Derek Sivers and the Art of Enough

Why your happiness depends on defining enough.

Who is Derek Sivers ?

Derek Sivers is an American entrepreneur and musician (now living in New Zealand) who was the CEO of one of the first digital music stores “CDBaby" in the early 2000s.

Derek Sivers might be one of my favorite writers and entrepreneurs. I came across Derek’s book Anything You Want   a few years ago when I was reaching burn out amounts of stress from juggling being a full time teacher in a tough school district, running a coaching business and also trying to be a good husband in a new marriage. 

My goal is to pack as much Sivers wisdom into one spot so you won’t have to go crawling through the internet for it.  Enjoy!

#1 The Pursuit of Enough

It is the inability to define what “enough” is that is society’s greatest cause of unhappiness. We walk around with ideas of success thinking that certain things will bring us lasting joy. Usually what we think we want isn’t even our own idea but was rather planted there by someone or something else. 

Kurt Vonnegut and Joseph Heller were at a party at a billionaire’s extravagant estate. Kurt said, “Wow! Look at this place! This guy has everything!” Joseph said, “Yes, but I have something he’ll never have…Enough." 

Just think about it: How many times have you seen some ad for a 17 year old kid telling you the single secret to building wealth from his mom’s basement? How many times have you seen some weird guy in front of a rented leer jet on a YouTube pre-roll ad trying to convince you to invest in Bitcoin? How many times have you seen a sports car and sighed wondering when you will get your big break…? 

As Derek’s success grew monetarily in CD Baby his happiness inversely went down. Is that the case for everyone? No. But, it was the case for Derek and that’s an important lesson to understand.

The single most important lesson I learned from Derek was to ask myself “Am I doing this because I genuinely want to, or am I doing this to impress an invisible jury that exists only in my head?”

#2 No Roads, Only Directions

When I was being evacuated by the U.S. State Department from Ukraine in 2014 as Russia invaded, I was told probably one of the single most impactful things by my Ukrainian taxi driver to the airport.

Ukraine spends more money than any other country in Europe on roadwork but still has some of the worst roads (corruption) so as we tried to avoid the pot hole my driver joked: In Ukraine, there are no roads, only directions . 

This is kinda like business: You might think you have all these wonderful schemes, plans and tricks up your sleeve to scale, make money and create incredible products for your clients only to have them quickly blow up in your face. Instead of scheming Derek suggests you simply “answer the cries for help” instead.

#3 Hell Yeah! Or Hell No!

Deciding what to do in life should meet one metric: If you aren’t saying “Hell Yeah!” It is an automatic “Hell No!”

As a peoplepleaser by nature I’ve ignored this advice only to end up hurting relationships, business deals or customer trust in the long run. It comes down to FOMO. We don’t want to miss out on living a larger life so we collect lukewarm commitments that clog up our day too much to make space for rare “Hell Yeah!” opportunities that may pop up.

“If you’re not saying “ Hell yeah!” About something, say no. When deciding whether to do something if you feel anything less than “Wow! That would be amazing! Absolutely! Hell yeah!” Then say no. When you say no to most things, you leave room in your life to throw yourself completely into that rare thing that makes you say “ Hell yeah! ” 

It seems that in some cases, you may need to say Yes to things that don’t make you say “Hell Yes” to at least break into a particular sphere or develop relationships.

The latte boy in the DC lobbyist office doesn’t necessarily want to be everyone’s errand boy, but he knows that a year well spent networking will set him up for what he really wants to do in the long run: deal making. The unpaid graduate assistant coach sleeping on the couch in the locker room of an SEC football program probably has a girlfriend wondering what the heck he is doing, but he knows he is there for the network first.

Again, the root of this idea is defining enough - defining the limits of what makes you energized and what drains you.

#4 Execution, Execution, Execution

Steve Jobs wasn’t the first person to try making a smartphone. Uber wasn’t the first ride sharing app idea. Tesla wasn’t the first electric car idea (in fact electric car plans have been around as long as the Model T Ford). It was their execution on these ideas that turned these good ideas into good businesses.

Good ideas aren’t automatically good businesses.

…ideas are worth nothing unless they are executed. They are just a multiplier. Execution is worth millions…To make a business, you need to multiply the two components. 

I have been such a reflector in my own life - filling up tombs of journals and notebooks with ideas, theories and notes but it dawned on me looking at all these notebooks: Where was the execution? What if instead of sitting on 1.5hr’s of reading and notes per day I decided to ship, publish and take action instead? I think some reflection is healthy. But I’ve often used idea formation as a crutch to excuse my own inaction.

#5 The Market Wants What It Wants

It’s important to tinker early and often because you won’t know what people like until you put something in front of them to accept or reject. In Seth Godin’s marketing work and in my own experience it is abundantly clear that people aren’t always rational. Even if they say they would pay x amount for your product or idea you just won’t know if that’s true until they do. 

So, until your market buys it hasn’t bought.

Until your course receives sign ups the market doesn’t want it. Until your consulting service is used the market doesn’t want it. This is why it's important to iterate nimbly. Don’t sink all you money into developing a product that people only say is a good idea. 

It’s only a good idea if they buy.  

Derek talks about how what he thought CDBaby did was very different from what his paying customers thought it did. He thought “it was just a credit card processing service” but it turned out his clients saw CDBaby as a democratized online CD storefront. 

In my own coaching business I thought was just coaching high school kids how to kick better, but overwhelmingly the parents and players I worked with saw my business as helping them navigate the weird world of college football recruiting. 

What you think your business does isn’t usually what your customers think it does. Why your customers come to you usually isn’t why you think they come to you. Be ready to pivot.

