📖 Backstory

Recently, I found myself trapped in an endless cycle of overthinking about my life – convinced that somewhere deep inside me was my real purpose, and if I could just think hard enough, analyze deeply enough, I’d finally unearth that hidden answer. I spent countless hours journaling, soul-searching, and trying to logic my way to clarity, believing my true calling was buried in my head just waiting to be discovered through enough introspection.

Until recently, having read Designing Your Life and actually trying to do the exercises and put its lessons into practice. In this newsletter, I’ll share what I learned from Burnett and Evans, and how their approach challenged my belief that I could think my way to answers, showing me instead how to use design-thinking tools (like brainstorming multiple futures and running small experiments) to actively build a life I love, rather than endlessly searching for it in my own head.

💡 The Big Idea

The big idea in Designing Your Life is that you can’t engineer a fulfilling life by pure thought alone – you have to design and build it through action. Burnett and Evans argue that many of us approach life wrong: we obsess over finding a single “perfect” plan or passion, or we get stuck worrying and analyzing, hoping to think our way to clarity. Instead, they suggest treating life as a design project, where you start where you are, empathize with yourself, ideate lots of possibilities, then prototype (experiment) to see what actually works. Real life isn’t a linear problem to solve; it’s a creative, iterative process. The authors emphasize that there’s no one “right” answer or singular path you’re supposed to discover. In fact, their research shows that fewer than 20% of people have a single identifiable passion guiding them – so the rest of us can relax and stop beating ourselves up for not having “one true calling.”

What makes this book stand out is its mindset shift: it’s okay to not know exactly what you want. Designers don’t start with answers; they start with curiosity and problems to solve. Designing Your Life teaches you to reframe “dysfunctional beliefs” (like “I should have my whole life figured out by now” or “I just need to find my passion and everything will fall into place”) into more helpful perspectives. The core argument is that a well-designed life comes from trying things out, learning, and continuously adapting – rather than sitting in your head attempting to logically deduce your future. This inside-out approach resonated deeply with me as an overthinker. It gave me permission to get out of my head and into the real world, where I could test my ideas and learn by doing, not just by researching. Covey’s 7 Habits taught me about principles and character; Designing Your Life taught me about process – a way to navigate the uncertainty of career and life choices by building my way forward one experiment at a time.

5️⃣ Build Your Way Forward

Idea 1: Stop Overthinking – Bias to Action

The first major lesson for me was to quit overanalyzing and start doing. I’m the type of person who loves reading, researching, and imagining every scenario – essentially trying to think my way to the perfect life plan. Burnett and Evans call this out and encourage a “bias to action.” This hit home for me. It turns out, no amount of sitting at my desk pondering will compare to getting up and trying something in real life. For example, I spent months deliberating whether I’d enjoy working in a different industry. I made pro-con lists, read articles – you name it. Finally, inspired by the book, I set up a casual prototype experience: I shadowed a friend for a day at their startup. That single day taught me more about what I liked (and didn’t like) in that field than endless Google searches ever could. The design approach is all about actionable data: you try something small, see how it feels, and use that feedback to guide your next step. As a lifelong overthinker, embracing this “try stuff and see” mentality was liberating. It broke the paralysis and gave me momentum – I didn’t have to solve my whole life, I just had to do the next experiment.

Idea 2: There’s No “One True Purpose” (So Don’t Fear Getting It Wrong)

Another powerful insight from Designing Your Life is that there isn’t a singular, pre-destined life purpose for most people. Many of us (myself included) have been afraid of committing to a path because we worry, “What if it’s the wrong one? What if every moment I’m not on my ‘true calling’ is wasted time?” The authors debunk this mindset as a dysfunctional belief. In reality, life can be lived in multiple fulfilling ways. Rather than one grand “purpose,” think of it as many possible lives you could live – and all of them could be meaningful. This idea blew my mind a bit: it’s not about choosing the one right thing, it’s about designing a good life within whichever path you’re on. Once I internalized this, my fear of “choosing wrong” started to fade.

For instance, I had been agonizing over whether I should stick with my current career or pivot to something entirely different that might be my true passion. Designing Your Life taught me to reframe that dilemma. Instead of looking for a perfect answer, I acknowledged that both paths (and others) could lead to rewarding futures. The key was just to pick a promising option and fully commit to it for a while to see what I can make of it. Interestingly, there’s research noted in the book about decision-making: people who “go all in” on a choice tend to be happier with the outcome than those who keep second-guessing or leave themselves an out. In other words, part of designing your life is making a choice and then embracing it instead of constantly regretting or wondering about the alternatives. Personally, once I chose to pursue a new qualification (after months of hemming and hawing), I decided to let go of the FOMO about other paths. Unsurprisingly, I felt more peace and excitement – my energy was finally invested in building that choice into something great, rather than endlessly questioning it.

