8 Unconventional Lessons from Derek Sivers to Help You Become More Successful

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Unconventional Success

A friend shared this video from Derek Sivers recently. I’d seen a (different) version of same material a couple of years before on Sivers’ YouTube channel, and was reminded how much I’d enjoyed it then.

Derek Sivers may not be a household name, but many self-published authors will have come across BookBaby; the company that is an offshoot of Sivers’ original company CD Baby.

He talks about the history of CD Baby, how he came to sell it for $22 Million, and how he gave it all away. I’ll let him tell that story.

This version of the presentation at Chris Guillebeau’s World Domination Summit 2015, is a timeless reminder to anyone who’s obsessed with counting the future, setting goals and thinking they will become a map for getting to year’s end, or that they even bear any resemblance to how that might look.

It’s not so much about unconventional success, as an unconventional way of getting there. I don’t know that I agree with everything — or at least I have a different perspective on the same point — but I think it’s a fun presentation and they lessons are a great way to access a new way of thinking — to push yourself to think, rather than follow the message from Divers, or any message from anyone — a point echoed in the video.

Don’t pursue something that someone said you should want, instead of what you really want.

(All the quotes in this piece are from Derek Sivers, by the way, from the video)

Uncommon Sense

The video isn’t really anti-goal-setting, in fact, Derek Sivers doesn’t specifically mention goals (although I’m guessing they don’t drive what he does at all!). He talks about what he did, and what he means when he refers to ‘uncommon sense’.

I love it when people share what they did. It’s great story, of course. But they are not telling us what to do, there is no prescription, only description, and from that we make what we will of it.

Here are eight of the principles I extracted from watching the video — a quick read if you like to skim and, if you’re intrigued, I encourage you to give the video a chance.


He started his ‘little’ website, CD Baby, in 1997, and he said that by 2002, five years later, it really felt like it was turning into something.

There were milestones along the way — thousands of musicians, customers, staff, some senior hirings — but nothing felt like it was ‘real’, until it was.

Ten years in it felt too big, too much responsibility.

The next year he sold for $22 million.

Lesson: don’t get frustrated a few weeks in; give it time.


Most of us go with the flow most of the time, well I do at least ;-).

We do what we think is ‘normal’ without really thinking about what’s important to us. That’s OK, but admit it, and don’t imitate what everyone else is doing, or what you read in this year’s popular book or Medium post.

The most important thing (according to Sivers, and what’s not to agree with?), is that you should avoid the deathbed regret that you did what someone else wanted, rather than what lit you up.

Optimise your life for what you want.

To do this we have to know what matters to us most, what it’s all for (in business, but I think this applies to everything).

Is it money? Fame? Recognition? Freedom? Something else? Know it so well that you focus on it, that you choose it, and that you don’t diffuse and diversify your efforts.

For me, I’m less about the outward markers of success, than knowing where I’m coming from, and I trust that the expression of life will take care of itself. But, sometimes it’s fun to aim for something in particular; to choose a game and play to win.

Learn to say no. Learn that you will need to let go; perhaps you can’t have money and fame. If you have to make a choice, which is it?

Be aware that, whatever you choose, people will always tell you that you’re wrong. It’s inevitable — they think you could do it differently, better.

Maybe you could but stick to your guns, and choose what matters to you.

Lesson: if you hate it, don’t do it. Do the thing that you will regret not doing.

I’m so with him on this!


As a former economist, I find it astonishing how much weight people put on forecasts — business, economic, weather… we know they’re wrong more times than they’re right. The most accurate forecast of what will happen tomorrow is actually what happened yesterday.

Counter-intuitive as that may be, the future won’t turn out the way you expect. And, if that’s true, why do we spend so much time and effort trying to plan for it?

Sivers prefers to think like this:

Don’t commit to one idea of the future, commit to a problem that you want to solve.

There are many ways you can solve a problem.

It’s OK to let go of attachment to what any specific solution might look like. If you’re committed to telling stories that people love, or you’re committed (as he was at CD Baby) to help musicians get their work in front of a wider audience, then go with the flow of any possible solution.

Lesson: the future won’t look the way you expect. Don’t keep aiming for something that isn’t real.


What you think you’re going to sell might actually be different to what you do sell. Be prepared to adapt when people tell you what they want.

