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Book Summary: When to Jump – If the Job You Have Isn’t the Life You Want

If your life were a story, what would you want the plot to be like? And what’s the difference between the life story you dream of and the life story you have? “When to Jump” is a collection of case studies with clear guidance on how and when to leave one career path to pursue a very different one. In this book summary, you’ll learn the key principles of jumping and read inspiring stories from people who were brave enough to do it.

A practical guide on how to follow your dreams and be true to yourself.


  • Want to lead a life you’re proud of
  • Feel like there’s something missing in your life but aren’t sure what
  • Enjoy learning about inspiring people who took risks and never looked back


In May 2014, Mike Lewis sat in a Boston airport with a one-way ticket to New Zealand in his hand and a year’s worth of clothing and supplies crammed into a blue bag next to him. He had just jumped from his job at Bain Capital to go on a world tour and become a top-ranked professional squash player. It was a bold move that propelled Mike well out of his comfort zone, but in the end, it paid off by letting him realize his athletic dreams, meet hundreds of incredible people, and ultimately pave the way for founding his own company that would help countless other people make smart moves to fulfill their dreams.

Book Summary: When to Jump - If the Job You Have Isn’t the Life You Want

In hindsight, Mike’s adventure sounds exciting, but making the jump required hard choices and diligent preparation. To start off, Mike wasn’t even in the top 300 squash players, and sometimes didn’t score a single point for an entire match! Mike left behind a successful career, a big income, and community he loved to pursue this niche sport that he wasn’t even good at yet.

What life experiences do you dream of having? What’s keeping you from having them? In this book summary, you’ll learn about how Mike and others made their jumps, along with four key concepts to making yours. Specifically, you’ll learn:

  • How to listen to the little voice in your head.
  • How to make a plan.
  • How to let yourself be lucky.
  • Why you should never look back.

You’ll also learn about how the famous “Humans of New York” project got started, and how one brave woman bounced back from what seemed like a failed jump.

How to Listen to the Little Voice in Your Head

Do you ever feel like something isn’t quite right even though everything is going well? By all conventional standards, Mike should have been satisfied with his career at Bain. At the young age of 23, he was meeting entrepreneurs and gaining valuable business acumen, earning a hefty salary, and using his two weeks’ annual leave to go to exotic places like Angkor Wat. He was living the life of many people’s dreams. Yet a little voice in his head told him that there was something very different that he wanted deep down. By listening to it, he realized that he was pursuing this life because it was the life that he thought he should be living. He was actually in love with the game of squash, and after pursuing it as a hobby for years, he couldn’t get the idea of playing professionally out of his head.

If you want more than your current life allows you to do, you’re not alone.The people you bump into at your job, on your commute, or in your favorite cafe, all may seem to be content with their current states and careers, but many of them aren’t. Some of them, perhaps like you, also hear this whisper, telling them that they were meant to do more. The majority of people neglect those voices. It’s easy to get caught in the daily grind, ignoring these thoughts, or even actively suppressing them since they might interfere with your success. But if you ignore these thoughts, you run the risk of having regrets later in life.

Mike decided that it was important for him to find out what the voice in his head was telling him, so he began reading books about other people who had jumped to live life on their own terms. He made a list of companies that had been founded by people with nontraditional backgrounds, and the risks they had taken to start the company. He also began cold-calling people who did cool things, from alumni from his college to people he had read about in the newspaper. He spent long hours after work meeting more and more people, learning about more and more successful jump stories. Finally, he decided that he really should listen to the voice in his head and make a jump plan.

How to Make a Plan

Many people imagine jumps as simultaneous decisions that transition quickly into dynamic adventures and fairy tale endings. This couldn’t be further from the truth.

When preparing for his own jump, Mike had a helpful interview with an exbanker who transitioned to professional cycling. The cyclist didn’t waste time telling Mike about her training schedule or what it was like to be an elite athlete. Instead, she told him about the behind-the-scenes preparations: how she had saved money, how she prepared herself for the worst-case scenario, and how she told her boss that she was quitting. Mike took her advice. Instead of immediately quitting his job to play squash, he spent nearly two years taking steps toward his goal before leaving his job. Those included saving up money, adopting a professional athlete lifestyle, beginning to compete on the weekends, and most importantly, continuing to ask hundreds of people for what they had learned from their personal jump experiences.

