“How to Live” Derek Sivers’ Smorgasbord of Mindsets

Derek Sivers details 27 distinct mindsets in “How to Live.” He concludes that each should choose how to integrate them into their life choices.

“How to Live” Derek Sivers’ Smorgasbord of Mindsets

While “How to Live” is not quite a book of poetry, Derek Sivers has polished a number of insights into succinct phrases spread over  112 pages. This is a book that bears re-reading. Sivers self-published it and offers a nice combination package where you can get the hardcover and multiple digital formats:  epub, mobi, pdf, mp3, html (no DRM).

He opens with: “Please read slowly. One line at a time.”
He concludes: “This is an orchestra: You are the composer and conductor.”

Derek Sivers on How to Live
There are 27 instruments in the orchestra and 27 mindsets explored in the book. I could not discern a mapping between the instruments and the mindsets, but Sivers is a musician and may see it differently. Or his metaphor may only extend to the orchestra and not the individual instruments. I put his conclusion first because it took me a few sections to appreciate that Sivers was not advocating for a particular perspective but instead offered a tour of 27 possibilities to choose or remix as you see fit. I was reminded by the help page for “life” on an old timesharing system, “Life: You will have to figure that one out for yourself.” He was inspired by “Sum” by David Eagleman, a collection of 40 possible afterlives. I have not read the book, but you can read Sivers’ review here.

It’s up to you how you arrange and integrate one or more of the following 27 mindsets:

  1. Be independent.
  2. Commit.
  3. Fill your senses.
  4. Do nothing.
  5. Think super-long-term.
  6. Intertwine with the world.
  7. Make memories.
  8. Master something.
  9. Let randomness rule.
  10. Pursue pain.
  11. Do whatever you want now.
  12. Be a famous pioneer.
  13. Chase the future.
  14. Value only what has endured.
  15. Learn.
  16. Follow the great book.
  17. Laugh at life.
  18. Prepare for the worst.
  19. Live for others.
  20. Get rich.
  21. Reinvent yourself regularly.
  22. Love.
  23. Create.
  24. Don’t die.
  25. Make a million mistakes.
  26. Make change.
  27. Balance everything.

This book offers a lot of excellent advice and many valuable perspectives. Some sections did not resonate with me, but overall, this is a well-crafted masterpiece. I have selected the most useful advice for bootstrapping entrepreneurs and added my perspective.

Unless otherwise attributed, all quotes are excerpts from “How to Live” by Derek Sivers.

Be Independent

Being independent means you can’t blame others.
Decide everything is your fault.
Whoever you blame has power over you, so blame only yourself.
When you blame your location, culture, race, or history, you’re abdicating your autonomy.

The core truth here is that you must examine your behavior and choices to assess your level of contributory negligence. Some things are not under your control, and “bad things” can happen to “good people” due to bad luck or rare events. We are occasionally innocent bystanders, but it’s best to assess how to prevent a recurrence.

You can’t be free without self-mastery.

Managing oneself requires self-knowledge that allows you to leverage your strengths and self-control to work around or compensate for your weaknesses.

Own your own business with many small customers to avoid depending on any big client.
Offer products, not a personal service, so your business can run without you.
Create many sources of income like this.

I think services are easier to adjust than products. The practical and low cost path to a fast start is offering services to a few customers. But products offer leverage once you have debugged product-market fit.


Find a community of like-minded people.

You can find more than one community to support your efforts to improve in different areas.

Trust helps your happiness more than income or health.

This one made me think hard, but I realized that Sivers is correct. You would risk money or your health to help a friend or someone your trust.

When people say you’re a person of good character, they mean you’re not just good, but consistently so.
You’re defined by what you do repeatedly.
Your habits create your character.

You won’t build character or trusted relationships if you only honor commitments when it’s expedient–whether it’s to yourself or others. Building trust involves pain and sacrifice, putting others’ needs ahead of yours. The best way to be trustworthy is to be meticulous about making your commitments, so you are confident about meeting them.

Fill your senses.

I did not find anything that resonated in this section. Your mileage may vary. Please note that I scored very poorly on the VIA Strengths Survey for “Appreciation of Beauty.”

Do nothing.

The ideas I found helpful in this section related to “first do no harm,” right actions at the right time, and what Nicholas Nassim Taleb calls “via negativa,” or the road to be avoided. In Anti-Fragile, Taleb writes, “The learning of life is about what to avoid. You reduce most of your personal risks of accident thanks to a small number of measures.”

People will appreciate your silence, and know that when you speak, it must be important.
Shallow rivers are noisy.
Deep lakes are silent.

