Note: While reading a book whenever I come across something interesting, I highlight it on my Kindle. Later I turn those highlights into a blogpost. It is not a complete summary of the book. These are my notes which I intend to go back to later. Let’s start!

  • Designers love questions, but what they really love is reframing questions. Reframing is one of the most important mind-sets of a designer. Many great innovations get started in a reframe. In design thinking we always say, “Don’t start with the problem, start with the people, start with empathy.” Once we have empathy for the people who will be using our products, we define our point of view, brainstorm, and start prototyping to discover what we don’t yet know about the problem. This typically results in a reframe, sometimes also called a pivot. A reframe is when we take new information about the problem, restate our point of view, and start thinking and prototyping again. You start out thinking you are designing a product (a new coffee blend and new kind of coffee machine) and reframe when you realize you are actually redesigning the coffee experience (Starbucks). Or, in an attempt to make an impact on poverty, you stop lending money to the wealthy class in a country (as the World Bank does) and start lending money to people considered too poor to pay it back (micro-lending and the Grameen Bank). Or the team at Apple comes up with the iPad, a complete reframe of what the portable computing experience is about.

  • The reframe for the question “What do you want to be when you grow up?” is this: “Who or what do you want to grow into?” Life is all about growth and change. It’s not static. It’s not about some destination. It’s not about answering the question once and for all and then it’s all done. Nobody really knows what he or she wants to be. Even those who checked a box for doctor, lawyer, or engineer. These are just vague directions on a life path. There are so many questions that persist at every step of the way. What people need is a process—a design process—for figuring out what they want, whom they want to grow into, and how to create a life they love.

  • A well-designed life is a life that makes sense. It’s a life in which who you are, what you believe, and what you do all line up together. When you have a well-designed life and someone asks you, “How’s it going?,” you have an answer. You can tell that person that your life is going well, and you can tell how and why. A well-designed life is a marvelous portfolio of experiences, of adventures, of failures that taught you important lessons, of hardships that made you stronger and helped you know yourself better, and of achievements and satisfactions. It’s worth emphasizing that failures and hardships are a part of every life, even the well-designed ones.

  • Problem Finding + Problem Solving = Well-Designed Life

  • If it’s not actionable, it’s not a problem. It’s a situation, a circumstance, a fact of life. It may be a drag (so to speak), but, like gravity, it’s not a problem that can be solved.

  • The key is not to get stuck on something that you have effectively no chance of succeeding at. We are all for aggressive and world-changing goals. Please do fight City Hall. Oppose injustice. Work for women’s rights. Pursue food justice. End homelessness. Combat global warming. But do it smart. If you become open-minded enough to accept reality, you’ll be freed to reframe an actionable problem and design a way to participate in the world on things that matter to you and might even work. That’s all we’re after here—we want to give you the best shot possible at living the life you want, enjoying the living of it, and maybe even making a difference while you’re at it. We are going to help you create the best-designed life available to you in reality—not in some fictional world with less gravity and rich poets. The only response to a gravity problem is acceptance. And this is where all good designers begin. This is the “You Are Here” or “Accept” phase of design thinking. Acceptance. That’s why you start where you are. Not where you wish you were. Not where you hope you are. Not where you think you should be. But right where you are.   
  • From the earliest days of civilization, thoughtful people have recognized that it pays to be healthy. And by “healthy” we mean being well in mind, body, and spirit—emotional health, physical health, and mental health. The relative importance of each of these aspects of health is up to you. How you measure your own health in these areas is your call. But once you’ve figured out how you define “health,” you need to pay attention to it. How healthy you are will factor significantly into how you assess the quality of your life when answering that “How’s it going?” question. Work. By “work” we mean your participation in the great ongoing human adventure on the planet. You may or may not be getting paid for it, but this is the stuff you “do.” Assuming you’re not financially independent, you usually are getting paid for at least a portion of your “work.” Don’t for a minute reduce work only to that which you get paid for. Most people have more than one form of work at a time. Play. Play is all about joy. If you observe children at play (we’re talking more about finger painting with mud than about championship soccer here), you will see the type of play we are talking about. Play is any activity that brings you joy when you do it. It can certainly include organized activity or competition or productive endeavors, but when those things are done “for the joy of it” they are play. When an activity is done to win, to advance, to achieve—even if it’s “fun” to do so—it’s not play. It may be a wonderful thing, but it’s still not play. The question here is what brings you joy purely in the doing. Love. We all know what love is. And we all know when we have it and when we don’t. Love does make the world go around, and when it’s lacking, our world can feel like it’s not moving us much. We won’t attempt to define love (you know what you think on that, anyway), and we have no formulas for finding your one true love (there are lots of other books about that), but we do know that you have to pay attention to it. Love comes to us in a wide range of types, from affection to community to eroticism, and from a huge array of sources, from parents to friends to colleagues to lovers, but they all share that people thing. That sense of connection. Who are the people in your life, and how is love flowing to and from you and others?

