Tag: entrepreneurship

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On judgment-based decisions

On April 1, 2016, I was excited and full of optimism. After months of negotiation, we were about to sign a purchase agreement to sell our company. Although I had mentally braced myself for the buyer saying the deal was off in an attempt at an April fool’s joke, we closed the deal that day. Three years later, the real trick was revealed.

Dr. Bob Knight, the founder of our company, had recruited me to become CEO in January 2009. Bob, an engineer in his mid-sixties, was ready to retire. Our company focused on commercializing new technology in the utility and energy industry, and we worked on a broad range of projects including ways to commercialize fuel-cell vehicles, emission control technology at power plants, and new approaches to make buildings more energy efficient. 

Our company’s growth had been fueled by the 2008 economic downturn. In response to the devastating impacts of the recession, the Obama administration earmarked billions of dollars in federal stimulus funding to support “shovel-ready” jobs related to energy projects, including the retrofit and weatherization of buildings. When I realized most of the money would flow to state and local governments, we developed a strategy to help governments quickly implement energy retrofit programs that would make homes and buildings more energy efficient and create jobs. Our strategy worked. We won multiyear contracts valued over $60M, and our company grew overnight from fifteen to fifty employees. 

I learned a lot from this experience. But years of battling onerous regulatory requirements and red tape prevented us from implementing our best ideas and made me feel like a fighter going up against a much larger opponent with one arm tied behind my back. I was ready to move on to my next chapter.

I had an idea for a startup. In fact, we had already begun work on the new idea, and as a condition of selling the company, I negotiated a small team to go with me to pursue it. My new company was called UtilityScore. We built software that estimated electricity, natural gas, and water bills based on property information, local utility rates, and climate data. We contracted with Zillow and other real estate websites to give buyers a good picture of the total cost of ownership of a particular property before they made a purchase. Every home was assigned a score related to the cost of utilities so homebuyers could compare homes in their area.

Because utility costs are 20%-40% of housing expenses in most of the U.S., we expected that homebuyers would be eager to have such information. Contractors could also use our data to show potential customers how much they could save by installing solar or upgrading their air conditioner or heater. 

Life was good and about to get better. I had money in the bank from the sale of the business and a great team I looked forward to working with every day. And in early June, we were accepted into the summer 2016 batch of Y Combinator (YC.) Getting the stamp of approval from the most famous startup accelerator in the world gave us a boost of confidence.

YC has helped some of the most successful high-growth startups including Stripe, Airbnb, Cruise Automation, DoorDash, Coinbase, Instacart, Dropbox, Twitch, and Reddit. And as soon as we got into YC, several angel investors decided to invest. YC Demo Day is the main event of the program, providing an opportunity to pitch several hundred investors. The amount of money raised by companies varies, but many of the companies raise a $1M to $2M seed round in the weeks following Demo Day. 

Clouds roll in

We raised a total of $0 dollars after Demo Day. Not a typo! I think we were the only company not to raise any money in that batch. I felt demoralized and embarrassed. I had entertained no illusions that we were going to be a top company in the batch, but I had certainly expected to raise at least a few hundred thousand dollars to buy us time to continue our mission. Telling my team and existing angel investors that we didn’t raise any money was difficult and sent a terrible signal.

Shortly after Demo Day, things went from bad to worse. Around 5 a.m. on October 6, 2016, I was pulling out of my garage to go to the gym when the front left tire of the car broke off the axle, making it impossible to drive or even return it to the garage. Determined to get in my morning workout, I went back upstairs, asked my girlfriend to call AAA, and changed into my running shoes. 

Early morning light was just beginning to bathe the streets of San Francisco’s SOMA district when I started running down 7th street. My lungs were full of the cool air as my body put up its normal fight against running so early in the morning. 

As I approached the intersection at 7th St and Brannon, I saw a car slowing down for the stop light. The pedestrian walk light was illuminated, so I proceeded to run into the intersection as I watched the car approach. By the time I realized the driver did not see me and had no intention of stopping for the red light, it was too late. The car struck my right side. I flew into the air, smashed down on the hood of her car, and violently bounced off onto the hard pavement — shattering my left knee on impact. Doctors had to drill nine screws and support hardware into my bone to hold my knee together. 

