251: Taking the Leap Into your Dream…the Smart Way with Mike Lewis

Pete Mockaitis
Mike, thanks so much for joining us here on the How To Be Awesome At Your Job podcast.

Mike Lewis
Great to be here, thanks for having me.

Pete Mockaitis
Well, I’d love it if we could start… It’s fun that this is not only a fun fact but a key part of the story behind your wisdom. But could you tell us the tale behind you becoming the 112th best squash player in the world?

Mike Lewis
Sure, absolutely. And thanks again for having me, it’s a real treat to be on. I grew up in Southern California, my dad was a squash player. For those who don’t know squash, you’re in the majority. It is a sport like racquetball or even like tennis indoors, but west of New York City there really aren’t many players who compete at the high levels, particularly as a junior, as a kid.
When I was 14 years old and discovering the sport, my dad had obviously played it before. Like I said, he had played on the East Coast as a naval surgeon, and our family moved. I was born in the city, but moved to the South and then to Santa Barbara. And when I was 14, came across the sport on my own actually, ironically, at the one gym that had four courts or five courts within 100 miles from our town, and it just happened to be down the road.
So, I fell in love with it and I think I loved the idea of the adventure behind it. The idea that I could really create my own story from playing the sport, and really go my own path with it. So, at that point I thought, “I’m going to do this someday”, I just didn’t know exactly how that would happen. There was probably five of us, like I said, west of New York City, who were competing as kids. And first I had to get better to play in college and at some point I’d say, “Well, if I could do that, maybe I could get even better.”
And shortly after I started playing, there was a traveling pro who was coming through town for a tournament we hosted at our local club. And I remember I was around 14; he was I think just 5-6 years older, but described this adventure of playing a sport we both adored and using it as a way to see the world – playing on mountains in Brazil and cities in Asia and towns that dotted the Pacific. And I just knew at some point I would do that.
So, like I said, I found a way to get to play in college, I got to play for four years, I was the captain of the team my senior year, and then while I was in the working world for several years going forward after graduation I just kept it up. And I said to myself, “If I can just keep going and find a way to get better and eventually get sponsors and maybe even compete part-time, I’ll be able to maybe someday be able to do this full-time for a bit.” So, long story short, which we can get into, but I was able to do it and get as high as… And my goal was to rank 200 in the world, and I got to 112.

Pete Mockaitis
That’s good. It’s so funny – as you relate the story, it’s like I want to play squash and travel the world. It sounds awesome.

Mike Lewis
It really was awesome.

Pete Mockaitis
And so, now I’m just so curious. What fascinates me when it comes to professional anything, and sports I think is interesting in that world, particularly because I think if you’re like the 122th best basketball player or American football player, there are huge financial rewards. Can you enlighten us what sort of compensation does a 112th best squash player in the world see?

Mike Lewis
Well, the short answer is, not a lot. The pro squash tour is like the pro tennis tour, but the ugly stepsister, almost. So, you’ve got your Wimbledons of the world, but because we are a lot less popular, invisible and don’t have the marketing dollars and the brand sponsorships or the TV deals, there just isn’t that much money.
So, Wimbledon has several million bucks for the men’s and women’s champion; the Wimbledon in our world, the champion might bring home 50K at most. There is money in endorsements and camps and other stuff, but largely there’s just not much money. And then where I play, 112th in the world at my peak… You have to remember I started I think at 380 or something. You really are getting off the bottom in what was akin to the AAA Satellite tour – our version of Bull Durham and the minor leagues. And it’s nothing against those tournaments, but those were 16, 32 guys in a draw splitting $5,000.

Pete Mockaitis
Right, okay.

Mike Lewis
And yeah, you just wouldn’t bring much back from that. So, largely what the opportunity provided was exposure. You could get better, you could get yourself off the ground and get up the ladder a bit, but also it was the experience. A lot of these tournaments offer to pair you with host families, just like how we hosted that gentleman coming through town when I was a kid. That’s how I spent nearly every night of my 200,000-mile, 50-something country, nearly 2-year adventure. I was with other people along the way.

