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When Pigs Fly: My 100-Word Ideas for a Year
Doing this book was like writing a flash fiction story a day for a year, but not just little stories — philosophical speculations, jokes, mystical musings, practical tips, autobiographical tidbits (real and imagined), social commentary, etc. Some you might consider profound, others stupid (or worse), but at only 100 words each, if anything angers or annoys or even bores you, it’s on to the next for something entirely different.
375 pages, Kindle Edition
Published March 8, 2025
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Displaying 1 - 24 of 24 reviews
August 15, 2025
If you’ve ever wondered what it’s like to crawl inside the swirling, caffeinated brain of an author mid-creative explosion, this is the book for you— just bring snacks and maybe a helmet. The novel’s concept is inspired, or at least delightfully unhinged: a collection of 100-word musings on wildly varying subjects. We're talking everything from a Cosmic Timepiece (tick-tock, dread), to Housebot (your friendly neighborhood tea-brewing robot), to Tired Magic— which is basically every wizard after working retail hours.
There’s also Gastronomic Debauchery, which might just be a fancy way of describing my weekend diet, and of course, My Demons— because what quirky literary collection would be complete without them making an appearance and overstaying their welcome?
I particularly bonded with My Chronic Dizziness— finally, a piece of writing that understands my wobbly, salt-deficient soul. My doctor tells me to “increase sodium,” which is a polite way of saying, “enjoy your life slightly saltier and infinitely more boring.” Thanks, Doc. I cringe, as I hate the taste of salt.
The author has clearly mastered the art of cramming a novella’s worth of angst, wit, and wisdom into tight 100-word parcels, like literary tapas. Some entries are genuinely funny, others deliciously dark, and a few left me blinking uncomfortably at the page like, “Oh, so we’re going there, huh?” But hey, when you're trying to cover everything from metaphysical concepts to tea-making robots, you’re bound to hit a few speed bumps— or emotional potholes.
What’s impressive is that despite its chaos, the whole book never reads like the literary equivalent of an unhinged YouTube comment thread. It’s actually coherent. Somehow. A tidy, experimental, borderline-stream-of-consciousness journey which demonstrates that you can bounce from topic to topic like a caffeinated squirrel and still make perfect sense— without being full-on schizophrenic or turning the reader into a confused puddle.
In the end, it’s a mixed bag, sure— but one of those intriguing mixed bags where even the weird licorice piece makes you think deeply about your childhood. Compelling, unexpected, and guaranteed to poke your brain in the ribs at least once.
There’s also Gastronomic Debauchery, which might just be a fancy way of describing my weekend diet, and of course, My Demons— because what quirky literary collection would be complete without them making an appearance and overstaying their welcome?
I particularly bonded with My Chronic Dizziness— finally, a piece of writing that understands my wobbly, salt-deficient soul. My doctor tells me to “increase sodium,” which is a polite way of saying, “enjoy your life slightly saltier and infinitely more boring.” Thanks, Doc. I cringe, as I hate the taste of salt.
The author has clearly mastered the art of cramming a novella’s worth of angst, wit, and wisdom into tight 100-word parcels, like literary tapas. Some entries are genuinely funny, others deliciously dark, and a few left me blinking uncomfortably at the page like, “Oh, so we’re going there, huh?” But hey, when you're trying to cover everything from metaphysical concepts to tea-making robots, you’re bound to hit a few speed bumps— or emotional potholes.
What’s impressive is that despite its chaos, the whole book never reads like the literary equivalent of an unhinged YouTube comment thread. It’s actually coherent. Somehow. A tidy, experimental, borderline-stream-of-consciousness journey which demonstrates that you can bounce from topic to topic like a caffeinated squirrel and still make perfect sense— without being full-on schizophrenic or turning the reader into a confused puddle.
In the end, it’s a mixed bag, sure— but one of those intriguing mixed bags where even the weird licorice piece makes you think deeply about your childhood. Compelling, unexpected, and guaranteed to poke your brain in the ribs at least once.
August 16, 2025
Odyssey Through the Human Condition
Having been utterly fascinated by Ray Gregory's 'Old Souls', I eagerly dived into 'When Pigs Fly', and once again, this author proves himself to be a master of unconventional and deeply thought-provoking insights.
This book is a unique treasure: a collection of over 360 short entries, like distilled diary notes, each 100 words long. Yet, within these concise paragraphs, Gregory packs an astonishing density of meaning, forcing you to slow down and truly absorb every carefully chosen word.
The themes are as vast and varied as the human experience itself, spanning from profound reflections on God and human connection to candid observations on first crushes, social commentary, and even mystical musings. It's a journey through the author's sharp, often dark, but always bitingly true viewpoint of the world. A particular quote that resonated deeply with me, echoing a favourite poem by Robert Frost, stated: "Not some cosmic cataclysm but internal strife will be the demise of our kind." Entries like "Unconditional love", "Barbara", "Psychiatric Mom", and "Porn Numbed" burrowed into my thoughts, showcasing Gregory's ability to evoke complex emotions and stark realities in minimal prose.
'When Pigs Fly' is an intensely rewarding read for anyone who appreciates literature that demands active engagement and rewards careful consideration. It’s a remarkable testament to the power of brevity, offering a profound and incredibly true reflection of life. I highly recommend this book for readers who enjoy intellectual sparring and the kind of wisdom that lingers long after you've closed the page.
Having been utterly fascinated by Ray Gregory's 'Old Souls', I eagerly dived into 'When Pigs Fly', and once again, this author proves himself to be a master of unconventional and deeply thought-provoking insights.
This book is a unique treasure: a collection of over 360 short entries, like distilled diary notes, each 100 words long. Yet, within these concise paragraphs, Gregory packs an astonishing density of meaning, forcing you to slow down and truly absorb every carefully chosen word.