And, of course, actions speak louder than words.

“It is remarkable how much long-term advantage people like us have gotten by trying to be consistently not stupid, instead of trying to be very intelligent.”
Charlie Munger

Think super-long-term.

Delay gratification.
Today’s discomfort brings future rewards.
When you have a clear view of the future, you won’t mind the small sacrifice.
You never regret not indulging.

In general, this is good advice. But sometimes, entrepreneurs try to live on too little or start making “stupid cheap” choices that reduce their startup’s robustness and resilience because they are forcing themselves to operate right on the edge of failure. Of course, new spending should follow new revenue, not anticipate it–or worse, depend on it. Still, as you gain traction, you should allocate a portion of new revenue to compensation increases for the founders and any employees working “below market.” There are also considerable morale benefits to be gained from the team sharing a meal together at least every few weeks and it’s nice when the company can pay for it.

When you choose a behavior, you choose its future consequences.

Founders must be very cautious about having one set of rules for themselves and another that they apply to employees. When you are establishing culture, people look hard at your actions.

Intertwine with the world.

If you want a successful network of connections, what matters is not how many people you know but how many different kinds of people you know.
Building relationships worldwide brings more opportunity, more variety, and more chance for circumstance.

The Internet has dramatically reduced your cost of discovering and connecting with interesting people worldwide. The combination of professional networks like LinkedIn, extremely low-cost audio and video communication tools like Skype and Zoom, and the ubiquity of email have made a worldwide network of connections possible for any entrepreneur.

Make memories.

I have selected just this quote that I think is good advice but it’s not representative of the thrust of the chapter.

Journal every day.
Write down your activities, thoughts, and feelings for future reference.

There are four complementary ways to do this:

  1. Always carry 3×5 cards with you. I keep a handful in my shirt pocket to jot down sudden inspirations I would otherwise forget. Writing a short note on an index card does not break the flow of a conversation when typing on your phone or opening your laptop might. Paper is also devoid of the cornucopia of distractions that any Internet-connected device keeps only a few clicks away.
  2. Keep a few sheets of paper and a pen on your nightstand: now you can record those brilliant insights that occur just as you are falling asleep or persist as memory fragments from dreams.
  3. Maintain one or more documents online or on your computer to capture your “good ideas” so that you can get them out of your head so that you don’t forget them–and you can get back to what you should really be working on. It’s probably best to have a primary scratchpad document that you review periodically to sort and re-assign different ideas to more specialized documents.
  4. Sometimes the flow of your ideas is so swift that the mechanical overhead of writing them down or typing them might lose some or break the flow. Consider capturing your thoughts as voice notes on your phone or a pocket recorder. While picking up your phone might tempt you to check your mail or surf the net, a pocket recorder offers no distractions. Services like Otter and Rev do a good job of producing useable transcripts from single voice audio at a low cost.

This next quote comes from the “Make a Million Mistakes” chapter but seems thematically related to “journal every day.”

Keep a log.
A mistake only counts as experience if you learn from it.
Record what you learned, and review it.
Otherwise, it was a waste.

I have blogged about the value of journals and logs in

Master something.

Mastery is the best goal because the rich can’t buy it, the impatient can’t rush it, the privileged can’t inherit it, and nobody can steal it.
You can only earn it through hard work.

Marcelo Rinesi has documented these same implications for the “Expertise Light Speed Barrier.” It takes years to develop expertise. While some methods of acquiring expertise are more effective than others, there are no real shortcuts.

The pursuit of mastery helps you think long-term.
It keeps your eyes on the horizon.
You spend time intentionally.
The most rewarding things in life take years.

I think people who achieve mastery do so because they can enjoy the journey.

Define “success” for yourself.
Describe the outcome you want.
You can’t hit a target you can’t see.

I like Eric Berne’s definition of a winner as “a person who fulfills his contract with the world and with himself. That is, he sets out to do something, says that he is committed to doing it, and in the long run does it. […] If he accomplishes his goal, he is a winner.” Of course, for someone to become a winner, they have to describe the outcome they want. Berne suggests there are four requirements:

  1. A winner fulfills his contract with the world and with himself.
  2. A winner says,  “I made a mistake, but it won’t happen again.”
  3. A winner knows what he’ll do next if he loses, but doesn’t talk about it.
  4. A winner says, “I won’t let that happen again,” and doesn’t.

Focus means head down.
Big picture means head up.
The more you’re doing of one, the less you’re doing of the other.
If you’ve been head-down on a task for too long, lift your head up to make sure you’re going the right way.
Don’t do well what you shouldn’t do at all.

