to shoulder the burden of our care when they have their own busy lives (see #2 above). I do want them to visit often, of course. I realize that you never got to this point, but I’m wondering what you think about retirement communities, what questions you have, and how this all looks from up there.

Til next time.

biggest hugs, Debbie

P.S. Did you see a therapist towards the end of your life? Do you think I should??

Questions for readers

• Do you have a friend or family member, who’s no longer with us, that you like to talk to?

• What’s your approach to the physical changes and disabilities of old age? Do you ignore them, say nothing about them, or discuss openly?

• How are you finding this new series, Letters to Lucy?

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writes exquisitely about something exquisitely painful… and that is the death of her husband. I’ve been married for 53 years, to a man I am still in love with, and the idea of losing him is unbearable. Reading Mary’s experience of grief after three years since her husband’s death is unsettling; she offers a glimpse of something that is so private, so immense, so frightening—a topic that is almost too hard to think about, let alone write about.

But with her pen, Mary makes it accessible, even beautiful, for a reader like me. A reader full of that particular fear. She writes, “Almost daily, I find myself stunned by some small remembered sweetness, or an unresolved hurt. Sometimes I’m ambushed by a longing so intense I need to stand still, eyes closed, waiting for it to subside.”

Mary’s Writer, interrupted is a two-time Substack Featured Publication, read by nearly 6,000 subscribers. She also writes about Minnesota winters made even colder by the presence of ICE, her burgeoning spring garden (ravaged by rabbits), and more. Whatever the topic, she draws us in with the rhythm and specificity of her writing, and through the emotion we can feel so clearly behind her words, and connect with. Her essays are as good as any you’ll find in The New Yorker. As one of her readers put it recently, “You open the door and I simply do not want to leave.”

At the same time, like most good writers, Mary does not write alone. She is an active participant in ’s Conscious Writers Collective, and as you’ll read below, she credits that experience with sharpening her craft and making her a better writer.

For a behind-the-scenes with a very [b]old writer, read on.

Debbie Weil: Mary, tell us how you became a writer, and an enviable one at that.

Mary Roblyn: I’ve been a writer since I was seven. But as I grew up in a family which discouraged such things, I kept my writing a secret. Despite – or because of – their opposition to girls’ education, I moved out at 19 and worked to support myself as a full-time student, graduating from the University of Minnesota with a degree in anthropology and linguistics. I got married at 23. We had a daughter and a son; I stayed home with them for several years. Although I published a few things in literary journals, I never earned an income from my creative work. I worked in philanthropy, as a grant writer, and as a book publicist. None of the jobs I held were satisfying, and mental health issues kept me from pursuing fulfilling work. But I kept writing. I took classes and joined a writer’s group. I even got my MFA in my 40s.

It wasn’t until I began my Substack that I became a paid writer. And now, a bestseller. I’m incredibly grateful for the generosity of my subscribers.

DW: You spent a long time taking care of your dying husband; how are you taking care of yourself these days?

MR: It’s been challenging. As I wrote about in a recent post, All Things Must Pass, I had to say goodbye to my 23-year-old cat, Mini. She was a wonderful companion for two decades, and saw me through the death of my husband and the three years since then. I cared for her when age took its toll. She slept in my bed every night. It’s a big loss.

I have a daughter and son who live nearby. They will say things like, “Mom, you need to get out more.” And they’re right. Now that it’s spring, I’m spending time in nature. I live in the Twin Cities, near the Mississippi River. There are bike paths and walking trails everywhere. I have great neighbors and wonderful friends. A six-year-old girl lives next door. Everyone should have a six-year-old in their life.

And then there’s the Writer, interrupted community! My readers sustain me. I could not do this without them. There are many times when I think I should send out a post, but I know it’s not ready. My readers deserve my best work.

Writing is at the very core of my being. It brings a huge sense of purpose, which I think is the key ingredient to aging well. And the writers on Substack are extraordinary. I try to be a good literary citizen by promoting others, buying their books, and taking out as many paid subscriptions as I can afford.

I love Substack. I’ve found my home.

DW: You’ve been so forthright in writing about your grief, as in your recent What I Learned in My Third Year as a Widow. Does writing about it ease the pain?

MR: Oh, absolutely. I wrote in my journal – in fact, I ended up filling six journals during the year after my husband’s diagnosis and between his death – about everyday details. The things you might otherwise forget. I’d found Substack through George Saunders’ Story Club, from a random email that arrived in my inbox. That gave me the idea that I, too, could start a Substack. I sent out my first post in November, 2023, six months after I became a widow.

It was so rewarding. It gave me the idea that I could get through grief by writing about grief. And I found this to be true.

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My 74-year-old husband is in relatively good health: active, not overweight, and enjoying a productive life as a retired physician. But daily he reminds me that the surgeon had to “cut his leg off” as part of the TKR (total knee replacement) he had… three months ago. Sam has a dry sense of humor_, so it’s hard not to giggle; but as much as I love my husband (and his sense of humor), I’ve grown a bit weary of his kvetching and whinging. His unexpectedly slow–and painful–recovery from this surgery is, shall we say, the topic du jour in our household.

Sam is not normally a chronic complainer, but like most physicians he’s a very bad patient; he catastrophizes over worst-case scenarios, including infection, disability, and other long-term outcomes that, as a non-medical person, I’ve never even thought of. For his left knee, he tells me, these include continued pain and not regaining full flexion, which, according to his surgeon and his PT aides, are highly unlikely to be the ultimate outcome.

