Derek Sivers: “Your Music and People” - 12 Timeless Lessons and Insights

Derek Sivers is a colorful and successful entrepreneur, musician, speaker, and writer. He wrote a couple of insightful books, one of them is his bestselling work “Anything You Want“, which I describe in one of my most well-received blog posts. 

An interesting story that I can share is that I got in touch with Derek after publishing a blog post, and we exchanged a few emails. Our conversation was inspirational and I decided to explore his works further. 

He recommended his book "Your Music and People" - a work about building a dream lifestyle and remaining independent. The grand theme of this book is:

“A philosophy of getting your work to the world by being creative, considerate, resourceful, and connected.“

Derek Sivers often described as the “philosopher-king” is an interesting person who has a lot of insights, wisdom, and often counter-intuitive viewpoints on building business, following a passion, curiosity, and living life as a series of grand experiments. 

I’m a huge enthusiast of Sivers’ approach to entrepreneurship, creating, living independently, finding a mission, and achieving excellence. It’s all in a minimalist, down-to-earth narrative that has nothing to do with suits and MBA degrees. Business is just as creative as art, so express yourself and find your own way to success!

Here are 12 timeless insights from Your Music and People by Derek Sivers.

1. Art doesn’t end at the edge of the canvas.

“The way you present your art, and what people know about it, completely changes how they perceive it. Therefore, your art doesn’t end at the edge of the canvas. Your creative decisions continue all the way to the end. “

The way Derek Sivers thinks about the marketing and selling craft is different and even counter-intuitive to what most people think. He thinks about marketing as being a considerate and continuous, never-ending process.

Every creative step of doing your art is the expansion of your original idea. Whether it’s painting, music, or business. Let’s take a painting.

You start with a tiny notion for a picture, then you choose the kind of canvas, then colors, mix them with others, add textures, then you come up with the title and the overall visual look to present it.

Each of the abovementioned steps was an extension of your initial idea. And the process of putting your art into the world can be just as creative as creating it.

Your creative process hasn’t stopped by canvas. The way you present your art, how you make your work available, and telling the story behind the picture are also the steps of the creative process. These steps are all the continuation of your creation.

In short, marketing is an extension of your art and can be creative as well. Improvise, experiment, and have fun with it. Try some things that nobody else has done before. There's more to it than putting things on the Internet and announcing it like everyone else.

2. Everything you do is a test

“Everything usually feels so serious — like if you make one mistake, it’ll all end in disaster. But really everything you do is just a test: an experiment to see what happens. My favorite times in life started with a “see what happens” approach.“

An interesting approach that Sivers shared with us is to do everything with the conviction that it’s all a test. And there’s a productive benefit behind that attitude.

If it’s all a test that’s impossible to fail bacause your mission was only to see what happens.

And the range of possible applications of this approach, firstly, is wide enough, and secondly is positive and productive to start using it day-to-day to improve our lives on many levels.

The encouragement could be that the best moments in my life started with a "see what happens" approach. And it happened to Derek as well.

Sivers also shared a couple of examples of this approach:

“Let’s see what happens if I run my vocals through my guitar pedals.

Let’s see what happens if I invite that famous producer out to lunch. “

This is only a test. Try everything because there’s no downside.

3. Restrictions make you better

Someone says, “Write me a piece of music. Anything. No restrictions. Go!” You’re stumped. It’s the blank page syndrome.

Instead, someone says, “Write me a piece of music using only a flute, ukulele, and this toy piano. You can only use the notes D, E, and B. It has to start quiet, get louder, then end quietly. Go!”

Aha! Now that’s an inspiring challenge!

Another insightful and broadly applicable approach that Sivers shared is to set yourself some creative limitations if you feel stuck. And the more specific the constraints, the better and easier they’ll be to fulfill.

You can use it for business purposes, but I also found that it seems to be highly practical in personal life, and you can think about restrictions in various aspects.

You can spend a week only contracting people you’ve never contacted before or spend your weekend without electronic devices. I find it very refreshing and inspiring.

Whenever you’re feeling uninspired or unmotivated, use creative restrictions and they set you free.

4. Embrace your persona

“When communicating with your fans and contacts, don’t try to sound bigger than you are. Don’t use the corporate “we”. Say “I”.

Fans want to connect with you as a person, not as a brand. Don’t appear flawless. Show a charming flaw. Confidence attracts, but vulnerability endears.

Your fans are your friends. Prove you’re a real person. Write every post or email as if it was from you to your best friend“

We could summarize this chapter by saying that you should take pride in saying “I” instead of “we”, but there is also worth bringing up lessons and philosophy for independent creators.