Pete Mockaitis
I don’t know why the first question that comes to mind when you mention all these different host families is, what have you settled in on as optimal mattresses and pillows, since you’ve tried them all?

Mike Lewis
You know what? It depends on the country and the continent. Some places I was just lucky to have… I remember my first place I stayed was right before I left Bain Capital, where I was working, I ran into a woman right nearby. I was going back to work after going to the gym, and she had told me, “Oh, you’ve got to play in the South Pacific.”
And I Googled when I went back to my office “squash in Fiji”, and a squash tournament in Tahiti popped up. And like two weeks later I was staying with the organizer of the tournament under a mosquito net in his daughter’s former childhood bedroom. It was decorated with princesses and glow-in-the-dark stars. And that, I can tell you, is not the Ritz-Carlton, but it was what I was hoping for. We picked the daughters up from school, we went to family outings, there was a birthday party at their neighbors’ that I went to, I sang karaoke. It was so much more than just the squash.

Pete Mockaitis
That is so cool. Okay, alright. So then, for everyone salivating, wanting to have their own sort of adventure in their own kind of a way, why don’t you lay out for us what’s When to Jump all about and can we hear who it’s for and why it’s important now?

Mike Lewis
Yeah, absolutely. So, When to Jump really came out of my own personal struggle to figure out when I was supposed to chase this dream. Like I said, it had been years, a decade since I first had this little voice in my head. And I was going about my job every day and I’m sure folks listening to this show can relate – you start to get a sense of circularity to your life. I knew what I had to do at work, it was fine. There was nothing too treacherous I could mess up. I kind of knew the playbook like the back of my hand. And on the other side there was this thing I really wanted to do.
So, I first Googled “when to chase dreams”, because I was like, “When do you do it?” And what I found was stuff that’s either too prescriptive, too self-helpy, or too inspirational where it’s almost just lost in the fluff of what you’re actually supposed to apply to your own life. And so, where I came out on it was, “What if I just talk to people who left something comfortable to go do what they cared about?” And I collected their stories and those stories could become proof that it wasn’t totally insane for me to do this.
And that’s what I did – I just started reaching out to people – first friends of friends, then colleagues, then passengers on the bus next to me, then a bartender down the street. And then all of a sudden as you start to peel back the layers, more and more stories became available.
And what was fascinating was that I wasn’t getting just that sexy, glossed-over photo, scoop or snapshot of the update from LinkedIn that only talks about the good stuff. This was the nitty-gritty, unsexy steps that come with chasing your dream. And people were giving highly vulnerable, real honest versions of what that looks like. And so, to me that’s what I wanted, that’s what made it feel realistic. They talked about the middle of that journey.
And so I remember speaking to a woman who was a Wall Street banker turned cyclist, and she had left Wall Street to try being a cyclist. And had largely failed for a while, but ended up making, after years and years, the Olympic team, and competed in London and then in Rio. And the conversation I thought would go something like this: “How was it to be a cyclist?”, “It was amazing, I made the Olympics.” And that would kind of be it. And instead it was: “How was it to be a cyclist?” And she was saying, “Well, here’s the hardest conversation I had with myself. Here’s what I was most scared of. Here’s what failure tasted like. Here’s why I kept going anyway.”