In Sivers’ case, he started CD Baby as a payment processor for musicians, they became a ‘record store’ when someone asked, and then a distributor when Apple came knocking.

Where you end up won’t look the way you expected. Back to the previous point though — you’ll still be doing the work you want to do, solving the problem you want to solve.

Lesson: listen to what your customers are asking you to sell them.


CD Baby had a very simple business model that took it from zero to $10 Million — one fee to set up the CD online, and one fee for each CD sold. Plus they paid the artists weekly.

They only call it a revolution after you’re successful.

Five years in, CD Baby started to get press coverage for revolutionising the music business. They didn’t start out with the idea of revolution — they started out just providing a service to friends. Not everything has to have drama.

Serving people better… often that’s all there is to it.

Lesson: forget about disrupting the status quo, just do good stuff.


We know how tough it can be to face rejection, and how we have to be consistent to get to where we want. There’s a difference between persistently trying to sell something that no-one wants to buy, and consistently doing your work, week in week out.

Derek Sivers talks about his years as a musician, and how hard it was.

When I started CD Baby it felt like I’d written a hit song, he says.
Now I know what it feels like, I know the difference between easy, and hard.

It reminds me of an interview I heard with Michael Morpurgo recently — the children’s author who wrote the book of the hit film War Horse. The book didn’t sell brilliantly when he wrote it, but that didn’t stop him writing books.

And then, someone came along and wanted to make it into an animated stage play. “Great,” he said, “I didn’t think they would actually do it!” But they did, and , later the phone rang, and it was Steven Spielberg asking if he could make War Horse into a film.

It’s a story we’ve heard from so many successful people — that we do, and then we do again. When Morpurgo’s book wasn’t selling so well, do you think that stopped him writing?

You might think your idea is brilliant, that your book is the best thing you’ve ever written, but if it people aren’t buying, let it go and write something else.

Back to Sivers,

Success comes from persistently improving and inventing, not persistently pushing what’s not working.

Lesson: not everyone will understand or share your vision. Let it go and move on to the next thing. You’ll know when it becomes easy.


Just get something out and see how people respond. We know this from The Lean Startup, the idea of the MVP — minimum viable product.

In the video, Sivers talks about someone he met who, for two years, had been trying to get funding for a music recommendation service. They were so focused on the product they neglected doing any testing.

“Why don’t you just turn around to someone at a concert, ask him or her what they like to listen to, and then give them a suggestion?” To Sivers that’s the 0.1 version of a music recommendation service.

But no, we stay attached to our idea, and we want to invest time and energy and perhaps also money into it. It could be a project at work, or a business idea or a passion project. That’s all good, but the magic, in my opinion, is in the co-creation — the dance between what we think we want and what the world wants to create with us — to see that is to indeed see where impact comes from.

For Derek Sivers, ideas on their own are worthless; the value gets added when you execute them.

Lesson: just do it. Ship, as Seth Godin says. Get something out because then you can learn and then you can improve.


The final part of the video is more specific to CD Baby and the quirky things that they did that got musicians coming to them, staying with them, and recommending them to their friends.

It matters less what these are (you can watch the video for the stories), than to know it’s about doing the things that humanise you or your company. Forgetting the facelessness of the internet and reminding your customers that you are a real person.

Most people don’t, and you’ll be the one who stands out. And make sure it’s you, the authentic you. I’ve seen people do this as exactly themselves and I’ve seen people see someone else implement a good idea and think “oh that’s a great idea, let me try that!”, and it doesn’t quite land. It might take a while but stick with who you are, not what you think is cool in someone else.

Lesson: be human, be weird, and, remember, it’s the small things that make people ecstatically happy.


The way I see it, goals are an expression of what we think we want; they don’t represent what will make us happy, or what will make others happy, or even have any merit of their own — no matter what ‘society’ tells us. They are false idols for sure.

We can’t predict the future, people we interact with, colleagues or customers, will like what they like, not what we want them to like. Success is about showing up and following the path of what is working, rather than forcing what is not.

If we don’t set goals, if we do the work, maybe, just maybe, we’ll get more done and have more fun doing it.

With love,


What if making an impact was part of your everyday? Stories to light up your soul. Read more and free courses: https://cathypresland.com/find-out-more

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