057: You+ vs. You 2.0 with MBS
8 Dec 2025 · 37 min
Jenny Blake talks with Michael Bungay Stanier about his new book How to Begin. They explore the difference between improving yourself within your current stage versus making a leap to the next one, and what it costs to pursue ambitious goals.
Chapters
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This is your time. How can we earn twice as much in half the time with joy and ease while serving the highest good? That is our guiding question here at the Freetime Cafe, your home for heart based business. I'm your host Jenny Blake. Join me for conversations with authors, friends and fellow business owners as we explore ways to free your mind, time and team to do your best work. Now onto today's show.
Hello friends. Today is a very exciting day. One of my longtime friendors and greatest mentors, Michael Bungay Stanier. His brand new book launches today. It's called how to Start Doing Something that Matters. This is a beautiful book. I absolutely love it. And fun behind the scenes. Michael and I were accountability buddies for each other. We did this tiny sprint as I feature in free time where we would send each other a check mark every day in the month of December and partly into January. Did we Write at least 100 words today? It was that tiny and that simple. And in doing that, both of us wrote books that are coming out just months apart. I also feature MVS in the section of the intro on Escape Velocity. Here he was a free time guest and two time Pivot podcast guest. Before that he was here episode 51 talking about his big goal of transitioning out of the CEO role of Box of Crayons, the learning and development company that he built for nearly 20 years. I love that conversation. And soon I'm going to have a chat with Shannon, the CEO who took over for him, about her side of that experience and what it's like running the business now. But Michael's someone who has always given me such wise, sound, sharp, contrarian advice for my business. He's been absolutely instrumental in building the licensing programs that I have. He's just one of those people that can make any room laugh and also deliver such brilliant zingers of wisdom. In honor of MBS's book launch today, I asked him if I could replay the conversation that we recently had for his show, Two Pages with mbs. Typically people read their favorite two pages from any book and then the guest and MBS discuss. It's a great show. I encourage you to check it out and subscribe if you haven't already. In this case, Michael invited a handful of people to almost flip the mic a little bit and he chose two pages from his new book how to Begin that he would read. And I might have misunderstood the ask when we showed up because I kind of thought I was interviewing him about these two pages of his book. But I think maybe he was going to interview me or you know, what's an interview with two friends who've known each other 10 years and trade polos every day? I mean, not right now, but when we were writing and working on things. So it ended up just being me asking him a lot of the questions that I have about working on these big goals, as he calls them, ones that are thrilling, important and daunting. So I hope you enjoy this conversation from Michael's two pages podcast. Be sure to check out the brand new book how to Begin. Oh, it is so masterfully, beautifully laid out. These little icons and markers and the typography, the COVID I know I'm like really kind of OTT right now over the top, but it's masterful. It's masterful. And coming from having just a couple months ago sent my book to the printer, I did not even have the energy to do the level of design work and vision that MBS tends to do and have. It's one of his superpowers for sure. Last thing before we dive into the episode. Michael's also hosting co hosting an event with Apollo Ono and Whitney Johnson, who are also launching books in January 2022. So if you do order, submit your proof of purchase and you'll get exclusive access to the Begin, Grow, Pivot and Learn summit. You can visit mbsworks or howtobegin.com and now onto our conversation.
So writing a book can be a lonely, lonely, scary, confusing business. And that's when it's going well, when it's going badly. It's much worse than all of that. And one of the things that has been brilliant about writing how to Begin is my friend Jenny Blake. Because Jenny's been a friend of mine for many years now. I first met her when I gave a talk at Google, I know, more than 10 years ago now. And she worked at Google at the time and helped introduce me and coordinate that which is wonderful. And then, glory be, we stayed in touch, we've become friends and I feel like in the last year or so that friendship has deepened because we have been traveling companions in writing books. Jenny's had other books written before she's had other podcasts. So we're kind of similar in a lot of things that we think about, but Jenny and I have been kind of encouraging each other and exhorting each other on to write a book. So when I thought of who would be the small number of people who I'd love to preview the new book with and have a conversation about it, honestly, Jenny was just on a unmissable top of the list person because she's been with me the whole way. So it's very exciting to talk to Jenny as it always is. So, Jenny Blake, welcome.