  • A way to take stock of your current situation, the “You Are Here” for you, is to focus on what we call the health / work / play / love dashboard. Think of this like the gauges on your car’s dashboard. Gauges tell you something about the state of your car: Do you have enough gas to complete your journey? Is there oil in the engine to help it run smoothly? Is it running hot and about to blow? Similarly, the HWPL dashboard will tell you something about the four things that provide energy and focus for your journey and keep your life running smoothly. Dysfunctional Belief: I should already know where I’m going. Reframe: You can’t know where you are going until you know where you are.

  • We all have different mixes of health, work, play, and love in our lives at different times. A young single person, fresh from college, might have an abundance of physical health, lots of play and work, but no meaningful love relationship yet. A young couple with children are going to play a lot, but in a different way from when they were single or when they didn’t have children. And as we age, health becomes a bigger concern. There will be an appropriate mix for you, and you will have a sense of it, at whatever stage of life you are in.   
  • Since life design is an iterative process of prototypes and experimentation, there are lots of on ramps and off ramps along the way. If you’re beginning to think like a designer, you will recognize that life is never done. Work is never done. Play is never done. Love and health are never done. We are only done designing our lives when we die. Until then, we’re involved in a constant iteration of the next big thing: life as we know it. So the questions remain: Are you happy right now with where your gauges stand in each of these four areas? Have you looked at them honestly? Are there areas that need action? Have you perhaps come up against one of your wicked problems? That is possible, even this early in the process. If you think you have, make sure to check first for a “gravity problem.” Ask yourself if your problem is actionable. Also, look for some expression of balance and proportionality in your dashboard—very important for design—without imagining that there is some perfect symmetry or balance between all the areas in your life. It’s unlikely that health, work, play, and love will divide neatly into four equal parts. But when life is really out of balance, there can be a problem.

  • You need two things to build your compass—a Workview and a Lifeview. To start out, we need to discover what work means to you. What is work for? Why do you do it? What makes good work good? If you discover and are able to articulate your philosophy of work (what it’s for and why you do it), you will be less likely to let others design your life for you. Developing your own Workview is one component of the compass you are building; a Lifeview is second. Now, Lifeview may sound a bit lofty, but it’s really not—everyone has a Lifeview. You may not have articulated it before, but if you are alive, you have a Lifeview. A Lifeview is simply your ideas about the world and how it works. What gives life meaning? What makes your life worthwhile or valuable? How does your life relate to others in your family, your community, and the world? What do money, fame, and personal accomplishment have to do with a satisfying life? How important are experience, growth, and fulfillment in your life? Once you’ve written your Workview and your Lifeview, and completed the simple exercise that follows, you’ll have your compass and be on the path toward a well-designed life. Don’t worry—we know that your Workview and Lifeview will change. It’s obvious that the Workview and Lifeview you have as a teenager, as a young college grad, and as an empty nester will all be substantially different. The point is, you don’t have to have it all figured out for the rest of your life; you just have to create the compass for what life is about for you right now.

  • Our goal for your life is rather simple: coherency. A coherent life is one lived in such a way that you can clearly connect the dots between three things:
    • Who you are
    • What you believe
    • What you are doing
  • For example, if in your Lifeview you believe in leaving the planet a better place for the next generation, and you work for a giant corporation that is polluting the planet (but for a really great salary), there is going to be a lack of coherency between what you believe and what you do—and as a result a lot of disappointment and discontent. Most of us have to make some trade-offs and compromises along the way, including some we may not like. If your Lifeview is that art is the only thing worth pursuing, and your Workview tells you that it’s critical to make enough money so your kids have everything they need, you are going to make a compromise in your Lifeview while your children are dependent and at home. But that will be okay, because it’s a conscious decision, which allows you to stay “on course” and coherent. Living coherently doesn’t mean everything is in perfect order all the time. It simply means you are living in alignment with your values and have not sacrificed your integrity along the way. When you have a good compass guiding you, you have the power to cut these kinds of deals with yourself. If you can see the connections between who you are, what you believe, and what you are doing, you will know when you are on course, when there is tension, when there might need to be some careful compromises, and when you are in need of a major course correction. Our experience with our students has shown that the ability to connect these three dots increases your sense of self, and that helps you create more meaning in your life and have greater satisfaction. So now it’s time to build your compass and set out on your quest. Right now your quest is simple (and it’s not to find the Holy Grail). Your quest is to design your life. We may all want the same things in life—a healthy and long life, work we enjoy and that matters, loving and meaningful relationships, and a hell of a lot of fun along the way—but how we think we’ll get them is very different.

