All posts by Jackie Pick

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About Jackie Pick

Jackie Pick is a former teacher and current writer living in the Chicago area. She is a contributing author to multiple anthologies, including Multiples Illuminated, So Glad They Told Me: Women Get Real about Motherhood, Here in the Middle, as well as the and the literary magazines The Sun and Selfish. She received Honorable Mention from the Mark Twain House and Museum for her entry in the Royal Nonesuch Humor Writing Competition. Jackie is a contributing writer at Humor Outcasts, and her essays have been featured on various online sites including McSweeney's, Belladonna Comedy, Mamalode, The HerStories Project, and Scary Mommy. A graduate of the University of Chicago and Northwestern University, Jackie is co-creator and co-writer of the award-winning short film Fixed Up, and a proud member of the 2017 Chicago cast of Listen To Your Mother.

How to Laugh at Death While Time Eats Itself*

Book Review, Books, Reading, Recommendations, The Folio

What I Read September 2025

This month I’ve been juggling eleventy kajillion calendars. This is not, as you might assume, because I am a particularly efficient or important person. It is because time, like most of my kitchen drawers, gets jammed on all the oversized things I try to cram in it. Items currently requiring my attention and scheduling: two schools, two adults working from home at somewhere between two and seventeen different jobs, volunteer activities, various kid activities and applications, and the all-important sacred day when the Halloween candy finally materializes on the grocery shelves. That’s the one holiday America does perfectly. Costumes, sugar, minimal chitchat.

Fittingly, every book I finished in September carried within it the godforsaken ticking of a clock – THE clock – with incessant urgency and inevitable silence.

In Replay, time is a wheel greased with déjà vu: die, reboot, repeat. Maggie Smith’s Dear Writer is profoundly gentler, insisting we use our time well and show up to the page. The end will come regardless but right now there is time to mark the paper purposefully, joyfully, fearlessly. Obitchuary treats death like a hot gossip item, grief delivered with a rimshot. Robert Benchley proves that even the most mundane of moments can be slapstick if you just untie its shoelaces.

Put another way: my eleventy kajillion calendars don’t lie, though they constantly contradict each other. We’re all quite busy running out of time, and what remains is how we spend it. There are jokes, stories, hope, relationships, and maybe a decent breakfast before the lights click off.

Which is all just to say here are the books I enjoyed enough to finish this month, in no particular order except the one I typed them:

  • Dear Writer by Maggie Smith
  • Replay by Ken Grimwood
  • Obitchuary by Spencer Henry and Madison Reyes
  • The Benchley Roundup by Robert Benchley

*If you’ve ever watched a week vanish into laundry, you’ve seen it happen.

DEAR WRITER by MAGGIE SMITH

In the opening paragraphs of Dear Writer, Maggie Smith writes, “I believe creativity is our birthright as human beings.” I like this. It’s a much better birthright than, say, a Costco card or bad knees. She doubles down a page later: “When you read a poem, or listen to a song, or watch a play, you’re not the same person afterward. You’re slightly rearranged.”

Smith organizes her book around ten principles, which incidentally sound like the syllabus for the world’s nicest graduate program: Attention, Wonder, Vision, Play, and more. Each comes with a note to “Dear Writer,” followed by essays, some prompts, and suggestions for further reading. It’s craft book meets pep talk, heavy on kindness and honesty, light on prescriptive rules.

The section on Vision is a banger. Smith advises us to “make your own uncool,” which is the kind of line I love because I am, in fact, deeply uncool, so this will take very little effort on my part. The gist: take risks, some people won’t like your work, and that’s okay. The chapter on Restlessness also hit home. Smith reframes that itchy dissatisfaction we all feel when a draft isn’t there yet as something generative.

Smith’s quotable lines are legion. In Tenacity: “Your creativity is calling. It needs you. Work on your endurance and stamina. Wring your mind out like a rag over a bucket, until it’s bone-dry. Get every drop.” In Hope: “If hope is imaginative, then pessimism is a failure of imagination.” And she drops a piece of advice from Stanley Plumly that I’m still chewing on: “Stay deep within yourself and stay alone there — that is where your poems come from, and that has nothing to do with an audience. You are the audience.”

