Book Review: Derek Sivers - "How to Live"
BACKSTORY (Skip to Review)
When I got an email from Derek Sivers with the subject line “Early Access to My Next Book”, I expected it to be your typical Sivers email: not too long on content and getting straight to the point. And I was right. The first sentence he wrote was “Please don’t tell anyone”. He went on to say that the message was only for his private email list, and that he just finished the book three days prior. I don’t know how many people are on Sivers’ “private” email list, but it’s nice to know that I’m on it.
I consider Derek and myself "internet acquaintances". We’ve never met in person, but our relationship is far from unidirectional. He is the type of person that will respond to every single email or chat or ping he gets, and I am the type of person to try to engage with people who are interesting, regardless of their social status or career or celebrity or any of that. I have been having a back and forth with him through email for almost 18 years. It’s crazy to think it’s been that long. I forget the exact circumstances, but I published my first full length album in 2003 - and I remember getting an email from Derek himself, congratulating me on my first (CD Baby) release. If it was a boilerplate email, it definitely could’ve fooled me. It was written with such compassion and detail, and it was almost like he took a listen to my music and said “Hey man, I think this stuff’s pretty good; I think you’ve got a good future ahead of you”. Being the skeptic that I am, I replied to the email as if he were a colleague, chatting him up and asking all sorts of questions; not really expecting an answer. I asked him about CD Baby, how he got to where he was (in ’03), where he was headed, and other questions on business and life. He answered quickly and countered with more questions about my music and my life. This went back and forth for a couple weeks. It was good conversation and it wasn’t forced. It just seemed like two guys, talking about music, business, life and whatever else, and it was cool to be having casual conversation (through email) with the CEO of a successful and rapidly growing company.
Since that first exchange, I released four more albums between 2004 and 2007. Each time I paid my registration fee, bundled up my CDs, and sent them off to the Portland OR warehouse, I got another note from Mr. Sivers. And each email begat another period of interesting back and forth through email. I really felt like we were friends, even though I was sure that he treated every single customer this way. I just happened to be more talkative than others, probably. In 2008 I started working on my sixth album, and I was fortunate enough to have my Father help me mix it in a new, state of the art studio the two of us built together in his new house. I titled this album “Elderly Drop Off”, mostly for the fact that I got a killer album cover photo by sheer luck and that name pretty much “had to be”. The songs on the album were fitting though, and the album itself was unfortunately prescient. After finishing mixing, then going to mastering, then printing 1000 copies and sending a whole bunch off to CD Baby, I was in probably the best point in my life in my relationship with my Father. We had an insane multimedia production house ready to book clients and the sky was the limit. Literally days after, he was diagnosed with stage IV cancer; untreatable; no chance of survival; and he was dead in less than four months.
My world was shattered. I was existing in a dense fog; a hazy state of just moving in any direction I could to keep from having to face any emotion. Every minor inconvenience was a complete catastrophe. I remember there was some sort of problem with my new album at CD Baby - something about the discs not ripping to mp3s properly. It was a simple matter of having to get the replication house to reprint a thousand discs due to an error on their part, but it was a mountain of madness and meltdown in my eyes.
By that point I had Derek Sivers on speed dial (well, just his personal email address), so I emailed him asking to help me out. After 5+ years, I would usually just shoot him a personal note whenever I had an issue with CD baby. So I wrote him a very long, intricate message, not only stating what I needed him to do for me “as a favor” to fix my CD Baby issue, but also pages and pages of how much I was struggling, suffering, and just unable to cope with the reality of death.
He was slightly taken aback, because the first thing he said in his reply was “Dude, I don’t work there anymore, I sold the company last year!”. I was shocked. It was like my entire world was shattered by a sudden death, and NOW Derek Sivers is no longer with CD Baby. It seems sorta trivial looking back, but I was really, really upset at the fact. I was sure that it was going to turn into a faceless/heartless/soulless conglomerate carcinogen, and that dealing with them and the broader industry would become a complete nightmare. Even though I was totally right, it’s not as big a deal today as it seemed then.
But Derek took only one sentence to address his status with CD Baby. The rest of the email was carefully chosen words of comfort; metaphors and true life stories of consolation, and a message of hope. At the moment I cannot find this email, but I’m going to keep digging because I would love to read it again. I was in such a state of confusion, grief, and abandonment, that it took multiple reads to really receive his message. I was so caught up with losing people that I lamented the fact I couldn’t email him for help with any CD Baby issues anymore. His response was something to the effect of “Don’t worry about any of that stuff. You have my personal email. Email me anytime!” He was just another normal dude, who was there for me if I needed him.
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All of that backstory is for you to get a sense of who is writing this review. I’m not a journalist, nor a literary critic, but I like to read and I read quite a bit. So think of this as a “review supplement" to all the other ones written by the pros for newspapers and magazines. And probably a thousand or so fans.
In Derek’s email, he said “How to Live” took him two years to write, and another two years to edit. Seems normal? I don’t know how fast a book should take to write. I suppose as long as necessary for the author to think it’s ready. And Derek definitely thinks it’s ready, saying “It’s the best thing I’ve ever written.” and “I’m so happy with it.”. What I found even more interesting than the amount of time he spent on the book was the subtitle, and what he had to say about it.
