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Forty Ways to Look at Winston Churchill
Warrior and writer, genius and crank, rider in the British cavalry's last great charge and inventor of the tank—Winston Churchill led Britain to fight alone against Nazi Germany in the fateful year of 1940 and set the standard for leading a democracy at war.
Like no other portrait of its famous subject, Forty Ways to Look at Winston Churchill is a dazzling display of facts more improbable than fiction, and an investigation of the contradictions and complexities that haunt biography. Gretchen Craft Rubin gives readers, in a single volume, the kind of rounded view usually gained only by reading dozens of conventional biographies.
With penetrating insight and vivid anecdotes, Rubin makes Churchill accessible and meaningful to twenty-first-century readers with forty contrasting views of the man: he was an alcoholic, he was not; he was an anachronism, he was a visionary; he was a racist, he was a humanitarian; he was the most quotable man in the history of the English language, he was a bore.
In crisp, energetic language, Rubin creates a new form for presenting a great figure of history—and brings to full realization the depiction of a man too fabulous for any novelist to construct, too complicated for even the longest narrative to describe, and too valuable ever to be forgotten.
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First published May 11, 2003
About the author
Gretchen Rubin
45 books146k followersNEW AUDIBLE ORIGINAL AUDIOBOOK
In "Get It Done: How to Complete Your Dream Project," bestselling author Gretchen Rubin brings her signature approach to help you finally complete your dream project.
Drawing on her decades of knowledge of how people successfully change behavior, Rubin offers tools to help you break down any big project, stay focused, and keep moving forward. LISTEN ON AUDIBLE
___
AUTHOR BIO
Gretchen Rubin is one of today’s most influential and thought-provoking observers of happiness and human nature.
She’s the author of many New York Times bestselling books, such as The Happiness Project, Better Than Before, and The Four Tendencies, Life in Five Senses, and Secrets of Adulthood, which have sold millions of copies in more than thirty languages. Her next book Secrets of Adulthood comes out April 2025.
She’s the host of the popular, award-winning podcast Happier with Gretchen Rubin, where she and her co-host (and sister) Elizabeth Craft explore strategies and insights about how to make life happier. As the founder of The Happiness Project, she has helped create imaginative products for people to use in their own happiness projects.
She has been interviewed by Oprah, eaten dinner with Nobel Prize-winner Daniel Kahneman, walked arm-in-arm with the Dalai Lama, had her work reported on in a medical journal, been written up in the New Yorker, and been an answer on Jeopardy!
Gretchen Rubin started her career in law, and she realized she wanted to be a writer while she was clerking for Supreme Court Justice Sandra Day O’Connor. Raised in Kansas City, she lives in New York City with her family.
In "Get It Done: How to Complete Your Dream Project," bestselling author Gretchen Rubin brings her signature approach to help you finally complete your dream project.
Drawing on her decades of knowledge of how people successfully change behavior, Rubin offers tools to help you break down any big project, stay focused, and keep moving forward. LISTEN ON AUDIBLE
___
AUTHOR BIO
Gretchen Rubin is one of today’s most influential and thought-provoking observers of happiness and human nature.
She’s the author of many New York Times bestselling books, such as The Happiness Project, Better Than Before, and The Four Tendencies, Life in Five Senses, and Secrets of Adulthood, which have sold millions of copies in more than thirty languages. Her next book Secrets of Adulthood comes out April 2025.
She’s the host of the popular, award-winning podcast Happier with Gretchen Rubin, where she and her co-host (and sister) Elizabeth Craft explore strategies and insights about how to make life happier. As the founder of The Happiness Project, she has helped create imaginative products for people to use in their own happiness projects.
She has been interviewed by Oprah, eaten dinner with Nobel Prize-winner Daniel Kahneman, walked arm-in-arm with the Dalai Lama, had her work reported on in a medical journal, been written up in the New Yorker, and been an answer on Jeopardy!
Gretchen Rubin started her career in law, and she realized she wanted to be a writer while she was clerking for Supreme Court Justice Sandra Day O’Connor. Raised in Kansas City, she lives in New York City with her family.
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Displaying 1 - 30 of 170 reviews
May 23, 2010
13 ways to look at Gretchen Rubin's 40 Ways to look at Winston Churchill:
1) Bathroom reading for the overeducated (apologies to Tom Hahn).
2) Lists are easy to write because they don't have to have thematic unity or cohesion.
3) Lists are easy to read and fun to quote from.
4) Lists of historical details are deceptively hard to compile accurately, but Gretchen Rubin does so, repeatedly.
5) Ways to look at Winston Churchill that were not considered in this book, but could have been: bricklayer, inventor, administrator, mirror of biographers' prejudices.
6) Ways to look at Winston Churchill that were wisely not considered in this book: acrobat, substance-abuse counselor, blogger.
7) Phrases not associated with Winston Churchill: “I do not know which to prefer,/ The beauty of inflections /Or the beauty of innuendoes”, “O thin men of Haddam”, “bawds of euphony”, and “He rode over Connecticut/ In a glass coach.”
8) Churchill appreciated brevity... in other people.
9) If Churchill had never been born, who would babies look like?
10) Life is fleeting and there is much reading to do, so if you're going to read one good book about Churchill, this is a good choice. It's short.
11) This book is like the unholy offspring of Reader's Digest and the History Channel.
12) This is a good book to read while listening to the much, much longer Churchill biography The Last Lion on your Ipod.
13) This book is Imodium for the logorrhea of other Churchill biographers.
You are invited to add additional ways.
1) Bathroom reading for the overeducated (apologies to Tom Hahn).
2) Lists are easy to write because they don't have to have thematic unity or cohesion.
3) Lists are easy to read and fun to quote from.
4) Lists of historical details are deceptively hard to compile accurately, but Gretchen Rubin does so, repeatedly.
5) Ways to look at Winston Churchill that were not considered in this book, but could have been: bricklayer, inventor, administrator, mirror of biographers' prejudices.
6) Ways to look at Winston Churchill that were wisely not considered in this book: acrobat, substance-abuse counselor, blogger.