  • A Workview should address the critical issues related to what work is and what it means to you. It is not just a list of what you want from or out of work, but a general statement of your view of work. It’s your definition for what good work deserves to be. A Workview may address such questions as:
    • Why work?
    • What’s work for?
    • What does work mean?
    • How does it relate to the individual, others, society?
    • What defines good or worthwhile work?
    • What does money have to do with it?
    • What do experience, growth, and fulfillment have to do with it?
  • Your Lifeview is what provides your definition of what have been called “matters of ultimate concern.” It’s what matters most to you.
    • Why are we here?
    • What is the meaning or purpose of life?
    • What is the relationship between the individual and others?
    • Where do family, country, and the rest of the world fit in?
    • What is good, and what is evil?
    • Is there a higher power, God, or something transcendent, and if so, what impact does this have on your life?
    • What is the role of joy, sorrow, justice, injustice, love, peace, and strife in life?   
  • Read over your Workview and Lifeview, and write down a few thoughts on the following questions (please try to answer each of the questions):
    • Where do your views on work and life complement one another?
    • Where do they clash?
    • Does one drive the other? How?
  • Double-check your Workview and Lifeview and make sure they align. Anytime you’re changing your situation, or pursuing a new thing, or wondering what you’re doing at a particular job—stop. Before you start, it’s a good idea to check your compass and orient yourself. Now that you have your compass, it’s time to “find your way.” This is a quest, after all. Dysfunctional Belief: I should know where I’m going! Reframe: I won’t always know where I’m going—but I can always know whether I’m going in the right direction.

  • Flow is play for grown-ups. In the life design dashboard, we assessed our health, work, play, and love. The element we all find the most elusive in our busy modern lives is “play.” You might think that we all have too many responsibilities to have much time for play. Sure, we can strive to have our work and our chores engage skills we like using, but face it—it’s work, not play. Maybe. Maybe not. Flow is one key to what we call adult play, and a really rewarding and satisfying career involves a lot of flow states. The essence of play is being fully immersed and joyful in what you’re doing, without being constantly distracted by concerns about the outcomes. When we’re in flow, that’s exactly what’s going on—we are fully present to what we’re doing, so present we don’t even notice time. Seen this way, flow is something we should strive to make a regular part of our work life (and home life, and exercise life, and love life…you get the idea).

  • The brain represents only about 2 percent of our body weight, and yet it takes up 25 percent of the energy we consume every day. It’s no wonder that the way we invest our attention is critical to whether or not we feel high or low energy.

  • High levels of engagement often coincide with high levels of energy, but not necessarily. A colleague of Dave’s, a brilliantly fast-thinking computer engineer, found arguing for his point of view an engaging activity, because it made him think on his feet. He was great at it, and often found other people at work asking him to make their arguments for them. But he noticed that getting into those arguments totally exhausted him, even when he “won.” He was not a contentious person, and though it seemed fun at the time to outwit others, he always felt terrible when it was over. Energy is also unique in that it can go negative—some activities can actually suck the life right out of us and send us drained into whatever comes next. Boredom is a big energy-suck, but it’s much easier to recover from boredom than from being de-energized, so it’s important to pay specific attention to your energy levels.   
  • There are two elements to the Good Time Journal:  
    • Activity Log (where I record where I’m engaged and energized)
    • Reflections (where I discover what I am learning) The Activity Log simply lists your primary activities and how engaged and energized you were by those activities. We recommend that you make Activity Log entries daily, to be sure to capture lots of good information. If every few days is easier, that’s fine as well, but log activities at least twice a week or you’ll miss too much. If you’re using a binder, you can make log sheets using the worksheet at the end of this chapter, which has little gauges for how engaged and energized you are by your activities
  • All of us are motivated by different kinds of work activities. Your job is to figure out which ones motivate you—with as much specificity as you can. It will take a while to get the hang of this, because, if you’re like most people, you’ve not been paying detailed attention to this sort of thing. Sure, there are times when we all come home at the end of the day and say, “That was great,” or “That sucked,” but we seldom sift through the particulars of what contributed to those experiences. A day is made up of many moments, some of which are great, some of which suck, and most of which lie somewhere in between. Your job is to drill down into the particulars of your day and catch yourself in the act of having a good time. The second element of the Good Time Journal is reflection, looking over your Activity Log and noticing trends, insights, surprises—anything that is a clue to what does and doesn’t work for you. We recommend doing your Activity Log for at least three weeks, or whatever period of time you need to be sure you capture all the various kinds of activities that arise in your current situation (some activities may only come around every few weeks). Then we recommend that you do your Good Time Journal reflection weekly, so your reflections are based on more than just a single experience of each activity. Write your weekly reflections on blank pages in your Good Time Journal.

