Design Your Life with Design Thinking

“Fail often so you can succeed sooner”

“Enlightened trial and error succeeds over the planning of the lone genius”

These are a couple of quotes out of a company called IDEO.  When I was an engineering student, I saw a then revolutionary ABC Nightline special about IDEO where they redesigned the common shopping cart in 5 days through the radical approach of using empathy to understand the customer and rapidly iterate to a meaningful product. I was hooked and decided that this is what I wanted to do in my career. 

Fast forward 20 years later and IDEO has been responsible for billions of dollars of created value, design thinking has become standard for pretty much anyone involved in creating new products or services, and an entire school at Stanford has been created around design thinking. 

As an engineer and innovation leader, I have spent 15 years in a career focused on new product development and can accurately call myself an inventor with over a dozen patents to my name.  In fact, I think that I am going to start wearing a button at all times shaped like a gold star with the word inventor written on it in impressive gothic font.  Entirely by serendipity I’ve also had the opportunity to attend a mini design thinking program at Stanford’s D-School, tour IDEO and meet Dave and Tom Kelley who I saw in that Nightline special back as an undergraduate.  With humility and gratitude, this kind of felt full circle for me.  For those interested in understanding a bit more about design thinking, Stanford offers some cool free resources.

Designing Your Life: the book  

As I decided to live my life outside the maze and began what I think of as this newest chapter in my life, a colleague of mine recommended a book called Designing Your Life.  It is the result of a couple of professors realizing that perhaps the biggest challenge facing their students was “What  do I do with my life?”  The professors thought, what if we took the innovation methodology that is design thinking and applied it to help answer this question?  There is a pretty good Ted talk by one of the authors of the book if you are into Ted talks:  

Based on my background, I decided that I would be a fool to ignore this book.  As a long time design thinker with a new passion for lifestyle design, it seemed a perfect fit.  I want to share a few takeaways that resonated with me from the book and also share some of my thoughts on how one designs a good life.  These are my unsponsored thoughts and opinions alone. There will be no affiliate links.

Overview: Designing Your Life

I found this a worthwhile and very fast read.  For anyone with design thinking experience, this book will immediately make sense.  It takes something that you already understand as powerful for solving open ended and wicked problems and applies it to building a well lived joyful life.  The diagram below illustrates my interpretation of the first half of this book. The first figure is the stages of design thinking and the second figure is my interpretation of how the listed sections of this book adapt design thinking to designing one’s life:

The first 5 chapters each include an exercise and build on each other toward laying out a life design as shown in the diagram above.  The progression starts with a self assessment of where you are at and identifying your personal life view and work view.  From there, one is asked to keep a journal over a period of time evaluating how energizing each of various tasks are and how engaged or in the flow each activity makes you feel.  Like spending time living with your customer, these exercises are a way to uncover insights since you yourself are the customer in your own life design.  Next, the book covers some brainstorming and mind mapping methodologies to ideate about your life.  It also helps those that feel stuck in a rut with some reframing exercises.  The 5th chapter of the book was the most fun for me and the most informative for how I may live my life outside the maze going forward.  In it 3 possible life plans are created.  Why three you ask?  The book actually cites research that indicates that 3 parallel plans iterated to a 4th is more effective than coming up with one plan and iterating 3 times to a fourth.  I do love research. Each 5 year plan has questions associated that need to be answered and the next chapter covers prototyping those questions because as any design thinker knows, prototypes are rough tools for empathy to answer a question on a design.  In this case, the prototyping comes in the form of prototype experiences, prototype interviews, and additional brainstorming.

From the midpoint forward, the book changes.  The last half of the book devotes a couple of chapters to finding a job and building a career, a chapter to choosing a path without agonizing, one to becoming immune to failure by the way you use it for good, and then one around building a team.