You don’t have to please anyone else in the room. You’re the damn room.

My personal underline-and-throw-exclamation-points-in-the-margin fest came in her section “On Feedback.” As someone who’s received workshop comments that shut me down for months, I found her take validating and humane. Feedback, she reminds us, isn’t about finding what’s “wrong,” it’s about clarifying, supporting, and helping the writer get closer to what they want.

If you’ve read Anne Lamott’s Bird by Bird, this book is its scrappy cousin. Same heart, different swagger.

My favorite read this month.

REPLAY by KEN GRIMWOOD


This month I’ve been juggling eleventy kajillion calendars. This is not, as you might assume, because I am a particularly efficient or important person. It is because time, like most of my kitchen drawers, gets jammed on all the oversized things I try to cram in it. Items currently requiring my attention and scheduling: two schools, two adults working from home at somewhere between two and seventeen different jobs, volunteer activities, various kid activities and applications, and the all-important sacred day when the Halloween candy finally materializes on the grocery shelves. That’s the one holiday America does perfectly. Costumes, sugar, minimal chitchat.

Fittingly, every book I finished in September carried within it the godforsaken ticking of a clock – THE clock – with incessant urgency and inevitable silence.

In Replay, time is a wheel greased with déjà vu: die, reboot, repeat. Maggie Smith’s Dear Writer is profoundly gentler, insisting we use our time well and show up to the page. The end will come regardless but right now there is time to mark the paper purposefully, joyfully, fearlessly. Obitchuary treats death like a hot gossip item, grief delivered with a rimshot. Robert Benchley proves that even the most mundane of moments can be slapstick if you just untie its shoelaces.

Put another way: my eleventy kajillion calendars don’t lie, though they constantly contradict each other. We’re all quite busy running out of time, and what remains is how we spend it. There are jokes, stories, hope, relationships, and maybe a decent breakfast before the lights click off.

Which is all just to say here are the books I enjoyed enough to finish this month, in no particular order except the one I typed them:

  • Dear Writer by Maggie Smith
  • Replay by Ken Grimwood
  • Obitchuary by Spencer Henry and Madison Reyes
  • The Benchley Roundup by Robert Benchley

*If you’ve ever watched a week vanish into laundry, you’ve seen it happen.

DEAR WRITER by MAGGIE SMITH

In the opening paragraphs of Dear Writer, Maggie Smith writes, “I believe creativity is our birthright as human beings.” I like this. It’s a much better birthright than, say, a Costco card or bad knees. She doubles down a page later: “When you read a poem, or listen to a song, or watch a play, you’re not the same person afterward. You’re slightly rearranged.”

Smith organizes her book around ten principles, which incidentally sound like the syllabus for the world’s nicest graduate program: Attention, Wonder, Vision, Play, and more. Each comes with a note to “Dear Writer,” followed by essays, some prompts, and suggestions for further reading. It’s craft book meets pep talk, heavy on kindness and honesty, light on prescriptive rules.

The section on Vision is a banger. Smith advises us to “make your own uncool,” which is the kind of line I love because I am, in fact, deeply uncool, so this will take very little effort on my part. The gist: take risks, some people won’t like your work, and that’s okay. The chapter on Restlessness also hit home. Smith reframes that itchy dissatisfaction we all feel when a draft isn’t there yet as something generative.

Smith’s quotable lines are legion. In Tenacity: “Your creativity is calling. It needs you. Work on your endurance and stamina. Wring your mind out like a rag over a bucket, until it’s bone-dry. Get every drop.” In Hope: “If hope is imaginative, then pessimism is a failure of imagination.” And she drops a piece of advice from Stanley Plumly that I’m still chewing on: “Stay deep within yourself and stay alone there — that is where your poems come from, and that has nothing to do with an audience. You are the audience.”

You don’t have to please anyone else in the room. You’re the damn room.

