Derek Sivers and the Philosophy of Obsessive Simplification

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Who Is Derek Sivers?

Derek Sivers is a writer, speaker, programmer, entrepreneur, musician, and–according to his website–“circus performer.” If you don’t know who he is check out these: [1], [2], [3].

Obsessive Simplification in His Work

I was recently listening to him on a podcast [4] talking about his philosophy on writing, programming, and creating. It all boils down to an almost obsessive process of simplification.

He does this in his writing—his book “Anything you Want” [5] is basically a compressed autobiography, at 88 pages long, it is still packed full of valuable insights and wisdom. It’s one of those rare books that you find yourself highlighting something on almost every page.

He does this with his website, which he programmed with only the most basic programming languages so that it will last for years and years without needing modifications. It’s a sparse, simplistic web of archives, ideas, articles, and connections in a way unlike any other website I’ve personally encountered [6].

Even his articles within the website are obsessively concise with an average of about 22 sentences each.

Why He Creates This Way

Some might be put off by the initial impression of scarcity in his work. Some might wonder if he’s just lazy and good at marketing. The truth is that Sivers is really just one step ahead of the rest of us.

In his book, he explains the process of selling his company (CD Baby) years ago for $22 Million, donating the money to a trust for independent musicians, and living off a percentage of that trust [7]. In other words, he’s writing for personal reasons, he’s set financially. It’s this position that allows him to really look at his writing from a completely unique and unbiased perspective. 

Sivers explains that with the amount of information that’s out there and the number of creators that create more and more every day, our world is basically being polluted with an exponentially growing amount of unnecessary information. He understands that there is a shift in attention span happening on a global level and because of this, approaches the process of creating with this constantly in mind. 

However, I think what is most interesting about his philosophy is that he isn’t creating to simply please a world with this changing mindset. Instead, he seems to see this shift as a net positive and challenges himself to provide the most valuable information in the shortest form possible. He’s one of those rare people who embrace the change rather than clinging to the past like much of the world tells us to. 

Obsessive Simplification in Writing

When it comes to writing, this philosophy really makes me question the fundamental purpose of writing. For instance, if the purpose of writing is to provide an escape or a gateway into someone’s unaltered thoughts then writing longer forms seems valuable. However, if we’re writing to pass on practical wisdom or information then obsessive simplification could be the best possible philosophy to embrace in order to provide the most value to our reader. 

It just doesn’t make sense to write like writers of the past—people like Hemingway, Faulkner, or James Joyce, who wrote long, beautiful sentences. It just doesn’t really apply to our modern world. Ideas are beginning to matter more than words and, honestly, that’s the way it should be. 

In this way, I think that Derek Sivers is creating a new movement in writing, and it’s essentially doing the opposite of what most people expect of writers. Don’t write to be heard, write to add the most value possible with the least amount of words. Don’t just edit, obsessively simplify.


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References:

  1. “Weird, or Just Different?” by Derek Sivers. TED, Video, 2010. URL = https://www.youtube.com/watch?v=1K5SycZjGhI
  2. “The Meaning of Life” by Derek Sivers. Video, 2014. URL = https://www.youtube.com/watch?v=zzcCWEb-tyk
  3. “About” by Derek Sivers. Article. URL = https://sivers.org/about
  4. “Making Decisions, Achieving Excellence & Finding Meaning” by Modern Wisdom. Podcast, 2020. URL = https://www.youtube.com/watch?v=qmMVd7B6iWk&t=1773s  
  5. Anything You Want:40 Lessons for a New Kind of Entrepreneur by Derek Sivers. Book, 2011. URL = https://amzn.to/3bHK92K 
  6. Sivers.org by Derek Sivers. Personal Website. URL = https://sivers.org/
  7. “Derek Sivers Sold CD Baby for $22 Million, Giving Most of It Away” by Eliot Van Buskirk. Article, 2008. URL = https://www.wired.com/2008/10/derek-sivers-so/  

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