The themes are as vast and varied as the human experience itself, spanning from profound reflections on God and human connection to candid observations on first crushes, social commentary, and even mystical musings. It's a journey through the author's sharp, often dark, but always bitingly true viewpoint of the world. A particular quote that resonated deeply with me, echoing a favourite poem by Robert Frost, stated: "Not some cosmic cataclysm but internal strife will be the demise of our kind." Entries like "Unconditional love", "Barbara", "Psychiatric Mom", and "Porn Numbed" burrowed into my thoughts, showcasing Gregory's ability to evoke complex emotions and stark realities in minimal prose.
'When Pigs Fly' is an intensely rewarding read for anyone who appreciates literature that demands active engagement and rewards careful consideration. It’s a remarkable testament to the power of brevity, offering a profound and incredibly true reflection of life. I highly recommend this book for readers who enjoy intellectual sparring and the kind of wisdom that lingers long after you've closed the page.
July 26, 2025
When I began reading When Pigs Fly: My 100-Word Ideas for a Year by Ray Gregory, I thought I was going to hurtle through this book because it is fast paced and snappy. However, this wasn’t the case, as to get the most from these tantalising brain teasers, I found myself rereading ones I particularly enjoyed or which challenged my beliefs and preconceptions (many of them!). The themes are seemingly limitless ranging from racism, self-awareness and motivation, love, faith, time travel, social habits, to name a few. There is humour and fun amidst the serious topics and although not every snippet appealed to me, there are plenty of gems here.
In the introduction, Gregory says these nuggets leap into his thought process when he awakens in the morning. If only, is all I can say, when I awaken my thoughts are typically: I wonder if there's any milk left / Is it Tuesday? No, that was yesterday, must be Wednesday / Yes, there is milk left, I remember now. Riveting, as you can tell.
I was spoiled for choice picking the musing which appealed most, but I have decided on The Enlightened Ones who ‘don’t need to talk to each other, for they know each other’s minds. They communicate with other humans by entering their dreams’. l often feel misunderstood, and never presume to fully understand another’s life experience, their emotions or inner conflicts.
When Pigs Fly showcases the author’s creativity and versatility, is thought-provoking, although that worn-out phrase doesn't quite cut it here, now I'm scratching my head – thought liberating? thought inversing? Mr Gregory is the wordsmith, will no doubt know the correct term to describe his fascinating book of ideas.
In the introduction, Gregory says these nuggets leap into his thought process when he awakens in the morning. If only, is all I can say, when I awaken my thoughts are typically: I wonder if there's any milk left / Is it Tuesday? No, that was yesterday, must be Wednesday / Yes, there is milk left, I remember now. Riveting, as you can tell.
I was spoiled for choice picking the musing which appealed most, but I have decided on The Enlightened Ones who ‘don’t need to talk to each other, for they know each other’s minds. They communicate with other humans by entering their dreams’. l often feel misunderstood, and never presume to fully understand another’s life experience, their emotions or inner conflicts.
When Pigs Fly showcases the author’s creativity and versatility, is thought-provoking, although that worn-out phrase doesn't quite cut it here, now I'm scratching my head – thought liberating? thought inversing? Mr Gregory is the wordsmith, will no doubt know the correct term to describe his fascinating book of ideas.
April 10, 2025
I’ve very much enjoyed short stories and a novella by Ray Gregory and this, though out of genre, didn’t disappoint.
When Pigs Fly is different. From everything pretty much. Certainly from fiction. It’s an intriguing collection of crystalline cameos — 100-word thought-provoking, incisive nuggets of … all sorts: a mix of considered seriousness, shrapnel shards of glittering humour and everything in between, crisply and elegantly written as always with Gregory’s prose.
His technique reminded me of peeling off layers of onion skin to reveal a cleverly phrased contradiction at the heart, or of unpacking brightly painted Russian dolls to reveal the exquisite final miniature. And they are not the quick read you might expect — there is no fluff, there are no loose links between them, and each vignette requires and repays the reader’s full attention. This excerpt (from Do Unto Others), “How better to appreciate that awareness than to purify it, strip it of all superficiality and distraction, and realize it’s merely a speck of the awareness that includes all awarenesses”, for me both exemplifies and describes Gregory’s approach.
Themes in the sense of topics? Many and varied. Philosophy, religion, language, dreams, sex, love, science, maths, the Iliad, time, metaphysics, imagination — in short, life and death and all that comes in between. With perhaps a loose connecting thread of freeing ourselves from self- or culturally imposed constraints.
And themes in the sense of style? I relished many examples of Gregory’s trademark tropes of nemesis, meta concepts, the sting in the tail, turning things on their head, eye-catching metaphors and analogies. Not easy to do neatly and naturally within the confines of 100 words, but he pulls it off every time.
There are also a number of “What if” endings — not exactly cliffhangers given the fragmentary structure, more needle-sharp prompts to think about the preceding kernel of thought. Such as this quote (from Possibilities) which for me is a fine example of Gregory’s deft cerebral acrobatics: “What if your lack of imagination is the only limit to what is possible? And what if fear is all that limits your imagination, and the thing you fear most is what you imagine about imagination itself? And what if that is your fear of the madness that could overwhelm you if your imagination were to upset the applecart of your reality?”
More questions and provocations than answers, this refreshing and original collection is thoroughly recommended.
When Pigs Fly is different. From everything pretty much. Certainly from fiction. It’s an intriguing collection of crystalline cameos — 100-word thought-provoking, incisive nuggets of … all sorts: a mix of considered seriousness, shrapnel shards of glittering humour and everything in between, crisply and elegantly written as always with Gregory’s prose.
