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When to Jump: If the Job You Have Isn't the Life You Want
When Mike Lewis was twenty-four and working in a prestigious corporate job, he eagerly wanted to leave and pursue his dream of becoming a professional squash player. But he had questions: When is the right time to move from work that is comfortable to a career you have only dared to dream of? How have other people made such a jump? What did they feel when making that jump—and afterward?
Mike sought guidance from others who had “jumped,” and the responses he got—from a banker who started a brewery, a publicist who became a Bishop, a garbage collector who became a furniture designer, and on and on—were so clear-eyed and inspiring that Mike wanted to share what he had learned with others who might be helped by those stories. First, though, he started playing squash professionally.
The right book at the right time, When to Jump offers more than forty heartening stories (from the founder of Bonobos, the author of The Big Short, the designer of the Lyft logo, the Humans of New York creator, and many more) and takeaways that will inspire, instruct, and reassure, including the ingenious four-phase Jump Curve.
Mike sought guidance from others who had “jumped,” and the responses he got—from a banker who started a brewery, a publicist who became a Bishop, a garbage collector who became a furniture designer, and on and on—were so clear-eyed and inspiring that Mike wanted to share what he had learned with others who might be helped by those stories. First, though, he started playing squash professionally.
The right book at the right time, When to Jump offers more than forty heartening stories (from the founder of Bonobos, the author of The Big Short, the designer of the Lyft logo, the Humans of New York creator, and many more) and takeaways that will inspire, instruct, and reassure, including the ingenious four-phase Jump Curve.
334 pages, Hardcover
First published January 1, 2018
408 people are currently reading
2711 people want to read
About the author
Mike Lewis
3 books6 followersMike Lewis worked at Bain Capital before chasing his dream of playing professional squash. He is the founder and CEO of When to Jump, a global community of people who have left one path to pursue a very different one. When to Jump has reached millions through media impressions, in-person events, and brand collaborations. When to Jump, a collection of case studies with clear guidance on how and when to jump, is Mike's first book. He received his BA from Dartmouth College and lives in San Francisco.
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Displaying 1 - 30 of 151 reviews
July 15, 2018
Interesting premise, but in execution of most use to Wall Street bankers, stock traders, venture capitalists and pretty much anyone who can set aside money to take a year or so off work.
If you've got bills to pay and family to support then there's not much you can get from this book beyond "make your jump, when you have a plan."
Seriously. That's it. I just saved you hours of time. You're welcome.
If you've got bills to pay and family to support then there's not much you can get from this book beyond "make your jump, when you have a plan."
Seriously. That's it. I just saved you hours of time. You're welcome.
February 16, 2018
A collection of mini-bios about people who made major career changes. It doesn't really offer any practical advice aside from telling people to just do it.
July 9, 2018
author left a Bain Capital job to play pro squash and couch-surf the world for a year and a half in his 20s, then returned to the states to write this book and develop a site and all that about people making bold career moves in an effort to increase life satisfaction. Got his cousin Sheryl Sandberg to write the foreword!
most of the book is short essays by other people who made career jumps. A limitation of the book is that they're entirely favorable toward doing so. a few acknowledge that their moves failed in conventional sense [e.g., one guy got sober himself but realized that running a recovery house wasn't the business for him after a year or so], and many were forthright about its having turned out to be a lot of work, or less lucrative than prior job, or a source of sleepless nights etc. etc., but all in the end believed it was a good move. It's not a tough call if it's the right idea 100% of the time, so i sense a bit of selection bias in the solicitation of contributors.
some of the jumps were broad [bond trader to photographer who started the Humans of New York site, for instance], while others [at least in my perhaps naive reading] seemed so slight as to not really qualify for the category -- ex. "a former advertising operations associate at LinkedIn... internally jumped into a sales analytics position within LinkedIn".
others struck me as meaningful changes of direction but not especially amazing -- with all due respect, the bartender who became yoga teacher for instance. lots of people change jobs in the course of their lives, and without actually knowing the stats i might have guessed that perhaps even a majority of 25-yo bartenders don't continue in that field another 40 years until retirement. And if you're going to leave it, yoga teacher is as good as anything else as a next move.
my angle on it is perhaps skewed as a 56-year old tenured faculty member with a family, health insurance from the job, etc. etc., but i sort of found all the ones who were young single people with no one depending on them and no great job security anyhow to be kind of unremarkable jumps. maybe more of a dividing line than jump/don't would be employee/entrepreneur, as it seemed that some of the writers with the most turbulence in wake of decision were the ones who elected to start their own businesses, as opposed to just being employed in a slightly or greatly different line of work.
most of the book is short essays by other people who made career jumps. A limitation of the book is that they're entirely favorable toward doing so. a few acknowledge that their moves failed in conventional sense [e.g., one guy got sober himself but realized that running a recovery house wasn't the business for him after a year or so], and many were forthright about its having turned out to be a lot of work, or less lucrative than prior job, or a source of sleepless nights etc. etc., but all in the end believed it was a good move. It's not a tough call if it's the right idea 100% of the time, so i sense a bit of selection bias in the solicitation of contributors.
some of the jumps were broad [bond trader to photographer who started the Humans of New York site, for instance], while others [at least in my perhaps naive reading] seemed so slight as to not really qualify for the category -- ex. "a former advertising operations associate at LinkedIn... internally jumped into a sales analytics position within LinkedIn".
others struck me as meaningful changes of direction but not especially amazing -- with all due respect, the bartender who became yoga teacher for instance. lots of people change jobs in the course of their lives, and without actually knowing the stats i might have guessed that perhaps even a majority of 25-yo bartenders don't continue in that field another 40 years until retirement. And if you're going to leave it, yoga teacher is as good as anything else as a next move.
my angle on it is perhaps skewed as a 56-year old tenured faculty member with a family, health insurance from the job, etc. etc., but i sort of found all the ones who were young single people with no one depending on them and no great job security anyhow to be kind of unremarkable jumps. maybe more of a dividing line than jump/don't would be employee/entrepreneur, as it seemed that some of the writers with the most turbulence in wake of decision were the ones who elected to start their own businesses, as opposed to just being employed in a slightly or greatly different line of work.