  • Bill’s reflection included these observations: He noticed that his drawing class and office hours reliably created flow states, and that teaching and “date night” were the activities that returned significantly more energy than they consumed. Doubling up on those activities would certainly be one way to energize his week. His weekly faculty meeting is sometimes full of interesting conversations and sometimes not, so he drew two arrows on his energy diagram. He was not surprised that budget meetings sucked energy out of his day—he’s never liked the fiscal side of things much (though he appreciates that they’re crucial). Bill adjusted his schedule to surround these less engaging activities with more engaging activities, and to give himself small rewards when he completes “energy-negative” tasks. The best way to deal with these energy-negative activities is to make sure that you are well rested and have the energy reserves needed to “do them right.” Otherwise, you might find yourself doing them again—costing you more energy than they should. Bill was surprised that coaching master’s students, the students he likes and spends the most time with, was such a drain on his week. After journaling a bit on that subject, he discovered two things: (1) he was trying to coach in a bad environment (the noisy graduate studio) and (2) his coaching interaction wasn’t effective—his students weren’t “getting it.” Those two observations resulted in a redesign of his Tuesday-night class environment (he changed classrooms) and a shift in the coaching structure from meeting one to one with each student to coaching in small groups, so students could help one another during the interactions. These changes worked so well that a few weeks later he was regularly going into flow during coaching sessions. The budgeting still sucked, of course, but it’s not that big a part of the job, and the new coaching flow moments help make it more bearable.

  • Getting great insights out of your Good Time Journal reflections isn’t always easy, so here’s a tool designers use to make detailed and accurate observations—part of getting good at the curiosity mind-set. It’s the AEIOU method3 that provides you five sets of questions you can use when reflecting on your Activity Log. Activities. What were you actually doing? Was this a structured or an unstructured activity? Did you have a specific role to play (team leader) or were you just a participant (at the meeting)? Environments. Our environment has a profound effect on our emotional state. You feel one way at a football stadium, another in a cathedral. Notice where you were when you were involved in the activity. What kind of a place was it, and how did it make you feel? Interactions. What were you interacting with—people or machines? Was it a new kind of interaction or one you are familiar with? Was it formal or informal? Objects. Were you interacting with any objects or devices—iPads or smartphones, hockey sticks or sailboats? What were the objects that created or supported your feeling engaged? Users. Who else was there, and what role did they play in making it either a positive or a negative experience?   
  • Take some time to reflect on your memories of past peak work-related experiences and do a Good Time Journal Activity Log and reflection on them to see what you find. Those memories have stuck with you for good reason. You can make a list of those peak experiences, or write them out as a narrative or story. It can be very enjoyable to set to words the story of that great time when you were on the team that planned what they’re still calling the Ultimate Sales Meeting, or when you wrote the procedure manual that they still pass out to new writers as the standard for doing it right. Having the narrative of your peak experiences written down will make it easier to extract from those stories the activities that most engaged and energized you, and to discover insights that you can apply today.

  • From your Good Time Journal, pick one of the areas of greatest interest to you, or an activity during which you were really engaged (e.g., balancing the budget or pitching a new idea), and make it the center of your map. Then generate a bunch of connected words and concepts, using the mind-mapping technique.

  • From your Good Time Journal, pick something you’ve identified as really energizing you in your work and life (e.g., art class, giving feedback to colleagues, health-care access, keeping things running right) and mind-map this out.

  • From your Good Time Journal, pick one of the experiences when you were in a state of flow, put the experience itself at the center of a mind map, and complete your mapping of your experience with this state (e.g., speaking in front of a large audience or brainstorming creative ideas). Now that you’ve done these three mind maps, we’re going to invent an interesting, though not necessarily practical, life alternative from each.
    1. Look at the outer ring of one of your maps and pick three disparate items that catch your eye. You’ll know which ones they are intuitively—they should literally “jump out” at you.
    2. Now try to combine those three items into a possible job description that would be fun and interesting to you and would be helpful to someone else (again, it need not be practical or appeal to lots of people or employers).
    3. Name your role and draw a napkin sketch of it (a quick visual drawing of what it is), like the one shown here. For example, when Grant (who was languishing away at the car-rental agency) did this exercise based on when he was engaged in his life (hiking in redwoods, playing pickup basketball, helping his niece and nephew), he ended up drawing a sketch of himself leading a Pirate Surf Camp for children.
    4. Do this exercise three times—once for each of your mind maps—making sure that the three versions are different from one another.
  • One of the most powerful ways to design your life is to design your lives. No, we haven’t hit our heads and that isn’t a typo. We’re going to ask you to imagine and write up three different versions of the next five years of your life. We call these Odyssey Plans. Whether or not three interesting variations of your next five years immediately leap onto the screens in the multiplex movie theater in your head or not, we know you’ve got at least three viable and substantially different possibilities in you. We all do. Every single one of the thousands of people we’ve worked with has proved us correct in this. We all have lots of lives within us. We certainly have three at any particular moment. Of course, we can only live out one at a time, but we want to ideate multiple variations in order to choose creatively and generatively.