And that’s when things really started to get dark. Intense pain shot through my knee for weeks. I lay on my couch, relying on my girlfriend and other people for everything. I could not even bathe myself. My head was so foggy from painkillers that I could barely focus on work.

But the clock was ticking, and I felt like a dark cloud was constantly looming above me. I got sick to my stomach watching my bank account shrink month after month. So I started going to the gym on crutches to strengthen my body and build back the muscle and range of motion in my left leg. Motivated to get back to work with my team as quickly as possible, I hobbled into the office, putting my leg up on a pillow on my desk.  

But Zillow, our biggest customer, continued to drag their feet and kept finding new reasons to delay implementation. We made multiple attempts to test new approaches and pivot, leveraging the assets we built. But we were not getting traction. 

Persistent or Irresponsible?

One of the hardest parts of entrepreneurship is knowing when to quit. Every successful entrepreneur tells stories of persevering against all odds when everything looked hopeless — making their eventual success seem even sweeter. “Don’t quit” had been seared into my brain. But it’s hard to know whether you are wisely pushing through adversity or just flushing money down the toilet and banging your head against the wall for no good reason. 

After three years of hard work and experimentation, we were out of ideas and money. We were speeding toward a cliff, and I needed to make a decision. I tried to sell the company’s assets, but multiple deals fell through. I had to shut down the company. 

The mental whiplash of making and losing millions of dollars in a short period of time shook me to my core. Questions swirled through my head. Why did we fail? What could we have done differently? What important signal did we miss? I became obsessed with uncovering and understanding my mistakes. My search for answers sent me deep down a rabbit hole to learn what I did wrong. I was determined to prevent it from happening again.

What I learned completely transformed how I think about building companies, making decisions, and solving problems. Much of what I learned is not intuitive and pushes against the way most of us naturally think.

Learning hard lessons

One of my most important lessons was learning to question my beliefs. You can end up making poor choices if you don’t frequently strip bare your beliefs, which requires rigorous questioning and inspection of assumptions. This process is even harder than it sounds, which is why most of us don’t do it. When was the last time you actively tried to disprove your beliefs like a scientist trying to poke holes in a hypothesis through testing? 

Your beliefs shape your perspective and influence your judgment, which affects your decisions. Your decisions shape who you are and the reality you live in. The stakes are high because your decisions will play a large part in determining if you succeed or fail. 

I played a very expensive trick on myself by pursuing solutions to a made-up problem. I should have tested my assumptions — my beliefs — without committing three years and millions of dollars to them. UtilityScore did not create enough value to justify the cost. My desire to help reduce energy use in homes contributed to my blindness and clouded my judgment. Be extra careful when you feel virtuous about your mission. It’s easier to fool yourself when your identity is tangled up in the mission and you are gaining a sense of purpose from your efforts.

Judgment is knowing the long-term consequences of your choices and making the right decisions to capitalize on them. Good judgment is a superpower, which is normally gained through trial and error. But it’s also a skill you can cultivate by learning to apply principles, processes, and tools. Good judgment leads to better decisions.

What you decide to work on is far more important than how hard you work. Tactics don’t matter if you have the wrong strategy, and your direction matters more than your speed. You can be an amazing engineer, marketer, or salesperson, but if you decide to build, promote, or sell the wrong product for the wrong market, you’re going to fail.

Decisions are not one-size-fits-all. Math-based decisions are straightforward and usually involve running cost-benefit analyses. These decisions are typically not controversial and easy to make. Judgement-based decisions call for taking action under uncertain conditions, often due to missing information. 

Some decisions are difficult or even impossible to reverse. Jeff Bezos, founder/CEO of Amazon, calls these decisions one-way doors. Make these decisions carefully and methodically, ideally after performing a detailed scenario analysis in consultation with key stakeholders. Decisions that can be easily reversed are called two-way doors, and these lighter-weight decisions should be made quickly by high-judgement individuals or small groups.

Just DO IT

Following a process helps you improve the quality of your decisions as it can help you structure your thinking. To help me remember the steps of my decision-making process, I created the acronym DO IT: Define Observe Imagine Test. With a little practice, applying this process becomes automatic.

Don’t make the mistake of needing to learn everything the hard way. We have unprecedented opportunities to access knowledge and training that can teach you how to question your beliefs, improve your judgment, and make better decisions. Learn as much as you can from other people’s experiences to minimize wasting time, losing money, or regretting your choices.