November 27, 2017
Watching my niece's gymnastics competition - I use the term "competition" loosely considering I changed her diaper less than 3 years ago - I'm struck by the difference in the little girls' faces as they jump from the balance beam. They are all the same age. They all have had similar classes. Yet, there is a hesitation and almost fear on the faces of some, while others leap without much of a glance at the ground. I was reminded of these girls while reading "When to Jump" by Mike Lewis.
Lewis has built a sincere compilation of both his own career change and the stories of over 40 other individuals who take that step into the unsure world of a new career. He organizes it in a way that lays out how to plan one's own career move. The variety of starting points and landing points is vast. Each individual's story is short and to the point, making this an easy to read and widely applicable volume. If you are considering a career change and want a way to organize the chaos that decision may bring there is plenty here you will find useful.
The only flaw to this collection is the sampling bias for the stories. Like many business or self-help books of it's kind, the advice is taken from individuals who succeeded in whatever the topic of the book is. There isn't a separate sample of individuals who did the same or similar and wished they hadn't or had to go back to their old ways even if they wished they didn't. I raise this critique simply to say the book offers great encouragement for those who want to plan a "jump." But it does little to remind readers of the adage wherever you go, there you are." Like many of the 40+ individuals detailed in the collection and the girls who leaped headstrong into their gymnastics dismount, who you are will determine a lot about how you view your landing.
I whole-heartedly recommend this volume to anyone considering a career jump. It certainly provides a well-considered path to doing that jump wisely.
I received an advance copy of this book through a LibraryThing giveaway.
Lewis has built a sincere compilation of both his own career change and the stories of over 40 other individuals who take that step into the unsure world of a new career. He organizes it in a way that lays out how to plan one's own career move. The variety of starting points and landing points is vast. Each individual's story is short and to the point, making this an easy to read and widely applicable volume. If you are considering a career change and want a way to organize the chaos that decision may bring there is plenty here you will find useful.
The only flaw to this collection is the sampling bias for the stories. Like many business or self-help books of it's kind, the advice is taken from individuals who succeeded in whatever the topic of the book is. There isn't a separate sample of individuals who did the same or similar and wished they hadn't or had to go back to their old ways even if they wished they didn't. I raise this critique simply to say the book offers great encouragement for those who want to plan a "jump." But it does little to remind readers of the adage wherever you go, there you are." Like many of the 40+ individuals detailed in the collection and the girls who leaped headstrong into their gymnastics dismount, who you are will determine a lot about how you view your landing.
I whole-heartedly recommend this volume to anyone considering a career jump. It certainly provides a well-considered path to doing that jump wisely.
I received an advance copy of this book through a LibraryThing giveaway.
July 8, 2018
2 stars
I will be honest, I skimmed a good portion of this book. I read all the sections from the author, as well as the recaps, but I only read about half of the case studies (mostly because a lot of them didn't seem relevant or interesting to me).
If I recall correctly, at one point the author says he didn't want this book to be just a series of platitudes without any concrete advice, but that's basically what it is. I found some of the words of encouragement, well, encouraging! But for all the talk of how important it is to have a plan, there isn't much elaboration on what makes a successful plan and what mistakes to avoid.
As many other reviewers have also pointed out, the author comes from quite a privileged background, and most of the guest writers do, too (I guess the fact that the foreword is by Sheryl Sandberg should have been a warning sign). It's kind of obnoxious to say "you need to have savings to jump!" and then almost exclusively talk to people who came from lucrative careers like finance. Easy to say when you're in an industry like that...
And beyond the matter of money, the author's "jump" is to play professional squash? Seriously? It also rubbed me the wrong way that the last few pages of the book are him saying that he never intended it to be a long term "jump" and was already planning his next... writing this book. Sincerely glad I didn't pay for this, and rather checked it out from the library, cuz Lewis is playing us readers. Honestly...
As I said, I skipped around with the case studies. I mostly read the ones that had to deal with creative careers (like writing, photography, fashion design, etc.), because those felt most relevant to my interests. Unfortunately I just returned the book to the library so I can't go back to find the name, but one of the guest writers spoke about how she got into photography, and how she had to do a "mini jump" by taking a job in her industry that wasn't her ideal job, but led to better things. She also said that she had taken more "meaningless" jobs while she planned in order to build up her savings. I thought her section had the most realistic and smart advice in the whole book. I also appreciated the advice from the cheesemonger lady, who pointed out that if you are so miserable in your current situation (job, partner, living situation, whatever), you really have nothing to lose and should just get started on your "jump." The longer you wait, the longer you have to live with that unhappiness when you don't have to! That's basically the place I found myself in last year before I decided to quit my job, so I related to that a lot.
I feel like the premise of this book had potential, and probably would have been more helpful and informative in better hands. I don't recommend it!
I will be honest, I skimmed a good portion of this book. I read all the sections from the author, as well as the recaps, but I only read about half of the case studies (mostly because a lot of them didn't seem relevant or interesting to me).
If I recall correctly, at one point the author says he didn't want this book to be just a series of platitudes without any concrete advice, but that's basically what it is. I found some of the words of encouragement, well, encouraging! But for all the talk of how important it is to have a plan, there isn't much elaboration on what makes a successful plan and what mistakes to avoid.