Wow. That might be my favorite podcast or any introduction of all time ever. Thank you, mps.
My pleasure. How would you introduce yourself, Jenny? Who are you?
It's such a good question. Whoever really knows, I would say a lifelong bookworm. Books, as I suspect they have been for you, given the name of your new podcast. Books have been my bomb. My best friends, my teachers, my business mentors. And every now and then one of those books comes to life, AKA I get to meet a friend or hero like you back in the day at Google and keep in touch. So I would on paper consider myself an author, speaker and podcaster. Speakers sort of went by the wayside the last year and a half, but age that opened up space for something new. I realized that instead of jumping on planes and trains, running around, speaking to others and kind of serving others and clients, I actually had a chance to pause and reflect and recalibrate and kind of take a moment to be truer to myself. What did I really want to talk about if I wasn't afraid? And you were so instrumental, as you said in the intro, you I will not forget this. Yes, we both had ambitions to launch a book and a podcast pretty much at the same time. And when I failed all these accountability check ins with you, you had said, Send me 1500 words twice a week. And I said, okay, MBS, you've got it. And I just didn't do it. Over and over I failed. And you said, I have a better idea. Send me a hundred words a day. Just send me a check mark. Just 100 words. It's seven sentences. You've got this. And that did it. That was it. In the month of December, you and I traded check marks just about every single day. And I was absolutely shocked to compile those efforts and find that there's a book draft there in January. So thank you for that and just thrilled to be here talking about your beautiful new book.
Thank you, Jenny. You know, I'm going To love to talk about my book because I'm excited about it. But before I read the two pages from my book and then we have a quick chat about it, tell me a little bit about your new book. What's it about? What's at the heart of it?
My new book is called Free Lose the Busy Work, Love youe Business. The heart of it is my passion to help all of us create smarter systems around some of the busy work and the minutiae in our life and our work. To do it in a way that's easeful and joyful so that we can free up our mind and our time to do our best work and also to be present in our lives. I feel that work becomes this all encompassing behemoth sometimes. And every time a new social media app is introduced, we acquire a new inbox and the inboxes never end and the pings and requests for our attention never end. And they're designed that way. So for me, Free Time is really a manifesto and a love letter, most directly written to heart based business owners. But I hope that even more can benefit. It's how I have grappled with these questions over 10 years of how do I continue to free my mind and my time so I can do more of my best work?
Yeah, I mean you're a great role model like that. You are this kind of hardcore. I am not going to be sucked into the narrative around over busyness and climbing the slippery pole and scaling the success ladder. I'm going to define success on my own terms and then I'm going to build systems and structures that allow me to do that in a way that is effortless and that creates free time. And I think the title of your book is so clever because it's about free time, but it's also about freeing time. So the free is an adjective and it's a verb and it's brilliant because of that. So I look to you as my wise teacher around building systems and structures, which I'm not that great at. And I'm very excited for the book coming out. When does it come out?
Thank you so much. It comes out March 22, 2022.
32222.
Yes, exactly.
Well, let's talk enough about you, let's talk about me. I thought you'd never ask, you know, the four or five people who have asked to do this with me. I said, look, tell me which chapter you'd like me to read from and then we'll talk about it. And I was really thrilled you chose chapter Six. So chapter six is called Way up the Journey and it's.
Probably the heart of the book and the kind of deepest part of the book. Because in the first part of the book, the first section, you kind of define a worthy goal and you go through process of drafting it. The final part of the book is you cross the threshold. How do you start the journey, how do you take get going on it? But this middle section.
I think of it as the moment in a tennis ball when you throw it up in the air and it pauses for a moment and it's neither going up nor going down. It's got that still heartbeat and it's when you decide whether you can really commit to it. And it's where I think so often our commitments to our ambitions go off the rails because we haven't fully understood what's the reward and what's at risk. And weighing up the journey is part of that. So thanks for picking this bit because I love this part of the book.
You got it. I'm so excited to dive in. And it's the perfect this and what you just mentioned, the previous chapter on prizes and punishments, it all, it's. You kind of hold our hands on this journey of what's at stake for you, what's going to be worth the prize, you know, giving up the prizes and what are the potential punishments like. I just love how there's this reality of weighing up the journey. And when we get to this chapter in the book and this moment and you kind of ask us how serious are you and are you going to make incremental change or are you really going to go for this thing that is thrilling and daunting and calling you forth to be a new version of yourself. So I just love how you, this is kind of that crucial moment in the book where you're calling us forth to really take the leap.