His technique reminded me of peeling off layers of onion skin to reveal a cleverly phrased contradiction at the heart, or of unpacking brightly painted Russian dolls to reveal the exquisite final miniature. And they are not the quick read you might expect — there is no fluff, there are no loose links between them, and each vignette requires and repays the reader’s full attention. This excerpt (from Do Unto Others), “How better to appreciate that awareness than to purify it, strip it of all superficiality and distraction, and realize it’s merely a speck of the awareness that includes all awarenesses”, for me both exemplifies and describes Gregory’s approach.
Themes in the sense of topics? Many and varied. Philosophy, religion, language, dreams, sex, love, science, maths, the Iliad, time, metaphysics, imagination — in short, life and death and all that comes in between. With perhaps a loose connecting thread of freeing ourselves from self- or culturally imposed constraints.
And themes in the sense of style? I relished many examples of Gregory’s trademark tropes of nemesis, meta concepts, the sting in the tail, turning things on their head, eye-catching metaphors and analogies. Not easy to do neatly and naturally within the confines of 100 words, but he pulls it off every time.
There are also a number of “What if” endings — not exactly cliffhangers given the fragmentary structure, more needle-sharp prompts to think about the preceding kernel of thought. Such as this quote (from Possibilities) which for me is a fine example of Gregory’s deft cerebral acrobatics: “What if your lack of imagination is the only limit to what is possible? And what if fear is all that limits your imagination, and the thing you fear most is what you imagine about imagination itself? And what if that is your fear of the madness that could overwhelm you if your imagination were to upset the applecart of your reality?”
More questions and provocations than answers, this refreshing and original collection is thoroughly recommended.
December 27, 2025
Bite-sized morsels, but a filling meal
What a charming and fun collection of writings! The central concept of this whole piece is a great one, and one that's almost got me inspired to try my own hand at the same idea. These 100-word musings are varied in their subject matter, tone, and level of profundity, but they were nearly all interesting and compelling in their own ways. The author here has demonstrated good economy of language, cramming so much into each 100-word entry, making this somewhat *dense* reading... it took me a lot longer to work through this collection than I originally expected! That's not a knock against it: think of this book as being like a massive assortment of appetizers set on a table--and after the first bite, you realize that each one is far more filling than it seemed to be. I've read books twice as long in half the time; each of these takes some thinking to digest!
Common themes across the collection include musings of religion and gods, one's purpose in life, love/relationships/sex, metaphysics, reality, and writing itself. They range from grounded depictions of a scene to poetic musings of philosophy (and everywhere between). A few had what originally felt like an anti-science sort of bend, and that struck me a bit uneasily, but there were also pieces scattered throughout the collection that redeemed this viewpoint for me as the author's perspective was developed one 100-word paragraph at a time. By the end, I see the author's appreciation for a certain ineffability to the universe, and I don't entirely disagree with their perspective... and even in the handful of entries that didn't align with my views, the perspectives presented were always compelling.
The editing is clean and unobtrusive; the writing is dense, but that's a necessary tradeoff for the format. A book like this could make for an enjoyable experience if it were read parallel to how it were written: a single entry per day, spread over a year, as fascinating little seeds of a day's musings. Not every single entry is a home run, but many of them had me smiling and nodding... no matter who's reading this collection, I'd bet there are entries that will resonate.
Overall, this book is a great piece of experimental writing that punches outside of its length-class. Recommended for people who love writing that makes them think!
What a charming and fun collection of writings! The central concept of this whole piece is a great one, and one that's almost got me inspired to try my own hand at the same idea. These 100-word musings are varied in their subject matter, tone, and level of profundity, but they were nearly all interesting and compelling in their own ways. The author here has demonstrated good economy of language, cramming so much into each 100-word entry, making this somewhat *dense* reading... it took me a lot longer to work through this collection than I originally expected! That's not a knock against it: think of this book as being like a massive assortment of appetizers set on a table--and after the first bite, you realize that each one is far more filling than it seemed to be. I've read books twice as long in half the time; each of these takes some thinking to digest!
Common themes across the collection include musings of religion and gods, one's purpose in life, love/relationships/sex, metaphysics, reality, and writing itself. They range from grounded depictions of a scene to poetic musings of philosophy (and everywhere between). A few had what originally felt like an anti-science sort of bend, and that struck me a bit uneasily, but there were also pieces scattered throughout the collection that redeemed this viewpoint for me as the author's perspective was developed one 100-word paragraph at a time. By the end, I see the author's appreciation for a certain ineffability to the universe, and I don't entirely disagree with their perspective... and even in the handful of entries that didn't align with my views, the perspectives presented were always compelling.
The editing is clean and unobtrusive; the writing is dense, but that's a necessary tradeoff for the format. A book like this could make for an enjoyable experience if it were read parallel to how it were written: a single entry per day, spread over a year, as fascinating little seeds of a day's musings. Not every single entry is a home run, but many of them had me smiling and nodding... no matter who's reading this collection, I'd bet there are entries that will resonate.
Overall, this book is a great piece of experimental writing that punches outside of its length-class. Recommended for people who love writing that makes them think!
April 17, 2025
Bite-sized morsels, but a filling meal
What a charming and fun collection of writings! The central concept of this whole piece is a great one, and one that's almost got me inspired to try my own hand at the same idea. These 100-word musings are varied in their subject matter, tone, and level of profundity, but they were nearly all interesting and compelling in their own ways. The author here has demonstrated good economy of language, cramming so much into each 100-word entry, making this somewhat *dense* reading... it took me a lot longer to work through this collection than I originally expected! That's not a knock against it: think of this book as being like a massive assortment of appetizers set on a table--and after the first bite, you realize that each one is far more filling than it seemed to be. I've read books twice as long in half the time; each of these takes some thinking to digest!