And when I hung up – this was January 2013 – I sketched a cover page to what I would call When to Jump. And I wanted to make a book of these stories with ideas and insights, but also to be able to create a space and a community where people could come together, have good drinks and snacks and food, and share ideas and stories with people in real life in a non-awkward, weird way, and come together.
And so, that was the idea. I told a buddy of mine I would make this someday. I put it on the back burner, I collected… I think I had one story from the US Senator from Maine Angus King – that was the one I had in the can, and then I kind of put it on the back burner, like I said.
And a year and a half later I had collected these stories totally really to give myself permission to jump. I had trained nights and weekends, I’d collected sponsors, I’d played anywhere I could, whenever I could, took sick days and holidays and half days. I had collected some sponsors using some material I’d put together at work on our own slideshow deck presentation templates, and all these different things, where all of a sudden the jump became more real.
And so, I left; I moved to New Zealand. Like I said, six months turned into nearly two years, and sadly while I was gone, my buddy, who was next to me at work, who I’d confided in around this idea of When to Jump, passed away in an accident. And at that point I said, “I need to finish this project.” And fortunately had the support of his brother and sister, and we talked and I was able to dedicate the project to him.
And over time, more people came forward with stories, from Michael Lewis, the finance author who wrote Liar’s Poker and Moneyball, The Undoing Project, to the second baseman for the Cubs who left the Cubs to go to college, all the way to the first female bishop in the Anglican church, who left PR to go into the Church.
So I had all of these interesting stories and slowly I was able to create a framework from the themes that I saw that kept coming back up again and again. And I came back in the end of 2015 and was approached by book folks, signed a book deal of this book that’s now coming out January 9: When to Jump: if the Job You Have Isn’t the Life You Want. And it’s 44 of my favorite stories with a framework that I call “the jump curve”. And it follows you through the different phases of taking a jump.
And what I found is that jumping can be for anybody. Some of us think that jumping is about changing jobs and moving to Bali and starting a company and doing drastic things. But what I found is that a jump is really having agency over your life. It’s about saying, “Okay, I want to change something, whether it’s the way that I commute to work, whether it’s a hobby that I want to develop or a new language I want to learn, or moving cities with my job, going for an internal promotion.”
But I think there’s this idea that you can do it; it just might not be pretty. And When to Jump exposes that through our community. And so when I signed the book deal, I ended up using the money to bootstrap a platform, and the platform has a bunch of different facets. We have a festival every year called Jump Club, which is part music festival, part beers with friends, part speaker series. Sheryl Sandberg keynoted our first Jump Club last year. She wrote the foreword to the book. Our festival grew nearly double to a weekend this year in New York, and I think we’ll be in London next year in October of 2018.
We started working with brands and we started to curate stories and we launched a podcast that’s now a top 10 business podcast on iTunes, all around these conversations. And so, what I found most, I think compelling, is that there isn’t one way to jump; everyone’s got their own jumps to make. But it really helps to know that you’re not alone, and that everyone goes through these hardships when they decide to make that step into the unknown. And often times the unknown is what will deliver the best parts of your jump.