This is good advice. You need to balance strategy and tactics: don’t get so lost in the details you lose sight of your critical objective.

Let randomness rule.

I found very little that resonated in this section. The quote I selected below is at variance with the underlying theme of “embrace randomness.”

Random stuff happens.
All you can control is your response.
Every day, you’ll practice how to react to chaos: with dignity, poise, and grace.

This reminds me of one of Viktor Frankl’s great insights:

“Between stimulus and response there is a space. In that space is our power to choose our response. In our response lies our growth and our freedom.”
Viktor E. Frankl

Pursue pain.

I don’t think Sivers named this chapter correctly. He is not advocating masochism but something closer to the Motto of the Royal Air Force, “Per Ardua Ad Astra: Through Adversity To The Stars.”

Everything good comes from some kind of pain.
Muscle fatigue makes you healthy and strong.
The pain of practice leads to mastery.
Difficult conversations save your relationships.

I find the anticipation of various kinds of pain is often worse than the actual pain the effort or experience entails.

But if you avoid pain, you avoid improvement.
Avoid embarrassment, and you avoid success.
Avoid risk, and you avoid reward.

People say they’re not doing the work because it’s hard.
But it’s hard because they’re not doing the work.

Getting started with something new involves being embarrassed by your mistakes, a slow rate of progress, and the need to ask others for help. It can also mean changing your routine to enable new habits and system improvements.

The right thing to do is never comfortable.
How you face pain determines who you are.

The easy road leads to a hard future.
The hard road leads to an easy future.

How do you force yourself to pick the hard road? I visualize who I am helping or protecting or what I am trying to bring into existence. Personnel decisions, firing, hiring, and promoting can be very challenging. You want to give people a chance, but you must protect the team from someone who is not pulling their weight. What can look like the easy road often entails a lot of risk if things go differently than expected. I assume it will take multiple iterations to make something new work–nothing new ever works the first time–and opt for “slow and steady wins the race” over assuming a shortcut will work the first time I try it.

Sometimes you realize that winter is coming. A Norwegian friend explained to me once what they call the farmer’s lament: summers are short, and you don’t have much free time between planting and harvesting. And it’s summer, so you feel like taking some time off and enjoying the warmth. But then you realize you don’t want to lament your failure to repair your roof or plumbing or fencing in the middle of winter when you have to live with the consequences until Spring.

I am fortunate to have business partners who ask me, “Did you get that task done you committed to the client? Have you finished that blog post we had scheduled for today? Then why are you starting this new tasks before we have cleared off what was on the list for today” Fortunate may not be strong enough; blessed is more accurate. If you don’t have a lot of self-control, find co-workers who will kick you in the butt when it’s called for.

Pain’s power relies on surprise.
If you expect it, it’s weaker.
If you choose it, it’s gone.
Choose pain in small doses to build your resistance to it.

I blogged about surprise being a key element of pain’s power in “Unfamiliar pain.” Unexpected setbacks are doubly painful because they blindside you after you have figured things out and are settling into a groove. Instead, you are upended by a new competitor, an organizational shuffle at a customer or key partner, or a change in the economy.

A first-time entrepreneur often has an unconscious expectation that things will get easier are violated. Many clients ask, “when does this get easier?” Of course, I ask my partners the same question from time to time.

Ghosts don’t leave until you’ve understood their message.
Problems persist until you claim them and solve them.
Face them directly and they’ll disappear.

Hardware startups spent two years of the pandemic continually adjusting their BOM as rapid and dramatic shifts in part availability and lead times made it seem like it would be easier to nail jello to a tree than freeze the design. It played havoc with their costs and ability to make commitments.The ones the persevered realized that supply chain issues were not going to settle down for a while and they needed to make logistics and materials management a focus area. Here are two blog posts on managing persistent or recurring problems

Do whatever you want now.

I found very little that resonated in this section, and the quote I have selected below is somewhat at variance with the underlying theme of “do whatever you want  now.”

Happiness is something to do, someone to love, and something to desire.
Heaven is not what’s at the end of the path.
Heaven is the path itself.

You have to enjoy the journey. Entrepreneurship is an emotional roller coaster. I have blogged about this multiple times:

Be a famous pioneer.

I like these two quotes but Sivers seems to go  off the rails for the rest of the chapter. He conflates pioneering with building a public persona and accomplishment with outlandish behavior to cultivate celebrity. Your mileage may vary.

Nobody had ever run a mile in under four minutes.
It seemed impossible.
But one day, Roger Bannister did it, and the news spread worldwide.
Over the next two years, thirty-seven people also did it.