Designing Your Life: The Good

As the book points out, we are often told to discover our passion and once that is done then one can move forward with creating a good life.  Worse, many of us operate under the assumption that if you are “successful” compared to your peers, then you will be happy.  With something as open ended and nebulous as designing your life, this book has a number of useful exercises that provide insight and help one ideate and prototype her life.  For me, this alone was worth the price of buying as well as the time spent reading this book.  It also has a number of reframes and exercises to get the stuck unstuck.  I think the authors correctly understand that many of their readers are intelligent and perhaps slightly neurotic about making mistakes.  Many of us also suffer from FOMO since you only live once (unless you are Hindu or Buddhist).  The “Getting “Unstuck” “Choosing Happiness” and “Failure Immunity” chapters are particularly geared toward these readers. 

Designing Your Life: The Bad 

The book kind of feels like the first half was written very process oriented while the 2nd half is a little bit more off the cuff.  While I found the first 5-6 chapters providing immediate insights, building on each other, and informing some fabulous options for my life, the 2nd half feels a bit less cohesive.  There is a chapter about how not to get a job and a chapter about building your dream job.  Both feel pretty spot on correct to me but seemed a little bit shoe horned in there.  As someone who has hired many and created a career of satisfying employment, these chapters were less helpful to me.  They may be hugely valuable, however, to someone just leaving school and looking to build an amazing career.  Also, the last chapter on building your team for life design seemed a bit generic and tossed off including some well trodden basics on teams and mentors.    

Designing Your Life: Conclusions

Designing Your Life, is an effective book at providing insights into what you may want to do with life, then ideating, prototyping, and testing to move you forward on the path. This is no easy feat.  It also understands the things that many of us get stuck on and provides some help there as well. As a young engineer I learned that design thinking is an iterative process of the 5 steps shown in the diagram above.  It keeps going over a product’s lifecycle.  Thus it should come as no surprise that Life Design is the same.  To quote the book:

“Designing your life is actually what life is, because life is a process, not an outcome.” 

“When you remember that you are always playing the infinite game of becoming more and more yourself and designing how to express the amazingness of you into the world, you can’t fail.”

My Advice on Designing Your Life

I called this site “Life Outside The Maze” because it is about an escape toward freedom.  For me this was initially financial freedom that allowed me to stop working for other people’s agendas to get financial security and start working for myself to have a happy and joyful life.  From this vantage point, I see that we are often so busy evaluating and manipulating the outside world for our benefit that our knowledge of ourselves is actually quite limited to stimulus and response.  I am angry, tired, nervous, etc.  However, life design starts with looking inward at your values.  What is based on habits of who you were in the past as opposed to who you are today and what you aspire toward going forward?  What in your life feels neglected?  Journalling and mindfulness exercises have helped me to see patterns in my behavior that I did not when I was going 1000 miles per hour on stimulus and response.  This helps one to understand better the types of things that would energize you or put you in a flow state as well as the types of endeavors that will prove meaningful based on your values.  My advice is to use the resources on this site and others to get on a financial plan that is sound and gives you certainty that you will get to financial independence rather than living and working on stimulus and response.  Leverage this empowerment to actively design your life.

If there are things that you have always said that you are going to do, it is worth asking why you have not done them. Some may be unrealistic. If you want the body of a Hemsworth brother but are actually not willing to do the diet and workout necessary, it may be worth making peace with that. For those that remain on your list, it is worth including the ones that stand up to your own scrutiny no matter how stupid or weird they may appear to others. It is worth doing these things as soon as you can fit them into your broader plan. None of us knows how long that our lives will be. I am making it a personal goal to ask the question of whether I would regret not doing something on my death bed. If the answer is yes, I work that thing into my life plan as soon as I can. Why wait, why risk regret, and why not live a life that I have designed based on a deep dive inside myself. Over time some things will fall in importance and maybe fall away while others will emerge. Doing this iteratively over a life is successful life design to me.

If you have read other books that you feel are useful in designing one’s life please share in the comments below. I would love to read them! Also, if you’ve read this book and want to offer another opinion, have a question, or just want to join the conversation please do below!