#6 The Best Way To Grow Isn’t To Grow.

You’ve earned a certain level of trust with your current customers. They love you. They think whatever you’re doing is better than sliced bread. You are giving them oxygen as they gasp for air. You are making them happy. You are helping them live a fuller life. Yet, what do most businesses try to do the second they taste moderate success? Grow.

Growth isn’t bad, but how it is done is often a problem. They seek to find new clients. Maybe higher paying ones. Maybe ones in different areas. Maybe to break into a new market. But more revenue usually just means more liability, more expenses and less of you to go around to your true fans who love you. 

Of course, this selfish pursuit of growth is justified as selflessness by believing that as a bigger business you can somehow now better meet the needs and wants of your current clients. But really, growth is going to take your focus further away from them. 

If you really want to grow, focus solely on your preexisting clients.

None of your customers will ask you to turn your attention to expanding. They want you to keep your attention focused on them.

The more my own businesses have grown and the more the businesses of my friends have grown the more headaches they’ve experienced.

Instead of trying to grow your business in volume or quantity grow it qualitatively.

Your current clients are going to be your best source of newer clients anyway.

#7 Exclude!

You can’t be all things to everyone. Yet, many business owners do exactly that. When you are trying to gain traction you market to everyone, take every call, take every appointment, and will be overeager to close new sales. The problem is no one wants to be at a club that lets just anyone in - not even you. 

Have the confidence to know that when your target 1 percent hears you excluding the other 99 percent, the people in that 1 percent will come to you because you’ve shown how much you value them.  

Being exclusive is a long term game you want to play with long term true fan customers. It will feel in the moment like you are saying no to more money, which you technically are, but in the long term you are actually saving yourself more in money and customer happiness.

Let’s say you let one lousy customer in who you know isn’t a good fit but, since they are willing to pay you a lot you say yes anyway. This customer then calls you day and night, berates your sales staff and sucks the air out of your limited time and attention for the customers you actually do enjoy working with. In fact, you’ve become so distracted that a few of your true fan clients have drifted away to other competitors now. Now this lousy customer has cost you money instead of making you any. 

It’s a fine line between being polarizing enough to rally your 1% troops and appearing crazy or arrogant. It’s only really up to the business owner to know the difference. But, everyone likes to have their own private club. You can give that to them.

#8 There’s No Right Way (Which Might Be Wrong)

I used to think my heroes playing in the NFL growing up were super men, different, or unique, but through my business I’ve met and made friends with quite a few of them. They’re just like anyone else. Some guys were All Americans. Some rich. Some poor. Some had it all. Some slept in their cars for a year. There’s no one exact right way into the NFL.

Most of the textbooks on creating a business are written by people who’ve never built one. You can’t study business. You need to do it. Just like most teaching textbooks are written by people who quit teaching to write a textbook on how to teach.

You can’t pretend there’s only one way to do it. Your first idea is just one of many options. No business goes as planned, so make ten radically different plans. 

You’re not going to be Steve Jobs or Jeff Bezos. It’s just not going to happen. But you might be able to be the Steve Jobs of your own little world. 

#9 The Business Will Self-Destruct In 5, 4, 3, 2, 1…

The goal of a business is to put itself out of business.

You exist to serve people and help them become who they seek to be. But, inadvertently, you can get stuck on perpetuating the very problem you sought to solve. Most companies’ mission statements should actually read “We wanted to solve the problem so we became part of it.”

…even well-meaning companies accidentally get trapped in survival mode. A business is started to solve a problem. But if the problem were truly solved, that business would no longer be needed! … Your company should be willing to die for your customers.  

Think about it: Juul was initially created to wean cigarette smokers off of cigarettes and now is a public health disaster. Productivity and focus apps that charge 9.99/mo now bombard you will addictive notifications that keep you even more distracted. Twitter wanted to democratize news but has now given a platform to demagogues.

If one day your clients wake up and they say “Thank you so much for all your help you’ve truly solved our problem, we’d like to close our account with you.” You’ll know you made it. You’ll also know its time to go check out your next business idea.

#10 Desperate Is Creepy (The Backwards Law of Money)

Money is a backwards law: it’s only when you don’t care about it that it cares about you.

When someone’s doing something for the money, people can sense it, like they sense a desperate lover. It’s a turnoff…We want to give to those who give.  

How we see money is how we see ourselves.

Money can’t fill a hole in one’s heart to feel love, feel generous and be OK with who they see in the mirror. Even on the biggest sales I ever closed numbering a couple thousand dollars (I know small peanuts) I still was the same person I saw in the mirror that next morning, I wasn’t any happier and, if anything, more money meant more taxes.

At best, money is just a symbol of doing work that someone found valuable. Money is only found on the way to making other people happy, it flees from people looking solely for it. 

#10.5 A Profile Is A Person

There are real people just like you or I behind every smart phone, tweet, post, snap, email or profile out there, but it’s hard to remember. 

When I’m protected by one ton of steel and locked car doors I feel perfectly entitled to yell all sorts of things that would make my grandmother weep at other “idiot” drivers. But, should that same person be right next to me at the grocery store I’m a much nicer, more forgiving person since I don’t have a car door to hide behind.

If you think I’m a monster, don’t worry, you are too in your own way.

Distance creates self-righteousness and the overuse of pronouns like “they”, “these people”, or “those people” to box off those we don’t understand.

Assorted Derek Sivers Resources: Talks, Podcasts and Articles.

Derek Sivers’s blog is where you’ll find most of his work here: dereksivers.org .