Straightforward Life Advice From a Successful CEO

Derek Sivers seems like a pretty cool guy. He calls himself a musician, producer, circus performer, entrepreneur, TED speaker, and book publisher on his website. He started a company called CDBaby and made millions from this. He then gave the company to charity, resulting in millions of dollars subsequently being used to help up-and-coming musical artists who need some monetary support to try and realise their dreams.

Sivers also reads a lot of non-fiction books that are focused on psychology, self-help and self-improvement. He has little reviews of these books on his website and gives them a score out of 10, which is great if you need a recommendation of what to read.

In 2016, Sivers tried to summarise all of the key points he obtained from reading many non-fiction books. Then, he put these key points into “do this” directives as a personal guide to various aspects of life. Derek first brought the directives to the public’s attention in the hugely popular ‘Tim Ferriss Show’ podcast. Then, because of the demand, Derek shared the remainder of these lists on Derek’s website He also plans on doing more with these directives in the future, including potentially writing his own book.

Below are his directives, as well as my opinion of them. Directives that I completely agree with will be in green. Directives that I disagree with or that go against scientific research will be in red.

group hand fist bump

How to be useful to others:

Get famous

  • Do everything in public and for the public.
  • The more people you reach, the more useful you are.
  • The opposite is hiding, which is of no use to everyone.

Get rich

  • Money is neutral proof you’re adding value to people’s lives.
  • So, by getting rich, you’re being useful as a side effect.
  • Once rich, spend the money in ways that are even more useful to others.
  • Then, getting rich is double useful.

Share strong opinions

  • Strong opinions are very useful to others.
  • Those who were undecided or ambivalent can just adopt your stance.
  • But those who disagree can solidify their stance by arguing against yours.

Be expensive

  • People given a placebo pill were twice as likely to have their pain disappear when told the pill was expensive.
  • People who paid more for tickets were more likely to attend the performance.
  • People who spend more for a product or service value it more, and get more use out of it.

people taking group photo

WHAT I THINK: While many famous and rich people are useful to others, many others are not. What is true is that if you are famous and rich, you can have more influence on others and do more positive things, such as Bill and Melinda Gates. However, you also have the potential to negatively influence more people too, such as Donald Trump. What you do with that power and exposure is up to you.

You can also make a difference to others without being rich or famous. Don’t underestimate the difference you can make as a teacher or coach or parent or volunteer or community member or any other role where you interact with others regularly. If you charge more, people will value your services more, and you will earn more money and then have a greater chance to be useful to others.

Do try to be informed before sharing your opinions publicly. For example, look at all the damage Jenny McCarthy did by sharing her opinions on vaccines and autism.


How to get rich:

Live where luck strikes

  • Live where everything is happening.
  • Live where the money is flowing.
  • Live where careers are being made.
  • Live where your role models live.
  • Once there, be as in the game as anyone can be.
  • Be right in the middle of everything.

Say yes to everything

  • Meet everyone.
  • Pursue every opportunity.
  • Nothing is too small. Do it all.
  • Like lottery tickets, you never know which one will win. So the more, the better.
  • Follow-up and keep in touch with everyone.

Learn the multiplying skills

  • Speaking, writing, psychology, design, conversation, 2nd language, persuasion, programming, meditation/focus.
  • Not pursued on their own, they’re skills that multiply the success of your main pursuit (e.g., A pilot who’s also a great writer and public speaker; A chef with a mastery of psychology, persuasion and design).
  • These skills multiply the results of your efforts, and give you an edge over others in your field.

Pursue market value, not personal value

  • Do what pays well.
  • Do not be the starving artist, working on things that have great personal value to you, but little market value.
  • Follow the money. It tells you where you’re most valuable.
  • Don’t try to make a career out of everything you love. For example, sex.

Shamelessly imitate success

  • Imitate the best strategies of your competitors.
  • The market doesn’t care about your personal need to be unique.
  • It’s selfless and humble to use the best ideas regardless of source, to create the best service or product for your clients.
  • Get great at executing other people’s ideas as well as your own.

Be the owner, not just the inventor

  • It’s tempting to try to be the ideas person, having someone else do the dirty work of making those ideas happen.
  • Ideas don’t make you rich. Great execution of ideas does.
  • A rule of capitalism: whoever takes the most financial risk gets the rewards.
  • The biggest rewards will always go to those that fund it and own it.
  • To get rich, be the owner. Own as close to 100% as possible.

