Designing Your Life: Lessons from a Favourite Book

Okay, we are three months into 2025 and maybe you're avoiding that vision board, feeling like you haven't made much progress. Sometimes, the space between planning and implementation can get murky or maybe you DO start and the world is just not playing along. One of the best books I discovered a few years ago is ‘Designing Your Life: How to Build a Well-Lived, Joyful Life’ by Bill Burnett and Dave Evans. Why? 

Burnett and Evans are engineers who have adapted product design methodology to life planning, which then became a popular Life Design course at Stanford University and eventually, this book. The design process has various stages, but the one I go back to every year is Chapter 5, on ideation and charting/ideating possible pathways for the different lives you could lead.

From a design perspective, they write: “So Many Lives, So Little Time: One of the most powerful ways to design your life is to design your lives. 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…because life is an odyssey – an adventurous journey into the future with hopes and goals, helpers, lovers and antagonists, unknowns and serendipities. This exercise will help you imagine multiple ways you could launch the next chapter of your life’s journey – your quest’. 

Here’s what that looks like in reality: 

Choose three different goals/plans (alternative versions of you) for the next five years. 

- Life One is centered on what you already have in mind, either your current life expanded or a hot idea you've always wanted to try. Life Two is the thing you’d do if Life One were suddenly not feasible for whatever reason. Life Three is the thing you would do or the life you’d live if money or image were no object. 

- Each life must include a visual or graphic timeline - stick men are fine, it only needs to make sense to you. 

- Create a 6-word title for each alternative life option. This is to personalise these lives so you can better imagine yourself living them. 

- Seek the questions that this alternative life is asking, to test (your) assumptions and reveal new insights between what you think it should take to get there and more creative ways to get there. 

- Create a dashboard to gauge resources (time, money, skill, contacts) to pull this off. (There is a LOT more stuff on the dashboard - see Image 2 below). 

This post was sparked by a friend agonising over having to choose between two different roles in her company. The money would be the same for both roles, the day-to-day tasks would not, and each role represents a different career path beyond the company. One role would enhance her current skillset, the other would take her into a new sector. I referred her to this book and exercise. 

Perhaps you’re at a juncture right now wondering what to do next? Instead of drowning in anxiety and choosing from a place of fear: get some coloured pens and paper and have some fun with your future. The best life might be one you haven’t even considered yet.

Lenina Rassool is a journalist from Cape Town, South Africa. She has worked for mainstream publications such as Femina and Cosmopolitan Magazines and has spent the past five years producing and presenting The Womxn Show, a TV show on gender-based violence, funded by the Ford Foundation.