Common themes across the collection include musings of religion and gods, one's purpose in life, love/relationships/sex, metaphysics, reality, and writing itself. They range from grounded depictions of a scene to poetic musings of philosophy (and everywhere between). A few had what originally felt like an anti-science sort of bend, and that struck me a bit uneasily, but there were also pieces scattered throughout the collection that redeemed this viewpoint for me as the author's perspective was developed one 100-word paragraph at a time. By the end, I see the author's appreciation for a certain ineffability to the universe, and I don't entirely disagree with their perspective... and even in the handful of entries that didn't align with my views, the perspectives presented were always compelling.
The editing is clean and unobtrusive; the writing is dense, but that's a necessary tradeoff for the format. A book like this could make for an enjoyable experience if it were read parallel to how it were written: a single entry per day, spread over a year, as fascinating little seeds of a day's musings. Not every single entry is a home run, but many of them had me smiling and nodding... no matter who's reading this collection, I'd bet there are entries that will resonate.
Overall, this book is a great piece of experimental writing that punches outside of its length-class. Recommended for people who love writing that makes them think!
What a charming and fun collection of writings! The central concept of this whole piece is a great one, and one that's almost got me inspired to try my own hand at the same idea. These 100-word musings are varied in their subject matter, tone, and level of profundity, but they were nearly all interesting and compelling in their own ways. The author here has demonstrated good economy of language, cramming so much into each 100-word entry, making this somewhat *dense* reading... it took me a lot longer to work through this collection than I originally expected! That's not a knock against it: think of this book as being like a massive assortment of appetizers set on a table--and after the first bite, you realize that each one is far more filling than it seemed to be. I've read books twice as long in half the time; each of these takes some thinking to digest!
Common themes across the collection include musings of religion and gods, one's purpose in life, love/relationships/sex, metaphysics, reality, and writing itself. They range from grounded depictions of a scene to poetic musings of philosophy (and everywhere between). A few had what originally felt like an anti-science sort of bend, and that struck me a bit uneasily, but there were also pieces scattered throughout the collection that redeemed this viewpoint for me as the author's perspective was developed one 100-word paragraph at a time. By the end, I see the author's appreciation for a certain ineffability to the universe, and I don't entirely disagree with their perspective... and even in the handful of entries that didn't align with my views, the perspectives presented were always compelling.
The editing is clean and unobtrusive; the writing is dense, but that's a necessary tradeoff for the format. A book like this could make for an enjoyable experience if it were read parallel to how it were written: a single entry per day, spread over a year, as fascinating little seeds of a day's musings. Not every single entry is a home run, but many of them had me smiling and nodding... no matter who's reading this collection, I'd bet there are entries that will resonate.
Overall, this book is a great piece of experimental writing that punches outside of its length-class. Recommended for people who love writing that makes them think!
March 14, 2025
Having devoured Gregory's previous works, I approached this collection with high expectations - and found them exceeded in "When Pigs Fly," which offers a year's worth of 100-word vignettes. These say more in a paragraph than most authors manage in chapters.
Gregory's genius lies in his ability to take you directly into the human psyche with surgical precision. Each vignette serves as a mirror, reflecting your deepest thoughts and occasional uncomfortable truths.
His musing on a young Jesus contemplating why an all-powerful God would need him is a perfect example of Gregory challenging conventional perspectives without disrespect.
The collection shines brightest when Gregory explores the boundaries between consciousness and unconsciousness. His encouragement to "let your unconsciousness rear up and do its thing" resonated.
In "INsight," he questions our acceptance of reality: "Instead of simply accepting the world is our sole frame of reference, what if we went inward and found our center there?"
His exploration of human sexuality in "Tawdry Sex" strips away societal pretences, asking why we can't simply be "normal decent people enjoying something perfectly natural" instead of relying on "outlaw bravado" or "fancy naughtiness."
Similarly, pieces like "Power Mom" and "That Old Girlfriend" reveal uncomfortable truths about relationships we've all encountered.
What makes this collection exceptional is its accessibility. Despite its depth. Gregory doesn't lecture but invites introspection.
Whether reflecting on fleeting beauty in "Too Lofty, Too Long," exploring gender identity in Halloween Revelation, or examining the intersection of religion and schadenfreude in "Holy Satisfaction," each vignette feels like eavesdropping on private contemplations.
Through the author's musings, you feel as though you know him. I especially related to I’d Rather Write, as I, too, prefer written words to speech.
"When Pigs Fly" is delicious. Dip in and savor it.
Gregory's genius lies in his ability to take you directly into the human psyche with surgical precision. Each vignette serves as a mirror, reflecting your deepest thoughts and occasional uncomfortable truths.
His musing on a young Jesus contemplating why an all-powerful God would need him is a perfect example of Gregory challenging conventional perspectives without disrespect.
The collection shines brightest when Gregory explores the boundaries between consciousness and unconsciousness. His encouragement to "let your unconsciousness rear up and do its thing" resonated.
In "INsight," he questions our acceptance of reality: "Instead of simply accepting the world is our sole frame of reference, what if we went inward and found our center there?"
His exploration of human sexuality in "Tawdry Sex" strips away societal pretences, asking why we can't simply be "normal decent people enjoying something perfectly natural" instead of relying on "outlaw bravado" or "fancy naughtiness."
Similarly, pieces like "Power Mom" and "That Old Girlfriend" reveal uncomfortable truths about relationships we've all encountered.
What makes this collection exceptional is its accessibility. Despite its depth. Gregory doesn't lecture but invites introspection.