  • Try not to think of your Odyssey Plans as “Plan A, Plan B, and Plan C”—where A is the really good plan and B is the okay plan and C is the plan that you really hope you don’t get stuck with but that you would accept as tolerable if absolutely necessary. Every Odyssey Plan is a Plan A, because it’s really you and it’s really possible. Odyssey Plans are sketches of possibilities that can animate your imagination and help you choose which wayfinding direction you will actually take to start prototyping and living into next.

  • Life One—That Thing You Do. Your first plan is centered on what you’ve already got in mind—either your current life expanded forward or that hot idea you’ve been nursing for some time. This is the idea you already have—it’s a good one and it deserves attention in this exercise. Life Two—That Thing You’d Do If Thing One Were Suddenly Gone. It happens. Some kinds of work come to an end. Almost no one makes buggy whips or Internet browsers anymore. The former are out of date and the latter are given away free with your operating system, so buggy whips and browsers don’t make for hot careers. Just imagine that your life one idea is suddenly over or no longer an option. What would you do? You can’t not make a living. You can’t do nothing. What would you do? If you’re like most people we talk with, when you really force your imagination to believe that you have to make a living doing something other than doing That Thing You Do, you’ll come up with something. Life Three—The Thing You’d Do or the Life You’d Live If Money or Image Were No Object. If you knew you could make a decent living at it and you knew no one would laugh at you or think less of you for doing it—what would you do? We’re not saying you suddenly can make a living doing this and we can’t promise no one will laugh (though they rarely do), but we are saying imagining this alternative can be a very useful part of your life design exploration.

  • Create three alternative versions of the next five years of your life. Each one must include:
    1. A visual/graphical timeline. Include personal and noncareer events as well—do you want to be married, train to win the CrossFit Games, or learn how to bend spoons with your mind?
    2. A title for each option in the form of a six-word headline describing the essence of this alternative.
    3. Questions that this alternative is asking—preferably two or three. A good designer asks questions to test assumptions and reveal new insights. In each potential timeline, you will investigate different possibilities and learn different things about yourself and the world. What kinds of things will you want to test and explore in each alternative version of your life?
    4. A dashboard where you can gauge
      • Resources (Do you have the objective resources—time, money, skill, contacts—you need to pull off your plan?)
      • Likability (Are you hot or cold or warm about your plan?)
      • Confidence (Are you feeling full of confidence, or pretty uncertain about pulling this off?)
      • Coherence (Does the plan make sense within itself? And is it consistent with you, your Workview, and your Lifeview?)
    5. Possible considerations
      • Geography—where will you live?
      • What experience/learning will you gain?
      • What are the impacts/results of choosing this alternative?
      • What will life look like? What particular role, industry, or company do you see yourself in?
      • Other ideas
      • Do keep in mind things other than career and money. Even though those things are important, if not central, to the decisive direction of your next few years, there are other critical elements that you want to pay attention to.
      • Any of the considerations listed above can be a springboard for forming your alternative lives for the next five years. If you find yourself stuck, try making a mind map out of any of the design considerations listed above. Don’t overthink this exercise, and don’t skip it.
  • Life design is about generating options, and this exercise of designing multiple lives will guide you in whatever’s next for you. You aren’t designing the rest of your life; you are designing what’s next. Every possible version of you holds unknowns and compromises, each with its own identifiable and unintended consequences. You are not so much finding answers in this exercise as learning to embrace and explore the questions, and be curious about the possibilities. Remember, there are multiple great lives within you. You are legion.