7) Phrases not associated with Winston Churchill: “I do not know which to prefer,/ The beauty of inflections /Or the beauty of innuendoes”, “O thin men of Haddam”, “bawds of euphony”, and “He rode over Connecticut/ In a glass coach.”
8) Churchill appreciated brevity... in other people.
9) If Churchill had never been born, who would babies look like?
10) Life is fleeting and there is much reading to do, so if you're going to read one good book about Churchill, this is a good choice. It's short.
11) This book is like the unholy offspring of Reader's Digest and the History Channel.
12) This is a good book to read while listening to the much, much longer Churchill biography The Last Lion on your Ipod.
13) This book is Imodium for the logorrhea of other Churchill biographers.
You are invited to add additional ways.
December 31, 2017
My daughter (an attorney who is currently writing a book), gave me this book last week as a Christmas present. I knew when I first flipped through it and read Churchill’s comment “all newborn babies look like me”, that this would likely be a fun read – which indeed it was!
I thought author Gretchen Rubin (also an attorney, now a writer) took a creative and entertaining approach to celebrate the life of one of the most famous men in history, about whom so many lengthy biographies have been written. This was a quick read, written in a breezy and interesting style, yet with more substance and thoughtfulness than one may at first suspect.
As the title indicates, Rubin provides an examination of the many and varied aspects of Churchill’s life, in a point-counterpoint, “let the reader decide” format (e.g. “Churchill as Liberty’s Champion” vs “Churchill as Failed Statesman”, “Churchill and Roosevelt were/were not Friends”, etc.). While clearly not meant to be an exhaustive analysis of Churchill’s life, and with a focus more on Churchill’s personal attributes and character than his political or battle strategies, “40 Ways” will give any reader a solid and quite candid overview of the man who saved England and the World during the Second World War.
Plus, who can really resist enjoying Churchill quotes like these:
“Nothing in life is so exhilarating as to be shot at without result.”
When asked whether he was flattered by the crowds attending his speeches: “It is quite flattering, but whenever I feel this way I always remember that, if instead of making a political speech, I was being hanged, the crowd would be twice as big”
An entertaining read about a unique and amazing man!
I thought author Gretchen Rubin (also an attorney, now a writer) took a creative and entertaining approach to celebrate the life of one of the most famous men in history, about whom so many lengthy biographies have been written. This was a quick read, written in a breezy and interesting style, yet with more substance and thoughtfulness than one may at first suspect.
As the title indicates, Rubin provides an examination of the many and varied aspects of Churchill’s life, in a point-counterpoint, “let the reader decide” format (e.g. “Churchill as Liberty’s Champion” vs “Churchill as Failed Statesman”, “Churchill and Roosevelt were/were not Friends”, etc.). While clearly not meant to be an exhaustive analysis of Churchill’s life, and with a focus more on Churchill’s personal attributes and character than his political or battle strategies, “40 Ways” will give any reader a solid and quite candid overview of the man who saved England and the World during the Second World War.
Plus, who can really resist enjoying Churchill quotes like these:
“Nothing in life is so exhilarating as to be shot at without result.”
When asked whether he was flattered by the crowds attending his speeches: “It is quite flattering, but whenever I feel this way I always remember that, if instead of making a political speech, I was being hanged, the crowd would be twice as big”
An entertaining read about a unique and amazing man!
January 6, 2010
Gretchen Rubin is a former lawyer that has been a clerk for Sandra Day O’Connor, provided legal counsel to an FCC chairman, and has been a professor at Yale Law School. In all her free time she wrote a book and started a family. Eventually she chucked the lawyer thing and decided to devote herself fulltime to writing, thus producing her second book; 40 Ways To Look At Winston Churchill.
This book is unique because it’s a short 300 page romp through an amazing life, where 40 questions are asked in the form of chapters about its namesake. Rubin knew she had to do something different in order to garner any kind of attention on one of the most recognizable figures in recent history. Among the piles of biographies on Churchill, this one stands out because it doesn’t tell the reader a linear set of facts that add up to a “business as usual” biography, but rather gives conflicting views of the man from diverse sources. It is up to the reader to decide, not the biographer, on the questions posed. The form of this book attracted me as much as the story of Churchill, because it represents in a non-fiction guise, what fiction authors have been arguing is the most unique quality to the art of fiction and reading; the reader is the co-author, the co-creator of the imaginative experience. Fiction authors will say that this is proof that reading is non-passive, but rather highly engaging for a reader that is experiencing story telling through their own mind’s eye, thus filtering the author’s story through their personal perspectives and interpretations to create a unique activity. By asking questions in the chapter headings, Rubin has given the reader a map to follow that points to the often conflicting notions of a character that resists definitive conclusions.
On the tactics of biographers:
Churchill biographers – like all biographers – decide their stories and include facts to support them. Someone portraying Churchill as the savior of his country chooses certain facts; someone debunking the Churchill myth chooses others. In deciding what facts to relate – where each detail must stand in for hundreds of omitted details – biographers act like novelists, using theme, irony, motif, metonymy, description, symbolism, morals, and the like to shape a particular image of their subject.
Winston Churchill’s own words:
“Success is going from failure to failure without loss of enthusiasm.”
“Perhaps it is better to be irresponsible and right than responsible and wrong.”
“All newborn babies look like me.”
An American critic talking to Churchill about Mahatma Gandhi and the subject of Indian independence and Churchill’s reluctance to give up British India:
“Before we proceed any further, let us get one thing clear. Are we talking about the brown Indians in India, who have multiplied alarmingly well under benevolent British rule? Or are we speaking of the red Indians in America who, I understand, are almost extinct?”
On Churchill the renaissance man:
There is something melodramatic – legendary – fantastic about Churchill, a figure galloping out of the past. Even his name has Dickensian aptness: sacred and lofty, with decisive, alliterative elements. Can the facts be true? Could he really have been a man who was not only a prominent world statesman but also rode to hounds, fenced, flew airplanes, played polo, owned racehorses, painted, farmed, and collected tropical fish? Who without a university education was a celebrated war correspondent, novelist, historian, and biographer – whose books were not only best sellers but also won their author the Nobel Prize in literature, in the same year it might be added, he accepted the Order of Garter? He was the only person to serve in the War Cabinet in both WWI and WWII; he served in the Army, Navy, and Air Force. At age 70, in shooting contest with General Eisenhower and guard officers, Churchill hit 9 shots in the center of a bull’s-eye and 1 on the fringe.
