Designing Your Life Workbook

What Actually Goes Into This Thing

The Designing Your Life Workbook is a companion to the book by Bill Burnett and Dave Evans, two former Stanford engineering professors who built a curriculum around applying design thinking to career and life decisions. The workbook itself is basically a set of guided exercises, worksheets, and prompts that walk you through the same frameworks. You don't need the book to use it, but most people buy them together. The exercises are intentionally sparse on theory and heavy on doing something. That's the whole point. Here's the practical sequence I'd recommend if you're sitting down with it for the first time. Start with the Good Time Journal exercise before you touch anything else. It asks you to track what you did over two weeks and rate each activity for energy given and energy received. Most people skip ahead to the big existential questions because that's what the book's title sells you on. That's the wrong order. The journal data gives you actual evidence about where you feel engaged versus drained, and without that baseline the rest of the workbook is just speculation dressed up as insight. After that, move into the Odyssey Plans. You sketch out three possible five-year futures: the one you're currently on, the one that happens if your current path disappears, and the one you'd pursue if money weren't a factor at all. This isn't a vision board exercise. The constraint of exactly three options is deliberate because it prevents you from falling into the trap of optimizing for a single path and then panicking when things don't go according to plan. People tend to produce one detailed plan and two vague shrug-adjacent sketches on their first attempt. Push past that. Each Odyssey should be equally fleshed out.

Then comes the Bias Letter, which is probably the most uncomfortable exercise in the whole thing. You write a letter from your future self advising your present self to stop worrying and take a specific action. The format sounds silly but it works because it bypasses the internal critic that normally hijacks decision-making. You write it fast. You don't edit it. If you catch yourself getting philosophical mid-sentence, stop and rewrite it like you're actually receiving advice from someone you trust. Reframing comes next. The workbook teaches you to take a problem statement like "I need to find a better job" and convert it into a how-might-we question. "How might I create work that uses my technical skills while giving me more autonomy over my schedule?" The difference between a problem statement and a how-might-we question matters more than most people realize. Problem statements close thinking down. How-might-we questions open it up. This single pivot changes everything about how you approach the rest of the process. Prototyping conversations are where the workbook separates itself from generic self-help. Instead of deciding and then acting, you design small experiments. You identify someone who's living the kind of life you're curious about and you ask them for twenty minutes of their time. The exercise gives you a script. Most people overprepare for these conversations and end up sounding rehearsed. The workbook's suggested questions are intentionally blunt because you want honest answers, not performative ones. Asking "What do you do on a Tuesday afternoon?" gets you more useful data than "Tell me about your career journey."

I ran into a specific edge case last year with a reader going through this process. They were trying to prototype a career switch into instructional design but kept getting stuck on the Odyssey Plans. Every version they wrote felt either too vague or too tied to their current industry. The workaround was to strip the constraint entirely and write the plans in a completely different domain first. They drafted an Odyssey as if they were a landscape architect, then translated the structural elements back into career language. It took about twenty minutes and suddenly they had three coherent paths instead of one wish and two blanks. The trick is that design thinking works on structure, not content. Once you have the pattern, you can populate it with anything.

What Most People Get Wrong

The biggest mistake is treating the workbook as a linear product to complete rather than a toolkit to reference. People buy it, do chapters one through five in a single weekend, and then close it for six months. The exercises aren't designed to be finished. They're designed to be returned to. The Odyssey Plans especially should be revised every few months. Your assumptions about what you want change faster than you'd expect, and the workbook assumes you'll notice that and adjust. Another common failure mode is rushing the prototyping phase. The workbook suggests three prototypes per week during the active phase. That's aggressive. If you're working full-time, two is realistic. The quality of your prototypes matters more than the quantity. A single fifteen-minute conversation with someone actually doing the work you're curious about is worth more than ten casual LinkedIn messages. The workbook knows this and structures the exercise around specific types of conversations: informant interviews, experience prototypes, and storyboarding. Each one serves a different purpose and they're not interchangeable. There's also a real limitation worth being honest about. The design thinking framework assumes a baseline of agency and resources that not everyone has. If you're in a situation where you can't realistically prototype a career change because you're working three jobs or dealing with a health crisis, some of these exercises will feel tone-deaf. The workbook doesn't adequately address this. The reframing exercise becomes almost insulting when your constraints are structural rather than psychological. I've seen people get genuinely frustrated by the Bias Letter when their problem isn't internal doubt but external systemic barriers. In those cases, the workbook is better used for small-scale experiments within your current situation rather than as a blueprint for a complete career pivot.

A counter-intuitive point that doesn't get enough attention: the workbook's emphasis on curiosity is both its strength and its blind spot. Curiosity-driven exploration works well when you have options. When you're choosing between two equally unappealing paths, curiosity doesn't help much. Decision theory and risk assessment fill that gap better. I'd recommend pairing the workbook with something more analytical if you're in a high-stakes situation where the cost of a wrong choice is significant. The design thinking approach shines in exploratory territory, not in crisis management. The downloadable version of the workbook is available through the authors' website and major book retailers. It's structured identically to the print edition, so there's no functional difference. If you're someone who prefers writing by hand, the print version is fine. If you want to reuse the worksheets or share them with a coach or mentor, the digital version saves time. Either way, you're getting the same content. Don't overthink the format choice.