“How to Live” is subtitled: '27 Conflicting Answers and One Weird Conclusion'. He called my attention to this, writing: “Note the words ‘conflicting’ and ‘weird’ in the title. Don’t expect a normal obvious book”. I don’t know what a normal obvious book would be, but I am sure Derek Sivers has never written one.
What he said after that was the dagger:
“I removed every unnecessary word.
It’s meant to be read very slowly.
One sentence per line.
You’ll see.”
I was captivated by this. I wanted to read it immediately. And I was eager to follow his instructions while reading the book. Like it was some sort of key to have a better read! I immediately coughed up the bargain price to get the PDF and start reading.
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REVIEW:
The book starts off with a bang. And it wasn't because my interest was piqued and I was in a unique state of calm excitement. Rather the subject matter is just so raw. It is simply there on the page with few words in short sentences. There is nowhere for any of the ideas to hide, because each sentence is it’s own idea, stated completely earnestly with no filler to float around in, on, or behind.
The first of 27 chapters is on the topic of Independence. It’s not-so-subtly titled “Be Independent”. It was surprising to me that with a subtitle like '27 Conflicting Answers…', each and every chapter is an imperative - telling the reader to do a specific thing, or to not do something. It works though, as the imperatives move to declaratives which the author states as fact to support his imperative argument - whether or not you agree. Sivers knows that his facts are true, because they are true to him, and that’s all he needs. But writing things such as “Have more than one romantic partner. Or none. To avoid emotional dependance, never have just one.” is a bold stance for an author to take with his readers - he is assuming (or trusts) that they are open enough to consider his calls to action (or inaction), as well as confident enough in the author to trust him in accepting his imperative statements as well as the declarative truths he has laid out.
My favorite line of the first chapter ends a paragraph in such a brutally honest way that it simply has to make sense: “Assume nobody will help you”. As a reader, I’m left with two choices - trust Derek, and assume no one will help me, thus doing all the other simple (and complicated) things in the chapter to become more and more independent - or - be a fool, and assume that someone out there, somewhere, will help me in a time of need. These are the kinds of hard choices I’m calculating after reading four sentences… slowly.
That’s what did it for me right from the beginning of “How to Live”. I went in taking Derek’s advice to read one sentence per line, very slowly, with the promise of “you’ll see”, if I did it correctly. And it really worked. His words are so very carefully chosen, and his sentences are so craftily short, that I was forced to read them, slowly, then read them over again, then read them slower, until these blocks of four short-sentence paragraphs each became a grandiose proposition to ruminate on.
Eventually I start to notice a pattern, where I realize that Sivers is providing us with a fair amount of choice for a book telling you “How to Live”. One paragraph of thought begins with “Live where you feel most free”, then goes on to tell the reader all the ways to find and fit in that place which is most freeing. But immediately after that he counters with “Or have no home at all”, and goes on to evangelize the nomadic lifestyle and the benefits of perpetual travel for the purpose of not being bound by allegiance or physical connection to a nation-state. So it appears that being independent, and doing things that will make you more independent, is not a straight line from point A to point B. Rather there are many different ways to be independent, and you will find that eventually, through all your doing and not-doing to become more independent, that wherever you end up or whatever you become, your independence is probably dependent on your state of mind.
It wasn’t a smack-you-on-the-head, forced realization that most of these 27 Conflicting Answers are about a state of mind, a mindset, and a viewpoint. But it wasn’t some huge personal revelation either. It was very easily drawn out of me through introspection and reflection after each section. I thought it might get repetitive halfway through, but I was wrong. Each chapter has its own quirks and no single one is ever dull. Sivers has a unique way of taking a different route to get to his desired destination each time he defines an imperative. He throws a dart somewhere on a map, that’ll be point B, and we’ll both start at point A together. But then he will drop you off at point C, D, G, and T and let you work your (own) way to get to your point B.