Indeed. All right, let me read these two pages. It won't take long because my pages are pretty short. So chapter six is called Way up the Journey and the subheading is called Grow in Layers.
In Alexandria, Indiana, hangs the world's largest ball of paint. It started life as a baseball and on January 1, 1977, the first coat of paint, blue, was applied. It's been painted many, many, many times since then. Somewhere north of 25,000 coats, it now hangs from a beam in a purpose built barn, has its own website and weighs in at close to 2 metric tons. And as an aside, if you're interested in this, I learned about this from John Green's wonderful book the Anthropocene reviewed. He has a podcast of the same name. So if you want to geek out about a paintball, definitely check out John Green's work because he is a genius. All right, back to the text.
It's not only a roadside attraction, it's a slightly awkward metaphor for how we can mistakenly think about our personal growth. Another day, another barely perceivable paint layer. Psychologist and academic Robert Keegan has one of the most robust models to describe the process of self growth. What's helpful to know for now is in each of his five behavioral stages, there's first growth within each stage and then a leap to the next stage. I frame it as the difference between u and u2.0.u is growth within the stage and it's akin to that. Painful. You work to fine tune yourself, getting better and more comfortable in the stage you're in. It's often everyday work. Another day older, another day wiser. But U has its limits. It's not like one of those charts where there's a straight line heading diagonally upwards. Rather, growth is an S curve. You start slow, move more quickly up the curve, and finally begin to plateau. To continue to grow, to unlock your greatness, you need to make the leap to the next S curve and onto the next stage. This is U 2.0. Your worthy goal can be a catalyst for this leap. Your worthy goal can break the limits of U and free you to step into your next phase of learning and growth.
That's the first two pages of the chapter. After that we get into the wait, what do you mean it's going to break me? That doesn't sound good. And I'm like, it doesn't sound good, but it's part of this process of what does it mean to become U 2.0? Anyway, thanks for picking that. Jenny. Let me ask you what struck a chord for you in hearing me read that and hearing those words again.
One thing that came to mind as I was reading this is that there was a zero to one moment for that paintball as well. That even though the layers accumulate day by day in the later stages aren't that transformative. Someone had to decide, I am going to take a friggin baseball, paint it, hang it in a museum and commit to this creative goal. You know, not knowing what's going to happen or what's going to result. Maybe he did, maybe he piloted with a secret baseball in his attic somewhere. But this moment of, of deciding and also transforming, and this is what is so impressive about artists and fine artists in particular is they just have this way of looking at something differently and saying, I'm going to take a baseball and turn it into art. And so there is that moment, what you call you 2.0. It went from you plus baseball to a baseball 2.0. And now we're here talking about it. And it was featured in the Anthropomorphine. That's a hard word to say in John Green's wonderful book as you write.
Yeah, the Anthropocene Review. John Green mocks it all the time. He's like, I've chosen the book with the hardest name to say in the world. You're living the dream for him.
Yeah, totally. We'll be right back just after this.
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I wonder for you. Mbs One of the things I love most about the entire book are your personal examples. And you are truly in process, which is rare for an author to share things that are in process in a book because a book becomes this fossilized artifact that we might get embarrassed about a year from now. Yeah, I wonder if you see yourself in this paintball metaphor or even this U to U 2.0. Where are you in that leap yourself as we sit here recording this and the book is just about gonna launch.
For me, I would say the thing that kind of catapulted me to a next level probably has been happening over the last year or so, and it's moving away from being the CEO at Box of Crayons, which is one of the examples I talk about in the book, because I'd spent 20 years being that person, the founder and then the leader of box of crayons. And inevitably, I just had a lot of identity entangled in that. And it was scary and brilliant. I mean, prizes and punishments for stepping away from that and. And letting Shannon. Not letting. Just having Shannon step in to be the CEO of the company, but it just meant that I didn't have any more layers to apply as the box of crayons person. And so I kind of moved to a new baseball and I went, okay, what's mbs? Who am I now? I mean, I started calling myself mbs. Parker's Michael Bungay Stanier is almost as difficult to pronounce as Anthropocene reviewed.
