Lessons Learnt

Hell Yeah, or Nah: Minimalism & Writing Routines with Derek Sivers

In the latest addition to our Lessons Learnt series, we have programmer, writer and entrepreneur, Derek Sivers, who is best known for founding CD Baby, the largest online distributor of independent music in the world.

In 2008, after starting and running CD Baby for over a decade, Derek sold the company for $22 million, and has been writing, speaking and publishing content since then.

I’ve been an avid follower of Derek and his writings ever since I discovered CD Baby in 2014. His unique way of thinking and constant stream of great content has provided me with valuable lessons on minimalism and saying no as well as helping me to identify as a writer and write more.

Lessons Learnt is a series by Balance the Grind profiling individuals, brands or companies that inspire us. For more profiles, check them out here.

Lesson 1: You can apply minimalism to certain parts of your life

If you take a look at Derek’s website, writing or even study his lifestyle, you’ll see that minimalism plays a huge part in how he lives his life. I mean, we’re talking about someone who gave away $22 million of his money to a charity.

Derek’s website,, is as stripped down as a website can get: no colours, barely any images, no fancy features, just the core essence of what Derek is trying to get across to the audience. His clear and concise writing is also stripped down to the core idea, and makes for very easy reading — something I’ve learnt is very hard to achieve as a writer.

I hate waste. I don’t like the feeling of having more than I need. It feels like clutter.

Yes this means I only own one pair of pants, have only two plates in my little apartment, and my computer is a 7-year-old clunky laptop that works fine.

But it also applies to tech: removing every line of website code that isn’t necessary, and hand-writing a site with no framework or libraries.

And it applies to my writing: spending 12 hours writing an article, saying everything on my mind, then editing it down to the few words that are really needed.

About | Derek Sivers

I wouldn’t consider myself a minimalist by any means, but I do like to apply minimalism to some aspects of my life, especially my work. As a writer, it’s often tempting to add in big words and more sentences to bolster authority and credibility, but in developing my craft, I’ve learnt that simplicity and clarity are the two most important writing traits.

Lesson 2: Hell yeah, or no

Perhaps the most widely circulated blog post that Derek has written – No “yes.” Either “HELL YEAH!” or “no.” People typically have a fear a missing out (FOMO) so they tend to commit to as many things as possible, only to want to back out later when the time comes In his blog post – Derek has a great strategy to deal with this, especially when you feel like you’re overwhelmed and being pulled from too many different directions:

When deciding whether to do something, if you feel anything less than “Wow! That would be amazing! Absolutely! Hell yeah!” — then say “no.”

No “yes.” Either “HELL YEAH!” or “no.” | Derek Sivers

Lesson 3: If you’re a writer, then write. And then write some more.

Listening to Derek talk about his writing routine on Growth Mindset University was inspiring.

In a nutshell: a few hours before bed, he’ll turn off the internet and write for a couple of hours before going to bed. He’ll naturally wake up at 5.30am every day and just write for 5-6 hours before even turning on the internet. After that, he’ll take a quick break to have some lunch, answer emails, before getting back into all over again. All in all, he writes for an average of 15-16 hours a day.

It’s like my dream. It’s amazing. This is why people quit their jobs so they can just do what they want to do all day. I’m living my dream.

The weather got cold, so I went down to Portugal for 10 days and just got a little hotel room. I don’t know anybody down there. I sat in my hotel room and wrote for 16 hours a day in the hotel room. It was wonderful.

Jordan Paris / Growth Mindset University – Derek Sivers

For the longest time, I struggled with the idea of being a writer. Even though I’ve been writing stories since I was 8 years old; even after cutting my teeth as a music and movie reviewer for (now; even after I got my break in the PR agency because what I wrote on my first blog.

As my career progressed, I shifted away from regular writing and more towards strategy and project management. It ended up being almost 5 years since I properly sat down and worked on what I considered a creative piece of writing. That first time back at the keyboard was hard, imposter syndrome kicked around my head – “who would want to read anything you’ve got to say?”

Yet, slowly and surely, with the motivational help from great writers like Derek and Jason Fried, I got back into the habit of writing every day. I realised that writing is a muscle, and I needed to put in my reps with consistency and frequency, just like I do at the gym.

During this COVID-19 pandemic, with gyms shut down, I put that energy towards getting back into writing. For the time being, there’s no more waking at 5am to hit the gym, instead, it’s waking up at 4.30am to write until 7am – 7.30am (or whatever time Frankie decides to wake up).

It was excruciating at first, staring at the blank page, I felt like I was learning all over again. But as I got back into the habit, I remembered this was what made me feel the most content; along in a room writing, with some lo-fi jazz vibes playing in the background.

Before you go…

If you’d like to sponsor or advertise with Balance the Grind, let’s talk here.

If you never want to miss one of our conversations about work, life & balance, subscribe to our newsletter.

Workflow is a new interview series by Balance the Grind: we talk to people from different careers and lifestyles about their unique working styles and workspaces.

About Author

Hey there! I'm Hao, the Editor-in-Chief at Balance the Grind. We’re on a mission to showcase healthy work-life balance through interesting stories from people all over the world, in different careers and lifestyles.