Whether reflecting on fleeting beauty in "Too Lofty, Too Long," exploring gender identity in Halloween Revelation, or examining the intersection of religion and schadenfreude in "Holy Satisfaction," each vignette feels like eavesdropping on private contemplations.
Through the author's musings, you feel as though you know him. I especially related to I’d Rather Write, as I, too, prefer written words to speech.
"When Pigs Fly" is delicious. Dip in and savor it.
May 30, 2025
I have read another of Ray Gregory’s books – a set of short stories – and I was impressed. He can clearly write fiction, at least, of the short variety. This book, however, is something different. It’s not fiction (entirely, though there is fiction in it), but it is short; it’s almost like a thought-for-the-day’ journal, for a whole year, but with 365 thoughts or tales all accurately compiled to be exactly 100 words. This is a writing exercise that requires some skill, to hone the art of precision, and 100 words is a common limit or target in flash fiction – short, pithy tales with just one point and the onus to make it in a thought-provoking way. But as I said, this largely isn’t fiction: the entries are more-often musings upon whatever takes the author’s fancy, and they cover a wide range. For example, the first entry is entitled ‘mystery’ and muses upon the nature of the mysterious, and there are thoughts on other concepts, like the use of metaphors, the nature of beliefs, dreams, and so on. Others consider human emotions or actions, from helping to achievement to loneliness to insight. There are also common themes that recur in different forms – such as on religion or aspects of this. And occasionally, there is a contentious piece – like ‘The White God’ – or a sexual entry, that demonstrate Ray’s instinct to be challenging.
There’s a lot here – the author is clearly a deep-thinking man. Naturally, in a long volume, some of the entries are truly thought provoking, and others are more pedestrian. I would also, personally, have liked a few more fiction entries, but that shouldn’t be seen as a criticism per se, more an acknowledgement of the author’s fiction quality. All-in-all, this is well worth a look, and whether you read it all in one go (probably not advisable), or pick at it – one or several a day, perhaps during ad breaks while in front of the TV – it will reward you.
There’s a lot here – the author is clearly a deep-thinking man. Naturally, in a long volume, some of the entries are truly thought provoking, and others are more pedestrian. I would also, personally, have liked a few more fiction entries, but that shouldn’t be seen as a criticism per se, more an acknowledgement of the author’s fiction quality. All-in-all, this is well worth a look, and whether you read it all in one go (probably not advisable), or pick at it – one or several a day, perhaps during ad breaks while in front of the TV – it will reward you.
March 14, 2025
This book is exactly what the author claims it to be—daily ramblings, like reading someone's journal but with more structure and variety. The commitment to keeping each passage precisely 100 words is impressive, though at times it leads to awkward phrasing or missing words. Still, for nearly all entries, the author pulls it off well.
The content is all over the place in a good way—political, cosmological, philosophical, theological, personal, strange, funny, cringey, weird, and everything in between. A major theme is a push to accept Jesus while also criticizing religious institutions, embracing the mystery of reality while confidently asserting that Jesus is the answer to it. There are philosophical contradictions throughout, but that actually adds to the book’s charm. It’s a raw, personal look into the author’s mind—not that of a polished guru, but of an imperfect human with thoughts that wander in all directions.
Some passages are uncomfortable, such as discussions of rape, but these are rare. Others are deeply personal or speculative, blurring the line between autobiography and imagination. The constant shift in topics keeps things engaging—if one entry doesn’t resonate, the next one will be entirely different. There’s some repetition, particularly around themes like past relationships, death, God, and enlightenment, but each take has its own style and perspective.
Overall, I really enjoyed this book. It’s unique, unpredictable, and thought-provoking. If you know what you're getting into—a mix of introspection, randomness, and deep dives into the author’s mind—you'll likely find it a fascinating read.
The content is all over the place in a good way—political, cosmological, philosophical, theological, personal, strange, funny, cringey, weird, and everything in between. A major theme is a push to accept Jesus while also criticizing religious institutions, embracing the mystery of reality while confidently asserting that Jesus is the answer to it. There are philosophical contradictions throughout, but that actually adds to the book’s charm. It’s a raw, personal look into the author’s mind—not that of a polished guru, but of an imperfect human with thoughts that wander in all directions.
Some passages are uncomfortable, such as discussions of rape, but these are rare. Others are deeply personal or speculative, blurring the line between autobiography and imagination. The constant shift in topics keeps things engaging—if one entry doesn’t resonate, the next one will be entirely different. There’s some repetition, particularly around themes like past relationships, death, God, and enlightenment, but each take has its own style and perspective.
Overall, I really enjoyed this book. It’s unique, unpredictable, and thought-provoking. If you know what you're getting into—a mix of introspection, randomness, and deep dives into the author’s mind—you'll likely find it a fascinating read.
March 17, 2025
As a journalist and editor, I always find the most concise way to tell a story. I used to tell my writing students ‘forget about the sun is shining, the birds are singing’, just tell the story. The premise of this book appealed to me for the notion that you can condense thoughts, musings and reflections into just 100-word summaries. For a year, Gregory wrote down his thoughts and trimmed them back into a cornucopia of succinct stories. In Facing The Dream, he invites readers to imagine heaven, or whatever is your bliss, to be your present reality and not a far-away concept, so that you can enjoy what you have now. In a similar theme, he suggests that maybe we don’t come with a soul, but rather we have to grow one. He explores the human condition, and time and space as more constructs of the mind, and offers interesting glimpses of the world around us, from miracles and belief to the benefits of picking up litter. The Problem with Democracy, written as one long descriptive sentence, contains adjectives that could describe a current world leader. The pieces are at times sensual, and always insightful and thought-provoking, and the idea would make a good editing challenge for students.