Pete Mockaitis
Alright, this is juicy stuff. And I want to go in deep on the jump curve. But I want to maybe first say, I’m thinking maybe this is Step 0, if you will, but the decision that a jump is worth doing in the first place – not so much how, but whether to jump. And so I’d like to start by getting your take on, how do you go about framing up and thinking through that very initial part of the equation?

Mike Lewis
Well, the first piece of the jump curve talks about, listen to the little voice. And I think like you said, Step 0 would be to just acknowledge what you’re thinking about and what your feelings are that keep coming back, because our body doesn’t lie, as former NFL running back Rashard Mendenhall told me when I interviewed him about his jump from football into writing.
When you find yourself going to certain interests or ideas or spending your time in certain ways, those are usually telltale signs that there’s something boiling up within you. So, I don’t think there’s a perfect way to jump; I just believe that there are things you can do that will make sure it’s a positive, worthwhile experience. Because you really don’t know how it’s going to end, but you know how it can begin, and that I think takes planning and being thoughtful and following this jump curve.

Pete Mockaitis
Alright. Now when it comes to listening to the voice, can you elaborate a little bit, in terms of, what are some telltale ways that the voice or your body speaking tends to materialize? The symptoms, if you will.

Mike Lewis
Yeah, so it’s actually listen to the little voice because it’s that little voice that you hear when you go to sleep at night or wake up in the morning, thinking about. It’s something that’s kind of nagging at you, but you’ve always ignored. And I think for me, I knew that that fear of not listening to it would ultimately be more scary of having to deal with it, just echoing and echoing and sitting there for years and years. Then if I tried it – if I planned and proceeded forward with my jump – even if it didn’t work out, if I did it the right way, if I took the right steps, it would be close enough to saying, “Hey, I tried. It didn’t work, but I did it.”
And I think that often times that little voice is right, and we do a lot to drown it out, whether it’s through staying super busy, through working late unnecessarily, through making our calendar super jam packed – there are a lot of things we do to try to drown out that noise. And so if you can just find some silence in your day – I know that sounds really cheesy – I am in San Francisco, we have to be pretty crunchy out here. But I would say if you can wake up and say, “Okay, for five minutes today I’m just going to sit and be bored.”
There is a reason that we come up with our best ideas in places like the shower, where we can just sit and have nothing to do but let ourselves think and unwind. Our brains aren’t programmed to be stimulated to the extent that social media and smart phones and notifications demand of us. So if you overwork them, they don’t have the chance to start to loosen and let different juices flow. And I think that’s where you get that little voice. That’s where you can really start, is to say, “Okay, let’s try to take out some of these noisy distractions, let’s lower some of the other voices and let’s listen to what this little one has to say.”

Pete Mockaitis
Okay, that’s awesome. Alright, so then what’s the next step?

Mike Lewis
The next step is to make a plan. So we go from the aspirational to more the pragmatic. And within that step there are three pieces. One is financial planning – obviously you want to make sure that you’re jumping with some sort of cushion to really give this a go, and you don’t want to jump before that’s prudent.
The second piece is pre-jump practice, and that means really understanding what your jump is before you go. So, if you want to go start a furniture shop and selling furniture, you’ve got to learn about how to open a business. Maybe you should talk to small business owners. You’ve got to probably shadow or learn from a master handyman or a furniture maker. Maybe you start by watching YouTube videos. There’s a lot of things you can do just to start preparing for that step well before you have to jump. And that’s the pre-jump practice.
And then the third piece is safety net sewing. So I worked at Bain Capital for many years before I left to play squash, because I knew that if that jump didn’t work, and even if this jump doesn’t work, I would have a foundation. I had good reputation I think, decent enough; I worked on good projects and interesting deals; I got along with my superiors and others. And so, doing that type of legwork is actually really important, because I think for me at least, I’m not courageous enough to just drop everything and jump. I really need to feel like I’m supported, and Bain was very supportive when I ultimately decided to go. So those are the things that at a high level go into making a plan.

Pete Mockaitis
Oh, I really dig that. And so I’d like to get into a bit of detail with some of these here. Now when it comes to the financial plan, different people prescribe different sort of metrics or X month savings. What’s your take on what is financially cushioned enough?

Mike Lewis
Well, it’s funny. I think that it really is interesting when you peel back all the layers of what you actually need to live. You’ve got electricity, you’ve got water, probably let’s say that you need to have the Internet, you’ve got grocery bills, you’ve got your rent or your mortgage. You’ve got to have some sort of miscellaneous for external spending purposes, but what is that – five categories? Those are not 30 categories, those are not, “I want to dress in this certain way or drive this certain car or get this certain latte after work.”
And so, people think that financial planning is actually tough. What it is is really just being disciplined; it’s actually just cutting stuff rather than trying to say, “I need to go extreme and not spend a dollar.” You have finite fixed, hard costs – that’s not what we’re saying to change. It’s more like, on the margin, what can you start to tuck away? I’ll give you an example: If you cannot get a latte every day, you save $4-$5 each day for a year – that’s nearly $2,000 in your pocket. That’s a pretty good cushion to start your jump on.

Pete Mockaitis
Okay, cool, thank you. And when it comes to safety net sewing, I’d love to hear your take on, I guess the opposite point of view, which is, I don’t know – who was the famous general – the “burn the boats” guy. It’s like, that’s what made the soldiers fight oh so fiercely, is they had no option of retreat. And you’re proposing just the opposite – don’t burn those boats. Nay, craft an excellent boat. How do you think through these two sets of ideas on that?