  • When we use the term “prototyping” in design thinking, we do not mean making something to check whether your solution is right. We don’t mean creating a representation of a completed design, nor do we mean making just one thing (designers make lots of prototypes—never just a prototype). Prototyping the life design way is all about asking good questions, outing our hidden biases and assumptions, iterating rapidly, and creating momentum for a path we’d like to try out. Prototypes should be designed to ask a question and get some data about something that you’re interested in. Good prototypes isolate one aspect of a problem and design an experience that allows you to “try out” some version of a potentially interesting future. Prototypes help you visualize alternatives in a very experiential way. That allows you to imagine your future as if you are already living it. Creating new experiences through prototyping will give you an opportunity to understand what a new career path might feel like, even if only for an hour or a day. And prototyping helps you involve others early and helps build a community of folks who are interested in your journey and your life design. Prototypes are a great way to start a conversation, and, more often than not, one thing typically leads to another. Prototypes frequently turn into unexpected opportunities—they help serendipity happen. Finally, prototypes allow you to try and fail rapidly without overinvesting in a path before you have any data.   
  • Once you’ve committed yourself to life design prototyping, how do you do it? The simplest and easiest form of prototyping is a conversation. We’re going to describe a specific form of prototype conversation that we call a Life Design Interview. A Life Design Interview is incredibly simple. It just means getting someone’s story. Not just anyone and not just any story, of course. You want to talk to someone who is either doing and living what you’re contemplating, or has real experience and expertise in an area about which you have questions. And the story you’re after is the personal story of how that person got to be doing that thing he or she does, or got the expertise he has and what it’s really like to do what she does. You want to hear what the person who does what you might someday want to do loves and hates about his job. You want to know what her days look like, and then you want to see if you can imagine yourself doing that job—and loving it—for months and years on end. In addition to asking people about their work and life, you will also be able to find out how they got there—their career path. Most people fail not for lack of talent but for lack of imagination. You can get a lot of this information by sitting down with someone and getting his or her story.

  • Prototype conversations are great; they’re incredibly informative and easy to come by. But you’re going to want more than just stories as input for coming up with your life design. You want actually to experience what “it” is really like—by watching others do it or, better yet, doing some form of it yourself. Prototype experiences allow us to learn through a direct encounter with a possible future version of us. This experiential version could involve spending a day shadowing a professional you’d like to be (Take a Friend to Work Day), or a one-week unpaid exploratory project that you create, or a three-month internship (obviously, a three-month internship requires more investment and a larger commitment). If you’ve conducted a good number of prototype conversations using Life Design Interviewing, then you will have met people along the way who you may be interested in observing or shadowing. So that variety of prototype should be pretty accessible for you. You just have to ask—and remember, people enjoy being helpful. Most people we work with are surprised how well their Life Design Interviews go. The people they meet with really seem to enjoy it. Asking to shadow someone at work is a much bigger favor than a thirty-minute cup of coffee, but after a dozen or so prototype conversations, you’ll be ready to make a bigger request. Try it—even if you have to try a few times. You’ll learn a great deal. Coming up with hands-on prototype experiences, in which you actually get to do stuff and not just hear about stuff or watch stuff, is an even bigger challenge. But it’s well worth the effort to get your hands dirty and really discover how something fits you. You wouldn’t buy a car without a test drive, would you? But we do this all the time with jobs and life changes. It’s crazy, when you think about it. Remember all the ideas we had that Elise could have tried before she actually bought and opened a deli—things like catering a few times or taking a short-term job bussing tables? Those are the sorts of ideas you’re looking for.

  • Before jumping into grad school, Chung could have set up a brainstorm session asking, “What are the functions of career counseling, and what encounters can we imagine to reveal what doing each of them is really like?” You also want to be careful not to include your solution accidentally in your question. This happens all the time with some of Bill’s clients. They want to brainstorm “ten new ways to make a ladder for a stockroom.” This isn’t a very good framing question, because a ladder is a solution (and they only want ten ideas). A better framing would be to focus on what a ladder does: “How many ways can we think of to…give a person access to inventory in high places?” or “How many ways can we think of to…give a stockperson three-dimensional mobility in a warehouse?” These questions do not assume that ladders are the only way to solve the problem, and they open up the solution space for more creative answers (user-controlled stockroom drones, anyone?).

  • In life design, the choosing process has four steps. First you gather and create some options, then you narrow down your list to your top alternatives, then you finally choose, and then, last but not least, you…agonize over that choice. Agonize over whether you’ve done the right thing. In fact, we encourage you to spend countless hours, days, months, or even decades agonizing.

  • Just kidding. People can waste years agonizing over the choices they’ve made, but agonizing is a time suck. Of course we don’t want you to agonize, and that is not the fourth step in the life design choosing process.

  • The fourth step in the process is to let go of our unnecessary options and move on, embracing our choice fully so that we can get the most from it.

