There are some things about being president that I still have difficulty doing. … For example, faking emotion. Because I feel it is an insult to the people I'm dealing with. For me to feign outrage, for example, feels to me like I'm not taking the American people seriously. I'm absolutely positive that I'm serving the American people better if I'm maintaining my authenticity. And that's an overused word. And these days people practice being authentic. But I'm at my best when I believe what I am saying.

One option was to sell Patagonia and donate all the money. But we couldn't be sure a new owner would maintain our values or keep our team of people around the world employed. Another path was to take the company public. What a disaster that would have been. Even public companies with good intentions are under too much pressure to create short-term gain at the expense of long-term vitality and responsibility. Truth be told, there were no good options available. So, we created our own.

That’s a very good question. I think I’m a very lazy writer and by that I mean that I do not battle, I don’t struggle too hard against it. If I have difficulties in the writing, I just go and do other things. I don’t feel a compulsion to write. Of course, when I start writing then it becomes a compulsive activity, because I’ve begun something and I want to continue, want to finish it. … I know there are other writers who sit down religiously every morning, they take their espresso, they put a clean sheet of paper there and they sit looking at that paper until they’ve finished or covered at least a number of those pages. No, I’m not like that. I have to be ready. It has to gestate it for quite a while and then it’s ready to burst forth.

It’s how we are made as homo sapiens. We are biologically organized to cover distances on foot. That’s what we did for tens of thousands of years until we started to use horses, of course, until the mechanical age. And I would not call it “walking” because it’s not going out for a stroll or going out for a “power walk” or ambling in your city. It’s “traveling on foot.” You are reading the world, learning the essence of the world.

The proudest achievement of my life at that time was that software. Wonderfully organized, extensible, and efficient: the culmination of everything I’d learned about programming in ten years. After a successful relaunch and Christmas rush, I was looking at my plan for 2008 and beyond. All my plans needed a huge effort for little reward, but were required for future growth. I had broken it into about 20 projects, each taking 2 to 12 weeks. But I wasn’t excited about any of them.

So for years I kept calling myself an entrepreneur until one day I realized like, wait a second, this is expired! Like somebody who is an athlete in high school can’t keep calling himself an athlete forever.

In the end, I had to pay $3.3 million dollars to buy back that 90%.

And this is my only pair of pants. These three glasses, I don’t even think about it because I just think about having enough.

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

My mentor heard it and said, “Derek, you’re just not a singer. You really need to stop trying. Admit you’re a songwriter, and find a real singer.”