Question and answer or not; you decide. That is the task of this book, because part of Churchill's mystique lies within our outlook. In this way, his likeness is seen through ourselves.
This book is unique because it’s a short 300 page romp through an amazing life, where 40 questions are asked in the form of chapters about its namesake. Rubin knew she had to do something different in order to garner any kind of attention on one of the most recognizable figures in recent history. Among the piles of biographies on Churchill, this one stands out because it doesn’t tell the reader a linear set of facts that add up to a “business as usual” biography, but rather gives conflicting views of the man from diverse sources. It is up to the reader to decide, not the biographer, on the questions posed. The form of this book attracted me as much as the story of Churchill, because it represents in a non-fiction guise, what fiction authors have been arguing is the most unique quality to the art of fiction and reading; the reader is the co-author, the co-creator of the imaginative experience. Fiction authors will say that this is proof that reading is non-passive, but rather highly engaging for a reader that is experiencing story telling through their own mind’s eye, thus filtering the author’s story through their personal perspectives and interpretations to create a unique activity. By asking questions in the chapter headings, Rubin has given the reader a map to follow that points to the often conflicting notions of a character that resists definitive conclusions.
On the tactics of biographers:
Churchill biographers – like all biographers – decide their stories and include facts to support them. Someone portraying Churchill as the savior of his country chooses certain facts; someone debunking the Churchill myth chooses others. In deciding what facts to relate – where each detail must stand in for hundreds of omitted details – biographers act like novelists, using theme, irony, motif, metonymy, description, symbolism, morals, and the like to shape a particular image of their subject.
Winston Churchill’s own words:
“Success is going from failure to failure without loss of enthusiasm.”
“Perhaps it is better to be irresponsible and right than responsible and wrong.”
“All newborn babies look like me.”
An American critic talking to Churchill about Mahatma Gandhi and the subject of Indian independence and Churchill’s reluctance to give up British India:
“Before we proceed any further, let us get one thing clear. Are we talking about the brown Indians in India, who have multiplied alarmingly well under benevolent British rule? Or are we speaking of the red Indians in America who, I understand, are almost extinct?”
On Churchill the renaissance man:
There is something melodramatic – legendary – fantastic about Churchill, a figure galloping out of the past. Even his name has Dickensian aptness: sacred and lofty, with decisive, alliterative elements. Can the facts be true? Could he really have been a man who was not only a prominent world statesman but also rode to hounds, fenced, flew airplanes, played polo, owned racehorses, painted, farmed, and collected tropical fish? Who without a university education was a celebrated war correspondent, novelist, historian, and biographer – whose books were not only best sellers but also won their author the Nobel Prize in literature, in the same year it might be added, he accepted the Order of Garter? He was the only person to serve in the War Cabinet in both WWI and WWII; he served in the Army, Navy, and Air Force. At age 70, in shooting contest with General Eisenhower and guard officers, Churchill hit 9 shots in the center of a bull’s-eye and 1 on the fringe.
Question and answer or not; you decide. That is the task of this book, because part of Churchill's mystique lies within our outlook. In this way, his likeness is seen through ourselves.
April 29, 2016
I didn't know much at all about Winston Churchill before I read this. It was markedly different from a typical, straightforward biography, but in a good way. There were 40 different chapters-one was a timeline, one was a map, one was true/false, one was all photos. Most of the others were information/analysis.
A chapter I liked a lot was one with funny quotes from Churchill. -Man: "Vote for you? Why, I'd rather vote for the devil!" Churchill: "I understand, but in case your friend is not running, may I count on your support?"
-"Never stand when you can sit and never sit if you can lie down."
-When voted out of office, his wife said: "It may be a blessing in disguise." Churchill: "Well at the moment it's certainly very well disguised."
It seemed thoroughly researched and attempted to be balanced. A chapter about his marriage presented the argument that it was happy, and that it was unhappy. There were similar chapters on Roosevelt, Churchill's purported depression, his alcoholism, and his parenting.
As Rubin wrote, "All biographers decide their stories and include facts to support them." This felt like a well-rounded, inclusive overview. I wish the JFK edition was readily available.
A chapter I liked a lot was one with funny quotes from Churchill. -Man: "Vote for you? Why, I'd rather vote for the devil!" Churchill: "I understand, but in case your friend is not running, may I count on your support?"
-"Never stand when you can sit and never sit if you can lie down."
-When voted out of office, his wife said: "It may be a blessing in disguise." Churchill: "Well at the moment it's certainly very well disguised."
It seemed thoroughly researched and attempted to be balanced. A chapter about his marriage presented the argument that it was happy, and that it was unhappy. There were similar chapters on Roosevelt, Churchill's purported depression, his alcoholism, and his parenting.
As Rubin wrote, "All biographers decide their stories and include facts to support them." This felt like a well-rounded, inclusive overview. I wish the JFK edition was readily available.
November 16, 2020
During my current quest to learn more about Winston, I raided the public library's website, ordered a stack of books and collected them later that day via curbside pickup - wow thank you for a great COVID system! :)
After devouring the YA and children's books, I got involved in this one, a most unusual biography. The author tackles facts about Winston Churchill's life in an open and objective way. Many chapters addressed two opposing statements such as "Winston Was Well Suited to High Office" and "Winston Was Ill Suited to High Office." Another chapter: "Winston Had a Happy Marriage" along with "Winston Did Not Have a Happy Marriage." Truly he was not a perfect person, yet he did great things.
I loved the balance and I loved reading about how biographers can tailor a person's life to live up to their own ideas of who that person was. "A biographer's choice to highlight or dismiss certain episodes - controversial, offensive, or poignant - can vividly color a portrait. Readers unfamiliar with the subject's life are blind to the artful selection that's taking place." (p.221) And then the author, though clearly concluding that "Churchill was one of the greatest heroes of his time,"continues to tell about certain shortcomings and unfortunate facts that "this account has downplayed," such as his deplorable attitudes toward race. And imperialism. And women's suffrage. Yes, he truly was not perfect even at the time, and certainly not by today's standards.