Despite their reassurances, he seems a bit depressed, as well as angry, about his slow progress. He compares himself to several contemporaries, all men, who had TKRs but had much quicker and easier recoveries. It’s as if recovery is a competitive sport (surely, as a physician he knows better), and he thinks he’s losing.

I should note that he is very diligent about doing his PT, and is walking quite well at this point; but he’s not running down the block yet. He’s not back to where he was before surgery; and, more to the point, in a better place, with a stronger, pain-free knee, which was the whole point. His favorite physical therapist recently told him that he would be in fighting form in 12 months.

That sounds reasonable to me but I’m not the one who’s temporarily lame. So far, I’ve taken to telling him how sorry I am that he’s in pain, reiterated that the stiffness is sure to go away, and pointed out that things could be much worse (he could have a chronic medical condition with no cure, for example). But honestly, I’m not sure what the best way is to encourage and support him. With a little humor? With a lot of patience? Maybe you have some ideas! I need help!!

Questions for readers

• What are your best recommendations for supporting your partner?

• How do you stay sane when your partner is going through it, whether it’s a physical problem, an illness, or depression?

• Do you find that you are balancing patience and sympathy with admonitions to snap out of it?

• How does humor play into it?

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I almost didn’t publish this, fearing that you would think me self indulgent for chronicling a three-week trip to Paris when many are having a hard time right now1, due to external events in the world, or personal situations. Then I said what the heck this is what turning 75 this year means; I’m tired of giving flying fucks… I’m doing this, publishing a day late, and feeling great about it.

Hope you enjoy!

Herewith, a selection from my Paris diary2. I’m writing in the casual style of Substack Notes rather than a proper essay. Meet me in the Comments if you’ve got your own Paris stories; I’d love to hear.

The art class

I signed my husband and me up for a two-hour class offered through AirBnB: Learn urban sketching in the Latin quarter. The description said no drawing or watercolor painting experience necessary. I thought why not… I don’t think Sam and I have ever taken an art class together.

We were directed to find our teacher, Kristina, in the charming Rue Mouffetard area on the Left Bank. She was wheeling a clunky old bicycle loaded with art supplies (including tiny folding stools), which she doled out to her four students. We walked slowly beside her, on a perfect sunny afternoon, as she chose three different spots for us to sketch and paint. Kristina was patient and kind and kept saying, there are no rules and no mistakes. I was fascinated by how different Sam’s style was from mine; more careful and precise, but also impressionistic.

Sam and I also took a baguette-making class. The process is quite complicated, with many steps of punching and folding and an exact formula for mixing the flour, water, salt, and yeast to make the dough. It was like being back in chemistry lab (which I flunked, and Sam, as a pre-med, was really good at).

Two day-trips: Giverny and Chantilly

We elected to take the train to Monet’s Giverny on a Thursday; the next week, on a Monday, we took a quick train ride to Chantilly to see the 16th century Château de Chantilly. Both times, we chose weekdays to try and avoid the crowds which are clogging Paris and environs.

Alas, Monet’s blooming flower gardens, the obvious influence for the palette of his paintings, were mobbed with tourists, even at 10 am when we arrived, after taking a very early train from Paris.

Since we last visited about 40 years ago, Monet’s house and gardens have been entirely (but tastefully) commercialized. No matter; it was a memorable, sensory-filled day. We had a long lunch at a nearby café, and were back in Paris before 6 pm.

The magnificent Château de Chantilly is far less known than Versailles but absolutely worth a visit. The château is filled with an impressive art collection; you can walk through a leafy forest and elaborate, formal gardens designed by Le Nôtre (who also designed the gardens at Versailles); and there is an enormous historic stable housing stallions we could almost stroke, as we admired them up close in their stalls. We even had some crème chantilly for dessert after lunch.

I cherish this factoid: when Louis XIV paid a visit to the château some 400 years ago, his valet went down to the kitchen to check on the fish for lunch (it was a Friday); upon learning that there was no fish to be had for the king that day, he fell on his sword and committed suicide.

Three major museum exhibitions

Sam and I have spent countless hours together at museum exhibitions on our many trips. It’s one of the things we do best as a couple (otherwise, we tend to argue about stupid things) because we both enjoy art history and love the great 19th and 20th century painters, and artists of earlier eras as well.

The Matisse show currently at the Grand Palais (until July 26, 2026) was especially stunning; a visceral experience. It’s a show about late-life reinvention, which is what Matisse did with his cut-outs and drawings in the years following WWII, up until his death in 1954.

The other two exhibitions we saw on this trip, and loved, are the Alexander Calder retrospective at the Fondation Louis Vuitton (until Aug. 16th); and Renoir and Love at the Musée D’Orsay (until July 19th).

Plus two Substack IRL meet-ups

One with Shellie Holubek, new to Substack and author of and another with the charming , a fount of useful information about Paris. A planned visit with Paris-based was called off when she got sick. We’ll meet up in November, when I plan to be back.

The Blue Hour

The French don’t really use this phrase but Americans love it; it refers to the extraordinary luminosity of the sky about an hour after sunset. If it had been a sunny day, we saw it just after 9 pm every night we were in Paris.

Finally, how come three weeks in Paris?

My mother was a Francophile and owned a tiny apartment in Paris which she rented to friends, and also stayed in often, with my dad. Before she died, she gave the apartment to her four children. Et voilà.