Just as a self-check, the next time you tell yourself “no one else can do what we’ve done” realize that the fact that you have solved the problem will change a potential competitor’s perception of what’s possible. The bigger risk is not having a plan for exploiting your breakthrough and building rapidly on your initial successes. The more that you can  be seen to be continually raising the bar, the more uncertainty you introduce into potential competitors’ plans as to what the target is that they have to meet or exceed.

Instead of announcing far and wide you are aiming at a significant market, focus on getting the word out just to your customers about what you have accomplished and how it can help their business. Think about how to use a dog whistle to get the word out, not a bull horn.

This is the power of the pioneer:
To enable the impossible.
To open a new world of possibility.
To show others that they can do it too, and take it even further.
Explorers used to find unknown lands and bring back stories of unfamiliar cultures, which encouraged others to go exploring.
The old finish line becomes the new starting line.

Whenever you see a rapidly evolving understanding of a new technology or application landscape, driven by waves of explorers wandering over it to bring back exciting and conflicting reports (think of the six blind men and the elephant), you are looking at a prime opportunity for startups. You can join the fray if your team has the minimum expertise necessary and a willingness to learn fast.

Be a Pioneer: In my experience, many of the most successful investments have entailed being early. While there’s no surefire route to investment success, I do believe one of the easiest ways to make money is by buying things whose merits others haven’t yet discovered.  When everyone’s eager to buy the same thing, it’s probably overpriced. And when no one is willing to buy something, it’s equally likely to be underpriced.

Howard Marks in “Dare to be Great” (Sep-27-2006) [PDF]

Chase the future.

I did not find anything that resonated in this section. But your mileage may vary. Despite the title, Sivers is talking about chasing novelty and fashion trends. Future products and technologies become useful to the extent they can be applied to many mundane needs.

“The entrepreneur always searches for change, responds to it, and exploits it as an opportunity.”

Peter Drucker in “Innovation and Entrepreneurship” (1985)

Some blog posts related to discovering and creating the future.

Value only what has endured.

The media focuses on what’s new, because that’s what pays.
Their attention makes new things seem important.
But only time will tell.

There is too much emphasis on prediction based on recent events. There needs to be more effort devoted to spotting long-term trends and putting current events in context with history so that we have a better handle on where we are. I strive to build models that provide context and a sense of the range of possibilities. Monthly, quarterly, and annual publications and books offer more insight than sites that update hourly, daily, or weekly.

The modern life is shallow and distracted.
The timeless life is deep and focused.

There are times when a quick take followed by the best bad plan you can execute is required. But if you are not careful, you can let the urgent crowd out the important. And your risk spending all of your time reacting to events and not shaping longer-term opportunities.

Master the fundamentals, not new tricks.
Learn the timeless aspects of your craft.
This knowledge will never lose its value.
In any given field, learn the oldest thing still around, since it’s the one most likely to last.

Some things change, others remain constant. It’s hard to see the patterns when you are enmeshed in them. You have to pause and reflect.

Technology changes fast; people change slowly. So you need a plan to renew your technical skills and those of your team continually. On the other hand, soft skills (people skills) have a much longer lifetime. A small but continual investment in developing your speaking and presentation ability will pay dividends for a long time, as well as becoming a more thoughtful and encouraging listener.


Learning is underrated.
People wonder why they’re not living their ideal life.
Maybe they never learned how.

You get healthy by learning healthy habits.
You get wealthy by learning valuable skills.
You build a great interpersonal life by learning people skills.
Most misery comes from not learning these things.

This is about becoming more than “book smart.” You have to apply that knowledge not just recite facts you have memorized. If we take learning a language as an example. Reading is probably easiest because you can control the pace and re-read a passage if need be, pausing to look up one or more words if you don’t understand the meaning.  Speaking is next because here again you control the pace of your speech. Speaking is easier in cultures that are more accepting of non-native speakers but harder than reading. Hardest is listening–and engaging in conversation–with a native speaker. They can speak more slowly and make it easier but ultimately everyday conversation is fast and filled with complex idioms that add nuance but resist simple dictionary lookup based comprehension.

The life skills that Sivers is talking about work much the same way. You have to be able to respond to events and make decisions in real time. And in the cases he mentions  of maintaining your health or building wealth  or developing good interpersonal relationships it’s not enough to know the right answer. You have to have the discipline to avoid poor choices and pick a good one. David Starr Jordan observed, “Wisdom is knowing what to do next; virtue is doing it.”

Knowledge fades and eventually disappears unless you keep it refreshed.
Internalize it.
Don’t expect to just look it up when you need it.
Integrate it into how you think.