As many other reviewers have also pointed out, the author comes from quite a privileged background, and most of the guest writers do, too (I guess the fact that the foreword is by Sheryl Sandberg should have been a warning sign). It's kind of obnoxious to say "you need to have savings to jump!" and then almost exclusively talk to people who came from lucrative careers like finance. Easy to say when you're in an industry like that...
And beyond the matter of money, the author's "jump" is to play professional squash? Seriously? It also rubbed me the wrong way that the last few pages of the book are him saying that he never intended it to be a long term "jump" and was already planning his next... writing this book. Sincerely glad I didn't pay for this, and rather checked it out from the library, cuz Lewis is playing us readers. Honestly...
As I said, I skipped around with the case studies. I mostly read the ones that had to deal with creative careers (like writing, photography, fashion design, etc.), because those felt most relevant to my interests. Unfortunately I just returned the book to the library so I can't go back to find the name, but one of the guest writers spoke about how she got into photography, and how she had to do a "mini jump" by taking a job in her industry that wasn't her ideal job, but led to better things. She also said that she had taken more "meaningless" jobs while she planned in order to build up her savings. I thought her section had the most realistic and smart advice in the whole book. I also appreciated the advice from the cheesemonger lady, who pointed out that if you are so miserable in your current situation (job, partner, living situation, whatever), you really have nothing to lose and should just get started on your "jump." The longer you wait, the longer you have to live with that unhappiness when you don't have to! That's basically the place I found myself in last year before I decided to quit my job, so I related to that a lot.
I feel like the premise of this book had potential, and probably would have been more helpful and informative in better hands. I don't recommend it!
March 21, 2025
won from librarything.com
got in mail today
got in mail today
April 12, 2019
Not what I expected. Constant stories of an already successful person moving to a different successful career. I just skimmed this as it really didn't relate to my situation in the least bit. I wanted some practical advice, not just a book full of braggarts.
January 22, 2020
This book provides you with 40 I-made-the-jump-successfully stories, such as switching from a nurse to a doctor at a later stage of life. If you are clear of what you are doing and just want a little validation from others who are not your friends and family, this is a book with inspiring quotes you can turn to. But if you are specifically looking for the useful tools to assist you when to jump as seen in the book title, sorry, this is not the book. To me, the closest thing the author has achieved relating to the book title is that he draws the experiences of himself and others to conclude that there are four commonly known phases to a jump: 1) listen to your inner voice; 2) decide to take action; 3) let yourself be lucky and 4) don’t look back.
March 18, 2018
I struggle to know what my 'passion' is - but it was nice to see how many people moved from one career to another, and talked about how it worked (or didn't!).
Sharing the concept of the book with a friend; and the author's 'passion' being squash, my friend was rather bemused. Understandably too, as it's hardly a profitable career path.
Sharing the concept of the book with a friend; and the author's 'passion' being squash, my friend was rather bemused. Understandably too, as it's hardly a profitable career path.
April 12, 2018
Some great stories and advice... and some that are pretty skip-worthy. Also, I had to power through the first part which was all about the author's life (it was a little too silver-spooned). I'm glad I stuck with it though and will be looking into some of the contributors' works.
October 11, 2018
I needed this book at this time in my life. It made me realize that I've already made a lot of jumps, both personally and professionally, throughout my life. Reading Lewis' story and the stories of so many others who made a major professional jump wasn't only inspiring: it was necessary because so many of them shared how even after making the jump, they were still afraid, still uncertain and still confused. But they feel the fear and do it anyway. This is a book that gets really real really fast and helps you to start to move your excuses out of the way. It takes you on an up & down ride that will make you look at all of the flimsy reasons you use to NOT jump. It just forces you to look at yourself in the mirror and ask yourself some tough questions, but you soon realize you're better for it.
April 23, 2018
2.5 stars. I would say this book is pretty hit and miss. Some of the stories were interesting and inspiring, more of them were a little blah or general. I was kind of put off by the number of stories in here where the person started off in some kind of high finance job. One or two would've been fine, but I felt like there were too many, especially given that working in that environment probably gives you the types of savings/investment contacts that would make a jump much easier (especially into a start-up concept). This focus also gave the book a narrowness that seemed as if Lewis mainly asked a bunch of his friends for some submissions.
I didn't really come away with anything new from this book, most of the advice was obvious. The act of listening to it did make me think of my own ambitions and goals, so I'll give it that. My favorite section was the Humans of New York guy because I liked how he really put it all down to the fact that you have to do the work. You can't just keep talking about something, you have to do it and keep doing it, even if no one is watching yet. One other pet peeve I had was specific to the audio version: the section recaps. I started skipping them, but it was annoying to listen to Lewis read off snippets from what I'd already just listened to. If I thought something was interesting, I'd note it down myself, thanks.
Meh. I wouldn't really recommend this. I think there are better "follow your dream" books out there.
May 28, 2020
A biographical collection of people describing how and why they changed their existing jobs. Each story is a few pages(3-4) long, and all different in terms of their individual jumps.
The basic idea is to listen to your passion, plan for the future and don't look back. This is sensible enough to know but not something to write about. I think this was better suited to a podcast rather than a book.
Unfortunately, book misses the mark by not giving a recipe as how to make a jump. All you've is anecdotal experience of different people, which adds to the confusion rather than give any clarity to the reader.
The basic idea is to listen to your passion, plan for the future and don't look back. This is sensible enough to know but not something to write about. I think this was better suited to a podcast rather than a book.
Unfortunately, book misses the mark by not giving a recipe as how to make a jump. All you've is anecdotal experience of different people, which adds to the confusion rather than give any clarity to the reader.
August 17, 2023
[audiobook version]
I really enjoyed that this book was written as an anthology! I enjoyed hearing from different people who had made jumps. Also, really liked that the audiobook version had almost each essay read by the person who actually made the jump!