I’m coming as often as I can, to hang out, improve my French, and use Paris as a jumping off point for other trips (like this one to Avignon for a week, to study with our favorite prof).

Hope you’ve enjoyed these quick glimpses of what has been a truly memorable and special trip with Sam (and yes, we’ve enjoyed 15 sunny days in a row in Paris, possibly a record). I’m keenly aware of how grateful I am to have this experience with him. Even though we are both approaching 75 in relatively good health, I’m not counting on this kind of trip happening forever.

🇫🇷 🍷 Questions for readers

• Do you have a favorite Paris experience you’d like to share?

• Do you keep a journal, either written or pictorial, when you travel?

• Even if you’re cutting back on alcohol consumption, do you drink wine when in France? (I do!)
  

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Welcome to [B]old Age, where I write about the bittersweetness of old age, from the blessings to the bullshit. I write revealing Personal Essays for paid subscribers (like this special article), publish Q&As with [B]old Women, and offer discussion posts open to all.

My guiltiest pleasure is shopping online, most often for clothes but for other things as well. “Guilty” because I know that shopping does not make you happy… except in my case, it does. I feel instantly soothed when I scroll a favorite site; it scratches an itch that, I am aware, is an addiction. In addition, I rationalize that I’m saving money because I often shop the sales, and I savor the colors and styles which are displayed to full effect online.

I sometimes offer myself this experience as a reward. If I finish a vexing chore (or a Substack draft!), I give myself permission to log onto my favorite sites. Of course, I have an account on each one, with favored “insider” status. Recently I came across Cartoons Hate Her, a svelte Millennial influencer and excellent writer, who was sharing her spring 2026 picks. Lo and behold, she recommended the EXACT SAME jeans that I buy online and that I’m obsessed with.

This coincidence emboldened me. Granted, I am not a fashion influencer, but it made me think you might want to know more about where I shop online and for what essentials. One of the contradictory truths of being an old woman is that the way I feel inside and the way I look on the outside do not match up.

I’m an old woman, turning 75 this year, and yet, just as I have for decades, I care a lot about what I wear and how it makes me feel.

On a typical day, it’s blue jeans (they’re the most essential), with a different sweater or scarf, and comfortable walking shoes. (I have a thing for scarves, which cover up my wrinkly neck, as Nora Ephron pointed out.)

Online shopping lets me choose what makes me feel most like “me,” what identifies me as a [b]old, even badass woman. So I like to think it’s more than an indulgence.

Here’s an inside peek at this [b]old woman’s essentials…

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Not all of the immersions have been as dreamy as that sounds. There was the week with Jean on Belle Île, who accused us of spilling red wine on the bed covers1; another with Claude near Bordeaux, who was floundering in the midst of a divorce and insisted on including his unhappy young sons at dinner with us (not a conversation starter).

But then we found Julie Gaudin in Avignon, and it’s been a magical experience ever since.

This is our fourth séjour linguistique2 with Julie and she has become a friend as well as our favorite teacher. Not that either of us is truly fluent, but we both speak passably well and enjoy tremendously the challenge of trying to improve, of doing it together, and of laughing all week with Julie.

In this little video, I speak with Julie about why we’ve chosen immersion as a way to improve our French.

A summary of the conversation with Julie

Debbie explains that she is spending a week in France with her husband Sam, and with Julie, their prof, in order to practice speaking French in a real-life setting and in a way that is both engaging and meaningful.

When she was 14, she spent a year in school in France and learned the language through daily life and interactions with her friends. That experience shaped her belief that the most effective way to learn is through immersion—by listening, speaking, and living in the language, rather than relying primarily on formal instruction.

Julie draws a clear distinction between speaking and writing. While grammar exercises are useful for improving spelling and written accuracy, she sees them as secondary to developing fluency in conversation.

During the immersion, Debbie and Sam benefit from Julie’s real-time corrections, which she offers gently and constructively. She also takes notes in a Google Doc which they can review and refer to later.

Finally, the experience includes cultural outings, such as their visit to the newly restored and magnificent Château Thézan in Saint Didier, about 30 minutes from Avignon. They also visit Venasque, a picturesque “village perché" (hilltop village).

More about Julie’s immersion course here: lefrançaischezjulie.com

Questions for readers

• Do you have a desire to learn a new language?

• Do you like the idea of immersing yourself in the culture as well as the language, the approach that Julie is so passionate about?

• Is there an experience you’ve signed up for once, and then kept coming back because you liked it so much?

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The previous “Bonjours” d’Avignon… in 2025 and 2023!

And the sounds of Avignon on my podcast in 2019:

Today’s video post is just for fun. I’m obsessed with the bittersweetness of growing old, from the blessings to the bullshit. I write revealing Personal Essays for paid subscribers on topics like Why I’m pushing back on living to 100 and Three realities of aging hit me last week. I also publish Q&As with [B]old Women, and offer discussion posts open to all.

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“Everything I’d been working on for 25 years was turning to dust [thanks to AI], and at the age of 72, I was facing the reality that I had to find a new way to make money and get artistic recognition.” -

I met Pamela Redmond when she bounced into the newsroom of the University of Wisconsin’s Daily Cardinal, eager as a puppy, her flaming red hair long and flying. This was a half century ago, when she and I were both reporters on the student newspaper. We lost touch in the intervening years, but we reconnected about a decade ago at Generation Women, a women’s multigenerational storytelling event1 in NYC.