As independent and small creators we have one huge advantage over corporations - we have personality and spirit, which no corporation can counterfeit. Take advantage of it.

Speak to your fans like real people, be weird, authentic and show your true personality. People are deaf to the bland language of big business because, as we previously noticed it has no personality and spirit.

Once again, take pride in saying “I” instead of “We” and show your personality and spirit! People are turned away by bland corporate speech.

5. Life is a high school

“When you’re in high school, it’s all about popularity, cliques, and being cool. When you go to college, the focus shifts to academic achievement.

Many people get out of college thinking the world will be like that — like the harder you work, the more you’ll be rewarded. But it’s not.

Life is like high school. It’s all about how you come across, how social you are, what scene you’re in, being likeable, and being cool. But you can make this work in your favor. “

People tend to think that there’s a clear boundary between high school and so-called “real life”, but in reality, these episodes of our lives have more in common than the opposite.

Life is like high school. It’s all about how you come across, how social you are, what scene you’re in, being likable, and being cool. And you can make this work in your favor. You can practice your social skills and be the kind of person that people like to help and be your idealized self.

It’s worth noting that people want someone to look up to. It takes great effort to look and act cool instead of normal, but you can develop it and consider it as a part of marketing, which means being considerate.

6. Success is your priority. It’s up to you.

“One of the top music industry lawyers in Los Angeles was speaking at a conference.

She’s an expert in copyright law, so someone asked her advice on a licensing problem. They had recorded their version of a famous song, but were unable to get the rights to sell it because they couldn’t get a response from the publisher.

The lawyer shocked the audience when she said, “Sell it anyway. Don’t wait for permission. Save the proof that you tried your best to reach them. If they contact you to ask for money some day, pay them then. But never wait.”

Coming from a copyright lawyer, that was a bold statement.

It was a reminder that your career is more important than its details.

Success is your top priority. Never let anything stop you.”

Great insightful story from Sivers. Remember, don’t wait for permission and assume that nobody is going to help you. But I find it empowering to know that all is up to me.

7. Get specific

“This is one of the most useful lessons I’ve learned in life. When you don’t know your next step...

When you’re feeling unmotivated...

When asking someone to help you...

When you’re ready to make a dream come true...

Get more specific about what’s needed.“

Besides setting some creative restrictions when you feel unmotivated and stuck, the good move is to get specific, and there are two ways to do so.

1) Write down every detail you know

When you have a big goal, break it down into specific ingredients, describe concrete milestones, and set the next small steps that allow you to achieve your goal and break it into actions that you can start doing today.

2) Research what you don’t know

When you don’t know your next step, you start procrastinating and feel unmotivated. But a little research can turn a vague desire into specific actions. And Derek Sivers gave one example of good research:

“For example: When musicians say, “I need a booking agent”, I ask, “Which one? What’s their name?” You can’t act on a vague desire. But with an hour of research you could find the names of ten booking agents that work with ten artists you admire. Then you’ve got a list of the next ten people you need to contact. “

Once you turn a vague goal into a list of specific steps, it’s easy to take action.

So remember, take the time to get specific. Break down your big goal, write down your milestones, small steps, and do good research. It helps you to take action and beats procrastination.

8. Be valuable to others — not just yourself.

“When I’m hot, it’s hard for me to imagine that others in the room are cold. I think it really is hot, not that it’s hot only for me. It feels like a fact, not an opinion. “

Derek Sivers pointed out the importance of being able to look through the lens of consumers, especially as creators, when we often fall into many biases.

One of them is that when we do so something cool and valuable to us, we like to generalize and immediately think that that's valuable to others.

And it’s understandable because our feelings feel like facts, but we should be able to see from the perspective of others and be empathetic. As a creator, it’s crucial to pay attention to how others react and what value you give them, not only how you feel because, as we noticed, it's often misleading.

“When someone creates something that feels important, powerful, and valuable to them, it’s hard to imagine that it’s not important, powerful, and valuable to others.”

This advice also includes the problem of a starving artist and shows one of the solutions. There are two ways of solving the problem of a starving artist and money is the proof of doing something valuable.

1) Focus on making your art and projects more valuable to others.

As we have often noticed, art doesn't end at the edge of the canvas, which means that the creative process is constantly going, and you should be asking yourself how you can be more valuable to others. Pay attention to feedback, and you will be more valuable.

2) Change your mindset and stop expecting it to be valuable to others.

Accept your art as personal and precious to only you and try to get your money elsewhere.