I would have liked at least *some* stories from people whose jumps didn’t turn out so great, but I know that probably wouldn’t have been as inspiring, but I think it could have been helpful?
The book took me a little over a month to finish because I was digesting and pondering thoughts about my own life and own potential jumps.
I really enjoyed that this book was written as an anthology! I enjoyed hearing from different people who had made jumps. Also, really liked that the audiobook version had almost each essay read by the person who actually made the jump!
I would have liked at least *some* stories from people whose jumps didn’t turn out so great, but I know that probably wouldn’t have been as inspiring, but I think it could have been helpful?
The book took me a little over a month to finish because I was digesting and pondering thoughts about my own life and own potential jumps.
December 25, 2023
Full of testimonies that encourage changing professions. Not a bad book at all, but best for those who have already decided they need a life change and just need some encouragement to make the leap.
These testimonies helped me see that I’m doing what I’m called to do, even if it isn’t always comfortable or if I don’t always feel welcome. The testimonies were one-sided, with none of them regretting having jumped. That’s what I realized — whichever path would make me feel more regret is the one I should avoid.
These testimonies helped me see that I’m doing what I’m called to do, even if it isn’t always comfortable or if I don’t always feel welcome. The testimonies were one-sided, with none of them regretting having jumped. That’s what I realized — whichever path would make me feel more regret is the one I should avoid.
November 6, 2022
Jump a job to your advantage!
As a person who has changed jobs before, I can totally relate to the writings in Mike Lewis's book "When to Jump". The author initially tells readers about his own jump from an office job into the world of squash sports, then adds to the bulk of the book stories of jumpers from all walks of life from their own perspectives. The stories they all tell of how they changed their lives after changing their professions can really strike a chord in the hearts of readers.
The people mentioned in the book share inspirational stories on their lives before, during, and after the change to a different job. Their experiences are a mix of positive and negative that helped them alter their mindsets as they went along with the changes. Most of them began in traditional office jobs then later found themselves working in entrepreneurial and creative roles. This includes becoming a karate instructor, creator of the car moustache, tailoring a fashionable item that was promoted by the singer Beyonce, and alot more fascinating professions.
At the end of each chapter readers will find a collection of quotes arranged by Mr. Lewis that reflect lessons learned pertaining to the specific chapter. These quotes are very motivational and serve as key points to keep in mind for those willing to take the risk in changing their jobs or starting their own thing as entrepreneurs. I admire the fact that the author compiled the quotes from the people mentioned, the majority of which are not very well known yet have done their own great achievements worth sharing to the world as a result of their jump to better jobs.
Summing up, "When to Jump" is an inspiring read and I highly recommend it to people who feel stuck in a crummy profession and half thoughts about moving. I also recommend the book to people who have creative ideas and want to feel motivated to make the ideas happen in reality. Don't be afraid; make the jump when you feel in your heart that you're ready!
As a person who has changed jobs before, I can totally relate to the writings in Mike Lewis's book "When to Jump". The author initially tells readers about his own jump from an office job into the world of squash sports, then adds to the bulk of the book stories of jumpers from all walks of life from their own perspectives. The stories they all tell of how they changed their lives after changing their professions can really strike a chord in the hearts of readers.
The people mentioned in the book share inspirational stories on their lives before, during, and after the change to a different job. Their experiences are a mix of positive and negative that helped them alter their mindsets as they went along with the changes. Most of them began in traditional office jobs then later found themselves working in entrepreneurial and creative roles. This includes becoming a karate instructor, creator of the car moustache, tailoring a fashionable item that was promoted by the singer Beyonce, and alot more fascinating professions.
At the end of each chapter readers will find a collection of quotes arranged by Mr. Lewis that reflect lessons learned pertaining to the specific chapter. These quotes are very motivational and serve as key points to keep in mind for those willing to take the risk in changing their jobs or starting their own thing as entrepreneurs. I admire the fact that the author compiled the quotes from the people mentioned, the majority of which are not very well known yet have done their own great achievements worth sharing to the world as a result of their jump to better jobs.
Summing up, "When to Jump" is an inspiring read and I highly recommend it to people who feel stuck in a crummy profession and half thoughts about moving. I also recommend the book to people who have creative ideas and want to feel motivated to make the ideas happen in reality. Don't be afraid; make the jump when you feel in your heart that you're ready!
April 12, 2018
I kind of cheated here as I did not read the whole book but only the parts that interested me. Being currently in "jump-mode" I read only the introduction and the final "Don't look back" section. Second cheat is that I did not purchase the book but was given to me on a promotion tour by the speaker.
The book has a pattern on what to do if you do not like your job and/or the career trajectory and how to move from there to where you want to be.
This theory has emerged from the life of the author and people that have interacted with him, so we are talking about pure epistimology here. The vast majority of "When to Jump"'s content is two/three page essays of different people around the world in each stage. From this perspective the book is essentially an great articulation of very well edited blog posts about one subject put in one place.
The whole premise felt like being in the category of books that one would love if given as a gift but would not buy. I would suggest to resist that tendency and give it a shot if you find it in a bookstore.
Reminder to future self: write about my jump.
The book has a pattern on what to do if you do not like your job and/or the career trajectory and how to move from there to where you want to be.
This theory has emerged from the life of the author and people that have interacted with him, so we are talking about pure epistimology here. The vast majority of "When to Jump"'s content is two/three page essays of different people around the world in each stage. From this perspective the book is essentially an great articulation of very well edited blog posts about one subject put in one place.
The whole premise felt like being in the category of books that one would love if given as a gift but would not buy. I would suggest to resist that tendency and give it a shot if you find it in a bookstore.
Reminder to future self: write about my jump.