Now we’re both in our 70s and Pam is busier, more productive, and (this part is important) more fearless than ever. You might be familiar with the hit Netflix series Younger, based on her eponymous novel. Pam is also the creator of Nameberry, the world’s largest and longest-running baby naming site. But it’s her new one-woman show that caught my eye recently.

Pam is keenly aware of the threat of AI to her baby naming business. What could she do that AI can’t, she wondered? The answer came almost immediately: Old Woman Naked, her one-woman performance where she strips off her clothes, on stage, in front of a large audience, as a way to reveal her deepest secrets and to make the point that, as a 70-something woman, she is not invisible. This would be my definition of fearless.

More fearlessness in the revealing interview below. Enjoy!

And be sure to read Pam’s essay, What the Body Knows, how the story of her body is really the story of her life.

Debbie Weil: You started your Substack, The Jubilarian, saying “I need a plunge,” quoting Mrs. Dalloway. What’s the plunge been like this past year?

Pamela Redmond: Writing that first Substack, getting in touch with that wish for a plunge, was the start of a huge creative renaissance for me. I’d just left my publisher after rewriting my novel 11 times over three years, finally concluding that we’d never agree on its direction. I was struggling to keep my website Nameberry alive after AI stole all our content, and with it my reliable income and funding for my retirement. Everything I’d been working on for 25 years was turning to dust, and at the age of 72, I was facing the reality that I had to find a new way to make money and get artistic recognition. A Substack that made no money was in no way the logical solution to those problems, but that was its appeal. Since everything I should be doing hadn’t worked, why not do what I wanted to do, what made no sense but presented a new challenge and new freedom?

It opened up the world to me in a way I hadn’t experienced since I launched the website in 2008 and started publishing novels in 2000. That creative energy from the newsletter led directly, if not logically, to the idea for Old Woman Naked and a completely new direction in my work.

I had the idea for Old Woman Naked this past July, finished writing it by late August, and performed it in New York on October 7.

Now a fancy NY director, Wendy C. Goldberg, is developing it to be performed on a bigger stage with a star in the lead role. The New York Times Style section has already written and photographed a piece I hope will run soon. Ed note: we will insert the link as soon as it’s published.

So, the plunge has been incredibly invigorating and has set my career on a completely new path.

DW: You’re either very brave or, er, totally crazy: take us back to last summer and the genesis of your one-woman show, Old Woman Naked.

PR: I am very brave and I wouldn’t call the show crazy, but original. The work I always aspire to, the very best work of mine and of other people’s too, is something that is both totally original and totally natural. Something you’ve never seen that way before, but as soon as you see it, you know that is the way it should be.

Exposing the truth about women’s bodies over their lifetimes feels like that kind of work.

The funny thing is that I remember the genesis of each of my great ideas very clearly. They happened quickly and (that word again) naturally. Old Woman Naked started with wanting to do something AI couldn’t do. That meant it had to be real, personal, live, indelibly human. So, a one-woman show of some kind.

But how would I get people to come to my show? I could take off my clothes, I joked to myself. And immediately thought: That is a great idea. Taylor Swift, Beyonce, Chapel Roan, Kim Kardashian take off their clothes and attract massive attention. But no old woman has ever done that.

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Thank you , , and many others for tuning into a LIVE conversation with my old friend, ex-Google blog editor . I first met Karen when I interviewed her for The Corporate Blogging Book, so we’ve known each other for over 20 years.

Karen tuned in from her longtime home in San Francisco’s Noe Valley neighborhood; I was in our apartment in New Haven, CT. The video starts four minutes before the top of the hour, when we were supposed to be in preview mode. Just start at 04:00 and you won’t notice.

Below is a summary of our one-hour conversation, generated by ChatGPT from the transcript. I’ve reviewed and tweaked it for accuracy and to add a few links. You can probably tell that I didn’t “write” this summary because it’s not really in my voice; no matter: this is a good use of AI.

One of the things we talked about was book writing and publishing. Below you’ll find Karen’s memo on Hybrid (aka Indie) Publishing.

When I sat down with Karen Wickre for a Substack LIVE, we began with tech glitches, laughter, and the realization that neither of us understands every intricacy of Substack’s platform, which, in its own way, felt appropriate. We’ve both been early adopters for decades—and we’re still figuring things out. (Well, that’s what ChatGPT surmised, but I’d say Karen has tech tools and AI pretty well mastered.)

Karen, a former communications leader at Google and later at Twitter, only recently joined Substack, as author of The Accumulator, after what she described as “more than a year of agonizing.” Her hesitation wasn’t about writing—it was about format. “I realized I don’t want a newsletter,” she said. “I want a blog.”

That distinction matters. The Accumulator is deliberately intermittent: no schedule, no niche, no pressure to produce. Instead, it reflects what she calls “a lifetime of ideas and memories and opinions.” In contrast, my own approach is more structured—and paid. Which led us into a lively discussion about money.

I admitted something I feel strongly about: professional writers should be paid; not just for the income, which is very welcome, but for what it represents—commitment and accountability on my part, and respect for the work, on the part of readers. Karen agreed, but has chosen a different path, at least for now. She doesn’t want to feel obligated to produce on a schedule.

From there, as we’re both turning 75, we went back—more than 20 years—to the early days of blogging. Karen helped build Google’s first corporate blog, at a time when most companies relied on dry press releases. Her insight was simple but radical: let subject-matter experts speak in their own voices. Not executives. Not corporate speak. Real people.

That model—now taken for granted—was once revolutionary. (I included a case study of Google’s multiple blogs in my book.)