Mike Lewis
Well, it’s funny because when we get going a little bit, it will actually be a little bit of both, and I’ll explain that to you when we talk again soon on the next steps. But the “burn the boats” piece is actually right to some degree. And like I said, there’s a part of that that’s true. But first you should make that boat really, really nice, and I’ll tell you why – because there are going to be people from your old life and your old jump that will come in again and again – references to you as you go for a new job, potential investors in your company or idea, customers of your new products.
And so, it just behooves you to not say, “Well, screw it. Guns blazing, middle fingers up, I’m out of here”, because the world is small, especially if you’re going to, let’s say, leave a cafe or a restaurant to start your own restaurant – you might want to hire someone from there eventually, you might want to get reviews from that person who runs the restaurant that you’re leaving, you might want to get tips on suppliers to buy from. So, there’s just a lot to do in terms of really maintaining a great relationship.
And I’m not saying that you will cross paths with those people and I think we’ll get to why it’s important to only look forward when you jump and not be half-in, half-out, but I think it will give you a piece of mind to feel like, “Maybe I’ll never run into these people again, but they all know why I’m leaving. If they were called by someone at some point needed to show a reference for me, they would say, ‘You know what? Mike’s a good guy. He’s not all over the place. He didn’t just show up one day, give us the finger and quit. He told us what he wanted to do.’”
When I started to play squash tournaments on the side, I told everybody because they got bought into it. And so later when the squash tour became a real possibility, they knew that I was looking towards doing that, they knew it was something I cared about. It would have been a lot harder to massage that story if I just brought it up on everyone one day. And sure, I could have done that, but now I look forward and the people that I let really understand my journey are folks that are still trying to be a productive piece to this next jump. And so I think that’s why you want to be able to sew the safety net.

Pete Mockaitis
Okay, cool. Alright, so have the Step 0 and Step 1, and what comes next?

Mike Lewis
So, the piece after that, which is really the hardest part, is to say, “Okay, you’ve planned as much as you can. Now you just have to take a jump and let yourself be lucky.” So that’s Step 3. And that’s a quote that Michael Lewis, the finance author, gave, which is, “If you look for luck you’ll actually find it.” It’s like when he described looking for money on the ground. Grown-ups leave it everywhere. You can find it, you just have to be open to it.
And the same goes for making a jump. If you look for those opportunities, if you make the plans, if you put down the pieces to what I call “let yourself collide with other people and things” – your odds are you’re going to find that luck. You just don’t know it until you jump. And obviously that’s just tough, because we as humans I think are rational to some degree, and when you leave a job you know what you’re giving up in salary, benefits, comforts, etcetera, but if you don’t know everything you’re getting in return on the next thing – that’s super hard.

Pete Mockaitis
I hear you. So you’re leaving a very clearly known, quantifiable piece for a quite unknown, unquantifiable upfront piece. So, could you give us some examples with regard to finding money lying around or colliding with people and opportunities? How does that appear in practice?

Mike Lewis
In what it looks like?

Pete Mockaitis
Right.

Mike Lewis
I think that what it is is, you don’t know what you don’t know. So, it’s really putting out a voice to it. It’s kind of going back to that little voice – you’ve now turned the voice up a lot. And so you’re saying, in my example, “I’m leaving, I’m moving to New Zealand. Everyone knows I love squash. Would love anyone’s thoughts”, etcetera. And the classic thing is, what happened?
Someone said, “Well, you should stay when you’re in Australia with my good friend who used to belong to my gym and he just moved with his family down there.” And then when I got down there, I met up with this gentleman and stayed with his family and they said, “Well, we have an extra apartment; we just moved. It was a corporate housing thing. Do you want to stay there?”
So all of a sudden I’m staying at no extra cost to stay with this gentleman and his family, and then he says, “Well, you should meet a friend of mine, who’s got a great podcast.” And it was Rob Bell. And I go on Rob Bell’s podcast last year as I was developing When to Jump, and through that podcast I received stories that are now in the book that’s coming out January 9 from people that were listening, and received amazing help from friends of mine who I would never have met, except for that they were listeners to Rob Bell’s podcast. And Rob Bell once surfed with a guy that I stayed with because our mutual friend heard my story in the gym locker room in Boston two months before I left.