March 1, 2023
This book really sparked the motivation to take inventory of my life and what I’m doing and accept I’m not happy in my current role. While the word(s) “jump”, “jumping”, and “jumped”, started to get annoying/corny eventually (this is me being nit-picky lol), the philosophy makes complete sense. I enjoyed the format of the book - people telling their own story of the changes they made to be happier and fulfilled. The only thing missing is advice in how to actually figure out what that next thing should be… I know I want to change, I’m motivated to change, but I can’t think of anything that I’m interested in or good enough at that could be used to develop a business or insert myself into someone else’s.
September 27, 2018
inspiring! the audiobook was made a bit more interesting by the anecdotes being read by the folks whose story it is. enjoyable compilation.
June 10, 2019
A collection of inspiring stories, quick read, and gives one plenty of food for thought.
Read
August 28, 2022Nate Chambers, a former mechanical engineer and founder of Fit Factory Gear, is co-owner of Roark Gyms in San Francisco.
"I needed my ex-husbands support--not his permission but his support--because our lives are very connected...and emotionally, I was not ready to accept his lack of support." pg 52
"There's a line from the Gospel of Thomas that I kept thinking about over and over and over again: if you bring forth what is in you, it will save you, and if you do not bring forth what is in you, it will destroy you." pg 53
"Things change that you can't control...Our lives are all transit; there is always going tao be a coming and going, regardless of whether we jump or not. Don't avoid jumping because of the illusion of stability you think you have." pg 53
We tend to react...
~by planning more to try and fully solve all uncertainties,
~by pushing back the jump date, or
~by deciding not to jump at all--concluding that the job we have and the life that it provides simply aren't worth jeopardizing.
"But I knew a lot of my success was somewhat fluke-is and that it would dry up the moment I was exposed as someone who was basically not interested. It's very hard to keep up with anything you're not really interested in." pg 164
"I'm more or less addicted to the uphill battle of making my life as hard as possible. I thought working a lot would make me happy. It didn't." pg 178
"I talked to as many people in the art industry as possible. I cold-called and threw emails across alumni directories, yellow pages, art museums--anywhere. After each person I met, I told myself I needed to get to one more person. And I would get coffee with people. I would ask to get drinks...I'd listen to their experiences in art. Are they positive? Are they negative? Did they like being an artist? Did they like being a gallerist? I ended up sitting down with a lot of the gallerists who failed. They were the most helpful. The conversations allowed me to figure out if this jump was right for me. Every day of the week, I found, and still find, a way to take someone in my industry out for coffee." pg 179
"Most importantly, I had started every thought, dream, and conversation by saying, "When I open my gallery..." I was going to make it work." pg 179
Abigail Ogilvy Ryan, a former technology operations manager, restaurant manager, and hardware cashier, is the owner of Abigail Ogilvy Gallery.
"As a kid in Nigeria, my dad couldn't afford to go to school, so he'd sit outside the classroom by the window until the teacher chased him away. He'd show back up the next day, and the next, until the school told my grandparents to find a way to send my dad to school so he could stop bothering everyone. They did, but they had money for only one school uniform. So he walked naked to class each day, holding the clothes in his hands to keep them clean." pg 182
"Like other immigrant fathers, my dad's greatest fear is that I would end up poor, that I'd have to live in a situation like the one he grew up in." pg 183
"Why the heck am I dancing? I knew it spoke to me, but I also knew I didn't want to teach full time. What is it? Why am I doing this thing? As I cycled through responses, I started to find ways to use my dancing to help out the community." pg 185
"I benefitted from not being distracted. I had set the stage for my jump, and I needed to go for it unapologetically. Preparation is one thing, but staying half-in, half-out leads to mediocrity." pg 211
"Six years in, I was in the habit of introducing myself to magazines and websites. One day I sent an e-mail introduction to a design blogger and he responded warmly and offered to feature my work in a blog post. The article quickly went viral and was soon picked dup by countless other meed outlets, newspapers, and magazines around the world." pg 211
"My college professor Charlie Wheelan liked to remind his students that there are no final rankings in life. He'd often say that obituaries don't conclude with, "John finished in 3,123rd place."" pg 223
Dan Kenary, a former commercial bank loan officer, is cofounder and CEO of Harpoon Brewery.
"Plus, that's why I moved to DC; to chase my dreams, work on cool projects, and make my future what I want it to be." pg 232
"I sent out emails left and right, prying at Special Olympics International's to see if they would hire me. After being either rejected or ignored, I finally got an email from the guy who had sat in the office next to me at the World Games..."
"I started the day mopping, I'll end the day mopping. I'll be back mopping before brunch service starts tomorrow. You always hear this fact about the restaurant business--how most don't make it, how seven out of ten will shut down. I have no idea if that's right, and truth is, I don't care. This business isn't pretty, isn't easy, and isn't for everyone. But starting my own place is what I've always wanted to do, and in 2016 I finally left my nine-to-five to give it a shot." pg 235
"When I started to think about going into sober homes, it was the exact opposite: "I can talk about this. I want to talk about it."" pg 248
"That's something I always tell people: Get out there. If you're thinking about something, go do it, and see if you actually like doing it." pg 258
"I learned the right questions to ask myself: What kind of lifestyle do you want? More basic, how do you want to be spoken to on a daily basis? Do you want to be yelled at? Or do you want to have seemingly adult conversations? Do you want to work late nights or early mornings?" pg 259
"The people in the cheese world are truly salt of the earth. I knew I wanted to be surrounded by these people. It was hard for me to relate to others in a job where core incentives were more financially driven...I wanted to be around my people. And my people, I feel, are people who care about the environment and who care about other people. A collaborative, lovely group of down-home people."