9. Whatever scares you, go do it

“Have you heard of rejection therapy? It’s a challenge — kind of a game — where you make it your mission to get rejected by someone every day. You have to do crazy things, like asking a stranger if you can try a bite of their sandwich. If they say no, you win for the day. The real point of the challenge is to overcome the fear of rejection by constantly exposing yourself to it. “

Sivers noticed that musicians usually send their music to places that won’t reject them, and it’s easier and feels better, but it doesn’t provide long-term benefits and growth.

The magic happens when musicians started to send music to places that reject most musicians, and once they get into of one these places, it’s the proof and credibility that sets them apart from the rest and opens more possibilities.

Keep in mind that you can also re-visit places that rejected you before.

When you can show that you’ve made it through the filters — the places that weed out the bad music — it puts you in finer company: the best of the best.

In short, expose yourself to unpleasant experiences and remember that pain is where the growth comes from. And once you get into the company of the best, it’s your unlimited tailwind.

10. Extreme results = extreme actions.

“You can’t just normal your way through this.

Extreme talent requires extreme practice — training like an Olympic athlete.

Extreme success requires extreme focus — saying no to distractions and leisure.

Extreme fame requires extreme ambition — taking the spotlight and its pressure.“

If you want to lead an extraordinary life, you can't do what everyone else does. You can't spend an entire weekend watching 48 hours of everyone's favorite TV show. It's worth remembering that achieving extraordinary results requires a lot of sacrifices. The more intense your actions, the better. 

Normal people will think that you’re insane, but it sets you free, and fellow achievers will welcome you to the exclusive club. 

When you’re not practicing, someone else does, and it’s more likely that he will win in the long term. 

You can’t get extreme results doing ordinary actions. Find what you truly love and let it kill you. 

For more insights on success, you can read my blog post on Sam Altman, The Success Equation.

11. Doing the opposite of everyone is valuable

“It’s supply and demand. The more people do something, the less valuable it is.

Everyone else is multi-tasking. So it’s more valuable to single-task.

Everyone else is hyper-connected. So it’s more valuable to disconnect.“

Two of the most insightful pieces of investing advice recommend us to be fearful when others are greedy and greedy when others are fearful and avoid the competition and wisdom of the crowd. 

The first one comes from Warren Buffett, but the second is from Peter Thiel, who expand this principle in his best-selling book, Zero to One.

And the advice Sivers was trying to convey is to do what others aren’t doing, in the spirit of Buffett’s approach and Thiel’s principle. Look at what your competitors do, then switch your approach. Don’t try to compete with them and beat them at their game, instead start playing a completely different game. 

“All happy companies are different: Each one earns a monopoly by solving a unique problem. All failed companies are the same: they failed to escape competition.” - Peter Thiel

Remember, your competition is only a reference, not the point to follow. Don’t be associated with them and be so different that people don’t even think to compare you. Create your own niche and be radically opposite.

12. Focus on fundamentals

“We have a desperate need for certainty, so we want someone to tell us what’s coming. But it’s impossible. Nobody can possibly know.”

No one knows the future, so forget trying to predict it and focus on what doesn’t change, on your fundamentals. Find in your actions and business essential things to know and do, just like we know that there will be gravity and water will be wet. Be stubborn with your vision but flexible with the details.

“Instead of predicting the future, focus your time and energy on the fundamentals. The unpredictable changes around them are just the details.“

Summary

I think that the best way to wrap up this short but valuable and worth-reading book is by sharing a quote, counter-intuitively from the into of “Your Music and People“, where Sivers summarized the entire book in several points.

- Marketing is an extension of your art. Business is just as creative as music.

- Marketing means being considerate. Focus on others. See yourself from their point of view. Being weird is considerate.

- All opportunities come from people. Stay in touch with everyone. Use a database.

- People skills are counterintuitive. To be helped, be helpful. Persistence is polite.

- Be resourceful. Ask for help, but never wait for help. Call the destination and ask for directions. Get specific about what you want.

- The music industry is run by cool people like you. Don’t put them on a pedestal.

- Describe your music in a curious way, and it will travel faster and further.

- Be extreme and sharply defined. Target a niche. Proudly exclude most people.

- Money is just a neutral representation of value. Be valuable to others — not just yourself. People like to pay.

- Decide if you’re at the starting line or finish line. Nobody knows the future, so focus on what doesn’t change.

- Whatever scares you, go do it.

Finally, Sivers added: 

That’s it! That’s the whole book. These 88 tiny chapters will explain these points.

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