Pete Mockaitis
I love that.

Mike Lewis
That could go on forever too.

Pete Mockaitis
Oh yeah. And it feels like an adventure. You think about the great sort of fantasy novels or movies of our time – that’s what happens. You go forth and then something happens, which leads to something else, which leads to something else, and it’s kind of unpredictable and cool and exciting. So, I dig it.
So, all you really did was say to the whole world, “This is what is happening, this is what I’m doing. Would love your input.” And then away it goes. And so, I think it’s pretty cool. It seems like there’s value in doing that, both in the broad and general “Hey everybody” Facebook, LinkedIn world – “This is what I’m doing”, as well as in the particular, like, “Hey, you lived in New Zealand for a little while. What do you know?” And so, kind of going in both directions there.

Mike Lewis
Absolutely. I remember having a spreadsheet where I’d just fill in anyone who had an idea for me once I said I was leaving. I think the thing that people really miss in a lot of this is telling other people about what you want to do, because people want to help. And they want to help way more than you realize, but you have to tell them what they can help with.

Pete Mockaitis
I love it. Okay, next step.

Mike Lewis
So the last one is, and this is the fourth and final step – don’t look back. And so that is the “burning the boats” one, is you don’t just kind of say, “Well, if this doesn’t work, I’ll always go back, or maybe I’ll do this three days a week, then two days here, and I’ll do this nights and weekends.” Because at some point you’ve just got to be all in.
And that’s what “don’t look back” means, is once you say you’re in, don’t look around and say, “I wonder if this is really what I should be doing. I wonder what my friends would think. What if this doesn’t work?” You just have to be all in. And I know it’s really hard, but when you jump you can only look straight ahead.
And we’ve got in the book cases of failures and jumps that didn’t work out, and I think that’s what makes it real and understandable to say, “It might not be what I thought it would be, but it’s still going to be productive because I’m doing along the lines of what I enjoy.” And I think that’s super important, is when you jump to say, “This is going to work and I’m not going to second-guess myself twice.”

Pete Mockaitis
Now it’s interesting, as I’m thinking about my own jump, leaving Bain Consulting this time, not Capital, which you were talking about how everyone confuses them. But when I left and said I want to do training stuff, speaker stuff; learning and development is what fires me up the most… So I guess talking about “don’t look back” – I had a spreadsheet talking about the financial planning piece, and I suppose I had some standard in which I say I will quit at this point.
And I guess my standard might be somewhat extreme or aggressive – it’s like, “I will stop this if I have $0. I will not go into sort of insolvency or a negative net worth, but I am going to spend every dollar I have.” And so, I guess in terms of “all in”, you can call that 100% but not 120%, in terms of my “all in” this. And so, I’d love to get your perspective on that. Are there any sort of parameters or rules or tripwire covenants? I can think of “all in”, even though it sounds absolutist, still, on a bit of a spectrum.

Mike Lewis
Yeah. There’s a great line that Ethan Eyler, who invented the Lyft mustache, if you remember that. He was a videogame marketer before he invented this mustache that could go on cars. And he says when you’re taking a jump – he’s actually featured in the book too – he says there is this “van down by the river” fear. I think that’s in a book called Cubicle Nation that talks about it, where you think that you’re just going to be a failure living in a van down by the river.
And that never really happens. It does in some cases, but that’s pretty rare, and it’s mostly in our mind of like the biggest failure possible. So, I think what you described is the right one, which is, “I’ve made a plan-ish. I’m as sure as I can be, and now I’m going to go for it.” And I think that’s the way you’ve got to be; otherwise then why jump?