Ultimately the right choices are integrated into your worldview and felt. Bootstrappers develop empathy for their customers, become prudent about the impact of their decisions on their team and business, and stay frugal without becoming stupid cheap with practice and feedback from team members and partners.

Practical learning must operate at the level of muscle memory. It’s a rare decision that requires a calculation to several decimal places. If you can find the right church there really isn’t a wrong pew. To incorporate new learning such that your actions become second nature, you must practice using it regularly.

Communicate knowledge to others to make sure you understand.
If you can’t explain it yourself, you don’t know it.

Learning how to succeed as an entrepreneur is like learning to ride a bike. You have to manage multiple interrelated tasks in parallel. You have to pedal to keep moving forward. You have to steer so you don’t crash and get to where you want to go. You must maintain your balance to complement your steering and avoid tipping over the bike. And you have to maintain your focus in spite of distractions you may not have anticipated, like a patch of gravel that starts a skid or a bee that smacks into your chest and decides to sting you. You cannot learn how to ride a bike in a class: real life is the test. And if you want to teach someone else how to ride a bike you have to show them and run alongside them helping them stay balanced until they feel how to do it. Teaching someone how to swim presents the same set of challenges.

Follow the great book.

This chapter embraces the concept that “a man has to have a code.” You have to align your actions with a higher purpose. Although Sivers labels this “follow the great book” he lets you pick your book.

Discipline turns intentions into action.
Discipline means no procrastination.
Discipline means now.
Choose the pain of discipline, not the pain of regret.

I think the keys to self-discipline are to create habits and systems that reinforce your decisions, join groups and communities that are aligned with your purpose and committed to helping you become what you are striving for.

Define a good life as more than shallow pleasure.
A good life is contribution.
A good life is resisting temptation.
A good life is being the best you can be.
A good life is diligently following your book.

I agree with these values, the guidelines are similar to those in “commit”, “think long-term”, and “pursue pain.” Your action always speak louder than your words. As Emerson observed about a man who continually praised himself, “The louder he talked of his honor, the faster we counted our spoons.” I am always on guard when someone says “Let me be honest with you” more than once in a conversation.

Laugh at life.

I like these insights, but there is an undercurrent in the chapter that “life is meaningless,” which I reject.

Humor is the spirit of life — a sign of a healthy, vibrant mind and soul.

A bad situation can feel all-consuming.
A laugh shows you’ve escaped.
Humor puts distance between an event and yourself.
Comedy is tragedy plus time.
Time belittles anything by showing it’s not as bad as it seemed.
Humor does that instantly.

If you can laugh at yourself to recognize your humanity, you can take away some of the pain in challenging situations. James Thurber observed that “humor is emotional chaos remembered in tranquility.”  Humor is part of bouncing back from setbacks and getting unstuck when you feel trapped. It’s a circuit breaker when you find your mind racing in tight circles of fear.

No matter what you need to do, there’s a playful, creative way to do it.
Playing gives you personal autonomy and power.
When kids play make-believe, anything goes.
To play is to be free from constraints.

Relax constraints by asking, “what if we could…” The answers will often suggest one or more experiments that lead to a creative outcome. I agree that the ability to “play” with a problem or challenge is essential to finding novel, creative, and useful solutions. Although, Ackoff has talked about the ability to identify self-imposed constraints, adding additional restrictions can lead to viable solutions that unlock new levels of differentiation (for example, make a 50% cut in cycle time, memory usage, or transaction cost).

“Creativity is the ability to identify self-imposed constraints, remove them, and explore the consequences of their removal.”
Russell Ackoff

Prepare for the worst.

Things are going to get harder.
The future will test your strength.

Just anticipate and prepare.

This is a a regret minimization approach to managing a range of potential challenges. A small amount of pessimism and worry and can be  constructive–if it spurs you to preparation. Constant anxiety is counter-productive.

In “Preventing Chaos in a Crisis,”  Patrick Lagadec observes: “The ability to deal with the unexpected is largely dependent on the structures that have been developed before chaos arrives. The complex event can in some ways be considered as an abrupt and brutal audit: at a moment’s notice, everything that was left unprepared becomes a complex problem, and every weakness comes rushing to the  forefront.” The best way to mitigate this is to do your homework in advance and work out a range of options. More on this in “Thomas Schelling on Strategic Surprise.”

Distinguish between what’s in your control and what isn’t.
If it’s not in your control, put it out of your head.
Trying to control outcomes makes you disappointed and resentful.
Focus only on your thoughts and actions.