My personal underline-and-throw-exclamation-points-in-the-margin fest came in her section “On Feedback.” As someone who’s received workshop comments that shut me down for months, I found her take validating and humane. Feedback, she reminds us, isn’t about finding what’s “wrong,” it’s about clarifying, supporting, and helping the writer get closer to what they want.

If you’ve read Anne Lamott’s Bird by Bird, this book is its scrappy cousin. Same heart, different swagger.

My favorite read this month.

REPLAY by KEN GRIMWOOD

The trouble with dying at 43 (or any age, really) is that you expect it to be permanent. So imagine Jeff Winston’s surprise when he keels over at his desk, only to wake up in his 18-year-old body, circa 1963, with all the memories of a man who’s already survived disco. From the opening pages, it feels more exciting than the life he just lost.

At first, Jeff Winston does exactly what most of us would do. He places major bets, invests wisely, and generally struts through life knowing how it all turns out. But then the loop resets. He dies at 43 again. And again. And again. Turns out living the same 25 years over and over, no matter what, is maddening.

Like Groundhog Day stretched across decades, the book shifts from fantasy to philosophy. Can you only enjoy being 18 if you’re actually 43 inside? What happens when you’re living as a teenager and a middle-aged man at the same time? Grimwood leans into those ripple effects where every choice remakes the world, but the ending never changes.

The pacing is tight. Grimwood spares us the tedium of every replay in full, fast-forwarding to the choices that matter like a cosmic remote control with a mercifully working fast-forward button. Yes, it reads a little late-1980s, but then again, so did the 1980s.

If you love books like 11/22/63, “what if” fiction with actual emotional depth, or have ever just wondered “If I had to do it all over again, knowing what I know now…” you might enjoy Replay.

Replay starts as wish fulfillment (i.e., the fantasy of having the opportunity to do it again and fix things) and becomes a philosophical exploration of regret, loneliness, and the dreadful suspicion that life only matters because it ends. The brilliance of Grimwood’s novel is in showing that inevitability can be both a curse and a peculiar sort of gift.

OBITCHUARY by SPENCER HENRY and MADISON REYES

I didn’t realize until after I got hold of this one and looked at the back cover that the authors are podcasters. This did not bode well. I like my podcasts like I like my books: unrelated.

I opened it anyway.

Obitchuary is breezy, irreverent, and laden with more-than-occasionally-gross death facts. If there is a Venn diagram of “Halloween enthusiasts” and “people who correct you on the Latin root of rigor mortis,” this book sits precisely in the overlap. Especially good for pub trivia enthusiasts during Spooky Season.

The tone at first is like listening to two slightly tipsy friends who’ve been speaking in inside jokes since middle school. Now set them loose on the surprisingly sober business of what happens to your body after death. It’s not wholly unpleasant, but it’s undeniably jarring.

By Chapter Two, they settle in. The humor shows up in the right places instead of everywhere all at once, and the information takes the lead. Honestly, they are funny, it just lands better when they don’t keep poking you in the ribs to make sure you noticed the joke.

What Obitchuary underscores, with a deliciously relentless cheer, is how people are quite odd about death. Before it, during it, long after it. Some readers will find this refreshing, others gratuitous, and still others will wonder if they’ve accidentally purchased the wrong book.

That’s gallows humor for you.

I finished it out of morbid curiosity (tip your wait staff). I read some sections twice, skipped others. That’s the great advantage of nonfiction. You can dip in and out.

But whatever you do, don’t skip the epilogue. It’s unexpectedly tender and inspiring.

This book might best be enjoyed by fans of the Obitchuary podcast, trivia junkies of the macabre, or readers who like their death culture delivered with a wink. If you think you might be the audience, flip through it first. You’ll know pretty quickly.

THE BENCHLEY ROUNDUP by ROBERT BENCHLEY

Robert Benchley was the sort of man who could look at a perfectly ordinary activity and turn it into a full-scale farce. He made being baffled by modern life into a writing career, which is no small achievement considering modern life’s eagerness to baffle.