Yet I especially loved this summary (p. 173): "Can the facts be true? Could he really have been a man who was not only a prominent world statesman but also rode to hounds, fenced, flew airplanes, played polo, owned racehorses, painted, farmed, and collected tropical fish? Who, without a university education, was a celebrated war correspondent, novelist, historian, and biographer - whose books were not only best-sellers but also won their author the Nobel Prize in literature, in the same year, it might be added, he accepted the Order of the Garter [to become Sir Winston Churchill]?"
No wonder the "shelves groan with Churchill biographies."
After devouring the YA and children's books, I got involved in this one, a most unusual biography. The author tackles facts about Winston Churchill's life in an open and objective way. Many chapters addressed two opposing statements such as "Winston Was Well Suited to High Office" and "Winston Was Ill Suited to High Office." Another chapter: "Winston Had a Happy Marriage" along with "Winston Did Not Have a Happy Marriage." Truly he was not a perfect person, yet he did great things.
I loved the balance and I loved reading about how biographers can tailor a person's life to live up to their own ideas of who that person was. "A biographer's choice to highlight or dismiss certain episodes - controversial, offensive, or poignant - can vividly color a portrait. Readers unfamiliar with the subject's life are blind to the artful selection that's taking place." (p.221) And then the author, though clearly concluding that "Churchill was one of the greatest heroes of his time,"continues to tell about certain shortcomings and unfortunate facts that "this account has downplayed," such as his deplorable attitudes toward race. And imperialism. And women's suffrage. Yes, he truly was not perfect even at the time, and certainly not by today's standards.
Yet I especially loved this summary (p. 173): "Can the facts be true? Could he really have been a man who was not only a prominent world statesman but also rode to hounds, fenced, flew airplanes, played polo, owned racehorses, painted, farmed, and collected tropical fish? Who, without a university education, was a celebrated war correspondent, novelist, historian, and biographer - whose books were not only best-sellers but also won their author the Nobel Prize in literature, in the same year, it might be added, he accepted the Order of the Garter [to become Sir Winston Churchill]?"
No wonder the "shelves groan with Churchill biographies."
October 15, 2015
The layout of the cover is rather blocky and unattractive. The tan and red color scheme doesn't help much either. Thankfully if you keep it on the shelf you won't have to look at it much. The fact that the pages are the same tan color as the cover is an issue for me as well. I like a book to have white pages and these have an ugly jaundiced look to them. The top of the pages are also covered with unsightly little brown spots. The possibility that these are tiny bug poops makes me hesitant to even thumb through the book.
All is not lost though. Appropriately for a book entitled Forty Ways to Look at Winston Churchill there are indeed forty pictures of Winston Churchill. I would have preferred 40 different pictures of Churchill but I suppose that is nitpicking. The picture that does appear is a bad one for a cover as it is a flesh colored churchill on a flesh colored background. This ends up being unattractive as a cover and not readable as a face at a distance.
overall I give the book 4 velvet siren suits out of 5
All is not lost though. Appropriately for a book entitled Forty Ways to Look at Winston Churchill there are indeed forty pictures of Winston Churchill. I would have preferred 40 different pictures of Churchill but I suppose that is nitpicking. The picture that does appear is a bad one for a cover as it is a flesh colored churchill on a flesh colored background. This ends up being unattractive as a cover and not readable as a face at a distance.
overall I give the book 4 velvet siren suits out of 5
April 1, 2022
What a clever structure! Author Gretchen Rubin (yes, of The Happiness Project fame) read a number of the 650+ biographies of Winston Churchill, and wrote this book of short chapters that present Churchill from opposing points of view — i.e. Churchill as good father, Churchill as neglectful father. I knew very little about Churchill before reading this book and, frankly, didn’t think I needed to know more. I was interested in Rubin’s structuring of the biography, not in her subject. However, despite my best intentions to stay ignorant, I learned a lot of fascinating information about Churchill. A thoroughly enjoyable read.
February 2, 2016
I had high hopes for this one and it was a bit of a let-down. In the introduction she does a good job of explaining the problems associated with creating a biography (biases, personal opinions, politics, hindsight....) and her attempts to get around all of those things. She tries to tackle each issue from multiple angles in an attempt to come across unbiased, but it just reads like a lot of regurgitated information that we all already know about Churchill. Ultimately in the end she admits that she wrote this biography about "her Churchill". There is no way to escape prejudice with this sort of thing, but I felt like all of the back and forth was a strange format. And honestly, after reading some of her other (cheesy) self-help books I couldn't really take her very seriously. Consider this a "lighter" , very surface-level biography.
January 15, 2016
I've been wanting to read more about Churchill. He's a fascinating character, but frankly, the amount of excellent information out there is daunting. Where to start?
This was an excellent place. Very good information, and a simple overview of his life, from forty different micro-perspectives. As always, you're in good hands with Gretchin Rubin's writing. Though very different from her usual topics of habits and happiness from what I'd previously read, she treats Churchill with great clarity, honesty, and affection.
I enjoyed the variety, if not the brevity, of the essays. A few were so clear in premise as to be almost elementary, but I've already thought of half a dozen people to whom I'll immediately recommend this book.
This was an excellent place. Very good information, and a simple overview of his life, from forty different micro-perspectives. As always, you're in good hands with Gretchin Rubin's writing. Though very different from her usual topics of habits and happiness from what I'd previously read, she treats Churchill with great clarity, honesty, and affection.
I enjoyed the variety, if not the brevity, of the essays. A few were so clear in premise as to be almost elementary, but I've already thought of half a dozen people to whom I'll immediately recommend this book.
August 20, 2024
If you are interested in Winston Churchill, but don't have time to spend hours of research on him (spoiler: he really isn't worth it), fear not: Gretchen Rubin has done the research for you and condensed her findings into a short and light read. This is not meant to be an exhaustive biography but a quick refresher on history, popular or not.
Here you have a look at conflicting perspectives of Churchill (ex. Good Parent, Not A Good Parent), lists, quotations, and interesting tidbits.
Here you have a look at conflicting perspectives of Churchill (ex. Good Parent, Not A Good Parent), lists, quotations, and interesting tidbits.