"On business trips I'd explore the food scene while I immersed myself in it from all sides. I helped out at a farmers' market nonprofit, joined the California Artisan Cheese Guild, volunteered wherever and whenever I could. I need to know if my fling for cheese could be satisfying as a hobby or if it was something more." pg 260
"This community was welcoming, kind, and collaborative."
"My mom couldn't get it: Work is work. So whatever you do, it's going to be work. And I said, "I just disagree.""
"The next thing I did was drive around the country for two and half months visiting cheese makers. I met a lot of folks who struggled to get their products to market."
Sarah Dvorak, a former retail inventory planner, back-of-house kitchen attendant, and retail merchandising associate, is founder and owner of Mission Cheese, and American artisan cheese bar.
Social entrepreneurship
"Renting out my rooms is what made my jump possible. Financially, it placed me in a situation where I was slightly uncomfortable, which forced me to push my business forward, and at the same time, renting the rooms provided enough cash so that I didn't have to go out and get another job, because it would have been impossible to do with jump without any other ride gig. I'm going overtime, full-time, all the time. I just don't have thee extra time for attention require for any part-time desk job."
"Before you jump, get really clear on your values. Dont' let your thinking become too lofty on one hand or too grimly rooted in reality on the other. You have to have both." pg 273
"Even while I was committed to banking, people would say, "You should sell painting and design clothes on the side. You can display your art in galleries. You can do XYZ." They always believed that my creative gene was being wasted sitting in the office." pg 280
Brenda Berkman sued the New York City Fire Department to eliminate job discrimination against women. When she won in 1982, she quit her law practice and became one of the first women firefighters in the FDNY. After twenty-five years and promotion to captain, Berkman retired in 2006 and became an artist.
"Say it was Friday. If the day went well, I'd feel great the whole weekend. If Friday went horribly, I'd spend all weekend miserable. I needed something that would create some pocket of air in my life, something that I could value other than trading." pg 288
"Maria Popova, founder of Brain Pickings, talks about the danger of prestige and the feeling it gives us: how good it feels to be doing something that makes us feel important. It locks us into places. Money wasn't the most tempting reason for me to stay--it was the feeling that I..." pg 289
"In my jump, I wanted to, for the foreseeable part of my life, attempt to make just enough money so that I could control my time. I focused exclusively on how I would spend my days. I would switch priorities and put time above money as the most valuable resource. Instead of structuring my life to have as much money as possible, I was going to structure my life to have as much time as possible. I thought if I did that, I could answer a simple, important question: What is it that I should be doing?" pg 290
"I set a modest goal: take some time off and photograph. I didn't have a lot of money saves and so my ambitions were basic; my only goal was to make just enough money to control my time."
"I started reading a hundred pages a day, and I did that every day for the better part of the next decade. It created discipline..."
"For the next foreseeable time of my life, I'm going to do only what I want to do. I'm gonna do it all day long. And that sounds simple, but here's the main thing: very few people actually put in the work to follow their dream. Look around New York City. Listen to all the people who tell you they're musicians, who tell you they're photographers, who tell you they're artists, who tell you they're painters. And then you ask them, "Oh, really? Tell me about your average day. What are you doing on a weekly basis to do these things?"And you learn, eight times out of ten, that the person is doing just enough work to own that identity, to be able to call themselves that."
"When done correctly, and very few people are doing it this way, jumping is nothing but hard work. That's all I did. I didn't go out. I didn't go to concerts. I didn't know anybody in New York. I didn't hang out with friends. All I did was photograph. I treated it like a job."
"Photography is all I did. It's all I did. That's the thing. It doesn't matter unless you're the kind of person with the discipline and the work ethic to work all day long at what you want" pg 292
"It got to be where it was discipline that was sustaining me--discipline that I built up after I flunked out of college, when I told myself I was going to practice piano for an hour every day no matter what. I was going to practice piano for an hour every day not matter what. I as going to exercise every single day no matter what. I did all three of those things every single day for years. That built discipline, and that's what got me through my jump and taught me how to do something every single day without fail, no matter how I felt. That's the key to making a jump. It's not passion. It's discipline." pg 293
"It took a year of working every day before I could fully pay my rent. But I never said to myself, "This is not working because it's not a good idea." I told myself, "This isn't working because I'm not ____ enough yet. I need to get better. I need to improve." Malcom Gladwell's Tipping Point gave me my. new mantra: that there's no way that I can fail because I can always get a little bit better. If I keep getting a little bit better, a little bit better, a little bit better, the work gets a little bit more interesting. It's going to reach a point where suddenly people are going to be checking it out, not because I'm telling them to, but they're going be checking it out because it's good enough and it's interesting enough."
July 2, 2018
If you're thinking or contemplating a life change. This is absolutely your next book!
September 17, 2018
Good advice for anyone looking to make a career change.
August 12, 2020
When to Jump collects stories from people who left their stable but unfulfilling jobs in order to pursue their dreams. It suggests various things to consider, both in terms of reasons to leave your current jobs and how likely you are to achieve the dream you are leaving it for.
A lot of self-help advice is wildly impractical, overly optimistic nonsense that will ruin your life if you try to follow it. Stuff like “Follow your dreams,” “Never give up,” “Something’s only worth doing if it’s extraordinary,” “Don’t let anyone doubt you.”
The problem with these cliches is that they have zero connection to how realistic your dream actually is. How good are you at it, including the less fun aspects of turning your endeavor into a business? Is there a market for it? Will you be able to make enough money to support yourself and your family?
Lewis does give some thought to these pragmatic questions, but in my opinion, not nearly enough.
There’s an enormous amount of survivorship bias in this book. Nearly all of the case studies are from people who succeeded, even though the reality is that the overwhelming majority of people who “jump,” or leave their secure job to follow a dream, will fail.
