Designing Your Life

Anya Ruvinskaya
6 min readFeb 15, 2021

I read Designing Your Life by Bill Burnett and Dave Evans. I don’t read many self-help type of books, especially don’t recommend many. This one is special for me. It resonated and I’ve actually recommended it to others. This book was suggested to me by a very good friend. I likely would never have picked it up if she didn’t suggest it to me. She also generally is not one for self-help books or recommending them to others but considered this one as one that can actually be useful based on where I was in my life at that point.

Photo by JOSHUA COLEMAN on Unsplash

I’ve been on an existential career search (and to find the meaning of life, the universe, and everything) for as long as I can remember. Particularly on the career front, I’ve obsessively explored options and contemplated different paths since my early 20s. This book helped me put some structure around this perpetual process as well as some more tactics to make me feel like it all may add up to something by matching it to my values and overall life view. Unexpectedly, it also helped me try out a new decision making approach. Decision making in my personal life from the many options I proactively pursue is something I struggle with (funny how much easier this is for me to do when it comes to product management aka work decision making).

The essence of the book is nicely summarized towards the end of it by letting us know there are five simple things we really need to do to design a well-lived life: (1) be curious, (2) try stuff, (3) reframe problems, (4) know it’s a process, and (5) ask for help.

Also, full disclosure: it took me nearly TWO YEARS to fully get through this book. I did take my time on and off with it as I was exploring (see my personal sabbatical story) and made sure to do all of the exercises suggested. Similarly to the happiness class, I think this book is only as good as the work you put into it. Doing the work is most definitely the hard part. Another piece of disclosure is this book may not resonate with everyone, depending on your circumstances. If you feel like you do not have many options in your life and you’re somewhat limited by your circumstances this book will likely either put you off or inspire you to think outside of the traditional constrained boxes. Thinking outside of your constraints is certainly more challenging if you have family or financial responsibilities and much easier if you have fancy degrees and savings to fall back on (wanted to make sure to acknowledge this).

Notes

We tend to start all of our life design brainstorms with the phrase “How many ways can we think of to…” to make sure that we haven’t limited our potential output.

A question/technique to try when trying to think outside of the box and brainstorm some ideas and options for yourself. I loved getting uncomfortable and trying out all of the design exercises mentioned in the book to get more creative like brain mapping, sketching, etc.

Positive psychology tells us that happiness is context-dependent, so, without a context — such as “my work” or “my social life” — no one knows where to start.

I’ve often had the problem of knowing where to start and asking myself too-big and too-general questions such as “what will make me happy?” and “what is my purpose?.” Introducing some context and constraints to those questions helped me attack them and feel like they were more manageable.

Balance is a myth, and it causes a lot of grief and heartache for most of us.

This one was tough to read. I talk about balance all the time. I’m still torn on this one.

There is no perfect job that you perfectly fit, but you can make lots of jobs perfect enough.

The concept of “good enough” is something I’m really trying to champion in myself.

Dysfunctional Belief: I am looking for a job.

Reframe: I am pursuing a number of offers.

I loved this reframe! Such a simple way to flip what has been engrained in our heads. Job seekers do not necessarily have the short end of the stick!

Designing a career and a life requires not only that you have lots of options and good alternatives, as we have discussed; it also requires the ability to make good choices and live into those choices with confidence, which means you accept them and don’t second-guess yourself.

Making good enough decisions efficiently in my personal life and letting go of the rest is a big challenge for me. More on this below.

In life design, being happy means you choose happiness.

The secret to happiness in life design isn’t making the right choice; it’s learning to choose well. It’s about how you choose and how you live your choices once they’re made.

Dysfunctional Belief: To be happy, I have to make the right choice.

Reframe: There is no right choice — only good choosing.

There is a better way to make decisions, being in anguish over choosing an option is not the only way. There is a four-step process described in the book:

Step 1: Gather and Create Options (approach with a bias to action versus overthinking)

Step 2: Narrow Down the List (we make our best choices when choosing between only three to five options)

You really can’t lose when you’re shortening your list of options. If you cross out the wrong ones, you’ll know afterward. You may have to go as far as crossing out seven of the twelve and rewriting that new, clean list of just five before you realize it, but if it’s wrong, you’ll know. Trust us when we tell you that you can trust yourself.

What I also found fascinating and a good reminder is that once you’ve managed to narrow down the list to 3–5 good options, you can’t lose. At this point any choice will be a good choice, so in a way, step 3 below is extra credit!

Step 3: Choose Discerningly

The part of the brain that is working to help us make our best choices is in the basal ganglia. It’s part of the ancient base brain, and as such does not have connections to our verbal centers, so it does not communicate in words. It communicates in feelings and via connections to the intestines — those good old gut feelings. In order to make a good decision, we need access to our feelings and gut reactions to the alternatives.

Invest in cultivating this gut intuition continuously, it will serve you well over your lifetime. Practices that help you cultivate this are things like yoga, meditation, poetry writing/reading, journaling, prayer, etc (I’ve been trying to focus on mediation and would like to also cultivate a practice that incorporates some physical movement as well). The book actually said investing in this is the most important recommendation they can give to sustain a well-designed life. I agree with the authors that this is an area of weakness especially in modern western society.

Step 4: A̶g̶o̶n̶i̶z̶e̶ Let Go and Move On

Reversibility is not conducive to establishing reliable happiness with a decision. Apparently, just the invitation to reconsider and “keep your options open” makes us doubt and devalue our choice. So let’s get better and better at building by getting better and better at letting go of the options we don’t need any longer. This is key to choosing happiness and being happy with our choices. When in doubt…let go and move on. It really is that simple.

Get off the hamster wheel. The choice that you made is the right choice. I loved the suggestion to make a journal entry about your decision, and re-read it when you get confused.

Dysfunctional Belief: We judge our life by the outcome.

Reframe: Life is a process, not an outcome.

Once you become a life designing person and are living the ongoing creative process of life design, you can’t fail; you can only be making progress and learning from the different kinds of experiences that failure and success both have to offer.

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

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Anya Ruvinskaya

personal: curious, exploring outside & in — professional: tech, product.