April 20, 2023
I couldn’t find any discussion questions, so here are some:
40 Ways questions
1. Give an example of something new you learned about Winston Churchill.
2. What do you think of this format for a biography?
3. In chapter 39, Rubin summarized her view of Churchill. How would you summarize your view of him?
4. What did you think of his relationship with Roosevelt and his interest in the United States?
5. Have there been other figures in history who have similar characteristics to Churchill?
6. Do you think Churchill was a man-of-the-people or out-of-touch with the people?
7. What did you think of Winston and Clementine’s relationship? What about his relationships with his parents and his children?
8. What do you think of Churchill’s political career? His being chosen as successor to Chamberlain? His changing of political parties?
9. What are examples of Churchill being unconcerned with other’s opinions or views of him? What are examples of him caring about other’s opinions or views of him?
10. Do you think Churchill was born (pre-destined) for the role he played?
11. Churchill’s life spanned amazing changes in technology. What are some examples of this and do you think that is something we have all experienced as well?
12. His life also spanned great social changes. What were some of those changes?
13. What are your thoughts on the 80th birthday portrait?
14. Did this book change your perspective on Churchill at all? And if so, how?
15. Do you think Winston Churchill was a man of paradoxes or just can be viewed through others lenses that way?
40 Ways questions
1. Give an example of something new you learned about Winston Churchill.
2. What do you think of this format for a biography?
3. In chapter 39, Rubin summarized her view of Churchill. How would you summarize your view of him?
4. What did you think of his relationship with Roosevelt and his interest in the United States?
5. Have there been other figures in history who have similar characteristics to Churchill?
6. Do you think Churchill was a man-of-the-people or out-of-touch with the people?
7. What did you think of Winston and Clementine’s relationship? What about his relationships with his parents and his children?
8. What do you think of Churchill’s political career? His being chosen as successor to Chamberlain? His changing of political parties?
9. What are examples of Churchill being unconcerned with other’s opinions or views of him? What are examples of him caring about other’s opinions or views of him?
10. Do you think Churchill was born (pre-destined) for the role he played?
11. Churchill’s life spanned amazing changes in technology. What are some examples of this and do you think that is something we have all experienced as well?
12. His life also spanned great social changes. What were some of those changes?
13. What are your thoughts on the 80th birthday portrait?
14. Did this book change your perspective on Churchill at all? And if so, how?
15. Do you think Winston Churchill was a man of paradoxes or just can be viewed through others lenses that way?
March 11, 2024
A genuine enjoyment. I probably found it more satisfying than most.
Shorter chapters with bursts of anecdotes on complex character. Despite all Churchill’s flaws, you come away believing he was the perfect man at an imperfect time.
Shorter chapters with bursts of anecdotes on complex character. Despite all Churchill’s flaws, you come away believing he was the perfect man at an imperfect time.
April 19, 2025
I really enjoyed this- a little taste of different Churchill biographies. Full of quotes, images, and various views (point, counterpoint) of who Churchill was. This would be a good starting point for launching into lengthier biographies.
January 4, 2021
Shortest book on Churchill that I have ever read.
September 9, 2022
short summary of a long eventful life — easy to understand, gives a good amount of perspective of churchill’s life & impact
June 11, 2022
Enjoyed.
August 22, 2011
I adore reading biographies...like Winston Churchill, the past is more important, compelling, and real to me than the future, and serves as a good road map for navigating the hazards of the present. But this biography I devoured. Not only is WC an heroic, tragic, figure larger than life...living during treacherous times that begat heroism and oratory, the author's treatment of WC is unique in that it begs the reader to come to their own conclusions, based on an extensive bibliography of sources, as to "who was WC?" and where should he be in a reading of history, particularly during the two World Wars?
The author does conclude the book with her personal opinion of WC, which brought me to tears, and in this world of abstemtiousness, cynicism, and relativism it is refreshing to read about someone so certain, eccentric, and archaic, who stood strong against an evil "bad man" (Hitler) and never wavered, offering only "blood, sweat, and tears."
I've alwasy been interested in WC as the Anglo/American mongrel he was. His forebears were lieutenants to George Washington and fought bravely in the Revolutionary War. But what I found most fascinating was Winston's post war vision that America and the UK should be reunited as one nation.
I have often pondered that thrilling possibility...all the English speaking nations of the world as one force for good...we share history, rule of law, and temperment. Granted there are several particularly sticky wickets, i.e. what would we do with your royal family on the dole? Plus the Parliamentary style of government is totally incomprehensible and chaotic to most Americans. However, good fodder for a clever novelist... the US and UK reuniting after WWII.
The author does conclude the book with her personal opinion of WC, which brought me to tears, and in this world of abstemtiousness, cynicism, and relativism it is refreshing to read about someone so certain, eccentric, and archaic, who stood strong against an evil "bad man" (Hitler) and never wavered, offering only "blood, sweat, and tears."
I've alwasy been interested in WC as the Anglo/American mongrel he was. His forebears were lieutenants to George Washington and fought bravely in the Revolutionary War. But what I found most fascinating was Winston's post war vision that America and the UK should be reunited as one nation.
I have often pondered that thrilling possibility...all the English speaking nations of the world as one force for good...we share history, rule of law, and temperment. Granted there are several particularly sticky wickets, i.e. what would we do with your royal family on the dole? Plus the Parliamentary style of government is totally incomprehensible and chaotic to most Americans. However, good fodder for a clever novelist... the US and UK reuniting after WWII.
June 6, 2023
Fun(ny) fact(s): Earlier this week, after being overwhelmed by the multiple shelves of thick, heavy (sometimes multi-volume!) biographies of Winston Churchill at my favorite used bookstore, I selected this slim paperback to purchase.
Favorite quote/image: "When someone told him that the best thing he'd done had been to give the people courage, he contradicted, 'I never gave them courage; I was able to focus theirs.'" (pg. 216)
Honorable mention: "After touring the United States in the 1930s, Churchill was asked whether he had any criticism of America. He answered, 'Toilet paper too thin! Newspapers too fat!'" (pg. 58)
Why: I was hoping for a broad, sweeping introduction to the life of Churchill, one that was willing to hold in tension multiple views of this complicated man and historical figure. This book does that, also acknowledging the difficult task of biographers and their inherent limitations. However, at times Rubin seems more interested in commenting about the genre of the biography then diving too deeply into the life of Churchill, making the book feel repetitive with several "filler" chapters to arrive at the ideal number of 40. But this is about "her Churchill" after all, and I cannot fault her for that.
