How do you change not just your habits, but your entire life routine? How do you lift yourself out of comfort and tackle something completely different than what you’re used to? Derek Sivers recently posted a transcript of an interview he did about this topic, and while it’s a long read, it’s well worth your time. Some highlights:

I felt like I needed to shatter my habits. So my little mini slogan was, “Wherever you used to say ‘yes’ say ‘no’ and wherever you used to say ‘no’ say ‘yes’.” Reversing all of the things you used to do and trying the opposite… I would use that even on a little micro level. I see the gorgeous girl across the room and I’m like “Ahhh!” terrified to talk to her! Then I remember, “Whatever scares you go do it! So here we go..” and I would just walk up to the girl that intimidates me and say hello. Then of course she’s wonderful or not, whatever it is, but I walk away no longer scared. Now I just have that approach through life. I think whatever scares you go do it, because then it won’t scare you anymore.


I wanted to make it impossible for me to get stuck in a rut. So my mission was to spend the rest of my life outside of the US, mainly because I loved it too much. Santa Monica in particular. When I got to Santa Monica, I just felt “This is it, I have arrived. Like I love this place. I love these people. I love the food. I love the weather. I love everything. This is it. This is my home. This is where I belong.”

But that feeling kind of scares me, because it’s like that thing when people get to a certain age and say “This is who I am. This is how I like my eggs. This is where I live.” I didn’t feel it was time to stop progressing, even in my physical location. So my challenge to my self is to live the rest of my life outside the US, because I love California too much.


I went to New York City for 3 days, passing through for a friend’s wedding, and I met this gorgeous girl and we had this great first date, we’re all swooning over each other. So on our second date I said, “How would you feel about leaving the US and never coming back?” She looked at me for a second, kind of squinted and said, “Yeah, I could do that.” And so then we had a third date and that’s my wife.

She’s joined me on this mission to spend the rest of our life out of the US, even if it’s uncomfortable. Even if it’d just be the easy and comfortable thing to just go back to Santa Monica to what I know well. It’s the idea of kind of forcing yourself to keep progressing.


It’s really tempting to think it’s the exciting quick fix adventure thing of hopping on a plane and quitting your job and breaking up your relationship. That’s fun but be really honest with yourself that maybe the thing to get you out of your rut is finally acting on the thing that you have been avoiding for years.

While reading the transcript all I could do is nod my head. I share a lot of beliefs with Derek, and even though we lead separate lives, the main drivers behind them (adventure, avoidance of comfort, tackling new challenges) are the same. I remarked upon this when I reviewed his book

I met the author of this book in Rio, after already having been a fan of his blog. We talked a little about life, business, and travel, surprised that so many of our beliefs were similar yet our paths so different. He poured his energy into music and business while I poured mine into women and writing. I hold him up to be a business role model, a guy on the same page as myself who brought value to his customers over several years and was greatly rewarded for it.

So it’s no surprise that when Derek speaks, I listen.

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