Designing Your Life

I spend an immense amount of my time reflecting, researching, reading, and stressing about what I want to do with my life. So it should come as no surprise that I’ve read almost every best-selling self-help book.

Are they helpful?

Mostly yes!

Has it made me a better person?

Not yet!

Contrary to popular belief, self-help books are not written by charlatans peddling snake oil. Many of the authors are psychologists with impressive academic pedigrees and a commitment to scientific methodologies, or tech entrepreneurs with enviable records of success in life and business.

Self-help books are not just about positive thinking. We can no longer ‘visualise’ our way to a better state of body or mind. Instead, we must chart our progress, count our steps, log our breathing, track our diets, record our negative thoughts—and then analyze the data, recalibrate, and repeat.

So when I picked up Designing your Life, a self-help book by Bill Burnett and Dave Evans, I didn’t expect the first question in the book to be:

“What do you want to do with your life?”

I felt like this question no longer applies to me.

Just a few years ago, the world seemed so big and full of exciting adventures. There were possibilities. I could do anything with my life.

Now, I feel like the more appropriate question is “what are you doing with your life?” and somehow this question seems so much more daunting because some days, what I’m doing with my life is eating cereal out of the box while watching an entire season of Queer eye on Netflix.

Still, I powered through (see my previous post on my obsession with completing tasks) and was pleasantly surprised with the results.

This book teaches us how to use design to figure out what we want to be when we grow up (both in its actual sense and a metaphorical one). It provides a step-by-step guide with activities to apply five design mind-sets (curiosity, bias to action, reframing, awareness, and radical collaboration) to build a life we love. (I’ll explain what these mean in a separate post)

Yes, the book assigns you homework!

I loved the emphasis on life as a work in progress instead of assuming that happiness and contentment can only be unlocked when we reach some final destination. If you’re one of those rare people who are 100% at peace with your life, enjoy your good fortune. But for the rest of us, our goals and paths keep changing – so applying design thinking to life planning was actually a very refreshing exercise.

There were tons of case studies and exercises on how to prototype our best life. But I’ll focus on the one that pushes us to build 3 potential lives (or futures) and assess them. Just as we would prototype a minimal viable product in a design thinking exercise, we need to test the potential lives through informational interviews and other techniques to try out the lives in a non-committal way.

I’ve been a Design Thinker for awhile, so the concepts here were not too foreign to me, but the application of them in my personal life very much was. Curiosity and prototyping are a crucial part of discovering what makes you happy in life. The prospect of pursuing as many different kinds of work simultaneously is great news for someone as fickle as I am, but also in line with what the future of work is inevitably going to look like.

I wish I had this book 10 years ago. That way, I’d have had a well-reasoned, systematic, and eminently practical approach to navigating the (ever-evolving) question of what I want to do with my life (and not become the neurotic mess that I am today).

The foundation of this book is about creating and evolving. The proposal is to place more effort in making choices that suit you as they offer greater potential for joy and sense of purpose than following a path created by someone else.

Sounds enticing? Let’s see if it actually works.

This is the first article in the series: The Hard doctrine of personal optimization – a comically committed exploration of current life-hacking wisdom in areas ranging from athletic and intellectual prowess to spirituality, creativity, wealth, and pleasure.

Stay tuned!

Photo by Daria Nepriakhina on Unsplash

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