The book could have greatly benefited from more examples of people whose jumps didn’t work out, both to give a better understanding of the consequences and to give examples of what not to do.
Looking at the example of Lewis himself can be instructive in what the book is lacking. Lewis left his investment banking job to be a professional squash player. But when he did this, he was 24, had no responsibilities, had saved up a bunch of money, and was only planning for this to be a temporary thing.
So he was able to spend a year and a half couch-surfing through Europe while earning a negative income playing squash, until he burned through his savings and went back to investment banking with cool stories of his adventures. Very few people have a similar lack of responsibilities or the ability to spend eighteen months with a negative income.
The book does have some useful advice, and is worth reading if you’re considering leaving your career. But it only gives half the picture, and you would need to give much more thought to the consequences of failure before you are truly ready to jump.
A lot of self-help advice is wildly impractical, overly optimistic nonsense that will ruin your life if you try to follow it. Stuff like “Follow your dreams,” “Never give up,” “Something’s only worth doing if it’s extraordinary,” “Don’t let anyone doubt you.”
The problem with these cliches is that they have zero connection to how realistic your dream actually is. How good are you at it, including the less fun aspects of turning your endeavor into a business? Is there a market for it? Will you be able to make enough money to support yourself and your family?
Lewis does give some thought to these pragmatic questions, but in my opinion, not nearly enough.
There’s an enormous amount of survivorship bias in this book. Nearly all of the case studies are from people who succeeded, even though the reality is that the overwhelming majority of people who “jump,” or leave their secure job to follow a dream, will fail.
The book could have greatly benefited from more examples of people whose jumps didn’t work out, both to give a better understanding of the consequences and to give examples of what not to do.
Looking at the example of Lewis himself can be instructive in what the book is lacking. Lewis left his investment banking job to be a professional squash player. But when he did this, he was 24, had no responsibilities, had saved up a bunch of money, and was only planning for this to be a temporary thing.
So he was able to spend a year and a half couch-surfing through Europe while earning a negative income playing squash, until he burned through his savings and went back to investment banking with cool stories of his adventures. Very few people have a similar lack of responsibilities or the ability to spend eighteen months with a negative income.
The book does have some useful advice, and is worth reading if you’re considering leaving your career. But it only gives half the picture, and you would need to give much more thought to the consequences of failure before you are truly ready to jump.
January 14, 2018
There are lots of books out there which promise you your dream life, job and love if you follow the authors simple rules and it can all seem like a bit of a pipe dream. Mike Lewis has tapped into something a little bit different with When To Jump. Using his own experience of taking the leap from venture capitalist to professional squash player as inspiration, Lewis sought out other people who have made the leap.
What I like about When To Jump, is that it isn’t full of rags to riches stories and people who have changed the world. It’s a collection of stories from ordinary people that have changed their own worlds. Some are complete changes in direction; Jeff Arch, for example, who went from karate school instructor to Hollywood screenwriter, or Rashard Mendenhall who went from professional football player to writer. But, some are as simple, and as frightening, as going for that promotion, or taking a side step into a different department in the same company you work for.
The common theme amongst these uncommon stories is to have a B plan. Yes, you can have that little voice telling you to give it all up and become a writer or to quit your lucrative management position to launch a start-up, but you need to be sensible and have a backup plan. It’s not all about ‘the jump’, it’s more about planning the jump so that you have a higher chance of success when you decide to take the leap.
I found the stories inspirational, motivational, and above all attainable. Many, many times whilst reading When To Jump, I thought ‘I need to get my jump plan together!’.
This is better than your average motivational read. Original, bite-sized stories which will get you thinking, and more importantly listening to your own inner voice.
Buy now at Booktopia! Copy given to me by the publisher in exchange for an honest review.
What I like about When To Jump, is that it isn’t full of rags to riches stories and people who have changed the world. It’s a collection of stories from ordinary people that have changed their own worlds. Some are complete changes in direction; Jeff Arch, for example, who went from karate school instructor to Hollywood screenwriter, or Rashard Mendenhall who went from professional football player to writer. But, some are as simple, and as frightening, as going for that promotion, or taking a side step into a different department in the same company you work for.
The common theme amongst these uncommon stories is to have a B plan. Yes, you can have that little voice telling you to give it all up and become a writer or to quit your lucrative management position to launch a start-up, but you need to be sensible and have a backup plan. It’s not all about ‘the jump’, it’s more about planning the jump so that you have a higher chance of success when you decide to take the leap.
I found the stories inspirational, motivational, and above all attainable. Many, many times whilst reading When To Jump, I thought ‘I need to get my jump plan together!’.
This is better than your average motivational read. Original, bite-sized stories which will get you thinking, and more importantly listening to your own inner voice.
Buy now at Booktopia! Copy given to me by the publisher in exchange for an honest review.
April 16, 2018
I actually finished a non-fiction! But this did not feel much like any other self-help books I read. I felt like I was reading the chicken soup books. It was a pretty easy read with bite size chapters. I love the fact that the book were inserted with stories of people who jumped, be it successful or otherwise. It was also close to the heart as I had been thinking of making another jump. It resonated with me for all the past jumps I made too. And how I could have made some jumps better than how it had turned out to be.
When to Jump is a book that tells the story of the little Voice in you, that tells you what you should be doing to be happier in your life - you know, the voice that you usually ignore in favor of what you think is the right way to live your life! Like studying and be the best in school so you can get a good job and start a family etc. But what if that does not make you happy? But yet, you do not want to live that life, just because you were expected to?
It can be a small jump or a big one. But a few important things to do before a jump - it has to have a plan, you will need a backup, get a lot of support from people who KNOW you and you need to have the courage to jump! This books tells you all about the four phases before a jump, and in between the phases, tells you stories of those who jumped. These were the interesting insights and the reflective thoughts of what kind of jump you will need, why you need to jump, when to jump and how to make that jump successful.
