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Wisdom from a Curious World Traveller—Meet Derek Sivers

August 14, 2016

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One of my favourite bloggers is Derek Sivers. I discovered Derek online several years ago, and was impressed with his love for learning and for sharing with others. His eclectic background is fascinating, as is his humbleness. In the past, he’s been an entrepreneur, programmer, circus clown, author, plus much more. A few years ago he wrote a wonderful, compact book called Anything You Want: 40 Lessons for a New Kind of Entrepreneur. It’s excellent; be sure to check it out.

Recently, Derek shared three short posts with his followership. I enjoyed them so much I asked his permission to share them with my readership. These three posts have gems of insight for leaders of all stripes. I encourage you to reflect on them and to also follow Derek’s life journey via his blog.

And if you haven’t seen Derek’s narrated video First Follower: Leadership Lessons from Dancing Guy”, viewed over four millions times, then take a moment to watch it.


Keep Earning your Title, or it Expires

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Until yesterday, I called myself an entrepreneur. Today I erased it from the top of every page on my site.

It’s been years since I started a company, so I can’t keep using that title.

Someone who played football in high school can’t call himself an athlete forever. Someone who did something successful long ago can’t keep calling himself a success.

You have to keep earning it.

Holding on to an old title gives you satisfaction without action. But success comes from doing, not declaring.

By using a title without still doing the work, you fool yourself into thinking future success is assured. (“This is who I am!”) That premature sense of satisfaction can keep you from doing the hard work necessary.

Stop fooling yourself. Be honest about what’s past and what’s present. Expiring old titles lets you admit what you’re really doing now.

And if you don’t like the idea of losing your title, then do something about it! This goes for titles like “good friend”, “leader”, or “risk-taker”, too.

I updated my home page to reflect what accomplishments are in the past. It’s liberating to speak in past-tense about what’s passed, and only speak in present-tense about what’s actually present.

I do plan to start another company some day. And when I do, I will have earned the “entrepreneur” title again.




Someone asked what I remember as the best times of my life.

They’re almost all times when I was being the most productive — when I was creating the most.

Turning my ideas into reality is what I want the most out of life. So that’s what gives me the deepest happiness.

Then I realized that all the best, happiest, and most productive times in my life, were when I was completely cut-off.

No internet. No TV. No phone. No people.

Long uninterrupted solitude.

When I was 22, I quit my job, and spent five months alone in a house on the Oregon coast. Practicing, writing, recording, exercising, studying, learning. No internet. No TV. No phone. No people. I only drove into the city once a month to see friends and family. The rest was completely disconnected.

In those five months, I wrote and recorded over 50 songs, made huge improvements in my instrumental skills, read 20 books (some of which changed my life), lost 20 pounds, and got into the best physical shape of my life. Not only that, but I was the happiest I’d ever been.

When I was 27, I moved to the woods of Woodstock and did that again. Months and months of lovely solitude. That’s how I started CD Baby.

It’s not that I hate people. The other best times in my life were with people. But it’s interesting how many highlights were just sitting in a room, in that wonderful creative flow. Free from the chatter of the world.

No updates. No news. No pings. No chats. No meetings. No surfing. No blogs.

Silence is a great canvas for your thoughts.

That vacuum helps turn all your inputs into output.

That lack of interruption is a great ingredient for flow.

Every business wants to get you addicted to their infinite updates, pings, chats, messages, and news. But if what you want out of life is to create, then those things are the first to go.

People often ask me what they can do to be more successful.

I say disconnect. Unplug. Turn off your phone and wifi. Focus. Write. Practice. Create.

That’s what’s rare and valuable these days.

You get no competitive edge from consuming the same stuff everyone else is consuming. But it’s rare to focus. And it gives such better rewards.


Derek 3I’ve been feeling extremely un-motivated lately. I don’t know why. I look at things that excited me just a few months ago, and I think, “Why bother? What’s the point?” I don’t feel like doing anything.

What do you do when you don’t want to do anything?

Well, I also have a list of things that I should do, things that really need doing, but I never feel like it.

Boring things. Necessary things. Things I’ve been putting off for years, but really do need to get done. The reason I never do them is I’m always more excited about something else.

Ah, but I’m not excited about anything now, am I?

So now, when I’m not excited about anything else, is a perfect time to do them!

So I made a list of these necessary things, and have been getting them all done. It’s not fun, but I use some caffeine, and get through it. It actually feels pretty good.

Conventional wisdom tells us to do the important and difficult thing first, but doing this boring work has moved me from a state of doing nothing to doing something. I’m just starting to feel like doing something important again.

So next time you’re feeling extremely un-motivated, do those things you never want to do anyway.


A work-only zone does wonders for your productivity. So, I prefer working at the office now. I spend 8 focused hours there, then I go home to be present with my family.
— Derek Sivers

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