We also talked about editing, a profession Karen believes is deeply misunderstood. “People think they need a writer,” she said. “But often what they really need is an editor.” Someone who can shape, question, and “see around the corners.” It’s a kind of wisdom role—one that feels closely aligned with what we also talked about: “modern eldering.”

That phrase comes from our friend Chip Conley and his Modern Elder Academy, which has influenced both of us. The idea is simple but profound: we now have decades of life beyond what used to be considered “retirement.” The question is not whether we’re done—but what we do next.

For Karen, that means staying engaged—with younger people, new ideas, and emerging technology. For me, it’s that and more. It also means slowing down, listening more carefully, and becoming a more intentional mentor.

We ended, inevitably, with thoughts about AI. Karen’s view is pragmatic. AI isn’t one thing—it’s many tools, some of them extraordinarily useful. But her most striking point was this: if you want to be a relevant elder today, you have to engage with AI. Not blindly, not uncritically—but actively. As she put it: “You better be using it and know how to use it.”

That, in the end, may be the through line of our conversation: from blogging to Substack to AI, the tools keep changing. But the mindset—curiosity, openness, willingness to experiment—remains the same.

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Traditional vs. Hybrid (aka Indie) Publishing

⬇️ Below is Karen’s very informative publishing memo, which she prepared with the help of Gemini:

Hybrid vs. Traditional Commercial Publishing For First-Time Nonfiction Authors by Karen Wickre

Executive Summary

For a serious nonfiction author, the choice between traditional and hybrid publishing is a trade-off between risk and control.

Traditional publishing minimizes financial risk (no cost to you) but requires a loss of control and a much slower timeline (18–24 months).

Hybrid publishing requires a significant upfront investment ($25k–$50k+) and places the financial risk on you, but offers speed (6–8 months), creative control, and higher potential royalties per copy.

Comparative Analysis

1. Traditional Commercial Publishing

The Model: You sell the rights to your manuscript to a publisher. They own the product; you earn a royalty.

Author Cost: $0. In fact, they pay you. You typically receive an advance against future royalties. For a first-time author, this might range from $5,000 to $50,000 depending on the topic’s commercial potential and your “platform” (audience size).

Author Workload:

→ Writing: High. You must write the manuscript (often after selling the book on a proposal).

→ Marketing: High. Contrary to popular belief, traditional publishers expect authors to do the heavy lifting on promotion. They provide distribution and some trade reviews, but you are responsible for speaking gigs, social media, and PR.

→ Production: Low. The publisher assigns editors, designers, and project managers. You have input, but they have the final say on cover, title, and interior design.

→ Timeline: Slow. Typically 18–24 months from contract to publication.

2. Hybrid Publishing

The Model: You pay a publisher to produce and distribute your book. You retain the rights and creative control; they provide professional curation and distribution.

Author Cost: High ($20,000 – $50,000+).

Industry analyst Josh Bernoff estimates that a high-quality hybrid campaign (including printing, design, and perhaps some marketing support) costs between $30,000 and $50,000.

You pay for everything: editing, cover design, proofreading, and printing.

Author Workload:

→ Management: Moderate to High. You act as the CEO of your book. The publisher serves as a high-end contractor. You don’t have to *do* the layout or editing, but you must review and approve every step.

→ Marketing: High. While some hybrids offer PR packages, the success of the book largely depends on your own efforts and budget.

→ Timeline: Fast. Typically 6–9 months. This is often the deciding factor for “serious contemporary topics” where the information might become outdated if forced to wait two years.

Key Difference: Risk vs. Reward

Traditional: The publisher takes the financial risk. If the book flops, they lose money, not you. You get lower royalties (typically 10–15% of net).

Hybrid: You take the financial risk. If the book flops, you are out your investment. However, if it succeeds, you keep a much higher percentage of earnings (often 40–85% depending on the model).

Part 2: Reputable Hybrid Publishers

For a “serious contemporary topic” (e.g., business, politics, social issues, big ideas), you need a publisher that specializes in thought leadership and has strong distribution into physical bookstores. The following firms are widely recognized as reputable (vetted by sources like Jane Friedman) and are specifically recommended by Josh Bernoff:

1. Amplify Publishing Group

Best For: Business, Politics, “Big Ideas”

Details: Includes imprints like RealClear Publishing (politics) and Amplify Publishing (business). Known for high production value and speed.

Recent Titles: The Age of Intent, Losing Our Elections.

Greenleaf Book Group

Best For: High-achieving authors, Thought Leaders

Details: A veteran in the space. Very selective with a strong airport bookstore distribution network.

Recent Titles: The New Experts, Optimizing Strategy for Results.

Ideapress Publishing

Best For: Business, Innovation, Trends

Details: Focuses on “non-obvious” ideas and business trends. Highly regarded for marketing support.

Recent Titles: Non-Obvious Thinking, The Disruption Mindset.

Page Two Books

Best For: Nonfiction, Strategy

Details: Based in Vancouver but serves the North American market. Specialized in strategy and nonfiction. Known for excellent design and handling complex projects.

Warning: Be cautious of “vanity presses” masquerading as hybrids. If a publisher accepts your manuscript immediately without vetting, it is likely a vanity press. Reputable hybrids are selective and will reject manuscripts that are not ready for market.

Sources & Further Reading

JaneFriedman.com: Offers a definitive list of “Best Known Hybrid Publishers” and guides on how to spot scams.

