How to use design thinking to robot-proof your career

I came across a book called Design Your Life. Design thinking is extremely influential in the Silicon Valley. Authors of the book, Bill Burnett, and Dave Evans, are both professors of the famous Stanford They asked this question:

How to apply design thinking to build a joyful, fulfilled life?

What is Design Thinking? If you have heard about iterating, prototyping, failing fast and failing often, then you got a fairly good idea of what design thinking means. Startups use this methodology to make sure they design products that customers want to buy in real life. They talk to potential customers to understand their needs; quickly redesigning products and getting customers' feedback. They keep going until they hit on a version that resonates with their potential customers.

This is all great, but I can't help thinking. How can Design Thinking help us robot-proof our career?

There are many junctions in our life where we have to figure out what kind of career we want to be in. It happens when we graduate from college, but it doesn't stop there. We get laid off. We want to do something we are passionate about. We want time with our family.

While we know our talent and passion, we are not exactly sure who will be interested in us. The result? We keep doing what we did in the past, even though it doesn't feel exactly right.

That is where Design Thinking can help.

Design Thinking helps you visualize various possibilities for your life and career.

Design Thinking gives you guidance on how to take small and meaningful steps to test out your career idea by talking to people in the real world.

Design Thinking helps us dream big AND 100% grounded in reality.

Design Thinking is about changing our mindset and the way we view our career as a journey. Here are a few ideas for us to get started today!

1. Stop believing there is one perfect career for our whole life

My father and my uncle both quitted their high paying jobs to start new careers in their 40s.

Aren't we suppose to choose and stay in one career for our whole life? I thought my family was weird.

Bill Burnett points out a (depressing) point in this book. As we live longer, we also work longer. In our 40-50 year career span, we will have at least 2-3 radically different careers.

President Reagan was a famous actor before he became President of the United States. Bill Gates was a CEO before he ran the largest Foundation to give back to the community. Martha Stewart was a stockbroker before she started her beauty-home media empire.

My family history turned out to be the norm, not the exception.

2. Not all your dreams can come true. And it's ok.


Happiness Expert Dan Gilbert, who also happens to be a Professor of psychology at Harvard, found a surprising result on our ability to predict what makes us happy.

The result? We are fairly lousy, and our assumptions about what will make us happy in the future are often wrong. It seems counter-intuitive, especially in our culture where we encourage everyone to dream big and conquer the world.

What he found out is that we always misjudge how we will feel in the future because we forget that the "us" in 2022 is different from the "us" in 2017. If there's no one perfect career, that also means not all our dreams could or should come true.

A couple of weeks ago, I somehow got the idea that eating three croissants in a row will make me very happy, and I went ahead and did that. Needless to say, I felt sick on the train ride home that evening.

Dan is right. I am terrible in predicting what makes me happy.

3. Think big and take small steps


Positive thinking has been huge in the past few years. We were told that by visualizing our success - getting that dream job, dating that dream girl - will motivate us to move closer to our goal.

Professor Gabriela Oettingen at the NYU took this idea for a test, and her research was surprising.

She found out that dreaming about the awesome future often makes us paralyzed with fear and unable to move. Luckily, she has an antidote: we should WOOP our life.


To put it simply, on top of dreaming big, we should also plan some concrete steps that we can take within the next 2-3 weeks to move us closer to the dream. We should also continue to learn, change and plan every 2-3 weeks. That sounds like iterating our life to me!

Lesson 3: While I cannot predict how to compete with robots of the future, yet, I can use design thinking and WOOP my career continuously to get ahead of the curve.