Benefit from human nature

  • Instead of complaining about the downside of human nature, find ways to benefit from it.
  • Instead of complaining about the rules, just learn the game, then play it.

bitcoins and u s dollar bills

WHAT I THINK: To get rich, it is important to know how humans think and act and find ways to benefit from this instead of wishing for things to be different. It is useful to see what has worked for others, learn how to do things in this way first, and then adapt the best things so that what you are doing is authentically yours. It is important to try to own the product or service you are trying to sell. If you don’t do this, your earning potential will always be capped and will generally always be less than your bosses.

While it is true that people need to be willing to spend money to make money, it’s not just about taking financial risks. There are many broke people out there who have spent too much on bad ideas. Figure out how to test your ideas or products first to see how the market responds before investing too much in it, and don’t be afraid to make changes or start over again if a better opportunity presents itself. Ideally, we aren’t just doing something for the money. If we love it, are good at it, and make a lot, we will be much happier than doing something just because we know that it pays well.

While it is true that we don’t know which opportunities will necessarily work out, we also can’t make much progress if we are saying yes to everyone and everything. Instead, meet and connect with the right people who are not just out for themselves until you find a great idea. Then pursue this project for a set period until you know if it is likely to make you rich or not. If not, jump ship as soon as you realise it and keep brainstorming and connecting and saying yes until you find your next great idea. Once you have this, learning to prioritise and say no might be even more important than always saying yes. Same with being in the middle of everything. It’s good until you know which path you want to go down. Once you know, distance from others can be just as good until an idea has been executed.

The last bit of advice that isn’t here is don’t gamble or invest in get rich quick schemes. Use debit cards instead of credit cards. Don’t buy the most expensive insurance options. Instead, invest in index funds and other trustworthy stocks regularly and as early as you can. Don’t change them around too much. Compounding interest will help you to gain a lot of money over time. But having heaps of money beyond what you need to meet your basic needs isn’t likely to make you a lot happier in the long run.

flight technology tools astronaut

How to thrive in an unknowable future:

Prepare for the worst

  • Since you have no idea what the future may bring, be open to the best and the worst.
  • But the best case scenario doesn’t need your preparation or your attention.
  • So mentally and financially prepare for the worst case, instead.
  • Like insurance, don’t obsess on it. Just prepare, then carry on appreciating the good times.

Expect disaster

  • Every biography of a successful person has that line, “And then, things took a turn for the worse.”
  • Fully expect that disaster to come to you at any time.
  • Completely assume it’s going to happen, and make your plans accordingly.
  • Not just money, but health, family, freedom. Expect it all to disappear.
  • Besides, you appreciate things more when you know this may be your last time seeing them.

Own as little as possible

  • Depend on even less.
  • The less you own, the less you’re affected by disaster.

Choose opportunity, not loyalty

  • Have no loyalty to location, corporation, or your past public statements.
  • Be an absolute opportunist, doing whatever is best for the future in the current situation, unbound by the past.
  • Have loyalty for only your most important human relationships.

Choose the plan with the most options

  • The best plan is the one that lets you change your plans.
  • Example: renting a house is buying the option to move at any time without losing money in a changing market.

Avoid planning

  • For maximum options, don’t plan at all.
  • Since you have no idea how the situation or your mood may change in the future, wait until the last moment to make each decision.

aerial view of city with lights during night

WHAT I THINK: It’s good to be creative, flexible, adaptable and open to change. These characteristics will become even more important in the future because change is likely to continue to happen at an even faster and faster pace. People back in the 14th century knew what to expect by the 15th century, but most people living now have no idea what life is likely to look like in the 22nd century. This doesn’t mean that we shouldn’t plan, and it definitely doesn’t mean that we should only plan for the worst. Life has continued to get better and better in so many ways, and it is likely to continue to get better in many ways too. It doesn’t mean it can’t get worse, but we shouldn’t all become doomsday preppers or not buy anything in case disaster strikes. Instead, try only to buy the things you need that will help add value to your life.

Especially if you have kids, stability is good, so don’t be afraid to set up roots. Buy a house, start a business where you live, and develop friendships with other people in your neighbourhood. Some people may leave, businesses may collapse, marriages may crumble. However, research still indicates that people have more satisfying relationships if they get married than if they live together but don’t get married. Married men are also both happier and healthier than single men. Divorce negatively impacts kids, especially if there is a lot of conflict. Learning how to overcome difficulties is better than always avoiding things or running away when things get tough or another seemingly desirable option presents itself. We always think the grass is greener on the other side, but when we get there, it’s often not as shiny or as different as we first thought (or better than we’ve previously had).