No matter how brave or excited you are feeling, before you quit your job, sell your car, or cancel your lease, you need to develop a very well-prepared plan for your jump. Although there is no such thing as a true failure when you make a jump, people who Mike spoke to who had been impatient and jumped without planning tended to struggle more to achieve their goals, or bounce back when things didn’t go as they had hoped, than the ones who had planned. Your plan will depend on the unique financial, professional, emotional, and social risks of your jump, but Mike recommends three common components: financial planning, prejump practice, and safety net sewing.

Financial planning includes budgeting for all of the costs that your jump will incur, and then setting aside savings or revenue streams to cover those costs. Elizabeth Hague learned the hard way how important this is. She quickly left her job as a secretary, moved in with her parents, and started a photography business, without properly calculating operating costs or developing a marketing plan. The business didn’t make enough money to pay the bills, so Elizabeth ended up having to shut it down. Today, Elizabeth doesn’t consider this jump a failure, as you’ll learn later, but she did learn a tough lesson about the importance of planning.

Pre-jump practice includes starting to work toward your goal now. For Brandon Stanton, who left bond trading to eventually start the “Humans of New York” project, that meant doing as many portraits as possible. You might be familiar with “Humans of New York,” a social media project that provides a worldwide audience with daily glimpses into the lives of a wide array of New York City residents. Because of the quality of today’s “Humans of New York” portraits, and the powerful biographies attached to each one, many assume that Brandon started out with top photography skills and a clear vision for what he wanted to do. In the early days, he actually was a new photographer with less than eight weeks’ experience, and he had no overarching vision. But Brandon knew that before doing anything big, he had to start by achieving a small goal, so he started by going out every day and taking an astonishing 40 high-quality portraits. After months of this, he set his pivotal goal of photographing 10,000 people in New York City. The first “Humans of New York” Facebook page grew from that goal.

Brandon learned that jumping to follow your passion requires much more discipline than passion. What skills or experience do you need to make your jump a reality? What are some things you can start doing on a daily or weekly basis to test the waters and prepare yourself? It might sound boring or tedious to dedicate loads of time to your passion, especially if your current life is busy, but it is absolutely worth it.

Safety-net sewing includes strengthening relationships with people who can support you, creating a professional “Plan B” in case things don’t work out, and beginning to tell your colleagues and mentors your authentic story so that they will help you make the transition.

One private equity investor transitioned into founding a men’s pants company after business school in this way, and it paid off. Rather than abandoning his original career trajectory immediately to raise funds or start making pants, he started by first taking a high-paying internship at a well known firm so that he could save up enough money to invest in the materials he needed to start the business, and also have the connections and résumé experience to go back into finance if his plan didn’t work out. He worked on his business during holidays and on weekends, canceling vacations with friends so that he could focus all of his spare time on his jump and still perform well at work. In the end, he had made enough progress toward his goal that by the time the firm offered him a full-time position, he was confident enough to graciously decline, leaving behind a group of executives who would have happily hired him if his venture did not work out.

Financial planning, pre-jump practice, and safety net sewing are not only practical and necessary, but also motivating. Creating a detailed plan can help you to get momentum and ensure that you are brave enough to make the leap. Think about the first steps that you might take, such as or opening a savings account to fund your jump, testing out your idea, or telling your boss or colleagues about your long term goals so that they can support your transition. Envisioning each step makes your jump seem less idealistic and more feasible, which will boost your motivation and discipline.

How to Let Yourself Be Lucky

Planning is important, but don’t let yourself stay in the planning phase forever. Before jumping, a lot of people get hung up on “what-ifs.” It’s important to create plans in case things don’t pan out as you hope, but obsessing over worst-case scenarios will ultimately prevent you from living up to your potential.

Mike, like most people, was tempted to wait before making his big jump. After two years of careful planning, he was in top shape, was close to the top 300 in the international professional squash league, and had hit his savings target. But he kept thinking of reasons to wait a few more months before jumping. His mom came to the rescue, urging him that if he was going to make this move, he should stop putting it off. This snapped Mike out of his procrastination. He picked a series of tournaments in New Zealand to attend, packed his bags, and bought a oneway plane ticket.

