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lifeshifting interview with CD Baby's Derek Sivers

Derek Sivers is the founder of the hugely successful company CD Baby, but he has also been a musician and studied to be a clown. He very kindly answered some questions I asked him which I think are not only fascinating but also very useful for potential lifeshifters and polymaths.

1.    Can you recall breakthrough moments when you realised something was possible after all? Or maybe a new thing you’d never considered? What brought on that moment?

I have this realization all the time.  It's almost like I never learn it, since I keep realizing it over and over again. My self-identity of what I'm capable of doing keeps growing.

When I was 17, a teacher told me I could graduate college in two years.  He showed me how, and I did it.  He taught me that there is no speed limit.  When the world tells you how something is supposed to work, that just means it's the lowest common denominator.  Anyone with ambition can do much more, much faster. Read the full story at

When I was 22, I was working a regular day job and was buying the normal line that this is something we all need to do.  But two things changed my mind:  (1) My girlfriend's hippy parents.  Neither of them had jobs, yet they had a cute house in the country and put their daughter through college doing random work.  (2) The book "Island" by Aldous Huxley.  In the utopia he imagined, nobody is allowed to do something for more than two years.  After two years, it's healthier to switch it up and change jobs to something radically different.  (A physics professor becomes a rock-climbing instructor.  A gardener becomes a judge.)  These two things combined made me quit my job, and vow to make a living by making music.  That was 1992.  I haven't had a job since.

When I was 28, I was helping some musician friends sell their CDs online, but it kept growing and growing until it was the largest seller of independent music online.  150,000 musicians, 2 million customers, $100M in sales, 85 employees, and a 30,000 square foot warehouse.  Looking at this big monster of a business I'd created made me re-assess what's possible for me to create.

When I was 38, I sold CD Baby for $22 million.  Among my close friends, it's the subject of jokes.  I find myself looking at two cans of beans on the grocery shelf, and choosing the one that's 50 cents cheaper.  My friend will say, "Yep.  Lifestyles of the rich and famous."  But it makes you look at other people who may be glorified on the cover of a magazine, and realize they're not super-human.  Just had a string of success.

But still, after all that, I find myself looking at something like a tropical resort thinking, "I could never do that!" Then I have to stop and question that.  I still find my self-image is pretty limited to what has come before.  It still takes work to expand it.

2. What is the most powerful motivator for you?

The death-bed regret.  If you were to get hit by a bus today, realized you were going to die in a few minutes, but had a few minutes to stop and ponder the things you never did, what would you regret most?

I'm hugely motivated to do those things ASAP.  It's a very short list, luckily

3.    What gets you up in the morning now- in the past? ?

Getting rid of my deathbed-regrets.  I'm acting as if I'm going to die in a year or two.

4.    Can you tell us any mantras, phrases, wise saws, you repeat to yourself when the going gets tough?

These are my two big ones:

Whatever scares you, go do it.  You can use this in so many ways, from huge plans to small moment-to-moment decisions, like saying hi to someone that intimidates you.

It's either "HELL YEAH!" or no.  If you're not feeling 100% psyched-as-hell to do something, say no.  Leave room in your life for those few things you're psyched about.

5.    Did you have any habits you had to overcome that held you back from achieving what you wanted to achieve?

Procrastination, like anyone.  Doing the timid things like surfing the web or hanging with friends, instead of the daring things like forcing yourself through a creative block or difficult challenge.

But then you find that the greater reward is that priceless feeling of accomplishment when you do the difficult things.

6.    How supportive were friends and family of your lifeshifts from musician, to clown and entrepeneur?

I don't know, and it didn't matter.  When I announced at 14 that I was going to be a musician for life, of course nobody was supportive of that decision.  So I got used to doing what I want despite the disapproval of others.  I still don't care what anyone thinks.  I still make decisions that everybody I know is totally against, but I know it's the best for me, so I don't let it bother me at all.

7.    How did your polymathic background feed into success as an entrepeneur? Anything specific?

Most people have a very pre-set notion of what it means to be an entrepreneur.  They think Steve Jobs, Mark Zuckerburg, or whatever heroes they admire.  But because I never meant to be an entrepreneur, I had no pre-set concept of what my life should look like.  I was just doing what makes me happy, and trying to be as helpful as possible.

What's funny is when you use that simple mission - doing what makes me happy, and trying to be as helpful as possible - to make little decisions like whether to put advertising on your website.  Does it make you happy? No.  Is it helpful to others?  No.  Then don't.

And yeah - my music background probably gave me some different insights into running a business.  It's always healthy to pull in expertise from outside the field you're in.  I'm sure a rancher and seamstress could bring in metaphorical lessons from their backgrounds, too.

8.    What is the main thing you notice in young people you think the current culture is neglecting?

The importance of solitude.  Most creative output, deep thought, and unique insight comes from solitude.  But our current trend is for every aspect of life to be "social".  I'm not social.  I don't want to be on top of things.  I want to get to the bottom of things.

9.    What did you have to sacrifice to do the things you have achieved??

I haven't had a TV since I was 18.  Apparently the world has watched millions of hours of TV, and spends millions more talking about it, but I've missed out on all that.

A lot of people seem to go "hang out", and just drink and shout at eachother in noisy bars.  I've never tried that, so I don't know if I'm missing out, but time spent on that doesn't seem to be contributing to anyone's life-goals (except maybe the nightclub owner.)

In short: nothing.  No sacrifice.  I'm always doing exactly what I want.  I wouldn't have wanted it any other way.

There is more on Derek's great blog-

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