You have to be guided by outcomes when you evaluate the impact of habits, decisions, and systems you use to manage your business and your life. But you should only yourself accountable for the things that are under your direct control. Following up with a prospect is a legitimate goal, closing the deal is a joint–or even committee–decision that you can influence but don’t control. Walk fifteen minutes or reduce your carbohydrate consumption can be on your todo list for improving fitness and losing weight. But lose 15 pounds is an outcome not under your direct control.

To appreciate something fully, picture losing it.

Imagine the people you love dying tomorrow.
Never take them for granted.

We lost power for a day last month when we had high winds. The house was dark and quiet, and I read by candlelight for a half-hour in the early evening. There was a gust of wind at one point, and I looked out the window to see my candlelit reflection holding a book staring back. Overall it had a strangely calming effect on me. I did not miss the green letters on a black screen my laptop routinely provides. I went to bed at 8 pm and woke up bright and early. Fortunately, the gas heater still worked so I could take a hot morning shower by candlelight.

But more important than the comforts in our life are the people who have comforted us. Don’t lose touch with folks who have made a difference in your life; don’t wait to reconnect if you have.

Live for others.

Never say, “Not my problem.”
We’re all in this together.
What’s good for your community is good for you.
Whatever affects others affects you.
The quality of your life is tied to the quality of your community, neighborhood, and country.
You can’t be healthy in a sick society.

I agree with this but I think you also have to “play your position” on a team. You have to help those around you but do it with their permission and without creating a dependency.

Be warm, open, and fully present with everyone you encounter.
Confidence attracts.
Vulnerability endears.

People tend to mirror and reciprocate your actions. If you great a stranger with a smile and handshake you are more likely get start off on the right foot. Especially in a leadership role you have be able to project confidence in your team but be wiling to ask for help when you need it.  Two very effective ways of inspiring and supporting others are by taking action and by acknowledging your own mistakes.

Sometimes you really need emotional support.
You’re going through a hard time or a big decision.
You need someone else’s perspective on your situation.

Friends or family can give wonderful comfort.
You share your problem, and they share the burden.
They care for you deeply, but aren’t as distraught, so you see yourself through their eyes, and realize it’s not as bad as it feels.

An objective mentor can give this effect even more so.
This person has less sympathy, and a dispassionate perspective.
You summarize the facts of your situation with less indulgence and hyperbole.
Hearing yourself tell this version of your story reduces the intensity of your emotions.
You see yourself as they do: as a smaller character in a bigger picture.

One of the most effective ways to help someone struggling with a challenge is to ask questions from a caring perspective. If you can help them clarify their understanding of the situation, the feelings it may have stirred up, and their goals, you will often provide more value than opening with advice.

Success in business comes from helping people — bringing the most happiness to the most people.
The best marketing is being considerate.
The best sales approach is listening.
Serve your clients’ needs, not your own.
Business, when done right, is generous and focused on others.
It draws you out of yourself, and puts you in service of humanity.

The essence of entrepreneurship is a free exchange of value–what the Romans called “quid pro quo”–that leaves all parties better off: no one loses. This does not preclude acts of generosity and kindness. Mastering the skill of entrepreneurship involves cultivating  the capability to take prudent risks to explore and learn. It embeds the realization that failure is a real possibility. A plan that anticipates how to survive a sequence of small failures (or “affordable losses”) is far preferable to incurring a substantial loss that bankrupts you.

It’s also been my experience that successful entrepreneurs also commit to self-improvement. They recognize their limitations and address them directly and by partnering with others who have complementary strengths. They rely not only on self-assessment to detect personal limitations and weaknesses but also actively  solicit feedback from team members, customers, partners, and other members of the communities they are are a part of.

Get rich.

Money is nothing more than a neutral exchange of value.
Making money is proof you’re adding value to people’s lives.

I think “neutral exchange of value” is an excellent way to think of money. Money is the token, not the substance. Your customers have to make a profit from doing business with you: they have to gain more value from your product than you charge for it, or they won’t buy (at least not for long after they realize there are cheaper alternatives that meet their needs or they don’t need it at all). Your employer has to make a profit on your work: they have to realize more gain than they pay you. And when you hire people: it has to be a net positive for you. I am not arguing that you should pay people as little or as slowly as possible–quite the reverse since happy employees are more productive.

Instead of thinking of customers as leading to a sale, think of each sale as leading to a life-long relationship with a customer.

Relationships are more important than transactions. Winning a customer’s trust so that they invest effort in helping you improve your offering is much more valuable than any single transaction. So choose cheerfully refunding their money over losing their trust. a business relationship built on mutual trust and respect is your ultimate goal.