Although it might seem scary to fully commit to something that is not a 100% guaranteed success, once you’ve done your homework, start taking baby steps and letting the world know what you are doing. Then, when the time comes, don’t be afraid to make a big leap of faith. Remember that you are not jumping blind; you are well-prepared, and you welcome the results of your endeavors, whatever they may be.

Things could go worse than expected, but if you let yourself be lucky, they could go far better than expected. Mike initially intended his jump to take about three to six months, and to break into the global top 200 squash players ranking. Sixteen months, 50 countries, six continents, and 200,000 miles later, Mike was ranked the 112th best squash player in the world, and he’d connected with hundreds of generous hosts, new friends, and inspiring mentors along the way.

Why You Should Never Look Back

Jumping often entails facing unknown obstacles. It’s normal to rethink your decision to transition, especially when things don’t go according to plan. You might be afraid of giving up the stability of your current career, combined with the impressive status it may give you. But there comes a moment where you need to commit to your dream life, and stop obsessing over counterfactuals.

If your jump doesn’t go as you planned, it’s easy to beat yourself up or feel stupid for leaving the life that you had before. But the alternative is a life in which you take no risks, and wonder what would have happened if you had. While he was still working at Bain Capital, Mike told his co-worker Paige about his plan to become a top-ranked professional squash player. Paige was in the late stage of her career as an executive assistant, and had missed numerous opportunities to make her own jump. She told him that no matter the risks, he didn’t want to end up with unfulfilled dreams like she had, and urged him to courageously be true to himself.

Making a jump can be risky, so be persistent and don’t give up if you seem to fail in the beginning. Remember Elizabeth and how her photography business didn’t work out at first? Elizabeth learned two valuable lessons from her experience. First, she needed to find a job that wasn’t perfect, but that would prepare her for her next jump. Second, she had to believe in whatever she did next. Eventually, she got a temporary job on the set of photo shoots. It wasn’t glamorous and involved holding props instead of taking the pictures, but she approached it with a positive attitude and told her that it was getting her closer to her goal. Ultimately, she was so enthusiastic and good at what she did that her boss gave her a full-time offer at the photography company. She learned about how to run a successful photography business by spending time with the experienced professionals who worked there. Additionally, Elizabeth took the initiative to learn about digital branding so that she would become valuable to the company, and eventually got recruited by a dot-com company. There, she built up the funding she needed to make another jump, this time starting a digital media company that has been as success.

If you were guaranteed success, you probably wouldn’t work as hard to make your jump a reality, and you definitely wouldn’t value your success as much if you were fully expecting it. In other words, if you were moving along solid ground, it wouldn’t be much of a jump. So embrace the risk, enjoy the ride, and once you’ve made your jump, never look back.


In this book summary, you’ve learned:

  • How to listen to the little voice in your head.
  • How to make a plan.
  • How to let yourself be lucky.
  • Why you should never look back

What steps do you need to take before knowing when and how to make your own unique jump? Mike spoke with hundreds of people who made worthwhile jumps before he became fully convinced to make his own. And it still took him years of commitment and perseverance, to plan, begin, and execute his jump to become a successful professional squash player. Remember, don’t rush into your jump or give up on it just because you think it requires too much time and effort. Although jumps seem sudden and dramatic to observers, anyone who has made a jump knows that they actually require lots of careful planning and hard work behind the scenes before anything interesting happens.

And whatever happens, don’t feel scared or guilty for trying. Some people might think that you are crazy for quitting your job to pursue a childhood dream that could pay a lot less. But in the end, as Jeff Bezos told the Princeton class of 2010, when you are 80 years old, the story that will matter most to you will not be about your titles and money. Instead, it will be about the choices that you made and how they shaped you. Don’t you want to build yourself a great story?

About the author

Mike Lewis is now the founder and CEO of When to Jump, a global community of people who have left one path to pursue a very different one. Through When to Jump, he has helped millions of people through media presentations, in-person events, and brand collaborations. He received his bachelor’s from Dartmouth College and lives in San Francisco.