The Benchley Roundup, assembled by his son Nathaniel, gathers these short pieces into a single cabinet of curiosities.

It is what you might call a “panoply,” although I can’t imagine anyone actually using that word outside of a catalog.

Nathaniel admits up front that his father’s humor is hard to pin down: “I don’t think it can be analyzed. It is sometimes mad, sometimes penetrating, and sometimes based on nothing more than word associations, and the only generalization that can be made with any degree of certainty is that it is different—or, if you will, unique.” Which is another way of saying: abandon all hope of categorization. Benchley was, inconveniently, unique. And that’s exactly the appeal: Benchley never sounds like anyone else, even now. I would venture a guess that Benchley thought faster than the rest of us, and we’ve been trying to catch up ever since.

Many of these essays originated in magazines. Some land perfectly; others remind you that you are reading something written when people still wore spats with jokes and references that make you feel like you’ve walked into a party eighty years too late. Others arrive startlingly fresh, proof that certain absurdities never go out of fashion. Humor is like that: part fossil, part banana skin.

Reading Benchley today is like watching an old black-and-white film where everyone speaks in that brisk, so-called mid-Atlantic accent that once passed for sophistication and now just sounds faintly ridiculous. But that voice, that sense of time, is half the fun. His writing is unpretentious, seemingly effortless, and wide-ranging. You get the sense he could spin absurdity out of absolutely anything. And often did. This is either a tribute to Benchley’s talent or a condemnation of how little progress we’ve made as a species. Probably both.

The Benchley Roundup is a delight to dip in and out of. Some essays feel like artifacts, some land with fresh precision, but together they remind you why Benchley mattered, how he influenced subsequent generations of humorists, and why his style still feels different, even now. It’s smart, silly, and deceptively simple. As his son notes, the collection is best read in small doses, dipped into like a jar of peculiar sweets, because each piece is its own odd little universe. Some will feel like time capsules, others like dispatches from a mind still waiting for us to catch up. Benchley pointed out, with impeccable timing, just how gloriously inexplicable the world was and still is.

And there be the September reads. As always, I welcome any recommendations! What’s in your TBR pile?

A Modest Proposal for the Preservation of Civilization by Means of Group Chats

Humor, Ink Spatterings, Under 750, , ,

Encompassing but not limited to text chains, Messenger threads, WhatsApp dramas, Facebook comment kerfuffles, and similar circles of digital grievance.

It is a melancholy object, to those who dare attempt discourse, when they find conversations derailed by nuance, muddied with civility, or — ye gods! — conducted in person. Face-to-face conversations are notoriously unreliable, as they often involve people saying things that sound suspiciously like what they mean.

In this smoldering age, politicians argue, institutions creak, and somewhere, someone is inventing a new kind of paperwork.

I think it is agreed by all sensible parties (and at least three committees who have been trying to adjourn since 2006) that the sheer multiplicity of human communication is a public menace. Who amongst us has not endured the inefficiency of speech, the peril of eye contact, or the muppety flapping of arms to emphasize a point? No politician, pundit, or professor can preserve us.

Therefore, I modestly propose (usually preferable to immodestly proposing) that the group chat be the model and indeed the mechanism by which all of society is preserved. All communication, be it domestic, political, or sextual, should be confined henceforth to group texts, Facebook comment threads, and other online bitching arenas. All comments can be observed, recorded, and weaponized as needed. I propose these places not because they’re good, but because they’re reliably bad, which these days is the closest thing we have to safe.

We have already seen its power. A PTA chat of fifteen mothers and one father who replies “sounds good” can coordinate massive amounts of allergen-free snacks with more efficiency than the Pentagon deploys aircraft. A college roommate chat can process four marriages, two divorces, and one regrettable tattoo with fewer delays than family court. A midnight “you up?” has sparked (and derailed) more talks than Geneva.