Favorite quote/image: "When someone told him that the best thing he'd done had been to give the people courage, he contradicted, 'I never gave them courage; I was able to focus theirs.'" (pg. 216)
Honorable mention: "After touring the United States in the 1930s, Churchill was asked whether he had any criticism of America. He answered, 'Toilet paper too thin! Newspapers too fat!'" (pg. 58)
Why: I was hoping for a broad, sweeping introduction to the life of Churchill, one that was willing to hold in tension multiple views of this complicated man and historical figure. This book does that, also acknowledging the difficult task of biographers and their inherent limitations. However, at times Rubin seems more interested in commenting about the genre of the biography then diving too deeply into the life of Churchill, making the book feel repetitive with several "filler" chapters to arrive at the ideal number of 40. But this is about "her Churchill" after all, and I cannot fault her for that.
August 15, 2011
Really 4.5 for this one. I loved this biography! It was short, easy to read a little bit at a time, but still thoughtful and unique. The author looks at Churchill from several different perspectives and explains why each perspective may be right in its own way. It feels like an authentic way to look at a person's life. Read it!
October 27, 2019
This is my first non-human nature/happiness/improvement-related Gretchen Rubin book, and I’m happy to report I loved it. She looks at Winston Churchill through 40 different lenses: Churchill As Parent, Churchill and Sex, Churchill and Hitler, Churchill and Symbols, etc. It’s a fascinating way to examine a biographical subject – and any human, for that matter. For many of the ways, she provides a point and a counterpoint, both supportable by facts, to illustrate how Churchill was nuanced, dichotomous, and sometimes contradictory – just like all of us. I loved that take. It’s so different from many biographies and histories, where it feels like the writer settles on an agenda or point of view and then cherry-picks facts to support those views. This book lets the reader form their own opinions of Churchill as they go along and learn new information about him.
🎩🚬🥃✌🏻
I knew very little about Churchill going into this, but now I’m obsessed with him. What an insane life he led for all 90 of his years! He was born at the apex of the British empire and as a young man fought in one of the last battles where lances were used. LANCES. He died the year after The Beatles came to America. He saw so much, did so much (his productivity makes Leslie Knope look like a slacker), met so many people, and lived through so many milestones in history. His witticisms, one-liners, and speeches are writers’ gold. And I loved learning factoids about him that revealed the wonderful weirdo he was, like how he wore pale pink silk underwear and that he refused to wake up before 8 a.m. unless Britain was being invaded. Overall, I was struck by his intensity and how he applied that indomitable quality to the land he loved, England. His devotion to it in romantic theory and in often devastating practice was so moving. Matt and I watched/listened to some of his speeches on YouTube last night and I was in tears. What a deeply fascinating, flawed, heroic human. I definitely want to read more about him.
🎩🚬🥃✌🏻
I knew very little about Churchill going into this, but now I’m obsessed with him. What an insane life he led for all 90 of his years! He was born at the apex of the British empire and as a young man fought in one of the last battles where lances were used. LANCES. He died the year after The Beatles came to America. He saw so much, did so much (his productivity makes Leslie Knope look like a slacker), met so many people, and lived through so many milestones in history. His witticisms, one-liners, and speeches are writers’ gold. And I loved learning factoids about him that revealed the wonderful weirdo he was, like how he wore pale pink silk underwear and that he refused to wake up before 8 a.m. unless Britain was being invaded. Overall, I was struck by his intensity and how he applied that indomitable quality to the land he loved, England. His devotion to it in romantic theory and in often devastating practice was so moving. Matt and I watched/listened to some of his speeches on YouTube last night and I was in tears. What a deeply fascinating, flawed, heroic human. I definitely want to read more about him.
August 11, 2018
There were two main reasons the author claimed she wrote this biography: One was to allow someone to know about Churchill without knowing everything about Churchill. This she accomplished. As someone who knew only the basics about the former Prime Minister, I found this book to give me a more complete picture of the man without having to know every detail of his life.
The second reason she said she wrote this biography was to rectify the supposedly conflicting details about Churchill's life. This is where I feel that she failed. There were only a few chapters that dealt with these supposed conflicts, and each chapter was divided in two; one dealing with one side of the conflict, one with the other. However, instead of melding the two sides together, she wrote both sides as two completely opposing arguments with no way of making them mesh. So instead of me walking away seeing how one person could view Churchill as an alcoholic and the next person not (for example), she simply outlined both sides and left it at that. Which made me even more confused about these conflicts than before.
The chapter about Churchill's "sex life" was probably the most useless chapter in the book. She tries to explain that the reason she included it is because we as admirers are allowed to be curious. And then she spent a few pages to state the simple fact that Churchill wasn't really into sex. Why did this need to be included again? I'm not really sure.
Overall, this book was extraordinarily entertaining! For a person who doesn't read many biographies, I quite nearly flew through it and am looking forward to reading another Churchill biography soon.
The second reason she said she wrote this biography was to rectify the supposedly conflicting details about Churchill's life. This is where I feel that she failed. There were only a few chapters that dealt with these supposed conflicts, and each chapter was divided in two; one dealing with one side of the conflict, one with the other. However, instead of melding the two sides together, she wrote both sides as two completely opposing arguments with no way of making them mesh. So instead of me walking away seeing how one person could view Churchill as an alcoholic and the next person not (for example), she simply outlined both sides and left it at that. Which made me even more confused about these conflicts than before.
The chapter about Churchill's "sex life" was probably the most useless chapter in the book. She tries to explain that the reason she included it is because we as admirers are allowed to be curious. And then she spent a few pages to state the simple fact that Churchill wasn't really into sex. Why did this need to be included again? I'm not really sure.
Overall, this book was extraordinarily entertaining! For a person who doesn't read many biographies, I quite nearly flew through it and am looking forward to reading another Churchill biography soon.