April 4, 2025
To be honest I really wasn't sure what to expect with this book. I had been taken in by the title and the idea that it might be something off the beaten track to enjoy on my kindle. I was right on the money. When Pigs Fly is a truly eclectic collection of thoughts, philosophies and musings, all of which are 100 words long and cover each day of the year. You cannot help but be impressed by such an original idea and the ability to contain each entry to 100 words.
What I enjoyed most was the truly diverse subject matter, meaning you want to keep reading even if one entry is not to your liking, as you know the next will be something completely different. With such a tight word count the author takes you right to the heart of the topic at hand and I can honestly say each entry was food for thought.
This is the kind of book you can pick up once a day and spend ten minutes away from your screens and other distractions just enjoying whatever that entry serves up for the reader. It's not meant to be life changing philosophy but, at the same time, there are some pearls of wisdom you might just hang on to as you go about your day.
In a book market that seems to be increasingly crowded with the same kind of content, When Pigs Fly is a breath of fresh air for your crowded mind.
What I enjoyed most was the truly diverse subject matter, meaning you want to keep reading even if one entry is not to your liking, as you know the next will be something completely different. With such a tight word count the author takes you right to the heart of the topic at hand and I can honestly say each entry was food for thought.
This is the kind of book you can pick up once a day and spend ten minutes away from your screens and other distractions just enjoying whatever that entry serves up for the reader. It's not meant to be life changing philosophy but, at the same time, there are some pearls of wisdom you might just hang on to as you go about your day.
In a book market that seems to be increasingly crowded with the same kind of content, When Pigs Fly is a breath of fresh air for your crowded mind.
May 24, 2025
A Year-long Dose of Quick, Quirky Wisdom
This book - When Pigs Fly is a delightful literary experiment that combines discipline with creativity. Comprising 365 entries, each exactly 100 words, this collection offers daily musings that range from philosophical reflections and whimsical humor to practical advice and imagined autobiographical snippets. The author's commitment to brevity ensures that each piece is concise yet thought-provoking.
I love the diversity of this collection. I especially enjoyed the blurb for the chapter titled: “Porn Numbed.” There is modern life satire, sacred stuff, risqué content, poignant observations about human nature and a range of other nuances. This variety kept me engaged and impacted positively on the reading experience keeping it fresh and interesting. I feel that readers will resonate with different entries in the book, based on their personal interests.
The author's writing style is accessible and unpretentious, inviting us to reflect, laugh, and sometimes challenge our own viewpoints. The format is perfect for those seeking a quick yet meaningful read during a coffee break or as a daily ritual. This book is year-long exploration into the eclectic mind of its author, offering insights that linger long afterwards.
This book - When Pigs Fly is a delightful literary experiment that combines discipline with creativity. Comprising 365 entries, each exactly 100 words, this collection offers daily musings that range from philosophical reflections and whimsical humor to practical advice and imagined autobiographical snippets. The author's commitment to brevity ensures that each piece is concise yet thought-provoking.
I love the diversity of this collection. I especially enjoyed the blurb for the chapter titled: “Porn Numbed.” There is modern life satire, sacred stuff, risqué content, poignant observations about human nature and a range of other nuances. This variety kept me engaged and impacted positively on the reading experience keeping it fresh and interesting. I feel that readers will resonate with different entries in the book, based on their personal interests.
The author's writing style is accessible and unpretentious, inviting us to reflect, laugh, and sometimes challenge our own viewpoints. The format is perfect for those seeking a quick yet meaningful read during a coffee break or as a daily ritual. This book is year-long exploration into the eclectic mind of its author, offering insights that linger long afterwards.
November 17, 2025
A Hundred Windows Into One Wild Mind
This book is one of those rare collections that feels both playful and quietly profound, offering a year’s worth of tightly crafted 100 word bursts that linger far longer than their size suggests. The author jumps effortlessly between philosophy, humor, dream logic and raw honesty, creating a reading experience that’s best savored slowly, one thought capsule at a time.
Two of my favorite pieces, “Real or What?” and “The Door,” showcase just how sharply Gregory can turn short passages into a full existential pivot. In Real or What?, he questions the nature of the mind with a mix of skepticism and wonder, tugging readers toward that unsettling space between neuroscience and metaphysics. The Door, meanwhile, is a gentle, almost revealing reminder that beneath the noise of everyday life lies a private inner world, if only we remember to look for the door.
Not every entry hits with equal force, but even the quieter ones have a way of echoing. Curious, chaotic and unexpectedly moving, this book is a delightful invitation to think deeper in small, concentrated doses.
This book is one of those rare collections that feels both playful and quietly profound, offering a year’s worth of tightly crafted 100 word bursts that linger far longer than their size suggests. The author jumps effortlessly between philosophy, humor, dream logic and raw honesty, creating a reading experience that’s best savored slowly, one thought capsule at a time.
Two of my favorite pieces, “Real or What?” and “The Door,” showcase just how sharply Gregory can turn short passages into a full existential pivot. In Real or What?, he questions the nature of the mind with a mix of skepticism and wonder, tugging readers toward that unsettling space between neuroscience and metaphysics. The Door, meanwhile, is a gentle, almost revealing reminder that beneath the noise of everyday life lies a private inner world, if only we remember to look for the door.
Not every entry hits with equal force, but even the quieter ones have a way of echoing. Curious, chaotic and unexpectedly moving, this book is a delightful invitation to think deeper in small, concentrated doses.
June 6, 2025
I grabbed this book because I thought it would be an easy read.
I like to explore different genres and formats. Here we have a collection of daily thoughts or ramblings on a variety of topics by one author.
