I’ve known about Derek Sivers for a while now, including  reading his book Anything You Want about 3-4 years ago. But as always, there is more to a person than just a podcast, book, article so I was more than eager to learn more and see if there are some valuable lessons or ideas I could extract.  My own observations are below, but I would strongly recommend listening to the podcast in its original form.

— Being an aspiring professional musician, Derek would say yes to everything, just to be a professional musician, meaning he got paid for gigs, even if it meant playing for only $75 a gigat a pig show in the middle of nowhere. (taking buses across the state would cost as much as the pay for a gig) Lesson: when you are just starting, say yes to everything. You never know which one is the lucky lottery ticket.

— The now famous pig show eventually turned into him making 300$ a gig, while doing over 1000 gigs at a circus, and basically hosting the show. Eventually, Derek not only was able to make a living but also bought a house with that money.

— Derek realized (with the help of mentors) that his feeling of being self-conscious was because he thought that the attention of the circus crowd was on him — Derek Sivers — and NOT on the act that he was putting on. With a help of a mentor,  he learned to detach his own personality and ego from the act and realized that you get on stage to give the audience (any audience) what they came for, not for yourself. It isn’t about you, it is about the audience (customers, clients, partners etc. — this applies to many areas of life).

— Derek’s key to self-confidence –You are whatever you pretend to be. Having someone believe in you is a great plus ( a mentor/teacher who believes in you and supports you, and tells you upholding things often enough so that you eventually internalize it. Or as per Tim, having a specific  woman) but you can just choose to be confident at any moment.

— “standard pace is for chums”. Understand that most organizations are built around the lowest common denominator to keep up with everyone. You can go as fast as you want/can in any endeavor and life. Chose your own pace. Sivers learned the same amount in 4 2-hour highly qualified tutor sessions as he would in 4 years of music college. He tested out the first 2 years of college, just from those 8 hours of “personal training”, allowing him to graduate from a 4-year college in just 2 years. The lesson here is to seek out these “hyper jump” experiences and tutors who can help you shave years and years of effort and get you to your goals faster.

—Constantly question what you are doing and why you are doing it. Look for the shortcuts, by critically examining the way most people do things and questioning not only the validity and efficiency of what they are doing as well as the reason behind it. Quite often you will find that there is no particular reason behind a customary way of doing it, aside from it being just that — “customary”.

— Going all out, trying to achieve 100% efficiency and effectiveness and productivity is not a good approach (at least for Derek). After months of regularly going all out on a trail bike, huffing and puffing and more or less always completing the trail at the same time (down to a fraction of a minute most of the time), he tried to take it just a bit easier and slow down and enjoy the ride more. The result was much more pleasure, unexpected lessons, many more things observed along the way and,  surprisingly,  only a tiny increase in the overall trail ride time.

— Stop before anything gets stressful. Derek uses internal pain (psychological, not physical) as the internal trigger to stop doing things that “hurt” or slow them down, because that is a sign of doing things that don’t need to be done, or are not in alignment with who he is or what he is striving to achieve. Internal psychological pain is as strong of a signal as physical pain, and should be treated accordingly –– with respect and attention.

— Derek has no advice for the people who want to “push” their ideas onto the world. His original business, CD Baby had only succeeded because of the “pull” of the world, where people asked him to help and provide some service to them. Most of the products and services that Derek has built were to help other people solve their problems and make their lives easier/simpler/less painful. His philosophy is to respond to demand, instead of creating demand. Derek simply answered the call for help, by sharing what he already has/does/knows how to. He calls it a co-op model, where the incremental cost of adding more “clients” to his service/product is small and value added is significant.

— Communicate like a human with your customers. People want to know that there are actual humans on the other end of the line (phone, email, website) etc. No one wants to be served by a robot (well some do, but most people want to buy/get served by people). We all seek connections, and if you are not connecting with your clients, you are missing a great opportunity. Make people smile and make their life a bit more fun and easier and they will be more than happy to share and consider you remarkable (by definition “make a remark on you”).

— put aside the numbers for a moment, and consider what is “good for the world”. Think how to make people you serve, your clients, your customers, your employees a bit happier and joyous. It is good for the world and the business. There is so much more to business than just the money.