Bernoff.com: Josh Bernoff’s blog offers deep dives into the “ROI of hybrid publishing” and detailed cost breakdowns for business authors.

At the end of the memo are Karen’s four recommended hybrid publishers, a list I heartily concur with: Amplify, Greenleaf, Ideapress, and Page Two.

Well-known Substack writer , mentioned in our Live conversation, and author of eight books to date, has recently left her traditional publisher for hybrid publishing. Her recent article, The rise of the ‘authorpreneur’, makes the case for why this path is so appealing.

Comments or questions?

Questions and comments about publishing, AI, blogging or anything else we discussed in the LIVE are welcome. Either Karen or I will respond.

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The last time I felt vibrations like these was when I turned 50. I had the articulated sense that if there was something big I really wanted to do, I better get on with it. At the time, I knew exactly what that “something big” was: write a book. After a lot of hard work, and a few lucky connections, I published a nonfiction book with a big-name publisher1. It wasn’t a bestseller; but it was well received. Goal accomplished.

Now, as I turn 75, I’m hearing a different call. What drove me at 50 was ambition; I needed tangible proof that I could make good on a long-held dream. This time, the big thing is something new, something less defined, but something just as felt.

This time, the call sounds something like:

I want to lead, to live my values, and to create a legacy.

That sounds a bit woo woo, something I normally resist. I don’t picture myself as a crone, a female symbol of truth-telling and wisdom, an ancient woman who commands respect. The word is in fashion, but to me it conjures a witchy old woman with a wart-y nose.

That’s not me, at least not yet.

And speaking of popular female archetypes, maybe I have “queen” energy, since it’s more than likely I possess at least some matriarchal wisdom. I may even be stepping into my true self these days. Still, I can’t say any of these terms aloud without slightly… gagging. They’re just not my style.

So for now, I’ve decided to name this unexpected thing Eldering. The word also appeals to me because I’m a repeat student at Modern Elder Academy in Baja, MX.

As an elder, I can lead gently but with authority. As an elder, I can live my values unapologetically. As an elder, I can leave my mark.

But what is eldering, really, and how can I decipher its sudden call? I feel a sense of urgency; it’s not that my time is newly or unexpectedly limited, although I’m pretty sure I won’t live to 1002. It’s that I continue to doubt myself, and I might finally be ready to stop.

This essay took several weeks of thought and revision! Paid [B]old Agers compel me to do the work.

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I keep my annual fee as low as possible. If you absolutely cannot afford to pay, email me at debbieweil@substack.com and I will comp you.

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Despite the advice in and ’s just published Good Writing, I’m going to leave in “very.” The co-authors point out very as a crutch word which should be ruthlessly eliminated (they might strike out ruthlessly too; it’s a little redundant next to eliminated).

I don’t care.

Very belongs here; the word emphasizes the unending pull of my love for my mother, even if I never felt quite seen or fully valued by her.

In the last three years, I’ve experienced missing her in nearly every form: sometimes as a passing thought, other times as a gut punch.

Close to a decade ago, I was reading The Story of Babar to a four-year-old granddaughter. She was nestled in my lap and nodding her head attentively as we turned the first few pages. The story, as you might recall, concerns a young elephant whose mother is killed by a hunter, after which he goes to the city where he is befriended by a kindly Old Lady. “But wait!” Josie said, as I read quickly, hoping to move past the killing. “What happened to his mother?!” Her instant horror made me wince; I wanted to protect her. Because losing your mother is unthinkable, but then it happens.

We hear often about the depth of a mother’s love for her child; just this week actor Jessie Buckley won an Oscar for Best Actress for her role as the mother in Hamnet; wailing like a grief-stricken animal when her son dies.

But what about the other way around–especially, daughters who love their mothers despite everything? That’s what I want to hear about from you today.

If you are older like me, your mother is likely deceased. But perhaps your mother is still alive; maybe you long for her because of missed connections, or for other reasons. Or maybe you had a lovely relationship and it’s a different kind of missing. Tell us more.

I want to hear from you

• Whether your mother is deceased, or alive, do you find that you miss her?

• Sometimes I wonder if I miss my actual mother, or the idea of what she could’ve been to me. How do you reconcile the relationship you crave with your mother vs. the one you have?

• What do you do with overwhelming feelings of loss?
  

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I have drawers, shelves, and boxes filled with sex toys! Periodically I distribute those I no longer want to my friends. They smile when they see me arrive with a sack! - Joan Price

If I had to credit one person for helping me to think more expansively about the definition of sex, it would be . Joan, 82, is a senior sexpert who is renowned for her practical and sympathetic advice. I found her work online almost a decade ago and have been following her ever since. I interviewed her on my podcast several years ago (it was one of the most popular episodes) and got back in touch recently when I saw that she had new editions of her two most popular books1.

Her frank and “spicy” (her word) explanations of desire, sex, and what constitutes intimacy have helped me to understand changes in my 70-something body, especially what to do about the phenomenon of decreasing libido. Don’t wait to feel aroused, she counsels; start fooling around first and desire will come afterwards. That came as a surprise to me and my husband of 53 years; very reassuring.

Four years ago, Joan was quoted in the widely-read New York Times Magazine cover story, The Joys (and Challenges) of Sex After 70. Just last week, she and her 82-year-old boyfriend were profiled in the NYT about their sexual relationship.

And now live, a relaxed and conversational interview with Joan on the NYT Modern Love podcast—that reveals all about her sex life as an older woman!