At first, I was curious, but quickly grew tired. Despite splitting the reading over several days, it felt like I spent a long time with one person.
Some of these speculations were amusing, others — less so.
My favorite one was about the soul that is not handed to you on a silver platter. You have to grow it. And another one about trading minds with the genius physicist.
One of the recurring questions was “What if your lack of imagination is the only limit to what is possible?” Maybe you could heal yourself or others, choose the afterlife you enjoy, travel in time and space, and so on.
I decided I prefer to read longer stories with a plot rather than random thoughts, but all readers are different, and I’m certain there will be those who will find this collection entertaining and thought provoking.
I like to explore different genres and formats. Here we have a collection of daily thoughts or ramblings on a variety of topics by one author.
At first, I was curious, but quickly grew tired. Despite splitting the reading over several days, it felt like I spent a long time with one person.
Some of these speculations were amusing, others — less so.
My favorite one was about the soul that is not handed to you on a silver platter. You have to grow it. And another one about trading minds with the genius physicist.
One of the recurring questions was “What if your lack of imagination is the only limit to what is possible?” Maybe you could heal yourself or others, choose the afterlife you enjoy, travel in time and space, and so on.
I decided I prefer to read longer stories with a plot rather than random thoughts, but all readers are different, and I’m certain there will be those who will find this collection entertaining and thought provoking.
August 26, 2025
this is actually a really good book, the third by ray gregory i’ve read and easily the best so far. the concept is simple but powerful: 100-word bursts of thought, crafted almost like prose poetry. some are whimsical or funny, others sharp and biting, and quite a few feel profound in the way they capture something true about human life in so few words. gregory did an excellent job in the discipline of boiling down philosophy, humor, or social commentary into such a tight space without losing depth.
it feels sometimes like flash fiction, at times like a diary, and at times like philosophy, but it always manages to keep my attention because each page is fresh and different. the writing is sharp and thought-provoking, and i found myself being continously surprised and intruiged after certain sections. while the cover design feels low quality, the interior is far superior... thoughtful, clever, and original. i especially liked the pieces that leaned into philosophical musings with a poetic edge.
it feels sometimes like flash fiction, at times like a diary, and at times like philosophy, but it always manages to keep my attention because each page is fresh and different. the writing is sharp and thought-provoking, and i found myself being continously surprised and intruiged after certain sections. while the cover design feels low quality, the interior is far superior... thoughtful, clever, and original. i especially liked the pieces that leaned into philosophical musings with a poetic edge.
April 10, 2025
Having read three of Ray Gregory’s works, I knew what to expect: sharp, wry, witty stories. This, however, is an altogether different offering. ‘When Pigs Fly’ is an extensive collection of Gregory’s thoughts and musings, and what they all have in common is that every entry is exactly one-hundred words in length. Affording the reader a glimpse into his inner world, Gregory shares his opinions and ideas on a plethora of topics: faith and religion; end of life; love; sex; family; female body parts; how to be a good citizen, failed romantic relationships, democracy and politics, high school crushes and so on. He even let’s us in on his dreams, revealing in one entry about a beautiful woman he meets. As with his short stories, this vast collection of ideas, which you can dip in and out of, is still typical Gregory: playful, sardonic, provocative. Overall a very enjoyable read.
May 17, 2025
I didn’t really know what to expect when I picked this up, but I’m glad I did. When Pigs Fly is like a year-long brain teaser—but not in a crossword kind of way. More like philosophical flash fiction, or little slices of what-if thinking that are sometimes funny, sometimes odd, and occasionally unexpectedly deep. The 100-word format keeps things moving, which I appreciated—it’s easy to dip in and out without feeling like you’re committing to a big read.
Some ideas made me laugh, others made me pause and reread, just to let them sink in. There’s a lot of creativity here, and I admire the author’s ability to come at everyday things from strange and interesting angles. It’s a fun reminder that there are always different ways to look at the world, even if the view is a little weird sometimes. Definitely a cool little book to keep on your device for inspiration or a mental reset.
Some ideas made me laugh, others made me pause and reread, just to let them sink in. There’s a lot of creativity here, and I admire the author’s ability to come at everyday things from strange and interesting angles. It’s a fun reminder that there are always different ways to look at the world, even if the view is a little weird sometimes. Definitely a cool little book to keep on your device for inspiration or a mental reset.
June 2, 2025
When Pigs Fly is not your typical book. It’s unpredictable, philosophical, strange, and funny. The experience of reading all of these ideas mixed together reminded me a bit of when I read the Shel Silverstein poetry books Where the Sidewalk Ends and A Light in the Attic as a child. That is to say, I didn’t read them straight through, but nibbled at it, paga by page, so I could muse over a joke or commentary or charm. The end result is a dreamlike experience where images flash before your eyes and you catch a glimpse of something profound and then it evaporates and is replaced by another idea until you don’t remember details necessarily but rather bask in the mood of the whole thing. This book would be great for writers to read since it can spur thoughts with occasional randomness and anyone who wants a dose of unpredictable creativity should check it out. Highly recommend it!
June 6, 2025
This book it out of my usual interest area. I’m a Sci-Fi reader who also dabbles in self-help books. So, when this was recommended to me, it took me a moment to commit. But, I’m glad I did.
This is a truly unique take on a book and it’s so timely. I applaud the author, Ray Gregory, for the novel approach. “Why Pigs Fly: My 100-Word Ideas for a Year” is a plethora of micro-story bites. The stories range in genre and they each are truly all just one page in length. In an age of “now” and reduced attention spans, this is incredibly fitting. Some of the stories are funny and others are sad and everything else in between.
What I think is really fascinating is the perspective each of these stories takes. It’s truly like looking into someone’s mind without them know. This book is unique, well written, and definitely has my recommendation.