Essentially, having plans and making commitments is better than having none, as long as you are also open to making tweaks and even big changes if things really aren’t working out. Research indicates that having too many options makes it too hard to choose, and not making a decision can be really stressful and physically and emotionally draining. Also, research indicates that we tend to become happier with our choices over time once we have made them, as long as we commit to our choices and don’t keep trying to doubt ourselves or leave all the other doors open.

four women standing on mountain

How to like people:

Assume it’s their last day

  • Everyone talks about living like it’s your last day on earth.
  • Instead, to appreciate someone, live like it’s their last day on earth.
  • Treat them accordingly. Try to fulfill their dreams for the day.
  • Really listen to them. Learn from them.

Be who’d you’d be when alone

  • You could live in a crowd, pleasing only others.
  • You could live in solitude, pleasing only yourself.
  • But ideally, when in a crowd, be the same person you’d be when alone.

Assume men and women are the same

  • Men think women are so different from them.
  • Women think men are so different from them.
  • But the differences among men and differences among women are far greater than the differences between men and women.
  • So, counteract your tendency to exaggerate the differences.

Always make new friends

  • As you grow old and change, old friends and family will be unintentionally invested in maintaining you as you were before.
  • Let go of people that don’t welcome and encourage your change.

Avoid harming the relationship

  • For long-term relationship success, it’s more effective than seeking the positive.
  • A friendship that may take years to develop can be ruined by a single action.

Act calm and kind

  • Regardless of how you feel

Don’t try to change them

  • unless they asked you to.
  • Don’t teach a lesson.
  • Stop trying to change people who don’t think they have a problem.

Find wisdom in your opponents

  • Really engage with those who think opposite of you.
  • You already know the ideas common on your own side.

Purge the vampires

  • Get rid of people that drain you, that don’t make you feel good about yourself.
  • They make you hate all people.

men s white button up dress shirt

WHAT I THINK: It is great to really try to appreciate others, and understanding that some people may die soon is a helpful way to ensure that we don’t take others for granted. The Tail End by Tim Urban is an awesome blog post that nicely highlights how little time we actually have left with the important people in our lives. We should try to make the most of our time with them while we still have it, so we don’t regret it later.

We can learn a lot from others if we ask them about their life and experiences and beliefs and really listen, even if they have different ways of looking at things. But we shouldn’t try to give advice or teach lessons to others unless someone has asked or agreed to it first (or they’re reading your blog post!).

While it is good to minimise how much time we spend with people that drain us or don’t accept us for who we are, it is also important to try and maintain our old friendships. Having both old friends and family to keep us grounded and new friends to help us learn and grow is having the best of both worlds.

Men and women are different in some ways, and it is important to understand how and why. Of course, we should still see each other as individuals and not just a gender, but this is the same with people from a different culture, ethnicity, nationality, religion, and any other group different to yours. If we can understand group norms, it can help us to understand others a little bit better. Still, we should also be willing to change our perceptions of others based on what they say and do, rather than hold onto rigid, unhelpful or even discriminatory stereotypes.

While it’s impossible to always be 100% ourselves around others, the more authentic we can be, the more energised around others and connected with them. Similarly, we shouldn’t always act calm if we really are upset or angry or worried and need to express our feelings or what we need. However, we can express this in a kind and considerate way to not unnecessarily burn any bridges.

Thanks for reading!

Dr Damon Ashworth

Clinical Psychologist

Published by Dr Damon Ashworth

I am a Clinical Psychologist. I completed a Doctoral degree in Clinical Psychology at Monash University and a Bachelor of Behavioural Sciences and a Bachelor of Psychological Sciences with Honours at La Trobe University. I am passionate about the field of Psychology, and apply the latest empirical findings to best help individuals meet their psychological and emotional needs.

16 thoughts on “Straightforward Life Advice From a Successful CEO

  1. Hmmmm. Just suppose, that we all woke up one morning and overnight, a new nationwide federal law had been passed completely banning all Motivational speakers and also banning all businesses from posting inspirational of motivational quotes on any billboard, bus or signage.