Idea 3: Tackle Real Problems, Not “Gravity Problems”

One of the most eye-opening concepts in the book is what the authors call “gravity problems.” A gravity problem is a situation or constraint that you just can’t change, at least not right now – it’s as pointless to fight as gravity. For example, wishing that the 9-to-5 work culture would disappear or that your industry didn’t require a certain certification might be a wish, but railing against those facts won’t get you anywhere. If you find yourself stuck on a problem and making no progress, ask: Is this actually solvable, or is it a gravity problem I need to accept? I realized I had my own gravity problem: I was frustrated that I’m an introvert in a field that rewards networking. I kept thinking, “If only I were naturally outgoing, changing careers would be easier.” That’s not a problem to solve – it’s essentially gravity. I’m me, and I’m not going to magically turn into an extreme extrovert.

Once I accepted that, I reframed the situation. Instead of trying to “solve” my personality, I looked at workarounds: I can leverage one-on-one coffee chats (which I enjoy) instead of large networking events, and I can prepare better for socializing to ease my nerves. The book’s advice is blunt: if you’re not willing to (or cannot) take action on a problem, it’s not really a problem – it’s a circumstance. Acceptance is the only sane response. Paradoxically, accepting a gravity problem can be incredibly freeing. In my case, once I stopped lamenting “I wish I were different,” I could put that energy into strategies that do work for me. Designing Your Life encourages us to focus on designable problems – challenges we can actually do something about. It’s a great reality check: whenever I catch myself obsessing over an unchangeable situation (be it my age, a past decision, or some external condition), I remind myself to either accept it or reframe how I approach it, rather than banging my head against the wall.

Idea 4: Three “Odyssey Plans” (There’s More Than One You)

To bust out of narrow thinking, the book has a fantastic exercise: create 3 different Odyssey Plans for your next five years. The premise is that there are multiple versions of you tucked inside – so why not imagine a few? The authors often ask their students, “If you could live out all the lives you dream of in parallel universes, how many would you want?” Most people come up with several (the average answer is around 7½ lives!). In other words, you contain a multitude of potential futures. The Odyssey Plans exercise forces you to ideate beyond your default life path. You sketch out Plan #1 as if you continue on your current trajectory (but add all the improvements and bucket-list items you can). Plan #2 assumes your current career or gig suddenly disappears – what would you do next? And Plan #3 is the wild card: what you’d pursue if money or image were no object.

When I did this, it was incredibly fun and eye-opening. I drafted one scenario where I climb the ladder in my field and become an expert (my “current path” plus enhancements). Then another where I completely switch gears to work in outdoor education (the thing I’d do if my main career evaporated). And a wild-card plan where I move to a small town and start a bed-and-breakfast business with a friend. Laying these out side by side, I realised all three futures appealed to me in different ways – and none of them was terrible or life-ending. It drove home the book’s point: there’s more than one “you” possible, and more than one way to live a satisfying life. This took a lot of pressure off trying to find the perfect path. Interestingly, after sharing these Odyssey Plans with a mentor (as the book suggests), I also noticed common themes across them – clues to what I really value. Whether I was a corporate expert or a teacher or an entrepreneur, in each plan I had elements of creativity and mentoring others. That insight helped me refine my direction no matter which path I pursue. The three-path exercise showed me that life is not a single-track railroad; it’s more like a garden with multiple pathways, and you get to explore more than one if you want.

Idea 5: Prototype and Experiment (Try Stuff!)

If Odyssey Plans are the big picture brainstorming, prototyping is how you start testing those ideas in the real world. This is perhaps the most actionable (and relieving) part of the whole approach: you don’t have to commit 100% to a huge life change to see if it’s right for you – you can experiment first. A prototype in life design is a small, low-risk experiment to gather information. There are two flavours the book talks about. First is the prototype conversation: find someone who’s doing what you think you might want to do, and talk to them. Basically, ask them about their story – how they got there, what their day-to-day is like. This kind of informal interview can give you a realistic sense of that line of work or lifestyle. I tried this when I was curious about moving into nonprofit work; I reached out to a family friend who’d done it and had a frank chat. She graciously shared not just the positives but also the tough realities. I walked away with a clearer head – in this case, realising the nonprofit path wouldn’t fit the things I most enjoy doing (at least not in the way I imagined).