A Widow’s Guide to Sex (NYT Modern Love Podcast, March 18, 2026)

Here’s the transcript of the podcast with an intro by Anna Martin, host of the Modern Love podcast, and fabulous photos of Joan by Lauren Segal.

Today, we get our very own view behind the scenes with Joan to find out more about her life as a [b]old woman.

Debbie Weil: First, how is your recovery from your car accident?

Joan Price: In April 2025, an unavoidable car crash left me with three neck fractures. You can read more about it on my blog. Recovery is still an ongoing process. Luckily I’m able to do everything I could do before – even teach my line dance classes! I still have discomfort and tire easily. Many thanks to my physical therapist and my wonderful Pilates trainer/ bodyworker for helping me get to this point.

DW: What does [b]old age mean to you?

JP: [B]old age to me means accepting, even celebrating the aging process, adjusting to my body’s ever-changing needs and demands with all the tools I can summon, and trying to find optimism and humor even when the challenges seem massive. One of my mottos: “As long as this is my reality, what can I take charge of?”

DW: You and your partner, Mac Marshall, live by choice in separate abodes in northern California’s Sonoma County. Do you think that distance contributes to a more robust sex life for the two of you?

JP: Absolutely. We see each other when we want to. Living apart gives us solitude and independence. When we come together, we’re ready for connection!

DW: What’s your response to why so many of us are hung up on PIV (penis in vagina) as the definition of sex??

JP: It’s what we were taught was “real” sex.

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Not so long ago, I wrote about using ChatGPT to edit one of my drafts and how it made my editor, , cry. She writes her own newsletter, FREQUENT CRIERS CLUB, but this was different. Was AI going to put her out of business as an editor? I’d felt seen and understood by ChatGPT’s input on my rather personal essay, but it turned out that a number of the chatbot’s assumptions were incorrect; I’d been fooled. So the answer was… No!

Not wanting to prompt any more tears from Erin, nor wanting to fall again into a rabbit hole of confusion and doubt about whose words and ideas I was using (mine or the bot’s), I swore off ChatGPT for writing.

But now I’m learning to use AI in non-creative ways that are both mind-expanding and productive. I want to share a few of them with you; then I very much want to hear how you are using AI, and, if not, why. I hope you’ll meet me in the Comments.

Brainstorming

When I began to think about the complex topic of the 100-year life (and why I’m pushing back on it), I went right to ChatGPT1 with key questions. What are studies and stats I can refer to (the likelihood of living to 100, for example)? Recent articles in MSM? How might I organize this essay?

Then, I paused, pulling back to separate myself from AI, to consider what my goal was in writing this… to be factual and accurate but also to convey emotion.

I feel comfortable with this brainstorming approach for multi-dimensional essays—as long as I draw a clear line between research and creative output. I do NOT accept the bot’s offer to start writing for me, even if it’s just the first sentence or paragraph.

But there’s more to using AI as a thinking partner, especially if you want to think bigger—something I’m trying to do with [B]old Age.

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Read on for what I’m working on right now.

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Ever since I attended a creativity workshop1 with and in Baja, MX, I’ve been fired up about radical permission.

I keep wondering: what would it mean to give myself radical permission when it comes to this newsletter? What am I drawn to write about that I’ve been holding back on, that feels taboo? Here are a few things:

• GRIEF: the liberating, flip side of grief we don’t hear enough about

• MONEY: inheriting money from my father; the questions it raises

• SEX: the truth about sex in my 70s; there’s so much I haven’t figured out yet

The flip side of grief

When I lost both of my parents in the past three years (first my mom, then my dad), I had the dizzying sensation that I’d been unmoored. For over 70 years, they provided an inescapable reflection of who I thought I was; without them, who was that person? I loved both my mother and father very much, but their deaths—once the initial grief dissipated, once I’d gotten used to being untethered—offered something else… relief.

I am giving myself radical permission to tell you about this liberation, this feeling of freedom, because I suspect others have experienced something similar. It could relate to the death of parents who loved you conditionally, or perhaps the death of an abusive partner, or anyone you’ve had a complicated relationship with. I call it the flip side of grief; it exists alongside love, and neither cancels out the other.

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Three things happened last week that, taken together, reveal the deep truth about getting old. All three are painful; one is devastating.

Here are the three things, in the order of Good, Not So Great, and Devastating. As with a kaleidoscope, I’ve been turning the dial to see each one more clearly. I am still reeling.

1. I retreated to Baja for space to reflect with ; that opened up some uncomfortable realizations

2. Sam continues to recover from painful knee-replacement surgery; taking care of him evokes fear for the future

3. Lucy, one of my dearest childhood friends, died unexpectedly

First, revelations from a Baja retreat

This is what happened when I flew across the country from the East Coast last week to meet celebrity author : I realized I’ve been holding back in this newsletter. Liz asked us to explore what it means to “give ourselves permission,” and I realized that I’ve been hedging, even apologizing as I tell the story of growing old. I can’t do that anymore. I have to tell you the story more honestly. I’ve been holding back anger; I’ve been explaining myself too much; I’ve been afraid of disappointing or disgruntling readers. But I’m done auditioning for a slot in the “old woman celebrating old age” category; I’ve found my niche and that’s not it.

My story is ambivalence about old age. I am giving myself permission to tell this truth, more clearly and with more certainty. Sure, I know there are plenty of blessings (foremost for me, three children and six grandchildren), but the hard stuff (what I call the “bullshit”) requires bravery to face head on. And I’m not talking about wrinkles, sagging breasts, or extra pounds. It’s the hard truths about love and relationships, accepting the sadness of what I can’t change; it’s reckoning with legacy and accomplishment, and realizing my fierce ambition won’t drive me forward forever; it’s the growing awareness of precious time running out. It’s my story—and yours.