— CD Baby went against all the rules of the traditional music sales business model, basically creating the utopian ideal for an online music store with the goal to serve the musicians and not the “industry”. Some of the specifics were paying out weekly, transparent pricing, no musicians were dropped due to low sales etc. Derek didn’t really need more money, as he was already making enough for himself from his musician career (a great lesson in itself, to never act from a place of desperation).  Eventually, CDBaby became profitable and grew very fast. He enjoyed doing things for the right reasons, making the musicians using his site and customers happy, not the financiers and investors since he had none.

— Never underestimate the value of a discount and goodwill that it generates. Increase the price within logical limits, but be prepared to give discounts to any one who asks for it. In the case of CD Baby, Derek started charging $35 vs. $25 for CD setup. It still feels fair to both buyer and seller, yet creates tremendous goodwill on behalf of the client/buyer/customer when they get the “special” discount.

—Take ‘Hell Yeah/Hell No’ approach to life. Don’t spread yourself too thin by saying Yes to anything that is not an absolute ‘hell yeah’ because when a rare true ‘hell yeah’ opportunity comes along (and it doesn’t come along too often) you won’t have the space, energy or time to even recognize it and give it proper attention. Once Derek started saying No to pretty much everything that came his way, he had all the time in the world for the things he truly wanted to do. He is in control of his time now. According to Sivers, being busy is being out of control of your life. This applies even to personal things, not just work and business. Are you really truly ‘Hell Yeah’ excited about a particular person, activity, project? If not, drop it and create some space in your life.

—Automate yourself out of the day-to-day business decisions. It takes more work up front (it took Derek about 6 months with CDBaby) but it’s more than worth it in the long run. Document every rule, decision, and ideas so that it can be used by everyone else in the company. Make sure to create a story and explain the overarching ideas rather than document the tiny minute details, to drive the “spirit” of the company and not just a letter of procedures and rules.

— Books are Derek’s greatest mentors and guide his life. The problem for him was that he loved reading the book and thought that he would remember the lessons forever, yet he was finding himself not remembering a single thing from the book some time later. So in 2007 he started taking notes from the books he read and review them sometime later, to internalize the lessons from every book he has ever read (this review is partially inspired by Derek’s approach).

— Derek selects books to read based on Amazon reviews (many many 5 star reviews) and very occasionally on a recommendation of someone he respects and trusts. Being a slow reader (and liking it that way), he wants to make sure he is committing his invaluable time to the right cause. At the same time, he is giving up easily, if the book is not to his liking. This can be treated as a ‘fail early, fail fast’ approach to learning. Great book reviews can be found at https://sivers.org/book Top 5 books on that page are his highest rated.

— Distilling wisdom into directives, is extremely valuable yet so rarely done. Most of the material/volume in a book is ‘wasted’ on establishing credibility and to argue the source vs. the actual idea/steps to be done. So if you trust the source, you can skip the argument and just go to the distilled wisdom. That’s how the Do This Project was born, where Derek basically reviewed all the notes from the books above to compress it all into the “ultimate” wisdom of directives broken down by the situations and general areas of life.

  Geek in Japan is the book most given by Sivers as a gift. Understanding the philosophy of a place, country, city etc is extremely important to understand the culture better. In Derek’s opinion, this book explains the Japanese mindset better than he has ever seen before. If you plan on going to Japan or are interested in Japanese culture, this is the book to get.

— Advice to younger self (20 y.o.): “Women like sex”. This was said in all seriousness yet with a chuckle.

— Advice to younger self (30 yo): “Don’t be a donkey”, thinking short term is bad, long term is good — not everything has to happen this week. Meaning – don’t die of starvation and thirst, unable to decide to chose hay or water, because a donkey can’t see the future while a human can. You can do everything you want to do, you just need foresight and patience. If you have 5 different things you want to pursue, you can still do them for the rest of your life, use the future, that way you can fully focus on 1 direction at a time, without feeling like you are missing out and can’t do it at all.

— on a related note, (from Tim) most people overestimate what can be done in short term and underestimate what can be done in long term. Most people commit this mistake.  We feel pressure to pursue many many things in parallel, instead of pursuing them serially, which provides us with  much better results.

Please feel free to share these notes with anyone and anywhere you want, with a backlink and appropriate attribution. I would love to hear your thoughts and comments as well.

Podcast and additional notes can be found on Tim’s site: http://fourhourworkweek.com/2015/12/14/derek-sivers-on-developing-confidence-finding-happiness-and-saying-no-to-millions/