Pete Mockaitis
Alright, I’m with you. And I love it; I think that you’re right with the van down by the river. I remember I was thinking, “What happens if I spend my very last dollar?” And I thought, “Well, it’s not like I’m going to be homeless on the streets. It’s just I’ll have to pick a job that I might not find so interesting.” I always told myself that I would be doing cheese strategy, like some job at a giant corporate consumer packaged goods company like Kraft, doing cheese or something. I’m not passionate about, but I’m sure probably is interesting in its own ways. It just says optimization is intrinsically interesting for me and working with smart people, but it doesn’t light me up at the core. That’s really what is it stake, is, “Either we’re doing this or we’re doing cheese strategy. You’re not dying in the gutter.”

Mike Lewis
Right, exactly. You’re not going to die in the gutter.

Pete Mockaitis
Quote it! That’s the big quote for you: “You’re not going to die in the gutter.” Cool. And so then, a lot of these jumps have been in the career context. I’d love to get your perspective – you mentioned that sometimes when you’re referring to jumps it’s about hobbies or learning something new. How should we think about jumps in those contexts, where you can totally just keep doing the same job, but you’re still experiencing that adventure and that jump commitment action?

Mike Lewis
Yeah, I call it “internal jumping” and I think there’s three ways you can mix things up through the city you’re in, the office location, especially if you’re with a beer company. If you’re at the cheese company, you could do cheese marketing in Wisconsin or in France. You can change products – you can go from cheese to detergents if it’s a consumer packaged goods company, or maybe you could go from selling cheese and marketing it to the product and engineering of it. And so, that’s kind of like a role and type of jump switch.
And so, I think those three things or any combination of them would really lead to something that would be stimulating, because it changes that circularity. I interviewed on our podcast – I think it comes out in a few weeks – former CEO of eBay John Donahoe, who’s actually the former CEO of Bain as well. And he talks about this product or this concept, and I’m not going to remember the guy’s name, but he calls it “repotting”, which is this idea that every 10 years or 7 years or so you want to repot – take yourself out of one pot, put into another and let roots grow again.
And John actually, if you look at what he did at eBay, they would regularly switch cubicles of folks so that people can mix up and meet other people. And I think there are just things like that. Even going to work a different way or talking to the person on the bus next to you – that type of thing can mix things up and it’s a super incremental micro jump.

Pete Mockaitis
That’s good. So, Mike, tell us – what do you think would be the very first step if someone is having a little bit of that little voice going on? And is it just a matter of making time for the silence and the boredom, or what would be the very first thing you do?

Mike Lewis
Yeah, I would say, absolutely. The thing that’s no-stress, low-touch, light-weight, easy to do would be – and I do this every day – take five minutes in the morning before you look at technology, write in a journal, or maybe just make a Google doc or Evernote or whatever it is, and write down the things that you thought you did well yesterday. Get yourself into a mindset to be thinking of the positives.
And then if you want, start with one thing a day you’re going to get done, like a 24-hour goal. That stuff’s really easy. The CEO of 1-800-GOT-JUNK? told me about that – Brian Scudamore. And you can be as bite-size as, “Okay, I’m going to research things I’m interested in today” or, “I’m going to talk to a musician.” Something that just makes you curious. And I think if you give that 5, 10 minutes to yourself each morning, you’re going to get a little bit closer to that thing and that’ll get you on that curve. It’ll get your voice to kind of grow a bit. It’ll tune it up rather than tune it out.

Pete Mockaitis
Alright, cool. Well, Mike, tell me – anything else you want to make sure to mention before we shift gears and hear about some of your favorite things?

Mike Lewis
Yeah, I would just say if you want to learn more, our website’s WhenToJump.com. Our podcast is also called When to Jump, and you can find it on our website, also on iTunes and all that good stuff. We have a newsletter where we keep our community up-to-date once a month. Actually we just sent out our monthly one this morning. And then of course the book comes out January 9. So, I spent the better part of several years putting what I hope will be together the resources, the tools, the ideas and the people that give people a sense of permission. And I hope people enjoy the book, and obviously I would love to hear from you if you end up reading it.

Pete Mockaitis
Cool. Alright, now could you share with us a favorite quote, something you find inspiring?

