12 books to transform who you are, what you do & how you do it

What do you want to be? Who do you want to be?
More importantly, what do you want to do?

What do you want to do with your life, your business, your spare time, your body, your mind?

I’ve been thinking about this recently, trying to put it into some kind of order that makes sense, going through my bookshelves as I unpack after a recent move to a new apartment.

Here’s what I want to do. I’ve put together a monthly reading plan for the next 12 months that covers improving who you are as a person and an entrepreneur, and I honestly believe that if you follow it, you’ll be able to see some massive progress.

These are all books from my personal collection, and I’ve read and loved every single one of them. I’m doing this in 2 parts, because a few folks have told me that the longer posts here can be a bit overwhelming and tough to get through when they’re pressed for time. The next part will come out next week 🙂


Month 1. Courage.

Courage is the hardest thing to cultivate, and the hardest thing to lose once you have it. Courage makes the world go around a lot more than money every has, ever will, ever could. Courage is what makes great things happen, and stops terrible things from destroying everything else that we’ve built.

This month’s book — The Fellowship of the Ring, by J.R.R Tolkien

This was my first ever introduction to the truly inspiring power of courage. The courage that everyone shows in this book is breathtaking, and the words are so beautifully written. I couldn’t think of a better place to start.

Month 2. Productivity.

Being productive, wow that’s a real rabbit hole. You can spend so much time trying to be productive that you become less productive than ever before. But if you really want to do stuff, accomplish anything, make changes, shake the foundations, you’ll need to look at the tools and systems you use to get there.

This month’s book — Tools of Titans by Tim Ferris

This one is incredible. You can dive in just about anywhere, without trying to drag yourself through the whole book, and just find value on almost every single page. Mine used to have normal paper pages. It now has fluoro yellow pages because of how much of the book I’ve highlighted.

Month 3. Love.

Love is the most important part of your life. Don’t believe me? Wait until your life is almost over. Then we’ll talk. I’ve spent a lot of time worrying about a lot of things that don’t matter too much, and I’m only now working on spending more time and energy on love. Love for my family, my friends, the people who matter.

This month’s book — On Living, by Kerry Egan

Kerry Egan is a hospice chaplain, and in this book, she talks about the stories that her patients told her about their lives and values when they were at the end of the journeys. It’s about the importance of family and — yes — the vital importance of love.

Month 4. Your space.

We often fail to think about the way our own personal space affects our lives, but it does. The space we live in affects the decisions we make, the actions we take, the people we spend time with, the food we eat, the businesses we start, the jobs we take and turn down, the way we feel, the way we sleep, the time we wake up…its impact is truly massive.

This month’s book — Creative Space by Francesca Gavin

I bought this book years ago, when I was going through one of my poorer stages. Buying this book was going to cost me food money for a week, so I sold a bunch of my CDs to pay for it — largely because I knew I needed to change my living space and the energy that existed in it. It’s a book touring the studios and apartments of artists, designers, innovators and creative people, and it will inspire you to change your living space.

Month 5. Complications.

I know you won’t have to be told that life is complicated. But it’s worth remembering, all the same. Life is so full of grey areas, things we don’t understand, things we can’t understand, things that seem to exist outside of our reality in some way. The best example of this is often family. Your family will never be straight down the line, in black and white. There are shades of your past, and your sorrows and your joys that would exhaust the entire pantone collection of greys.

This month’s book — Fun Home by Alison Bechdel

This is my favourite graphic novel of all time. It’s Bechdel’s work about her Father and her family growing up, about his sexuality and how it impacted hers, about his choices and what they meant. It’s heartbreaking, funny, and a thorough exploration of the grey areas and complications of life.

Month 6. Business.

C’mon. I wouldn’t be me, if I wasn’t talking about entrepreneurship. I believe that starting a business — even a tiny little side business that just makes enough money every month to cover your social life or save a little extra — is something everyone should do.

This month’s book — The $100 Startup by Chris Guillebeau

I recommend this book all the time. I recommend it so much, I don’t even have to Google how to spell Chris’ last name anymore (sorry Chris Guillebeau). It’s a book about how to start a small business. A small business that can grow, or stay small, and can make money and make you feel empowered. It’s an incredible book.

Taking some old advice

Go to the profile of Jake Knapp

Today I’m leaving my job as design partner at Google Ventures. Instead of another full-time job, I’m focusing my energy on writing. I have about twelve books in mind, including some nerdy fiction. And I’m gonna go for it.

I’m typing this post to explain my decision to everybody, and also — because writing helps me think — to explain it to myself.

First, am I sure I want to leave? After all, this is my dream job. Over the last decade at Google and GV, I’ve had an absurdly great opportunity to experiment with my design sprint process and work alongside super cool startups. My colleagues are some of my closest friends. I can’t lie, walking away is painful.

But I’m not giving up this line of work altogether. I love running workshops and sprints. Honestly, I gather a lot of energy from it, so I can’t give it up. I’ll still advise startups on the side — but I’m putting writing first, rather than squeezing it in on the sides.

For years, I’ve done the bulk of my writing on weekends, late nights, and vacations. Last year, I published my first book. But check this out: I’ve been working on an adventure novel for seven years. Seven years! Why isn’t it done yet? Because I’ve been waiting for someday. I’ll have a little more time someday. I’ll finish it someday. And boy, will it be great. Someday.

Well, I’m done waiting for someday. Instead, I’m taking some old advice from my mom and dad.

In 1979, when I was about 2 years old, my family left Seattle for a small island in the northwest corner of Washington State. My parents had always wanted to live on a farm someday, and they decided to go for it.

They had seven kids and zero income lined up. Neither my mom nor dad actually knew how to farm, and they weren’t sure how they’d make ends meet (spoiler: not by farming). It didn’t make sense, but they had to do it. They wanted to make better use of their time on earth, and decided to pursue their crazy hippy dream.

It didn’t turn out to be a hippy dream. My dad had been a lawyer in Seattle, and he ended up taking a job as the local prosecuting attorney. My mom went back to school and became the high school English teacher. But they did get to do what they loved: feed animals, mend fences, and be part of a small town.

Growing up, I never totally understood that move. But now, I think I do. I have kids—only two of them, but they’re good ones—and I find myself telling them “take risks, find what’s true for you, don’t take the easy path.” But how can I tell them that if I don’t do it myself? If I want to write, but I don’t because I have to give up something great, how can I ever honestly ask them to take a chance?

A little over a year ago, my father died. I think about him every day. It’s been long enough I suppose I should be over it, but I’m not. I want to call him and talk things over. I want to hear his advice.

It was Alzheimer’s that got him. He was 85 when he passed away, but really started to decline around 80. As I type this, I’m 39 years old, and it’s hard for me not to think mid-life crisis thoughts. If I’m on his timeline, I’ve got 40 bucks in my pocket, and I’ve gotta think hard about how I spend each one. What am I gonna do with 2017? Buy another great year like the last five at GV or the last ten at Google? Or try something a little crazy?

If I could call my dad, I know what he’d say. If I was giving the advice to my boys, I know what I’d say:

Follow your heart. Do it, even if it doesn’t 100% make sense. It might not work out exactly how you imagine, but it’s probably less risky than you think. And either way, you’ll learn something.

So, okay. I hear you, dad.

Here goes.

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