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

If you have already decided that you need to do something drastically different in your career…but telling yourself

  • it’s a bad idea,
  • or too far afield,
  • or that that you shouldn’t take that feeling seriously,

then this book: Mike Lewis: When To Jump: If the Job You Have Isn’t the Life You Want is for you.


Lewis’s book is about jumping – the act of purposefully switching to a new career of your design. He was working a corporate job but longed to be a professional squash player. That might sound harebrained, but Lewis found comfort in others who had done something equally “crazy.” It affirmed his intuition to do what he needed to do. And now his book (and podcast, and Jump “school”) helps others realize that their own potentially “harebrained” career schemes might not be so crazy after all.

He outlines 4 stages of any jump.

Listen to What You Want

The first is to acknowledge your gut feeling, that inside voice where you’re borderline obsessing on your next thing. But what I really liked about this stage is that it’s not just about mindlessly tossing caution to the wind and taking a blind leap. It’s about how to tune into that little voice, while also remaining realistic and cautious. I feel like too much career advice of the moment is JUST DO IT! NOW! Like why are you still sitting in your cubicle?! When really, you do have to think through how long you need to save up to pay your bills, how to test out your plan, and how not to burn bridges in case you need to jump back into your current field. How to remain in your 8-5 for benefits and steady pay while you put in some hours at nights and on weekends to explore what your little voice is telling you.

Plan for the Change

Stage 2 is all about making that plan: financial planning, practicing your new thing, gathering expertise in it to establish your commitment to it. And most importantly, the key takeaway for me was “safety-net sewing.” Meaning you need to maintain ties with your current job and industry and honor the experience you have now because if your next thing doesn’t work out, you need to be able to return to something. Lewis outlines how he carefully and thoughtfully scheduled both work and social time with “anyone who had invested in my work” so he could explain his plans and tighten those connections. 

Welcome Luck

The third stage of the jump process I didn’t understand clearly. It was to let yourself be lucky, to be open to opportunities big and small, and to be open to the support that does come your way. I felt like the message here was muddled. In the other stages, it’s about making thoughtful milestones and careful progress in a step-wise fashion. Whereas here, he seemed to shift into “just do it already” mode. I wasn’t sure how that was different from the fourth stage: don’t look back. To not talk yourself out of it and go for it.

A Roadmap for your Career Course Correction

This book is good for those who want concrete examples, ample proof of people who have not only had “harebrained” ideas but made them happen, in spite of fear, societal or familial expectations, setbacks, and previous careers. The case studies are incredibly diverse, featuring folks who went from finance to food trucks, from tech startups to fashion, and from medicine (as in yes, MDs) to nonprofits. 

While the variety of case studies are a sure strength of Lewis’ book, I also left wanting far more from Lewis. Sure, it was nice to hear from all these folks – and in their own words – as they reflected on how they went about their jumps and survived. But when I put the book down, I really wanted more from Mike.

Lewis was incredibly strategic in how he went about his jump, but this book doesn’t say much about that. Instead, it’s more about proving the worth and validity of making a jump, by showcasing a community of those who have done it. And while I found many of the profiles fascinating, I grew tired of case study after case study after case study. Each stage of the book is set up with Lewis introducing that stage, and then a long series of case studies, and then a closing list summarizing the themes and commonalities that the case studies show. I personally would have liked more exploration of those stages, and fewer case studies. 

Despite that minor flaw, I really enjoyed this book. I’ll be tuning in to the podcast hoping to hear more insights about how Mike and his guests made their jumps happen. I recommend this book if you feel a strong pull to do something drastically different, but need to hear that your idea is not silly, and instead, is worth exploring. 

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