October 12, 2024
4.5
Winston Churchill has always been an enigma for me. He is a hero, a truly dedicated patriot, but at the same time he is stubborn, self-righteous, often an inconsiderate heel. He has been both heralded as the savior of Britain and the Free World and castigated for his obvious failures and blind spots. I have been grateful for his service and equally thankful that I never had to work with or live with him. Still he fascinates me, and I have read about his long life and career(s) most of my life.
It surprises me how insightful this very short book is in portraying the complexity of this singular man. Somehow Gretchen Rubin provided me with new and startling information that I had not found in longer, more studious histories of the man and his time. She also unflinchingly displays his tremendous attributes as well as his numerous shocking flaws. In the end this author provides her own final assessment of Churchill while at the same time granting her readers free agency to decide for themselves.
There is humor, pathos, and history in this sketch of Winston Churchill, in essence a man of the 19th century but one whose impact on the 20th century cannot be overstated. Rubin's book is by no means a detailed biography; yet it provides a unique and, for me, valuable image of the man that can too often be overshadowed by the avalanche of material exploring and explaining his long, active, and contentious life.
Winston Churchill has always been an enigma for me. He is a hero, a truly dedicated patriot, but at the same time he is stubborn, self-righteous, often an inconsiderate heel. He has been both heralded as the savior of Britain and the Free World and castigated for his obvious failures and blind spots. I have been grateful for his service and equally thankful that I never had to work with or live with him. Still he fascinates me, and I have read about his long life and career(s) most of my life.
It surprises me how insightful this very short book is in portraying the complexity of this singular man. Somehow Gretchen Rubin provided me with new and startling information that I had not found in longer, more studious histories of the man and his time. She also unflinchingly displays his tremendous attributes as well as his numerous shocking flaws. In the end this author provides her own final assessment of Churchill while at the same time granting her readers free agency to decide for themselves.
There is humor, pathos, and history in this sketch of Winston Churchill, in essence a man of the 19th century but one whose impact on the 20th century cannot be overstated. Rubin's book is by no means a detailed biography; yet it provides a unique and, for me, valuable image of the man that can too often be overshadowed by the avalanche of material exploring and explaining his long, active, and contentious life.
May 16, 2020
Book Report “40 Ways To Look At Winston Churchill”
Name of the book: “40 Ways To Look At Winston Churchill”
Author: Gretchen Rubin
Date: 5/8/20
Characters who I like and reasons: Winston Churchill is a man that is so crazy and calm, amazing, and terrible and almost indescribable. This man may very well be the most intricate and unexplainable man of the 20th century.
Summerize in three sentences: “40 Ways To Look At Winston Churchill” is the story of Winston Churchill through the eyes of his many books and biographies written about him. Winston Churchill’s life is explored through this book and teaches you many lessons that only this amazing man can teach you.
Most impressive sentences or parts and reasons What you feel or learn from this book: The most impressive part of Winston Churchill’s life, in my opinion, is how Winston Churchhill was able to survive the Gallipoli campaign and still become Prime Minister.
My judgment: “40 Ways To Look At Winston Churchill” provides a very interesting and unique view to the life of Winston Churchill that is like no other.
Whom you can recommend and why:
I can recommend this book to anyone who is a fan of WW2 politics and or Winston Churchill fan.
Name of the book: “40 Ways To Look At Winston Churchill”
Author: Gretchen Rubin
Date: 5/8/20
Characters who I like and reasons: Winston Churchill is a man that is so crazy and calm, amazing, and terrible and almost indescribable. This man may very well be the most intricate and unexplainable man of the 20th century.
Summerize in three sentences: “40 Ways To Look At Winston Churchill” is the story of Winston Churchill through the eyes of his many books and biographies written about him. Winston Churchill’s life is explored through this book and teaches you many lessons that only this amazing man can teach you.
Most impressive sentences or parts and reasons What you feel or learn from this book: The most impressive part of Winston Churchill’s life, in my opinion, is how Winston Churchhill was able to survive the Gallipoli campaign and still become Prime Minister.
My judgment: “40 Ways To Look At Winston Churchill” provides a very interesting and unique view to the life of Winston Churchill that is like no other.
Whom you can recommend and why:
I can recommend this book to anyone who is a fan of WW2 politics and or Winston Churchill fan.
August 18, 2020
It is refreshing to read a book by an American woman in the "Great Man" genre of biography. The thesis of the book is that Churchill is ultimately deserving of the "Great Man" label, but that every biography written about him will highlight or downplay facts to suit the biographer's conscious or unconscious bias. By arranging this book in themes, the bias of a conventional, linear biography is presumably reduced.
This was published in 2004 and since 2020 is (sigh) a year increasingly defined by cancel culture, I felt this was a helpful book to read. The author provides plenty of ammunition for those looking to "cancel" Churchill: his views towards women, India, non-whites, office harassment, and others are pretty cringe-worthy with ~80 years of hindsight.
On a happier note, I can also see this book being useful for decades as a teaser for young readers to learn more about Churchill. Some of the short, fun chapters around things like the map of the British Empire, the true/false statements, and people he rubbed shoulders with are all bite-sized pieces of content I can see reading with my son at an early age.
This was published in 2004 and since 2020 is (sigh) a year increasingly defined by cancel culture, I felt this was a helpful book to read. The author provides plenty of ammunition for those looking to "cancel" Churchill: his views towards women, India, non-whites, office harassment, and others are pretty cringe-worthy with ~80 years of hindsight.
On a happier note, I can also see this book being useful for decades as a teaser for young readers to learn more about Churchill. Some of the short, fun chapters around things like the map of the British Empire, the true/false statements, and people he rubbed shoulders with are all bite-sized pieces of content I can see reading with my son at an early age.
May 25, 2023
A nicely packaged bits and pieces of the man who made conventional medicine look like science fiction.
I like the comparisons in this book. Winston shared a few things with Hitler, like painting and being ignored by their fathers. In all other aspects, they were complete opposites.
Did Winston go through hell and ice just to impress his father? Most likely. Most people respect their parents but few are challenged by them with such offputting and unabridged negativity as to provoke this unyielding strive for achievement. Both Churchill and Hitler overachieved their father, driven by their utter and unabridged disinterest and hate.