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Welcome to [B]old Age, where I write about the blessings AND the bullshit of growing old. I’m pro-aging, but I’m also honest, brave, and obsessed with the bittersweetness of old age.

Read on for a travel diary of this week… and a special hello to my new compadres from Baja!

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Waves curl and pound this wide stretch of beach on Mexico’s Pacific coast, the permanent soundscape to a place I’ve visited a half dozen times but never tire of. Just a few days ago, I came within a hair of not getting on the plane to make the long trek from the East Coast.

My husband had just undergone knee-replacement surgery; yet he assured me that he could manage on his own (and that, as a clumsy nurse, I was driving him crazy). But I’ve never wavered so many times on whether to take a planned trip. Wasn’t it selfish to go? I finally decided that Sam would be okay and that I couldn’t pass up meeting (yes, THE Liz Gilbert) and her, to me, mysterious co-presenter .

Still, as much as I wanted to come back to MEA (the “wisdom school” I’ve written about), I was skeptical. As famous as she is, what could Liz really offer in a group workshop? I scribbled in my journal on the plane: “What does she have to teach me about purpose, joy, self-acceptance, creativity, bravery, etc. We’ll find out… “

And also, who was Tererai, and what was her role in a workshop on creativity? Wikipedia told me: “Tererai Trent is a Zimbabwean-American woman whose unlikely educational success has brought her international fame.” That was interesting!

A few highlights

The workshop opened with a short video recognizing Terarai Trent as “Oprah’s Favorite guest of all time.” I was blown away. Tererai grew up in a cattle-herding village in Zimbabwe, was married at 14, with no education, and had four children by the time she was 18.

Read more

After working with my amazing editor, , for 2 1/2 years, it was time to take a deep dive into our collaboration, from the logistics to our creative partnership to lessons learned about writing and publishing on Substack. This was a relaxed, free-flowing conversation and I hope you’ll have as much fun watching the replay as I did chatting with Erin. Be sure to subscribe to Erin’s Frequent Criers Club!

Thank you , , , , and so many others for tuning in!

Summary of our Live conversation

and I discuss what it really takes to sustain a weekly Substack—both the practical systems and the emotional/creative realities. I explain that I began writing in June 2023. My mother died in February of that year, my grief was complicated, and my podcast producer urged me to start writing again. Even with decades as a professional writer and editor—and the long-running podcast—weekly publishing initially felt like “a nightmare,” fueled by perfectionism and constant second-guessing, to the point of “rewriting” drafts in my dreams. (Spoiler alert: that doesn’t work.)

Finding Erin through a Q&A interview where she explained her editing process led to a collaboration that quickly calmed that spiral: I could hand off a draft, trust a second brain, and publish weekly with a very smart co-conspirator.

A central theme in our conversation is what a good editor actually does: preserve the writer’s voice while advocating for the reader. Erin emphasizes she isn’t a co-writer—she helps shape, refine, and clarify, often by offering example lines and inviting me to tweak. I accept almost all of her suggestions because it’s a kind of mind-meld; she understands what I’m trying to say; she also pushes me to be clear. This partnership has improved my writing, without a doubt, and it makes the process more fun, echoing what I loved about podcasting: creative work thrives with “another mind.”

We also talk about a key sustainability strategy: a mix of content types so every week doesn’t require a full personal essay. For [B]old Age, that includes:

• Q&As with [B]old Women (a lower lift than an essay, but still requires research, tailored questions, and a strong intro).

• Discussion question posts that spark high engagement and community (including a standout thread like “Do you lift your own bag into the overhead bin?” which opened up talk about aging, strength, chivalry, independence—and whether to go carry-on or check).

• Occasional lighter formats when traveling (photo diaries, short updates), while still honoring the weekly commitment.

Our conversation highlights how weekly cadence creates momentum—and how breaks can make restarting harder. I tie this to my journalism training: if you commit to publishing, you honor it. Erin adds that a publishing calendar (our shared, color-coded Google Calendar) reduces stress by planning post types even when the exact topic isn’t chosen yet—creating structure without killing flexibility.

We also address the complicated reality of Substack’s “social” layer (Notes). I find that Notes intensify comparison, envy, and self-doubt—especially when others get massive likes and restacks. Erin reframes this as a predictable psychological trap and suggests that having a trusted editor, writing group, or a few first readers can “turn down the noise” and keep the creator grounded.

Near the end, Erin shares her own newsletter origin story—which I’d never heard before! After a scary ER trip sparked by chest pains and fear of a heart attack, she felt a strong push to create her own publication. That became , a once/twice-monthly newsletter with both personal essays and a “lower lift” recurring feature (“crying, numbing, sparking”).

Finally, we tackle the balance between writing for yourself and serving readers. I believe the work must start as self-clarification (“I write to find out what I’m thinking” — Joan Didion), but becomes “useful” through connection—especially the community created by comments. I aim for an honest middle path in writing about aging: not forced positivity, not pure despair—something truer and more complicated. We close with one of my guiding principles about writing: “It’s not real unless I publish it and put it out into the world.”

This AI-generated transcript summary was carefully edited by me, including clarifications of key points! - Debbie

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We’d love to hear from you!

- Debbie & Erin

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