And I feel like I started painting a new baseball. And I'm still painting that. It's pretty small at the moment. I'm still trying to figure this out, but it was understanding what I'm leaving behind, understanding what I'm trying to become now. And this book, how to Begin, is a manifestation. It's like a worthy goal that is part of. It's not. I figured it out. And therefore, this is my worthy goal. Writing and bringing how to Begin out into the world is how I become this next version of myself. It's part of the process. It's not an outcome in and of itself. So, yeah, I feel like I'm at the start of something.
You said something really interesting in there, which is that you felt that you had added all the paint layers you could as CEO of Box of Crayons. And now this new direction, U 2.0, is removing layers to go back to the core and say, who is MBS after all? Who is MBS? After 20 years of adding paint layers, I. I just. It's so fascinating to think of removing them.
Yeah.
And you know the saying, it's harder to read the label from inside the jar.
I do, yeah. It's a great.
Like, why is it that we go. Why is it so hard to see what U 2.0 looks like or to remove those layers and know what that baseball and remember what that core is? Why do you think it is such a daunting process to truly, truly make this leap that we're talking about from you plus the one thin paint layer back to something. A totally different manifestation of ourselves.
Jenny. I think it gets to the very heart of what this section of the book is about, which is, in summary, we are far more committed to the status quo than we realize. And it is kind of full on to kind of go, wow, what does it really mean for me to step away and.
Leave behind.
The benefits I get from things being exactly the way that they are now. And often it's a bit nuanced as to what those things are, because you can be in a time in your life where you're like, I'm busy. I'm overworked, I'm stressed. I'm a bit anxious. I'm a bit distracted. And you can feel all of that. And that's the foam on the waves of the ocean. But there's a deeper current, which is like, I'm comfortable. I understand it. It's familiar. I know what the patterns are. I know who I am. And so we just have a level of comfort. There can be a level of discomfort, surface y. And it's just a deep level of, you know what? Actually, status quo is. Okay. Like, I could have continued to be a slightly mediocre CEO at Box of Crayons for many more years. There's a bunch of things that stroke my ego.
Help my wallet, all sorts of things that I could do around that. But.
Sometimes it's really helpful to have something happen to you. And, I mean, I decided it was a unilateral decision by me to move away from this role as CEO, but it was a really great catalyst for me to step into this next thing. But this is the power of this section of the book, which is you gotta see how you're nourished by the status quo right now before you can really understand whether it's worth leaving it or not.
You mentioned something that was on my mind too. Sometimes things happen to you, or it's almost like U 2.0 asserts itself.
Right.
We can be cozy in, um.
Yeah.
And it's interesting as your friend and I feel very fortunate to be a good friend, that in different parts of the book, you talk about one of your gremlins or inner critic is the lucky amateur. Which is so funny to me from the outside because, I mean, it's not funny, but it's just fascinating because I saw you building layer by layer by layer for 20 methodical, strategic, passionate years of box of crayons. And I go, there's nothing lucky about that. I wonder, maybe this relates to you 2.0 asserting itself and sort of knocking on the door and going, hey, you let me in or wake up or I need you to do something for me now. But I also wonder.
I wonder with the paintball, you know this saying, it takes 10 years to an overnight success.
Yeah.
We cannot always plan when that moment. I actually feature you in free time in the introduction, and I Say you are a beautiful example of escape velocity, where you actually are so successful at building your business. And we all know the coaching habits sold probably a million copies by now. But that came from one layer of paint after the other. That gave you the opportunity to even step into U 2.0. And so maybe can you speak to how do we know when to make the big leap versus keep putting those paint layers and trust that there will come some kind of tipping point or catalyst that we don't always plan, we don't always know the timing of as it relates to you 2.0.
It's a powerful question, Jenny, without a good answer. I wish I had that kind of magic. And now, because that's like buying low and selling high in the marketplace, we all aspire to doing it. How do you do that? I have no idea. But you know, there's that saying, planning is useful. Plans are useless, but planning is useful. I feel like it's something like that, which is part of what you're doing in that incremental growth is building capacity, building confidence, building resource. And I think part of what I'm trying to provoke, and you do this as well in your work, is to also start people feeling a bit restless just looking around going, am I happy with this? Is this the mountain I want to be climbing? Have I got to the top of the mountain? What am I doing? And there's a way that you.
