Contextual Book Recommendations 2020

Contextual Book Recommendations 2020

Recommendations based on what you’re in the mood for!

Most book recommendations are along the lines of ‘If you liked (book 1), you will like (book 2)’ or ‘this was a very well written book’. This is a perfectly good way to recommend books, but I also think the books people enjoy reading depends on what sort of mood/state of life they are in. In that spirit, here are my 8 contextual book recommendations for this year! I’ve also tried to grab my favorite snips from the books so you can sample them as you read this post. Happy reading for the rest of the year! Let’s get started.


If you do any kind of creative work & have a couple of hours to kill, read Show Your Work by Austin Kleon

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An alternative, if you will, to self-promotion. I’m going to try to teach you how to think about your work as a never-ending process, how to share your process in a way that attracts people who might be interested in what you do, and how to deal with the ups and downs of putting yourself and your work out in the world.

I picked up this book on a Wednesday at 3pm and couldn’t out it away until I was done 2 hours later. This will change how you view your creative work and how you share it.

If you’re looking to read real, interesting, heart warming behind-the-scenes stories from the biggest businesses in the world, read…

Ride of a Lifetime by Bob Iger

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Don’t let ambition get ahead of opportunity. By fixating on a future job or project, you become impatient with where you are. You don’t tend enough to the responsibilities you do have, and so ambition can become counterproductive. It’s important to know how to find the balance—do the job you have well; be patient; look for opportunities to pitch in and expand and grow; and make yourself one of the people, through attitude and energy and focus, whom your bosses feel they have to turn to when an opportunity arises.

Can’t say enough nice things about the stories from this book. This isn’t a book about a business or advice, it’s a lot more valuable than that.

…or Shoe Dog by Phil Knight

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Just before getting on the plane home we signed deals with two Chinese factories, and officially became the first American shoemaker in twenty-five years to be allowed to do business in China. It seems wrong to call it “business.” It seems wrong to throw all those hectic days and sleepless nights, all those magnificent triumphs and desperate struggles, under that bland, generic banner: business. What we were doing felt like so much more. Each new day brought fifty new problems, fifty tough decisions that needed to be made, right now, and we were always acutely aware that one rash move, one wrong decision could be the end. The margin for error was forever getting narrower, while the stakes were forever creeping higher—and none of us wavered in the belief that “stakes” didn’t mean “money.” For some, I realize, business is the all-out pursuit of profits, period, full stop, but for us business was no more about making money than being human is about making blood. Yes, the human body needs blood. It needs to manufacture red and white cells and platelets and redistribute them evenly, smoothly, to all the right places, on time, or else. But that day-to-day business of the human body isn’t our mission as human beings. It’s a basic process that enables our higher aims, and life always strives to transcend the basic processes of living—and at some point in the late 1970s, I did, too. I redefined winning, expanded it beyond my original definition of not losing, of merely staying alive. That was no longer enough to sustain me, or my company. We wanted, as all great businesses do, to create, to contribute, and we dared to say so aloud. When you make something, when you improve something, when you deliver something, when you add some new thing or service to the lives of strangers, making them happier, or healthier, or safer, or better, and when you do it all crisply and efficiently, smartly, the way everything should be done but so seldom is—you’re participating more fully in the whole grand human drama. More than simply alive, you’re helping others to live more fully, and if that’s business, all right, call me a businessman.

Possibly the one book that I would recommend you read no matter what. I struggled to pick one single highlight to include from this book, but the one above only does partial justice to the story of how Nike came to be.

If you have just graduated from college/if you’re starting a new job/if you’re generally confused about the ‘what do I do with my life’ question, read Designing Your Life by Bill Burnett and Dave Evans

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We all know how to worry about our lives. Analyze our lives. Even speculate about our lives. Worry, analysis, and speculation are not our best discovery tools, and most of us have, at one time or another, gotten incredibly lost and confused using them. They tend to keep us spinning in circles and spending weeks, months, or years sitting on that couch (or at a desk, or in a relationship) trying to figure out what to do next. It’s as if life were this great big DIY project, but only a select few actually got the instruction manual. This is not designing your life. This is obsessing about your life. We’re here to change that.

Even if you already have most of the insights this book talks about, some of the exercises and insights will be new to you.

If you’re in the mood for a fuzzy, cute, romantic-comedy, read…

The Rosie Project by Don Tillman

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Amazing. She retains a professor of genetics, an alien of extraordinary abilities, to help find her father, she travels for a week, spending almost every minute of the waking day with him, yet when she wants the answer to a question on genetics, she goes to the Internet.

…or Eleanor Oliphant is Completely Fine by Gail Honeyman

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Eleanor, I said to myself, sometimes you’re too quick to judge people. There are all kinds of reasons why they might not look like the kind of person you’d want to sit next to on a bus, but you can’t sum someone up in a ten-second glance. That’s simply not enough time. The way you try not to sit next to fat people, for example. There’s nothing wrong with being overweight, is there? They could be eating because they’re sad, the same way you used to drink vodka. They could have had parents who never taught them how to cook or eat healthily. They could be disabled and unable to exercise, or else they could have an illness that contributes to weight gain despite their best efforts. You just don’t know, Eleanor, I said to myself.

There are 2 kinds of people on this planet. People who enjoy the warm, fuzzy feeling that good romantic comedies give them, and liars. These books are just as good as they are advertised to be. Recommend!

If you’re in any engineering job (especially software engineering) OR if you’re simply trying to change how you think about problems and solutions, read Pragmatic Thinking and Learning by Andy Hunt

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This book is different when compared to the others on this list. Written a lot more in a textbook-style format, this isn’t a book you binge or read passively. This is a book you have on your bookshelf and keep going back to until you’re able to internalize everything it talks about. I have a bunch of unfinished notes from this book if you prefer to get a taster for what it’s actually like. Email me if you’d like a pdf of the notes!

If you’re not the happiest about your day-to-day habits and want a no-nonsense self-help book, read Atomic Habits by James Clear

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You do not rise to the level of your goals. You fall to the level of your system

The only real self-help book that I would recommend you read. Again, like any other self help book, this could have been much shorter, but James Clear keeps everthing concise and straight to the point. One of my favorites this year.


I hope you find some value in these recommendations. If you have any books that you would like to put on this list, let me know! As the recommendations keep coming in, I will include them below. Just make them contextual! For example, “if you < mood or life event or other context >, you should read < book name >”. I look forward to adding your recommendations in!

Happy reading!


See you next week for a new post!

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