Boring industries have little competition: most people seek status in glamorous new fields.
Find an old industry and solve an old problem in a new way.

Invent for a very small niche of people who need something that doesn’t exist.

Instead of making a key, then looking for a lock, find something locked, then make its key.

The thread that runs all three of these pieces of advice is to focus on providing value. Starting out with a compelling value proposition for a small market dramatically reduces the challenges you face in getting established. Moreover, if you serve a small market well, it can act as a basecamp that enables your exploration of larger adjacent markets. Starting with the key and looking for the lock–or the more traditional formulation of picking up a hammer and looking for nails–is a common approach for technology-driven firms. But if you can proceed from a deep understanding of the needs of a small market, you are more likely to satisfy your early customers and less likely to face competition from larger firms. Larger established firms will find a small market less attractive than other larger markets they can pursue.

Money is your servant, not your master.
Don’t act rich. Don’t lose touch with regular people.
Stay frugal. Reducing your expenses is so much easier than increasing your income.

Cutting unnecessary expenses is always a good practice in preparation for bootstrapping a new startup. It puts a floor on what you need for living expenses and helps you to prepare mentally for the rigors of the journey. And, as Sivers points out, it puts more money in your pocket relative to the income your business provides.

You don’t need to tell anyone you have money.
You don’t even need to spend it.
Stay 100% focused on creating value.
Everything else is a corrupting distraction.

One good test is to carry money without spending it. Although paying cash for things may sound increasingly old-fashioned, there is a significant difference between swiping and signing and handing someone real money. It’s also worth periodically reviewing any recurring expenses you have signed up for, whether in your lifestyle or business. Not everything lives up to its promises or your expectations, and your situation can change: what was a good decision three months ago is no longer a good investment.

Reinvent yourself regularly.

Putting a label on a person is like putting a label on the water in a river.
It’s ignoring the flow of time.

I am very good at snap decisions, noticing a small kindness or a flash of insight that can give deeper insight into someone’s character or intelligence. Sometimes it’s realizing that they are staying calm when others are not. But I am also good at quickly labeling someone a jackass because of a small selfish action or unnecessarily blunt remarks to a junior contributor that were unkind. The challenge is to give the jackasses a second chance and to remain alert to the possibility that initial warmth or generosity was a calculated manipulation. By definition, a bad hire is a good interviewer.

Let go of your expertise.
You built that boat to cross that river, so leave it there.
Don’t drag it along with you.
The timid cling to achievements.
The wise keep their hands free.

It’s terrible to feel your expertise aging out, to realize you need to unlearn some rules of thumb to take advantage of more accurate guidelines. But you must recognize and act on early evidence that what got you this far won’t take you much farther. Clinging to past methods allows your competitors to understand the need for change earlier and get a head start on a new and valuable set of tools and skills.


Sivers defines love as a “combination of attention, appreciation, and empathy.” But I think he leaves out commitment and so did not find most of this chapter useful. He had one suggestion I liked:

Don’t try to change someone, or teach them a lesson, unless they ask you to.

Unsolicited advice is rarely appreciated. Even requested advice may not alter perceptions, much less inspire action. Probably the most challenging aspect of what we do is giving useful advice–advice that changes an entrepreneur’s plans and subsequent actions. I like this quote from Thurgood Marshall because it reminds me that I am effective when I am the least emotional but genuinely trying to suggest an alternate perspective on a challenge (or an opportunity) a startup team faces.

“What is the quality of your intent? Certain people have a way of saying things that shake us to the core. Even when the words do not seem harsh or offensive, the impact is shattering. What we could be experiencing is the intent behind the words.”
Thurgood Marshall


Suspend all judgment when creating the first draft.
Just get to the end.
It’s better to create something bad than nothing at all.
You can improve something bad.
You can’t improve nothing.

Go ugly early and get it out of your head. Write a bad version just to make a start. My experience has been that many successful entrepreneurs were B students in school: they understand that “good enough” delivered quickly often does much better than fantastic or perfect delivered after folks have lost interest or found an acceptable solution elsewhere.

Distribute your work as widely as you can.

I think there are two key aspects to this. The first is that you share drafts, work in progress, prototypes, outlines, or other intermediate work that will allow others to provide critique and suggestions. If you are working on a new product, this means confirming the boundaries and parameters of the problem you intend to solve or the need you plan to address. Then you can solicit comments on solutions you are considering. The second is that once you believe you have a valuable product, you must get the word out to encourage prospects to buy.

Don’t die.

Don’t try to be more right.
Just be less wrong.