Mike Lewis
I would say I’d have to quote my cousin Sheryl Sandberg, who wrote the foreword to the book, and to paraphrase her it would be – a question that I go back to, that she goes back to again and again is what she would do if she wasn’t afraid? And I think that’s the most important question we can ask ourselves.

Pete Mockaitis
Okay. And how about a favorite study or experiment or a bit of research?

Mike Lewis
I thought that Manoush Zomorodi, who wrote the book Bored and Brilliant basically found a way to see if we could lower the interactions we have on our cell phones and social media and all that, and see what kind of result that would produce. And it turns out that it makes us happier.

Pete Mockaitis
Oh, perfect. And do you have a quick tip, a bit from there, in terms of if we wanted to get a little piece of that value, what should we do?

Mike Lewis
Yeah. One thing that you can do that’s super easy, which was amazing is, when you commute to work, try not to have your phone on you. So not even in your pockets – put it in your backpack or purse. It does wonders. I actually now leave it when I go to the gym. And it’s little things like that to disassociate; it really will rewire your mind and let you be bored.

Pete Mockaitis
Oh, cool. And how about a favorite book?

Mike Lewis
Memoir-wise I would say Shoe Dog by Phil Knight and his story of starting Nike – the ultimate jump start in many ways. And then in a more serious and kind of meaningful tone would be Man’s Search for Meaning by Viktor Frankl, a holocaust survivor and an absolutely extraordinary man. I think everyone should read that book.

Pete Mockaitis
Okay. And how about a favorite tool?

Mike Lewis
I really like the microphone I use when I travel for podcasts. I know I don’t know what this one is I’m using now, but when I travel I have an H1 microphone and recording set. And it’s just awesome; it’s really simple and small and you can actually have a lot of fun with it. You can record yourself and notes to yourself, you can record conversations, podcasts, interviews. It’s very cool.

Pete Mockaitis
Oh, excellent, thank you. And how about a favorite habit?

Mike Lewis
It’s funny you ask that. Last night I actually for the first time looked back at how many mornings I’ve written in my journal to start the day. And I just write. I don’t really read it again, I just write down yesterday’s synopsis – kind of what I said earlier. And I knew I started January of 2015, I’m wrapping up my third year, and this year and last year I’ve written 140,000 words each, which is pretty surreal to me.

Pete Mockaitis
And so, are you saying that you’ve got pretty nice consistency, in terms of every single day rocking out there?

Mike Lewis
Every single day. It doesn’t even occur to me not to do it now. So it’s just habits.

Pete Mockaitis
Cool. And is there a particular nugget or piece that you share that seems to really resonate with your audience and community, and it gets them kind of retweeting and quoting it back to you?

Mike Lewis
Yeah, I think that it’s, “Think of when you’re 80 years old and you look back on your life. What are you going to be most proud of? What stories will you make for yourself?” And I think that’s what drives people to jump.

Pete Mockaitis
And if folks want to learn more or get in touch, you say WhenToJump.com is where it’s at?

Mike Lewis
WhenToJump.com – it’s the home base for us. Our newsletter sign-up is on there, podcast, you can pre-order the book. And starting in February of 2018 we will have a Jump Ambassador program, which will be a 10-week intensive online course for people who want to meet 19 other RAD applicants that have been selected from around the world, and get closer to their jump. So all that can be found on the site, WhenToJump.com.

Pete Mockaitis
Oh, RAD makes me think of Silicon Valley.

Mike Lewis
Yeah.

Pete Mockaitis
Oh, boy. And do you have a final challenge or call to action you’d issue to folks seeking to be awesome at their jobs?

Mike Lewis
Well, I would just say, write down what your goal is. It’s a perfect time to say, at the end of 2018, what does your job look like? What are you doing? How are you crushing it, to say it in Silicon Valley terms?

Pete Mockaitis
Okay, cool. Well, Mike, thanks so much for taking this time and sharing the goods. I wish you and all of your jumpers lots of luck in their adventures!

Mike Lewis
Thank you for having me. It’s pleasure to be on. I hope this was helpful.