Reconsidering the Future:
What Happened When I Put Designing Your Life to Work for Me

by Jennifer Ridgway

Over the last few decades there has been a big shift in the typical career trajectory. While people used to get hired and stay with the same company until retirement, many of us not only switch companies several times, but also make a few career changes along the way. I, for example, began my post-collegiate career in technology sales, made a brief foray into politics, and then moved into publishing. With my most recent transition to stay-at-home mom, I also began freelance writing. Designing Your Life, by Bill Burnett and Dave Evans, dropped into my life at the perfect time. Now that my twins are in school, I’ve started thinking about my future: What could my work, and overall life, look like? Should I go back to a full-time job? If so, when? Do I want to stay in my previous industry? Would I rather try to ramp up my freelance writing, or would I want to try to focus more on volunteering? After reading great reviews of Designing Your Life and hearing about it from former colleagues, I decided to give it a read to see if it could help me answer some of these questions.

Burnett and Evans’s book is based on their popular Life Design course at Stanford, which began as a class for the Design School and has become a phenomenon throughout campus and beyond the university. Using the principles and philosophies applied to design (often called design thinking), Burnett and Evans charted out a program for how to reassess your life and move forward. Design thinking requires you to reframe how you define the problem and how you arrive at a possible solution; it means combining logic and imagination while also removing the filters you tend to put in place while problem-solving. They argue that this process helps us to overcome unconscious biases and think creatively.

Designing Your Life isn’t a simple self-help or career book filled with tips and tricks — it really is a full class in a book. What does this mean for the reader who wants to get the most out of it? It means you have to be ready to put in the thoughtfulness required and work through all of the exercises in the book, which are pulled from the Stanford course. Some of these exercises take ten minutes, such as the Health/Work/Play/Love Dashboard, which helps you realize where you are by assessing these four areas of your life on a quick scale. (Users learn that design thinking can help you to move forward from where you are, but you need to know where you are first to make that step!) And some of the exercises can take months, such as Prototyping, which includes things like brainstorming, interviewing people who are doing work you are interested in doing, and/or finding ways to actually experience the possibility you’re exploring (for example, through job shadowing). The prototyping process is crucial to helping you make an informed decision, just as it is in product design — you have to make a prototype of a chair to ensure it works as intended before releasing it to the wider public!

Designing Your Life spread

As I worked through Designing Your Life to clarify my future, I noticed that design thinking was a shift away from what I, and many others, have grown up thinking a career search should be. This re-think is empowering and can move you toward creating a life that is a great fit for you. Burnett and Evans also include helpful and specific information on how (and how not) to actually look for a job. They dig into how job descriptions are written, how to write your resume, and how many people really find a job off of the internet. They also give some tips for interviews and ideas on how to find jobs that aren’t posted.

One theme that runs throughout the book is that of changing your mindset. For example, when it comes to careers, we tend to think that we’ll be happy if we just find that “perfect” job. However, Designing Your Life will remind job-searchers that there’s no one right thing — at any given time there are multiple right jobs for you, and those roles may change as your life and priorities shift with time. Having this idea in mind, and knowing that I can find happiness in many different directions, made me feel less pressure to make the right decision. It also helped me to realize that I can still change my career at any point, and that I’m never done designing my life. You are never done designing your life either! It’s a constant project — as factors shift and change, you can, and should, always be thoughtfully designing your life.

Tips for Using Designing Your Life Effectively:

  1. Be prepared to put in the work. You cannot just read the book cover to cover and expect a change.
  2. Understand that this is a process. Going through all of the recommended actions and exercises in this book could take weeks or even months; don’t expect immediate change.
  3. Form a group. The authors suggest forming a small group to work through the book together. I didn’t do that, and I really wish I would have. Having insight from others who know me would have helped generate ideas as well as create a support structure to keep me motivated throughout the process.
  4. Be ready (or almost ready!) to actually make the change, or be willing to accept that you aren’t there yet. Unfortunately, this book wasn’t the book to help me decide whether or not I was ready to go back to work (can someone write that book for me?!), but it did help me recognize that there’s no one right answer, which is crucial. It also helped me in reevaluating what I actually value in my work, both at a high level and in the day-to-day tasks and responsibilities. When I am closer to being ready to make a change, I will pull this book off the shelf to walk through the exercises again and with even more thoughtfulness.