Stuff happens to you all the time. Sometimes you're aware of it and you understand the opportunity that it offers. So when I moved to Canada, I lived in Boston beforehand. I'd quit my job as an unhappy consultant. I had another job as a consultant lined up in Toronto. Our flight out of Toronto was on 9 11.
So it all went to hell.
My job disappeared. I found a temporary job. I struggled through that for six months, making no real impact. And after six months, they finally fired me. Basically exactly the same time as my equivalent of a green card. My landed immigrant status arrived in Canada. So I was like, I can work for myself now.
The safer thing would have been to go find another job. And the thing I did instead was to start box of crayons going, I have no idea what it means to start this, but honestly, it was like, all right, it's a new baseball. I'm going to start painting a new baseball now. And as you said, what is true is that I then spent 20 years trying to figure stuff out and trying to build and succeeding in building a company and a business around some of those ideas. And of course what you see from the outside is me making a whole bunch of brilliantly strategic and successful decisions. And what you don't see is me making a whole series of not brilliant and unsuccessful decisions, which are also true.
Yeah, it's so hard to imagine those because every time you've given me advice, it's like the most transformative game changer. So certainly my experience of you is, is always just so much vision and talk about creativity. Here's a question for you. One of my gremlins is.
It'S a little dated now, but the kid that wants to play basketball when they grow up and somebody goes, we can't all be Michael Jordan. Like you, I share this ambitious goal, a worthy, daunting, thrilling goal of having a top rated professional podcast. But the gremlin on my shoulder is, who's to say that's in the cards for you? You might think you want that. You might declare it to the world, you might even write it in a book. But the little gremlin sits on my shoulder going, we can't all be Michael Jordan. We can't all be Tim Ferriss. We can't all be Joe Rogan. And I still don't feel that I have a strong sense other than intuition along the way. And you don't know till you know. But I guess what I'm wondering is.
We can declare u 2.0 all we want and do you believe that we can all pursue that or is there some other factor that just steps in? And then my question is, how do we know? I don't even know. This is your next book, probably.
It's called how do you know?
Yeah, or how do we know? I mean, that's kind of what pivot my previous book is asking is like, how do you know when to persevere? How do you know when to pivot? But I have a lot of question around you 2.0. And sometimes when I'm in the moment of taking that leap going, am I being delusional or am I onto something here? Beyond the intrinsic benefits of how wonderful it is to talk to friends while hitting record, you know, all that good, good stuff.
Well, it's another great question, Jenny. You know.
The sentence that's at the heart of this book? We unlock our greatness by taking on the hard things.
It's not we unlock our greatness by having and succeeding and winning the hard things, it's by taking it on. So I do think it's a commitment to a process where you're like, this is actually how I'm going to learn and grow and stretch and be nourished and have an impact in the world. And it is deeply true that there is no guarantee of success in that. I mean.
I look at my podcast and it's like, I love the design of it and the vibe of it, but it's also true that it's nowhere near 10,000 listeners, which is the goal I set in the book. And I've got two and a half months to achieve. And I'm like, I'm hoping to get it now. I'm going, maybe a thousand listeners per episode. If I could get there, that would be pretty cool.
So I'm like, okay. So.
Part of what I get to is going, if this fails utterly, was it still worth it? And I've got that. With every one of my books that I've written, I've hit a point where I'm like, damn it, this is a good book. I'm just going to go with this because this feels like.
I can stand behind this book and it's part of my body of work, and if nobody reads it, well, more fool them. And I've had this conversation with myself with the two pages with MBS podcast, where I'm like, okay, not as many people are listening to this as I hoped they would do. I give up on this. And I'm like, well, what's success for me in this? And I'm like, okay, real success is innovating in podcasting. I think the kind of the setup is a slightly innovative woe. And honestly, meeting some really cool people and having great conversations and feeling less lonely and feeling like I'm building a constellation of people who I would love to hang out with.