Good health is slow decay. It’s always a good idea to eliminate bad habits and poor practices, or at least engage in them less and less frequently. You have to plug the holes in your boat before you open up the throttle. If you treat people unkindly, make team members feel angry and embarrassed to work with you, or act in greedy and shortsighted ways, no amount of performance improvement can compensate.

Avoiding failure leads to success.
The winner is usually the one who makes the least mistakes.
This is true in investing, extreme skiing, business, flying, and many other fields.
Win by not losing.

You have to be mindful of the many ways that failure can occur without becoming afraid of taking action or exploring better methods. You need a margin for error that allows you to experiment and continue to improve, and that keeps you away from serious failures. Many minor but recoverable errors will enable you to avoid major mistakes and use trial and error to find better practices.

Keep your eye on death.
Avoid the mistakes that end life.
Avoid the negatives that wreck life.
Avoid the time-wasting that brings death sooner.

A robust entrepreneur keeps his options open, never going all in on any one opportunity and never making choices that destroy customer goodwill, team morale, and suppliers’ trust.

“Death twitches my ear. ‘Live,’ he says; ‘I am coming.'”
Virgil (70-19 BC) “Copa” (The Female Inn Keeper) last line.

Make a million mistakes.

Learn by hands-on experience.

You can learn by anticipating and avoiding mistakes you have made in the past. Practice reinforces this. You also learn when you’re surprised — when your previous idea of something was wrong. If you’re not surprised, then the new information fits in with what you already know, but you did not anticipate its impact or otherwise failed to act on it. Real life is the test: hands-on experience forces you to acknowledge what skills you need to master.

Your growth zone is your failure zone.
Both are at the edge of your limits.
That’s where you find a suitable challenge.
Aim for what will probably fail.
If you aim for what you know you can do, you’re aiming too low.

We ask new clients, “how many proposals are you winning?” If it’s more than half, we tell them they are probably exploring enough. Especially in a market you are unfamiliar with, you should plan on losing two-thirds of the opportunities just to map the contours and depth of the market. This does not mean every target should be low probability–or you are likely to win too few to survive. But you must push yourself to investigate new types of related opportunities to master a niche.

Make change.

All your learning and thinking is wasted if you don’t take action.

Be careful to distinguish between seeing the answer in your mind and sweating the details necessary to achieve it. Everything works well in our imagination. Unfortunately, real life is not so generous when we unwittingly skip a vital step or omit a crucial ingredient.

Go where there’s a revolution.
That’s where people are questioning old norms, and looking for new solutions.

When an industry is ripe for improvement, or even better, has gotten a taste of change and is hungry for more, there is an opportunity for new entrants. It’s customer expectations that matter. If suppliers in an industry are satisfied, but customers are anxious for new solutions, there is an opportunity.

Balance everything.

Schedule everything to ensure balance of your time and effort.
Scheduling prevents procrastination, distraction, and obsession.
A schedule makes you act according to the goals of your highest self, not your passing mood.

Schedule quality time with dear friends.
Schedule preventative health checkups.
Schedule focused time to learn.

A schedule is an effort to plan what you want to accomplish. You can leave room for inspiration by scheduling free time. Something that feels contradictory at first but is one way to minimize the impact of hours of the day that tend to be less productive. Guard the hours when you are normally energized and able to accomplish what you set out to do. Be gentle with yourself and give yourself time to drift as well.

Even creative work needs scheduling.
The greatest writers and artists didn’t wait for inspiration.
They kept a strict daily schedule for creating their art.
A routine triggers inspiration because your mind and body learn that ideas emerge at that time.
The world’s greatest achievements were squeezed into existence by deadlines.

By scheduling a regular time of day for certain activities, you can train yourself to be productive. Very little is accomplished without committing to a deadline. You can also use deadlines  to challenge yourself to sprint: set a timer for 20-45 minutes where you can only work on one task you are not making progress on. Often you will find yourself unblocked and working past the buzzer, but even in the worst case, you are likely to make some incremental progress.

One final thought from Annie Dillard:

“A schedule defends from chaos and whim. It is a net for catching days. It is scaffolding on which a worker can stand and labor with both hands at sections of time. A schedule is a mock-up of reason and order–willed, faked, and so brought into being.”
Anne Dillard in “The Writing Life

Related Blog Posts

1 thought on ““How to Live” Derek Sivers’ Smorgasbord of Mindsets”

  1. Sean – this is an excellent review and summary! It’s been added to my reading list for a more thorough perusal!

Leave a Comment

Your email address will not be published. Required fields are marked *

Scroll to Top