13 Things I Learned About Success From Derek Sivers

Derek Sivers

Last night my almost 2 year old daughter grabbed an onion and ran away hoping to successfully take a bite out it. I chased after her and told her, “You are not going to be happy if you succeed at that.” How many times do we need to hear that in life? Succeeding, and being happy is something we all want.

You may know Derek Sivers from https://sivers.org/, his TED talks,  his book Anything You Want: 40 Lessons for a New Kind of Entrepreneur (a must read) or CD Baby. His interviews and writing have really challenged the way I view success. When I have been lost, his advice has been a great compass, always reminding me which way I’m facing and where I need to go. He challenges many common views and really asks you to be intentional about your purpose and goals.

It’s impossible to get to everything I’ve learned from him but I want to hit on a few here. I hope that you can find as much value from these as I have.

#1. Build your perfect world through your business

Sivers says, “When you make a company, you make an utopia. It’s where you design your perfect world” How many hours do you work? What tasks do you do? Where is your “office”? You can answer these questions and more. Design your ideal job. Sivers also adds, “You get to make a little universe where you control all the laws.”

#2. Success has no price tag

“Business is not about money. It’s about making dreams come true for others and for yourself”, says Sivers. Some business owners make more money than they can spend, but they aren’t happy. How much money would it cost to sell your dreams? I’m guessing no amount would do.

#3. You’ve got to have a backup plan. 

Perhaps you know Sivers from his 2010 Ted Talk: Keep Your Goals to Yourself.  Many people don’t realize that he had a couple of other talks proposed. The subject that was selected was just a last minute idea. Sometimes we think we know which one of our ideas is the best. Many times though, it’s better to try all of our ideas and let the world decide. It should be obvious that being stuck to one idea can end up making you stuck.

#4. Execution is everything

Brilliance is nothing without execution. Everyone has an idea. You have an idea right now! Yes, that one, I know it’s there. However, it’s nothing without execution. The world has changed, not by our great ideas but by the execution. Don’t worry about people stealing your idea, have ideas worth stealing and make them happen.

#5. Judge your goals today

“Goals should only be judged by their ability to change your actions in the present” It’s all about personal improvement. You have to try to get better. Sometimes you have to work for the joy of working. Get in that flow where you can grow and improve. I love his Lego analogy, “You see a kid playing with Lego, you’re like, ‘Why are you doing that? What is the ultimate goal? You know, it could be a much better castle if you’d have somebody else doing that” How many times do we tell ourselves that when we play with the “Lego” of our life?

#6. Serve others in away that brings you joy

Sivers recommends only starting a business when someone is asking you to. It’s all about, “Forget me, how can I help you.” But to truly be helpful you must enjoy what your doing. It’s not about being a martyr. His advice, “Happiness is the oil in the engine” When you are happiest is when you will be the most helpful.

#7. Forget life style design

If your goals are all about “me, me , me”, don’t be surprised if others aren’t as excited about it as you are. Many want to be the master of their own world, controlling all of their surroundings. This is their success. Sivers points out, “If you want to be undeniably successful, you must need to both master yourself and help others” I have gained the most joy, not from when I made my life better, but from when I can improve the lives of those around me. Being surrounded by gratitude, inside and out, is the life style I would design.

#8. Rock your own boat

Do what you’re afraid of. When you’re not surprised, you are not learning. I grew up in California, in Oakland. It’s not common to hear residents point out that the San Francisco Bay Area is the best region, of the best state, of the best country in the world. I also spent sometime in Santa Monica, just like Sivers. Sometimes when you love a place too much it is time to make a change. Today, I live in Sao Paulo Brazil. Life is different here, but I would have never learned what I know now had I stayed in the bubble I had made for myself.

9. Let your possessions be “good enough”

Although you want to be great, your possessions can be “good enough”. Whatever you buy can only be enjoyed by the comparison against what you had. Yes, it’s cool now, but there will be something better. You will never have perfect possessions. Own what you need and no more.

10. Delegate enough but not too much.

A leader must be able to explain, “Do this and here’s why”. When a question comes up, answer it in a way that can give direction in the future. However, it’s possible to delegate too much and lose the focus of your work. It’s your dream.

11. Make decisions

“Don’t be a donkey” exclaims Sivers. He tells the story of a donkey standing between water and food. He looks back and forth but never makes ups his mind and dies. No matter what part of your life you are at, make a decision. You can work on it for ten years, and then change focus. You don’t have to be something forever. Have the freedom to change and the courage to pursue.

#12. Do ONLY what makes you happy

At the end of the day, what’s your goal? Why do you work? Ask yourself, “Why am I doing any of this?” Bringing joy to those around me brings joy to me. If I’m not doing this, I’m not living. Find what makes you happy and DO IT.

#13. Give yourself to the future

Perhaps the biggest lesson I’ve learned from him is about parenting. “I never say, ‘let’s go, time to go’, we just do something until he’s ready to move on”, Sivers says about his son. This meditative approach to spending time with my daughter has helped me learn much more about her than I ever could by forcing my adult ideas on my toddler. Her decisions and approach are different than mine and I’m so happy just to enjoy who she is without my directions.

I hope you can find as much value from these lessons as I have. Remember this is not necessarily what Sivers believes, but it is what I learned from studying his work.  Also be sure to check out https://sivers.org/ for yourself. He has a wonderful list of “Do THIS” directives I’m sure you will enjoy at https://sivers.org/d1 Thanks for reading.

Which of these lessons was the most helpful to you?  Let me know in the comments.

Thanks Joe C. for inspiring me to get deeper into the subject of success.

Also thank you to the following interviewers:

Jenny Blake


Srinivas Rao


Jonathan Levi


Robin Zander


James Altucher


Tim Ferris 

http://fourhourworkweek.com/2015/12/28/derek-sivers-reloaded-on-success-habits-and-billionaires-with-perfect-abs/ and http://fourhourworkweek.com/2015/12/14/derek-sivers-on-developing-confidence-finding-happiness-and-saying-no-to-millions/

Moe Abdou


More interviews with Derek at: https://sivers.org/i

I’m a business owner from California now living my dream in Brazil. I’m passionate about using business to help others. If you’d like to connect, send me an e-mail at craigrohlfing@gmail.com. I answer all e-mails and it would be a pleasure to hear from you. Many thanks, Craig.

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