And so it's about understanding what real success means, but also then also looking at the cost of it, which is like, this is costing me time and money and an opportunity cost to not work on other things because I'm doing a podcast, two episodes a week, and weighing that up and going, is now the time for me to stop doing this? Or I keep going, going along this.
Yeah, it's. It's so interesting. And there isn't always a super clear answer. You just kind of articulated later in this chapter that we're talking about. You do talk about external rewards and goals and status markers and then internal needs that something might serve, like an introvert's guide to making friends is just start a podcast. And qualities we're cultivating. I would also add there's another benefit, which is surprise benefits. Something I love about writing books and podcasts creating anything. I call it public original thinking. Just got to think out loud sometimes and then the serendipity that results is exactly what you said. And David White also has a version of the quote you shared. What you can plan is too small for you to live. So I can hear that.
I love that. That's great, isn't it?
What you can plan is too small for you to live. So I try to remind myself when I'm sort of in the forest of it all and let's say in, in my case, just like you, I've sort of taken the leap. Like I'm like standing naked out on the. Not to not to take your podcast in a wrong direction, but like very, very vulnerable, very, very stretched in every way. I just try to remind myself I won't even know all the rewards. Like at least I'm out there open for surprises and serendipities. And those are some of the most delightful things for me is just the stuff I don't see coming.
I think. And this is a perfect place to be finishing, I think, which is you're just coming. It's taking us back to the sense of. Part of what's exciting about setting a worthy goal is you're committing to a journey towards a worthy goal. And it's a cliche, but it works. Which is it's often that the journey is a thing that nourishes you and rewards you and the goal itself changes and shifts and becomes something different. Hey Jenny, thank you for being such a gracious podcast host. I was kind of thinking I was going to host this, but you just took the reins and went, I'm just going to ask you questions. I was like, oh, this is great. So thank you. You make me look smart.
I mean, what happens when you put two podcasters in a recording room?
It's like we're both exactly for people who want more Jenny Blake, of which many people will be saying yes. Where do they find you? How do they learn about your podcast, your and about you Wherever you're listening.
To this search for free time with Jenny Blake. You can also visit itsfreetime.com and if you're listening to this before March 22, I'm going to do a special pre order. If you pre order the hardcover, it's buy one, get one, give one. So if you pre order the hardcover, you'll get instant access to the audiobook and you'll get to gift one to a friend because that speaks to my delight of just giving things to others. So just go to itsfreetime.com and MBS. I just have to tack on one thing to the end of what you just said. Maybe the Easter egg to the whole book is that our worthy goal is always the same and it's just to become more of ourselves in the world. No matter what we write down on paper as we go through your book exercises, ultimately we're all on a similar journey of just of self actualization.
Jenny Blake, you are awesome. I loved having you walk this path with me, this journey. I feel I'm a better person for knowing you. So thank you.
Thank you so much. Likewise MBS words cannot express and my book would not exist without you. It's been an honor and a joy and I'm just so grateful to be here. Thank you and thanks to everyone for listening.
Hey, it's Michael here. Thank you for listening to one of the how to Begin episodes, part of the two Pages with MBS podcast series. So you're either listening to it before or after January 11, which is the launch of the how to Begin book. How to Begin Start doing Something that matters. If it's before January 11th, if you're happy and willing to make a pre order of the book, I would certainly be grateful. The pre ordering kind of really matters to authors. It's our chance to kind of get some notice of the book, to kind of get a bit of buzz going around it. It's one of those great gifts that a reader can do is to pre order a book for an author. You know, I wrote the book because a line came to me which is we unlock our greatness by working on the hard things. And when I think of my own personal growth and the difference I've made in the world and the impact I've had, it's when I've taken on something that feels thrilling and important and daunting and I wanted to share and write about a process to help others do that. So if you're looking to be more ambitious for yourself and for the world, to kind of connect to that ambition, and if you're really wanting to rethink goals as a, as a liberating force, and if you just want to be the best version of yourself and do work that makes a difference, whether that's work at work or work, you know, just in life outside your kind of a career, then I think this book might be for you. You can find out more about the book@howtobegin.com that will give you bonuses, that will give you pre launch extras. If you're listening before January 11th, and it'll just give you additional resources if you're coming to it after January 11th. Thanks for your support. You're awesome. You're doing great.
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