By my best calculations, a group text of six to thirty-seven people, on a topic of no importance or clarity, can continue for weeks without resolution yet with feigned enthusiasm, thus bonding the community like poorly-set epoxy. Likewise, a Facebook thread can be expected to produce on average 142 comments: 118 bad-faith accusations, 17 GIFs, and 7 people sincerely attempting to help. They will be ignored. Surely these numbers demonstrate the efficiency of the system. Surely, also they demonstrate the futility of resistance.

Also, I posit with the mathematical certainty of one who regularly zoned out in algebra class, that for every one thousand “k” reactions, at least five international conflicts may be prevented. Gross domestic happiness would increase by twelve percent.

Of course, rules must be clear: no muting, no leaving, no sneaking off to Buffalo Wild Wings for in-person jibber jabber. Every meme circulated thrice shall acquire the force of law.

Should anyone run afoul of these rules, the penalty shall be immediate banishment to an uncomfortably governmental Signal chat.

Some will cry out that this proposal reduces sincerity, nuance, and basic human decency. To which I reply with all possible graciousness: obviously. Have you met people? And have we not already reduced all discourse to bloviating, grievances, and emojis? I merely propose a proper filing system.

Others may object in favor of email, to which I say: That way lies madness. Group texts are the last good ship on the sea, and if we are to survive, we had better climb aboard. (Also, just admit it: your Gmail is a Mausoleum of the Unread.)

A third objection may be raised, that conversation face-to-face is preferable. This, in theory, I cannot deny; yet in practice, it has already ruined civilization, whereas the group text has not yet had the opportunity.

I profess sincerely that I have no personal stake in this. I have been ejected from three group chats, ignored in countless threads, and endured the indignity of someone attempting to mute me in person with a TV remote. My only motive is the preservation of civilization by its last remaining instrument: the perpetual ding of notification

A Meeting of the Mind 2

Creative non-fiction, Humor, Ink Spatterings, Writing, Writing process, Writing the first book

Sequels Are Always Better Than the Original, Right?

ME: Good morning, Every Part of My Brain. Welcome to this second and highly improbable gathering of the committee. Let’s welcome Dragon to the team. He gnaws on my free time like chicken bones.

DRAGON: Cease! There’s no time for kissing up.

ME: We’re going to skip the icebreakers. We all know each other, as last month’s axe-throwing social made painfully clear.

(cheers erupt as Hype Man roars and grinningly points to a massive scar on his forehead. )

ME: Here are the minutes from the last meeting, which I’ve canonized as “classic literature.”

CRITIC: So it’s achieved the distinguished state of being largely unread?

HYPE MAN: YEAH! Minutes! The sizzle reel!

ME: Right. Brilliant. Perfect start. (clears throat) Time is like a soufflé: delicate, prone to collapse, and –

DRAGON: – guarded by me.

MONKEY BRAIN: I call this meeting to chaos! All in favor?

ME: Hands down. FYI, this meeting was pushed to the 3rd quarter because –

MARKETER: – because I double-booked us with a webinar on “Optimizing Your Creative Brand in Twelve Excruciating but Photogenic Steps.”

DRAGON: (snorts a puff of smoke like an offended kettle) Pathetic.

ME: Next, Old Business.

ARCHIVIST: Every Business eventually turns into Old Business.

DREAMER: New Business is just Old Business we haven’t met yet.

CRITIC: Our Old Business hangs around like a bad smell, because none of you actually take care of anything. Except, you, Me.

(MONKEY BRAIN flings unwrapped Tootsie Rolls at everyone. Snacking ensues.)

ME: (bangs gavel) Yes, very good. Moving on. I’d like to discuss role consolidation. I propose merging Critic, Worrier, and Self-Doubter into one tidy Efficiency Pod.

CRITIC: Absolutely not.

SELF-DOUBTER: I don’t think I’m pod material.

WORRIER: I’m not pod-shaped.

ME: Fine. Separate disasters you shall remain. Please fill out your timecards accordingly.

DRAGON: You people waste time like it’s your job.

ME: Can we please talk about writing?

Archivist: Ah. The novel. How goes it?

CRITIC: Probably like an axe to the skull, right, Hype Man?