This is a truly unique take on a book and it’s so timely. I applaud the author, Ray Gregory, for the novel approach. “Why Pigs Fly: My 100-Word Ideas for a Year” is a plethora of micro-story bites. The stories range in genre and they each are truly all just one page in length. In an age of “now” and reduced attention spans, this is incredibly fitting. Some of the stories are funny and others are sad and everything else in between.
What I think is really fascinating is the perspective each of these stories takes. It’s truly like looking into someone’s mind without them know. This book is unique, well written, and definitely has my recommendation.
June 12, 2025
“When Pigs Fly: My 100 Word Ideas for a Year” is like a collection of poetry in prose form. The author has taken on the challenge of writing down his thoughts on nearly every subject imaginable and boiling them down to just 100 words. As such, it seems a shame to spend more than one hundred words describing this book!
The subject matter is extremely varied but there is an overarching feeling of skepticism and melancholy throughout. Some of the short essays were humorous, others thought provoking. Here is one excerpt for example: “If God is indeed love, he would surely rather have us be like him than believe in him. Maybe any religion that says otherwise shouldn’t be believed.” Here is another example from an essay titled Litter: "There are also people who will pick up more than one piece a day. That’s what it takes, enough good people doing something."
Appropriate for adults.
The subject matter is extremely varied but there is an overarching feeling of skepticism and melancholy throughout. Some of the short essays were humorous, others thought provoking. Here is one excerpt for example: “If God is indeed love, he would surely rather have us be like him than believe in him. Maybe any religion that says otherwise shouldn’t be believed.” Here is another example from an essay titled Litter: "There are also people who will pick up more than one piece a day. That’s what it takes, enough good people doing something."
Appropriate for adults.
August 29, 2025
Ray Gregory’s When Pigs Fly is a surprisingly meditative collection of 100-word entries—some light, some odd, and some that really make you stop and think. I didn’t expect a book this short-winded to feel so expansive, but that’s exactly what it does: it opens small windows into big ideas. One of my favorite pieces, Tick-Tock, plays with time—not just how we experience it, but how we assume it works. It left me lingering on the thought that maybe all moments do exist at once, and we’re just too caught up in the “flow” to notice.
That’s the beauty of this book. Some entries breeze by, others hit you sideways and stay with you. Not every idea lands equally, but the variety keeps things fresh. It’s the kind of book you don’t need to read in order, or all at once—it’s more fun to flip through randomly and see what sticks. And more often than not, something does.
That’s the beauty of this book. Some entries breeze by, others hit you sideways and stay with you. Not every idea lands equally, but the variety keeps things fresh. It’s the kind of book you don’t need to read in order, or all at once—it’s more fun to flip through randomly and see what sticks. And more often than not, something does.
March 27, 2025
When Pigs Fly is a wildly inventive ride.
Reading this book feels like stepping into the author’s mind for a moment at a time, only to be spun around and dropped into an entirely new idea the very next page. From mystical insights to irreverent jokes, philosophical tangents to practical tips, no two entries are the same. It’s like flash fiction meets a thought experiment, diary, and stand-up routine. Whether you’re inspired, amused, or even briefly offended, it’s impossible to be bored — you’ll always wonder what’s next.
Reading this book feels like stepping into the author’s mind for a moment at a time, only to be spun around and dropped into an entirely new idea the very next page. From mystical insights to irreverent jokes, philosophical tangents to practical tips, no two entries are the same. It’s like flash fiction meets a thought experiment, diary, and stand-up routine. Whether you’re inspired, amused, or even briefly offended, it’s impossible to be bored — you’ll always wonder what’s next.
December 8, 2025
This is a great book for the modern era. Don’t have the time or the inclination to read a 500 page epic? A full-length self help book? Read one (or more) of these bite-sized essays and see where it takes you. The topics are delightfully diverse, ranging from religion to relationships to science to personal stories to history and on and on and on. There is (purposely it seems) no rhyme or rhythm to the order, so you never know what you’re going to get when you turn the page. Some are serious, some are funny. They all are snappily written and will make you think. Then on to the next one!
September 9, 2025
For those who enjoy poetry, philosophy, and exploring random thoughts.
When Pigs Fly is a collection of 100-word musings, covering a range of topics from Helping and Unconditional Love to Are We Alone? and even Randomness – twice! The author dives into profound and sometimes weird reflections that often left me thinking long after I’d finished reading.
I particularly enjoyed the snippets on Faces, Facing the Dream, Litter, Age, and Time Travel. However, some entries were so philosophical that they made my head hurt a bit! There’s also a fair amount of adult content, with many references to sex, making this a read best suited for mature audiences.
If you enjoy poetry, philosophy, and exploring random thoughts, this book offers plenty to reflect on. The inclusion of a contents page would’ve been helpful, to make it easy to dip in and out of the entries. Definitely a unique read – very random (maybe that’s why Randomness was included twice), but thought-provoking.
When Pigs Fly is a collection of 100-word musings, covering a range of topics from Helping and Unconditional Love to Are We Alone? and even Randomness – twice! The author dives into profound and sometimes weird reflections that often left me thinking long after I’d finished reading.
I particularly enjoyed the snippets on Faces, Facing the Dream, Litter, Age, and Time Travel. However, some entries were so philosophical that they made my head hurt a bit! There’s also a fair amount of adult content, with many references to sex, making this a read best suited for mature audiences.
If you enjoy poetry, philosophy, and exploring random thoughts, this book offers plenty to reflect on. The inclusion of a contents page would’ve been helpful, to make it easy to dip in and out of the entries. Definitely a unique read – very random (maybe that’s why Randomness was included twice), but thought-provoking.
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