The second type is the prototype experience: a way to actually taste-test the new life in a small way. This could mean volunteering, taking a short course, shadowing someone, or doing a side project. For example, when I fantasized about starting a little online business, my prototype was simple: set up a one-week Etsy shop for a few handmade items just to see how I felt running it. That trial run was illuminating (I learned I loved designing products but hated dealing with shipping logistics!). The point is, prototypes give you data. It’s basically the scientific method applied to your life: you have a hypothesis (“I might like this”), you run a small experiment, and you learn from the outcome. Sometimes the experiment confirms your interest – great, you take another step in that direction. Sometimes it saves you from a big mistake – also great, now you can course-correct without having invested everything. Since adopting this prototype mindset, I feel way less anxious about making changes. I know I can try before I buy in a sense. And honestly, it makes life more playful. Even if an experiment doesn’t lead to a new career, it’s still an experience and a story. As the authors sum it up, “get curious, talk to people, try stuff, and tell your story” – that’s how you design a well-lived life.

🧾 Life Design Lab

Together, these ideas form a toolkit for continual life design. What I love about Designing Your Life is that it’s not a one-time solution or a rigid plan; it’s a repeating process you can use anytime you’re facing a decision or feeling stuck. In fact, I’ve incorporated these principles into a kind of personal “life design lab” for myself. I periodically sit down to review my current situation (empathize/accept), brainstorm new ideas for the future, and then choose some small experiments to try next. It’s an ongoing cycle: imagine possibilities, try them out, learn, and adjust. Instead of a traditional goal checklist, I have a more flexible Life Design Canvas where I keep track of my Odyssey Plans and prototype ideas. This keeps me accountable to actually do the experiments and reminds me that I always have alternatives – I’m never really “stuck” because I can design my way forward.

Why use a design-thinking approach for your life?

• It breaks the paralysis. Knowing I can try multiple paths removes the pressure to pick the “perfect” one. There’s less fretting and more doing, which ultimately creates momentum.
• It’s adaptable and forgiving. Life isn’t static, and our interests can change. The design method lets me pivot gracefully. If an experiment doesn’t pan out, it’s not a failure – it’s valuable data for the next iteration.
• It keeps curiosity and fun at the forefront. Viewing my life as a series of experiments turns even challenges into opportunities for discovery. It brings a sense of play and creativity to career planning that I never had before.

In short, Designing Your Life gave me a framework to approach my life proactively and creatively. I’m no longer waiting for “answers” to magically appear or trying to think my way into certainty. Instead, I’m out there testing ideas in small ways and evolving my life’s design as I go. It’s comforting to know that this is a practice, not a destination – I can come back to it anytime I need, whether I’m present to a new challenge or just ready for another refresh. (If you’re curious about the template I use to plan my Odyssey Plans and experiments, check it out here.)

💠 Connecting the Dots

• How Will You Measure Your Life (Clayton M. Christensen): A great complement to Designing Your Life on the philosophical side. Christensen (a Harvard Business professor) urges you to define what success and happiness mean for you in the long run. It’s less about design methods and more about ensuring you’re pursuing the right things – so that the life you design is truly meaningful, not just impressive on paper.
• Mindset (Carol Dweck): A psychology book that dives into the power of a growth mindset. Dweck’s research shows that believing you can grow and learn from failures makes a huge difference in achievement. This pairs well with life design, which is all about embracing experimentation. If you adopt a growth mindset, you’ll approach those prototype failures or detours as learning opportunities rather than proof that you’re not “good enough.” It’s the perfect antidote for overthinkers who equate trying something new with risking their identity – instead, you start seeing yourself as adaptable and capable of change.
• Other frameworks: The Designing Your Life approach plays nicely with other self-discovery tools. For example, the Japanese concept of Ikigai (finding the intersection of what you love, what you’re good at, what the world needs, and what can pay you) can provide inspiration or direction when you’re ideating your possible futures. Similarly, the classic “What Color Is Your Parachute?” workbook offers time-tested exercises for exploring your strengths and interests – think of it as old-school career design that can feed into your Odyssey Plans. While these frameworks aren’t as action-oriented as design thinking, they can spark ideas and reflections that you later prototype in real life. Combining introspection (Ikigai, Parachute, personal values exercises) with the Designing Your Life method (try stuff, talk to people) creates a powerful one-two punch: you generate thoughtful possibilities and you have a way to test them out.