  • In his 1960s sci-fi classic Stranger in a Strange Land, Robert Heinlein invented the word “grok” to describe a way of knowing that Martians employ. It means to understand something deeply and completely, so much so that you feel you’ve become one with it. Because of its rarity, Martians don’t just understand what water is or drink water—they grok it. Now grok has entered more common cultural use; “I grok that” is sort of like “I get that,” only more so. It’s “I get that” on steroids. When you finally get down to making a choice from your narrowed-down list of alternatives, and you’ve cognitively evaluated the issues, and emotionally and meditatively contemplated the alternatives, it may be time to grok it. To grok a choice, you don’t think about it—you become it. Let’s say you’ve got three alternatives. Pick any one of them and stop thinking about it. Choose to think for the next one to three days that you are the person who has made the decision to pick Alternative A. Choice A is your reality right now. When you brush your teeth in the morning, you do so having chosen A. When you sit at a red light, you’re waiting to proceed toward your destination related to living in Alternative A. You may or may not actually say things to other people about this—such as “Oh yeah, I’m moving to Beijing in May!”—because such statements will cause confusion later. But you get the idea: you’ll just live in your head as the person in an Alternative A reality. You are not thinking about Alternative A from your current reality as a struggling choice maker. You are living calmly as one who has chosen A. After one to three days of this (how long is up to you and a matter of taste), then take at least a day or two off to be your regular self and reset. Then do the same thing with Alternative B, then another reset break, then Alternative C. Then one more reset break and, finally, a thoughtful reflection on what those experiences were like and which one of those people you might most like to be. This technique isn’t guaranteed (no such techniques are), but you can see how the intention here is to allow your alternate forms of knowing—emotional, spiritual, social, intuitive—to have some room to express themselves to you, and thereby complement the evaluative, cognitive knowing, which, if you’re like most of us, is the dominant form of thinking and choosing you rely on.

  • Reed always wanted to be a class officer at school, so he started running for office as soon as he could, in fifth grade. He lost. He ran in sixth grade—and lost again. He ran for office every year, often twice a year, and lost every single time. By the end of his junior year of high school, he’d run for one school office or another and lost thirteen times in a row. During his last year of high school, he decided to run one more time—for senior class president. Over the years, Reed’s parents watched with agony as the losses mounted up. After four or five losses, they would wince every time Reed announced, “I’m going to run again!” They were smart enough not to discourage him, but inside they wished he’d just let it go and stop the bleeding. They couldn’t stand to see him going through all those failures. But Reed didn’t mind. Oh sure, he hated losing—but he wasn’t changing his mind. He knew that if he kept at, it he’d learn what he was doing wrong and eventually he’d win—or at least he’d learn a bit more. In his mind, failure was just part of the process. With each successive loss, losing got less painful, which allowed him to take risks to see if new approaches would work. It gave him the courage to try out for other things—sports, acting. Most of these didn’t pan out, but a couple did. Though he was delighted with his successes, he would have been just fine even if he’d failed at those, too. Failing over and over freed him to focus his energies on running the best campaigns he could. Each failure was a lesson, so when he ran, he never worried about losing. When he finally won and became senior class president, he was thrilled, but the point isn’t that he finally won—the point is how he kept running. It turned out to be a more important lesson than he realized. At twenty-two, to anyone who looked at him from the outside, Reed seemed finally to be winning at life. Boy Scout. Class president. Quarterback. Ivy League. Crew champion. When he graduated from college with a degree in economics, his life seemed set on a straight course for success followed by more success. He landed a job with a top firm and for the first few years, his new career was going great. His job took him on the road often, and during a business trip to the Midwest, Reed noticed a strange lump just below his neck. He went to a clinic during his lunch break to check it out, and by the time he boarded his flight home three days later, a doctor has confirmed his worst fears: Hodgkin’s disease, a cancer of the lymph nodes. When he got home, he immediately began chemotherapy. Cancer at twenty-five was not part of Reed’s life design. But it was now part of his life. A lifetime of experience dealing with failure had paid off. Pretty quickly, Reed was able to accept the reality of his situation and put all his energies into getting better. He didn’t get stuck asking, “Why me?” Nor did he believe he had failed at being healthy. He was too busy getting another campaign prepared—this time, a campaign to beat cancer—and then using it. For the next year, he wasn’t advancing his economic consulting career, as he had planned; he was undergoing surgery, radiation, and chemotherapy. He was also learning, at a very young age, just how fragile life is. When his cancer treatment was over and his cancer was in remission, Reed had no idea what to do next. Actually, he had one idea—one somewhat crazy idea. There was this little item on his Odyssey Plan that he hadn’t begun to prototype: taking a year off from everything and being a ski bum. He was conflicted. An all-American boy on the fast track to success just doesn’t take a year off to become a ski bum and get nothing done. Reed, however, was not your average Boy Scout any longer. He had just fought a war with cancer, and even though he knew the smart plan was to go back to building his career, and he worried that an additional year of employment gap might ruin his résumé and therefore ruin his life, Reed decided he wanted to live his life, not just plan it. He did some prototype conversations with businesspeople before he made his decision, because he wanted to learn how future hiring managers might look at that decision, and concluded that he could afford the risk, and that the kind of people he’d want to work with would view his post-cancer ski adventure as a demonstration of boldness rather than irresponsibility. As for how other people would see it—well, that was their problem. The point isn’t primarily that Reed “succeeded in beating cancer,” but that he was able to enjoy failure immunity during the process, which enabled him to direct his energy productively and to learn things he could use later. By turning his problem into an advantage, he was able to design the best life possible in the face of adversity. It beats the hell out of being despondently confused about why bad things happen. The failure immunity he began learning in the fifth grade just kept coming in handy. A few years later, Reed decided to go for his dream job—working for a professional sports franchise, in particular an NFL team. Though he didn’t have any family connections in that world, he had met an up-and-coming NFL executive while in college and had been slowly building a network into the sports world through prototype conversations. He made some overtures into the industry, looking for work. The worst thing that could happen was being rejected, but with rejection no longer scary to him, why not at least try? When his attempts at an NFL job failed, he let go and quickly redirected his efforts into his next, alternative plan. Over a year later, he finally got a chance to apply for a job negotiating player contracts for an NFL team. Up against dozens of other candidates, many of whom had industry experience, he made it down to the final two and lost—he didn’t get the job. It really hurt, but, again, he quickly redirected his efforts into an alternative plan, and he got a job in financial management, working for a great company. But he didn’t give up on the pro team. Despite being rejected, he kept prototyping that career. He stayed in touch with the NFL executives and spent hundreds of hours building innovative sports analysis models, which he would show them every now and then. This was not the usual behavior of people who lost a job. And, yes, he was eventually hired by that same NFL team, for a better job than the one he had originally tried for. He had worked there for about three years when he decided that pro sports wasn’t really where he wanted to be—he “failed” again. So he moved on to a health-care start-up, secure in the knowledge that, if that didn’t work out, the next thing—or, barring that, the thing after that—would. Reed is now completely failure-immune. He’s not protected from the personal pain and loss of failure, but he’s immune from being misinformed by failure—he doesn’t ever believe that he is a failure or that failure defines him, or, in fact, that his failures were failures. His failures educate him in just the same way that his successes do. He likes success better, but he’ll take whatever he gets and just keep failing his way forward. To meet Reed today is to meet what appears in every way to be a very successful and content young man. He’s happily married, with a beautiful baby girl and an irrepressibly delightful three-year-old son. He’s tall, good-looking, and healthy. He and his wife just bought their first house, and he’s doing well at a great young company, working in genetic testing and health care. Reed is certainly enjoying all his recent success, but he doesn’t think of it in those terms. He’s mostly just grateful, and knows that how well it feels life is going is much more about his mind-set than his current level of success. This is the real reason why Reed is winning at life.