HYPE MAN: Uncool, but still, high-five!

ME: It, I am happy to say, goes well.

DREAMER: (rolling in a corkboard) I took the liberty of creating a Vision Board of our progress. Behold: a vaping dolphin, a typewriter made of ice cream, and Keanu Reeves in velvet singing Elizabethan madrigals.

ME: What on earth?

CRITIC: That’s not a vision board. That’s a cry for help.

HYPE MAN: Love it! Everyone should vape out of their blowhole!

MONKEY: BLOWHOLE

WORRIER: Is Keanu singing madrigals, or is it the velvet jacket?

ARCHIVIST: Actually, that’s corduroy, not velvet.

ME: Let’s all stop –

WORRIER: Stop writing?

ME: What? No!

DREAMER: Taking a rest stop on the cosmic highway!

ME: No rest –

CRITIC: No rest?Sounds like your characters need better working conditions.

ARCHIVIST: Please be sure to log all character reassignments.

ME: I’m reverse outlining and rewriting in loops. Plot, character, theme, setting, subplot, then back around again. Everything in some sort of organized heap, then, adjusted until it works.

DREAMER: Have you considered a treasure map subplot? Or a phoenix? Or writing it in second person? Should only tack on what, 1-9 months to the process?

DRAGON: I’ve barely allowed you enough time to inhale, and you want to exhale treasure maps?

ARCHIVIST: I’ll need to research whether phoenixes and treasure maps can coexist in second person.

MARKETER: Forget all that. Pivot to a cookbook. Cookbooks sell.

MONKEY BRAIN: Iguanas!

ME: No treasure maps. No phoenixes. No second person. No cookbooks. No iguanas. No cookbooks for iguanas or (holds up a warning finger to MONKEY BRAIN) cookbooks about how to cook iguanas. I like my story and have committed to it.

DREAMER: Have you considered switching careers and becoming an organ grinder?

ME: Like in a play-the-barrel-organ way or in a Sweeney Todd way?

MONKEY BRAIN: I’m suddenly uncomfortable

CRITIC: You’re all deranged.

ME: Chair agrees.

DREAMER: [leaps to feet dramatically] I propose we devote the next month to exploring the concept of time as a sentient being.

CRITIC: Opposed. Hard no. Like, concrete-after-a-Chicago-winter hard no.

HYPE MAN: Also a no, but great idea! Imagine the tagline: What if time was alive? Boom! Bestseller! High five!

ARCHIVIST: Seconded, pending a trademark search for “sentient time.”

DRAGON: [snarls] Time is indeed sentient, and it hates you.

WORRIER: Motion for catastrophic preparedness: deadlines missed, mockery, general and specific humiliations. And typos.

HYPE MAN: Opposed! Fear is the mind-killer, baby!

MARKETER: I propose we conduct a comprehensive market analysis before finishing the draft. Demographics, comps, audience studies.

ME: Opposed!

CRITIC: Motion to stop overthinking.

WORRIER: Counter-motion to overthink harder.

HYPE MAN: Counter-counter-motion to stop thinking entirely.

ME: All right, team. The plan is simple: cooperation. If we can work together, we will finish this thing, and maybe even start other things. Right now we’re like a rickety cart pulled by twelve horses in different rodeos.

SELF-DOUBTER: This is delusional.

HYPE MAN: Delusional? This is destiny! Cooperation! Teamwork! No rickety carts!

DRAGON: I know I’m new here, but this sounds like a waste of time. Considering…(gestures at the group, chews a charcoal briquette, then belches).

ME: We’ll continue to work calmly, one voice at a time.

MONKEY BRAIN: (waves squished Tootsie Roll) Guess what this looks like! Guess! Wrong answer, it’s poo!

ME: Why do I bother?

CRITIC: That’s the real question, isn’t it?

HYPE MAN: Because you love it! Because this draft is fire! Because we’re unstoppable!

SELF-DOUBTER: Or because she doesn’t know how to quit.

ME: One of you has got to be right. All right, meeting adjourned. Spirit Halloween wants this space.