So many other names in history share a similar timeline. Alexander the Great, for example. It is quite possible that every great achiever out there owes some of that success to that one beef they had with their old man.
In any case, we can safely assume that legends are never born to a family of helicopter parents. Mark that in your calendars.
I like the comparisons in this book. Winston shared a few things with Hitler, like painting and being ignored by their fathers. In all other aspects, they were complete opposites.
Did Winston go through hell and ice just to impress his father? Most likely. Most people respect their parents but few are challenged by them with such offputting and unabridged negativity as to provoke this unyielding strive for achievement. Both Churchill and Hitler overachieved their father, driven by their utter and unabridged disinterest and hate.
So many other names in history share a similar timeline. Alexander the Great, for example. It is quite possible that every great achiever out there owes some of that success to that one beef they had with their old man.
In any case, we can safely assume that legends are never born to a family of helicopter parents. Mark that in your calendars.
August 29, 2019
I absolutely loved this biography of Winston Churchill. The back and forth between the positive and negative views of him, both of which have their own truth, lent a sense of humanity to this great figure from history. Great figures in history are just human but their nature and their circumstances combine to produce a character that is larger than life and hopefully an inspiration to subsequent generations.
I couldn't wait to read another installment every evening. The chapters were short and easily digested and always had a new perspective to reflect on. There were novel methods of presenting the information throughout the book like the True/False quiz in chapter 35. Ingenious.
I'm glad I read Gilbert's biography before this so I had a thorough introduction to Churchill's life so there weren't many surprises but a lot of details presented in a new light that it brought a new dimension to my understanding of the man.
I couldn't wait to read another installment every evening. The chapters were short and easily digested and always had a new perspective to reflect on. There were novel methods of presenting the information throughout the book like the True/False quiz in chapter 35. Ingenious.
I'm glad I read Gilbert's biography before this so I had a thorough introduction to Churchill's life so there weren't many surprises but a lot of details presented in a new light that it brought a new dimension to my understanding of the man.
June 6, 2018
Extremely readable, great for fans of Gretchen Rubin, and a great portrait of a very complicated person.
I thought he was 100% perfect except for his haha foibles haha like building brick walls for fun and drinking in bed. Then I talked to a friend who is Nigerian.
So listen, he's complicated. I mean he's very complicated. I prefer to focus on his fight against Hitler, and I think we all do. Maybe the wish of 2018 is that we can have someone who is totally 100% morally pure, even though I think that's just an AI. Maybe we're all being tricked into longing for an AI. I'm sure this is all engineered by AI and now the AI will tell other AI and this will be my last review.
My favorite sections are his weirdness with dressing: pink silk underwear and the fact that he invented the leisure suit, but in really nice fabrics. Google "winston churchill siren suit" and enjoy.
I thought he was 100% perfect except for his haha foibles haha like building brick walls for fun and drinking in bed. Then I talked to a friend who is Nigerian.
So listen, he's complicated. I mean he's very complicated. I prefer to focus on his fight against Hitler, and I think we all do. Maybe the wish of 2018 is that we can have someone who is totally 100% morally pure, even though I think that's just an AI. Maybe we're all being tricked into longing for an AI. I'm sure this is all engineered by AI and now the AI will tell other AI and this will be my last review.
My favorite sections are his weirdness with dressing: pink silk underwear and the fact that he invented the leisure suit, but in really nice fabrics. Google "winston churchill siren suit" and enjoy.
October 21, 2020
This condensed summary of Churchill was just right for me. I appreciated the pro and con perspectives on certain topics (depression, alcoholism, family life etc.). He clearly made the difference for Britain as it faced Nazi Germany alone. His oratory strengthened the country's resolve to endure horrible sacrifices. And yet his unabashed imperialism and condescension toward almost everyone was not appealing (and not that different from Hitler). From birth to death, WC was his certainly his own person. My conclusion is that he was not a hero over the course of his life but he was definitely heroic during the war years. The author also explored the art of biography with candor that I appreciated and will remember.
IQ: "A biographer's choice to highlight or dissmiss certain episodes--controversial, offecnsive, poignant--can vividly color a portrait."
IQ: "A biographer's choice to highlight or dissmiss certain episodes--controversial, offecnsive, poignant--can vividly color a portrait."
September 7, 2017
The author has taken many biographies of Churchill and distilled them into this one readable account. She allows for both sides to be told and then concludes with her own opinion of Winston in the last chapter. I enjoyed this format and learned quite a bit.
My own conclusion? He had his faults and was complicated but was in the right place at the right time. I like him.
"It is all true, or it ought to be; and more and better besides. And wherever men are fighting against barbarism, tyranny, and massacre, for freedom, law, and honor, let them remember that the fame of their deeds, even though they themselves be exterminated, may perhaps be celebrated as long as the world rolls around." :Winston Churchill
My own conclusion? He had his faults and was complicated but was in the right place at the right time. I like him.
"It is all true, or it ought to be; and more and better besides. And wherever men are fighting against barbarism, tyranny, and massacre, for freedom, law, and honor, let them remember that the fame of their deeds, even though they themselves be exterminated, may perhaps be celebrated as long as the world rolls around." :Winston Churchill
March 24, 2019
I am a fan of Churchill, so I was looking forward to a snapshot of different portions of his life. But I ended up not liking the book. It was too abbreviated, and most subjects didn’t get the attention that It should have. I understand the approach, but I was not a fan.
I did learn more about Churchill. I knew that he was a larger-than-life figure, but I didn’t necessarily know that much of it was an affectation. He was a great man, but he was plagued with issues of racism and warmongering.
Nonetheless, I have learned much and Churchill remains, I think, a man to be admired. Just taken with a grain of salt. And I might not have realized the extent of this until I read this book. So, for that, I am grateful to the author.
I did learn more about Churchill. I knew that he was a larger-than-life figure, but I didn’t necessarily know that much of it was an affectation. He was a great man, but he was plagued with issues of racism and warmongering.
Nonetheless, I have learned much and Churchill remains, I think, a man to be admired. Just taken with a grain of salt. And I might not have realized the extent of this until I read this book. So, for that, I am grateful to the author.
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