  • We know we don’t want someone to stand up at our funerals and say, “Dave had good written and verbal communication skills.” Or “Bill really demonstrated the ability to juggle competing priorities and move quickly.” Life is about more than a paycheck and job performance. We all want to know we mattered to someone. We all want to know our work contributed to the world. We all want to know we loved and we lived the best we could, with as much purpose and meaning as possible, and that we had a pretty fun time doing it. And you only understand that in retrospect, because a well-designed life isn’t a noun—it’s a verb (technically it is a noun phrase but you know what we mean).

  • In life design we only take on the question of how to design your life—not what life you should live or why one life is better than another. Our friend Tim graduated from college with a degree in electrical engineering and went to work in Silicon Valley. His first job was in a fast-pace, just-gone-public start-up where he was designing cutting-edge microprocessors. However, after his first design project got canceled, Tim re-evaluated all those long nights and weekends and came to the conclusion that work was not going to be the main focus of his life. He valued play and love much more, and realized that he needed to make some changes. He switched jobs to a more mature company, rose to a comfortable senior position, and then just stayed there. He’s been in that role for almost twenty years, having become very well respected as a technical guru in his firm, and has turned down promotions and the money that comes with one again and again. “You have to make enough money to pay the bills and have the things you need,” says Tim. In his case, this means supporting his family, making sure his kids have access to a great education, and having a nice house in Berkeley. “After that, what’s the point? I’d rather have more fun and more friends. Money, promotions, and more responsibility do not motivate me. The point of having a good life is to be happy, not to work.” Tim’s design is working, and he’s one of the most balanced guys we know. He is a great dad and the center of a vibrant social life, has lots of friends, plays music almost every week, has his own cocktail blog, on which he promotes his cocktail inventions, reads a lot, and is one of the happiest people you’ll ever meet. His health / work / play / love dashboard is full of green lights, and he plans to keep it that way. And he’s a great example of a well-thought-out life design strategy in which work isn’t the most important thing.

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