Derek Sivers

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Today I want to introduce you to Derek Sivers. He’s been described as a philosopher-king programmer, master teacher, and merry prankster.

I’m fascinated by this guy. Whether I’m listening to an interview he’s done or the audio version of his book I hit pause, “rewind” and listen again, OFTEN, because his brain works in a way mine does not. His philosophies on life, people and work challenge a lot of my assumptions. And that’s what keeps me going back to him. The challenge. He makes me think, deeply.

I hope you find him even a fraction as fascinating as I do.

You can find him here.

Interviews with Derek

When I read this, I felt understood!

Sarah Kay

Sarah Kay. Performing poet. Founder of Project VOICE.

Click that play arrow and watch Sarah. Don’t miss the last poem!

Then scroll down and let’s chat.

Sarah Kay. Performing poet. Founder of Project VOICE. Don’t miss the last poem!

A few of my favorite lines:

“But getting the wind knocked out of you is the only way to remind your lungs how much they like the taste of air.”

“No matter how wide you stretch your fingers, your hands will always be too small to catch all the pain you want to heal.”

“If you make me laugh hard enough, sometimes I forget what century I’m in.”


Step one: I can

Step two: I will

Step three: Doing the work is not enough. You must infuse your work with things specific to you, even when those things are changing.


In Sarah’s words, “Great stories start from the intersection of what you’re passionate about and what others might be interested in.”

Good To Great by Jim Collins

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I first read Good To Great by Jim Collins in the fall of 2006 and I’ve returned to it many times. Without reservation, it’s the best business book I’ve ever read.

Collins set out to discover the characteristics that cause a company to go from good to great and sustain the results for at least 15 years.


The Flywheel
There is no miracle moment, silver bullet or one killer innovation. Long term results start slow, build up momentum then achieve breakthrough. “Like pushing on a giant, heavy flywheel, it takes a lot of effort to get the thing moving at all, but with persistent pushing in a consistent direction over a long period of time, the flywheel builds momentum, eventually hitting a point of breakthrough” (page 186).

The Hedgehog Concept
Great companies have a deep understanding of the intersection of 1. What you are deeply passionate about 2. What you can be the best in the world at and 3. What drives your economic engine.

First Who, Then What
Get the right people on the bus (and the wrong people off) and then figure out where to drive it.


Timeless. Sound advice applicable to all business types. Concepts easily translate to personal pursuits.

Steven Pressfield

I can’t think of a more appropriate place to start this What I’m Learning series than with Steven Pressfield. If I could magically make a stranger part of my family I would choose Steven Pressfield and I’d be sure I was seated next to him at every family gathering.

His books The War of Art and Turning Pro have had a huge influence on my work. It wouldn’t be hyperbole to call it life changing. I tote Turning Pro around like it’s life’s playbook. Because…it is. When I’m distracted, ready to give up, etc. I whip that baby open to any random page and I’m quickly reminded: the muse rewards those who do the work.

My Top Takeaways

  • Resistance is real.

  • Resistance is your compass to True North. The higher the resistance, the closer you are to the work of your soul.

  • The muse rewards those who do the work.

  • Concentration & depth = pro. Shallow & unfocused = amateur

Final Thoughts

Simple. Profound. Life changing.