    This is not as negative as it my sound at first, for two reasons (in my opinion):
    1. Scanning through some of these quotes, above, (this may not be popular, but—-) a lot o’ these quotes sound ssoooo politically-correct or like they could have easily come out of Napolean Hill’s book “Think & Grow Rich”—-OR—-written by someone who has attended one-too-many AMWAY seminars. But there is also another reason:
    2. With ALL motivational quotes (especially on a businesses sign when you drive by), the very fact that any business feels they need any such quotes at all, to improve things, is just a vivid demonstration of how far the place has already sunk in the first place. The more of that kind’ve stuff they have/promote, the less I would want to work there? Why? Because you will be expected to “drink the Kool-Aid and be a true believer” in order to be considered a good employee. Better to work in a place where it simply doesn’t come up. Someone says: but what about Morale? I say: better that people can be themselves, or even be silent, rather than be be expected/compelled to tow some “positivity” corporate line. When this happens, people may “do” it, but its out of “survival” not sincerity.

  2. Absolutely brilliant Damon, I agree with what you say here, especially with regard to the views on men and women. I have found there are more difference within men and within women than between men and women. This is what needs attention not the dismissive attitudes of men toward women and vice versa. I The advice on how to progress with your work ideas, something much needed for focus. You have put a lot of valuable information in this post. I will share it. Thank you and I need to reread it again to absorb more.

  3. I feel like lists like this should always come with a caveat of ‘if you want your life to look like X’ A lot of what he lists would turn life into a living hell for me, so it’s also important to be self-aware and not aim for a life that’s antithetical to who you are. (Been there, done that, it’s a really bad idea.)

    Shaping my writing/art according to other people’s subjective whims instead of my own would completely undermine my reason for enjoying it in the first place. I’d just be gainfully employed elsewhere for the purpose of paying bills and to avoid starvation.

    Also: the part about preparing for disasters and always expecting the worst seems like it would be -terrible- advice for people that have anxiety and a problem with catastrophizing. (I’m glad you addressed that bit.) A lot of his list seems tailored to people that are neurotypical and healthy.

    1. Yes definitely. The thing about always preparing for the worst is in direct contrast to what I tell my patients. There are a million potential what ifs that I could think about, and trying to prepare for all of these would be both unnecessary and exhausting. Much better to focus on what is most realistic and most helpful in my opinion rather than always preparing for the worst. I couldn’t imagine doing work that I didn’t like just for money either, but if we can find work that we enjoy and that pays well too that’s pretty cool.

  4. A sound evaluation, Damon. His advice started off sounding like a bad cliche of USA capitalism – indulge impulsiveness, appease the whims of others, and focus on money and fame. Thankfully introduced a bit of a humanistic side (a much more ancient and durable recipe for “success”). I hope not too many read his stuff mindlessly without their own critical evaluation.

  5. When he says that “Money is neutral proof you’re adding value to people’s lives”, it just isn’t true. The money markets have proven again and again that there is destructive money-making. It looks more and more as if the lessons of 2008 have been forgotten.

  6. First off, I don’t like the word “directive” at all. The only time I have ever used it it was used to reflect something negative. I know there are other takes on the word, but it still rubs my fur the wrong way.

    I generally agree with most of your choices of font color. Not all, though. I do generally agree with all of your summary opinions.

    The fact is, a lot of those “directives” can be looked at in various ways. They’re not black and white statements. Those who think all of them are, are missing experiences and lessons that would broaden their thinking.

    I am not totally opposed to “How to succeed” posts/articles, but I see success in a broad way. What is success to one, isn’t to another. We don’t all value the same things. We don’t all live in the same sphere. Sometimes people that a CEO may label as a “failure” is actually far richer, in many ways. Some people who feel they’re highly intelligent, lack intelligence that they are unable to possess because of a certain limited experience. Struggle means different things to some than others. I can speak for myself in saying that what I viewed as “success” in my youth, is comparatively shallow to me now. I was a lot more grandiose back then with an overblown sense of worth. I was so impatient that I had blinders on or took on so many things, that a lot became a blur.

    When writing above, I’m not implying that someone who is frequently knocked down in life will emerge stronger, wealthier, or wiser than someone who hasn’t. Some people who struggle or experience tragedy never recover well. I guess one can’t pass blame. There’s no good time or place for that. I’m just saying that sometimes struggle and failure bring a wealth of sorts that can’t be found otherwise. The key, I believe, is in the way we decide to look at life and success. That can require a creative mind, a very open mind, and a willingness to give oneself a freedom from traditional definitions. I think my progress on such a journey has come with analyzing and challenging my thinking, and working hard to prioritize truly important things for the me of now. My journey continues, as will some of my thoughts on life (success, happiness, what contentment really means/requires, etc.)

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