It’s at this point you could take what I’ve written above, read the table of contents of “How to Live”, and apply your opinion to how you think each chapter will roll. But this book is so different and unique that there’s no way you could guess how every chapter would read, even if your bookseller lets you preview an entire section. The writing style is pretty consistent throughout the book, but the nature of the “Answers” in each chapter are so different that it never becomes a slog. It turns out living has a lot of components, and they are all very different from each other. To spare you the mental effort, here is my list of alternate (non-imperative) titles for all 27 chapters, along with a single poignant thought that I took from each one:
1IndependenceLive totally and absolutely for yourself. Learn to rely only on yourself. 2CommitmentYou’ll suffer choice paralysis forever if you don’t commit to something, or to some things.3PerceptionSensory overload is not a bad thing. You have five senses - overload them and enjoy them! 4Nihilism Sans CynicismDoing stuff is overrated. Why do you always feel the need to be ‘doing something’? You don’t “have to” do anything.5Beyond Life GoalsWhat do you want to do that will have profound impacts outside of yourself, long after you’re gone?6Getting Out and OverThere are billions of people out there, go meet your ‘kindreds’ on the other side of the globe… we are all connected.7A Life to RememberIf you live a long, healthy life, but can’t remember it, what’s the point? Having amazing memories is the prize of experience.8Becoming a MasterIf there is one thing in your life that you truly love and can master, why not go for it? It’ll be worth the while.9No Preset PlanWe try to construct patterns and causes to make sense of things, but embracing uncertainty brings excitement and joy.10Pain is not a Bad ThingAvoiding pain, or embarrassment or anxiety, is cheating yourself because you won’t grow without it.11Action is for the TakingWhatever benefits you the most at any given moment is what you should do at that moment, full stop.12First Time for EverythingEverything ever done always had someone do it first. You have the ability to do many things “first”.13Live for Tomorrow, TodayThe future is coming at us at increasing speed, embrace everything new, unique and interesting, (However...14What Goes Around, Comes AroundPlacing value in tried and true bedrocks is better than latching on to new gimmicks.15KnowledgeYou have more ways to learn more things than ever, and you can enhance your life immensely by learning as much as possible.16The Good BookEveryone has their own version of their Human Guidebook, utilize yours as best you can.17Laughter’s the Best MedicineLaughter is the language of the soul, and you probably should be laughing more, for myriad reasons. 18Disaster PreparednessWe’ve mostly got it so good we couldn’t imagine the worst, but it’s a good idea to at least think about it, and prep.19Altruism and GenerosityBeing selfish doesn’t get you very far, helping others has so many rewards beyond just the helper and the helped.20Money is Still ImportantMoney is a neutral means of determining value, and that’s it. All the projections by others about money is not your concern. 21Adaptation and IterationYour identity is not a static thing, it can change constantly. Your past does not dictate who you are now or in the future. 22All You Hold DearLove is not a feeling, it’s actions starting with attention, appreciation, and empathy. It is powerful.23Making ThingsThe way to live is to create - getting every single idea out of your head and into reality is essential. 24Life and DeathYou obviously want to do much more living than dying, so live while you can, carefully! 25Messing UpYou learn much more from mistakes, so you shouldn’t be afraid to make them. Trying everything while expecting failure is okay! 26Reshape the WorldIf you go your whole life without changing anything in the world, you have just been a casual bystander.27Stabilization“Virtue is in the balance of extremes” - Derek Sivers
Again, each of these chapters are structured the same, but their contents are quite different from each other. The succinctness of each sentence is really powerful, and it allows the reader to take in the bare minimum amount of information needed to form an opinion, create a thought, or get introspective. I am glad that I had a brief introductory instruction on how to read the book, because it really helped my focus, my connection to the ideas, and my imagination in generating new ideas and thoughts that served me in a positive way as I read. I should write a note to Derek and tell him that he should include a small blurb on the front of the dust-jacket:
“Meant to be read very slowly.”
“One sentence per line.”
“You’ll See…"
-D. Sivers
At times, you could argue that Sivers is contradicting himself from chapter to chapter, or even within a single chapter, but most people will not fall for that, as the contradiction is actually the freedom that we as people need to know we have. If you look at all 27 chapters, a lot of them pair up in a somewhat binary manner, one right after the other. “Be Independent” is immediately followed by “Commit”; “Fill Your Senses” is followed directly by “Do Nothing”. But being independent and committing are not mutually exclusive of each other, and it becomes very clear why in Sivers' short sentences. It took a few tries to stop looking for contradictions, but eventually all of the 27 parts cohesively aligned in my mind and became a neural network spreading like a web, rather than a start-stop game of 1's and 0’s. There is a meditation to reading this book. I got there, briefly, and I want to go back again.
I won’t spoil the conclusion vis-a-vis the 'One Weird Answer' here, (and it is very weird), but I will talk a bit about how it tied up the book for me.
The “Conclusion” is by far the most powerful part of the book. I’d say it’s easily worth the price of admission alone. Seriously. But I also think you need to carefully read all 27 chapters; reading single lines over and over until you feel their power; and reflecting on each chapter before moving to the next, to really feel the impact and experience the pleasure that is the conclusion. I have to admit I was surprised, and also a little miffed, with what was in the final chapter as far as content goes. But once I let it sink in, it really hit me. I will use two metaphors to describe how this book wraps itself up. First, there’s the easy and obvious sexual metaphor. Sex is great, and usually, the entire experience of having sex is wonderful; it’s just that those last few moments are incredibly more fulfilling and satisfying than what was leading up to it. Second, when I was a kid I loved lemon-flavored Italian Ice (I still do). I would scrape and shave that ice with a spoon, taking my time, and really enjoying each bite of the ice that was actually a lot of work to scrape out of that little plastic cup. But once you got close to the bottom, the normal ice that you were shaving away at started to disappear, and it revealed a hidden piece of ice that was unlike anything you’d tasted before that. It was this little puck of crystalline frozen sugary syrup, and it was so much more delicious than all of the ice you had previously eaten. But just like sex, you had to put in the work, and savor every moment, before you got to the sweetest part.
So don’t be that kid who flips the Italian Ice over and eats the frozen syrup first.
Read this book, very, very, slowly... and when you get to the end… savor it.