In the end, the most important thing to remember is that a jump makes you to be who you are. You will not regret it because you jumped, rather than wondering about the what-ifs had you not chosen the jump.
When to Jump is a book that tells the story of the little Voice in you, that tells you what you should be doing to be happier in your life - you know, the voice that you usually ignore in favor of what you think is the right way to live your life! Like studying and be the best in school so you can get a good job and start a family etc. But what if that does not make you happy? But yet, you do not want to live that life, just because you were expected to?
It can be a small jump or a big one. But a few important things to do before a jump - it has to have a plan, you will need a backup, get a lot of support from people who KNOW you and you need to have the courage to jump! This books tells you all about the four phases before a jump, and in between the phases, tells you stories of those who jumped. These were the interesting insights and the reflective thoughts of what kind of jump you will need, why you need to jump, when to jump and how to make that jump successful.
In the end, the most important thing to remember is that a jump makes you to be who you are. You will not regret it because you jumped, rather than wondering about the what-ifs had you not chosen the jump.
March 27, 2021
Typical Ivy league kid, talking about typical Ivy league issues, surrounding himself with like-minded Ivy league or elite school kids. This book is about a bunch of young, Ivy+2 schools league kids in their 20s, taking 'jumps' in their career and life. Everyone comes from such a plush elitist background, and have this nonchalant way of saying 'if I failed, and things didn't go as planned, at least I could lean on my parents!'. Not a lot of people had families to support - or if they did, the other half of the family would chip in to help support the family, nobody was sick around them, everyone was earning enough to put money aside for their passion project, and all were already from a pretty prestigious background that they could jump back into the comfy life if they wanted to.
Most of the episodes aren't worth reading because you need to come from a certain prestige and privilege to be able to relate to these people and their wants and jumps. I understand that your issues with your life shouldn't be discounted because you come from elite schools, but almost none of these stories rang on a genuine note, or held any relatability to the common person.
The only episode I found intriguing was the one with the person going to med school pretty late in their life, and the last one about Brandon Stanton - where he speaks a different language of advice than everyone else in the book. He doesn't focus on passion, he focuses on the act of actually doing it, staying devoted and having a really strict discipline to what you believe is your jump and passion - also, how success (attention) doesn't come instantaneously, and how you have to grind and build to get to a point where you deserve others attention to your work.
Most of the episodes aren't worth reading because you need to come from a certain prestige and privilege to be able to relate to these people and their wants and jumps. I understand that your issues with your life shouldn't be discounted because you come from elite schools, but almost none of these stories rang on a genuine note, or held any relatability to the common person.
The only episode I found intriguing was the one with the person going to med school pretty late in their life, and the last one about Brandon Stanton - where he speaks a different language of advice than everyone else in the book. He doesn't focus on passion, he focuses on the act of actually doing it, staying devoted and having a really strict discipline to what you believe is your jump and passion - also, how success (attention) doesn't come instantaneously, and how you have to grind and build to get to a point where you deserve others attention to your work.
January 17, 2023
Notes for book club
"Over the next year and a half, I picked up more when-to-jump insights... It became clear that there is a smart way to try for a dream, a certain discipline around responsible planning."
"Do it. Everyone will have a reason for you not to go: they'll saw you're crazy, you're losing your edge, you could be earning more money. But do i"
"I thought, incorrectly, that if I made enough slides, the unknowns would go away, and the risks from jumping would vanish. Turns out, it's not possible to make all the unknowns go away."
"Explore the idea of internal jumping; if it isn't an established norm where you work, odds are it will be soon enough"
"Over the next year and a half, I picked up more when-to-jump insights... It became clear that there is a smart way to try for a dream, a certain discipline around responsible planning."
"Do it. Everyone will have a reason for you not to go: they'll saw you're crazy, you're losing your edge, you could be earning more money. But do i"
"I thought, incorrectly, that if I made enough slides, the unknowns would go away, and the risks from jumping would vanish. Turns out, it's not possible to make all the unknowns go away."
"Explore the idea of internal jumping; if it isn't an established norm where you work, odds are it will be soon enough"
March 18, 2024
I’m not a venture capitalist so I don’t have the expendable income to “jump” however I like how the last page had a space for me to manifest my plans (to be a girlboss)
A lot of the short stories were about corporate jobs being unfulfilling and immoral etc evil banker turned baker stories. A lot of alienated labour … and it’s almost like when the worker owns the means of production … and is not aimlessly making profits by exploiting other people … makes them fulfilled and happy ? Who would of known !
Very Tiktok lucky girl energy from this book so three stars!!
A lot of the short stories were about corporate jobs being unfulfilling and immoral etc evil banker turned baker stories. A lot of alienated labour … and it’s almost like when the worker owns the means of production … and is not aimlessly making profits by exploiting other people … makes them fulfilled and happy ? Who would of known !
Very Tiktok lucky girl energy from this book so three stars!!
May 28, 2023
inspiring but repetitive
Mike, thank you for writing this book. It’s definitely super inspiring and proves that anyone can achieve anything they want, if they only set their mind and energy to it.
The reason why 3 stars because there are way too many examples, some of the stories repeating…I just wish there was deeper context on what to focus on before and after the jump than so many examples with their short msgs.
Regardless, definitely worth a read.
Mike, thank you for writing this book. It’s definitely super inspiring and proves that anyone can achieve anything they want, if they only set their mind and energy to it.
The reason why 3 stars because there are way too many examples, some of the stories repeating…I just wish there was deeper context on what to focus on before and after the jump than so many examples with their short msgs.
Regardless, definitely worth a read.
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