If you want to build your judgment faster and learn to apply principles, processes, and tools to make better decisions, get my free e-book on judgment and decision making. The e-book pulls together hard-earned wisdom and shares the best of what I’ve learned, including the how-to’s, frameworks, and mental models to save yourself the pain of learning the hard way.

Beyond the practical content, you can use these ideas as a sharpening stone to become a more independent thinker. Learn how to test your beliefs and insulate yourself from outside forces that want to control or manipulate you. Overcome the fears and desires that cloud your judgment. Tackle stressful decisions with confidence. Most importantly, learn how to think more clearly and make better decisions in order to build the life you want.

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Question your beliefs

Most of the time we believe what we hear. And too often we hear—and then believe—things that are not true. But imagine how hard it would be to question every fact and underlying assumption you hear or read throughout the day.

Your brain acts like a sponge soaking up conversations with family and friends, daily news reports on TV and radio, information in emails and social media posts. It would impossible to every day test and probe every sentence from every source for complete accuracy. Even getting through one hour—much less a day—would be almost impossible. I’m exhausted just thinking about it.

To efficiently navigate life, we learn to trust people and institutions. Your life runs on trust for many things we take for granted. You trust when you flip on the light switch that electricity will be available to power your light bulb. You trust that pipes coming in and out of your home will provide water to flush the toilet. You trust that the ambulance will show up if you dial 911. You trust that the money you deposited in your bank account today will still be there tomorrow.

Trust undergirds our financial system and our justice system and our transportation system and provides the glue to hold our social fabric together. Without trust we would live in a world of paralyzing fear and violence. However, it’s important to recognize when it’s time to switch off your trust autopilot and begin questioning assumptions. If you don’t, you can make painful mistakes and walk blindly into bad decisions.

I spent twenty years of my professional career working on the wrong problem. Blinded by a utopian vision of renewable energy, I didn’t apply critical thinking to test my beliefs. Renewable energy technology has a role to play in providing the power in some situations, but currently it represents 2% of global energy. The laws of physics prevent renewable energy from becoming an efficient and preferred source of energy to power society.

I was not alone in making this mistake. One of our worst decisions in the 20th century was to underfund and overregulate nuclear energy. We let activists, rather than scientists, lead the national conversation on nuclear energy. Unfortunately, we were told many things that were not true—and we believed them.

In the book How Innovation Works, author Matt Ridley shares evidence for nuclear energy being the safest form of energy we produce: “Per unit of power coal kills 2,000 times as many people as nuclear; bioenergy fifty times; gas forty times; hydro fifteen times; solar five times (people falling off roofs installing panels) and wind kills twice as many as nuclear. And these numbers include the accidents at Chernobyl and Fukushima.”

New nuclear technology in the form of many relatively small reactors has no risk of explosion or meltdown, produces very little radioactive waste, and cannot be used to make nuclear weapons. But our fears of nuclear accidents and nuclear waste have kept us from pursuing this energy solution. Instead of having energy that’s too cheap to meter fueling massive new growth and innovation, for the past fifty years we have been dealing with economic stagnation and unnecessary environmental impacts related to pollution, habitat destruction, and climate change.

Dig down to bedrock

How much of your perceived reality is grounded in truth? What would happen if you took a crowbar and pried under every assumption you have about the world. What would be left? What are your foundational beliefs? I know what I see, hear, smell, taste, and feel. But I have to recognize the limits of my perception. Peering through a microscope or out the window of an airplane enables me to see different perspectives and helps me understand that there are truths I rarely recognize.

Limited perception helps you focus and survive. Imagine if you were not shielded from unlimited awareness. You would likely be so overwhelmed by sensation and experience that you would not be able to function. But perception does not equal reality. Therefore, it’s important to probe and question your beliefs often.

My beliefs today have changed from yesterday. And my beliefs yesterday were different from what I believed last week, last month, last year. If your beliefs are not changing, you may not be learning. Some of my best ideas and beliefs have been wrecked on the sharp rocks of reality. I have learned that it’s useful to question what I believe and to keep a loose grip on my opinions because my perspective changes with new experience and knowledge.

When I dig deep down to bedrock and question my understanding of the world, I see patterns of creative destruction—cycles of growth trying to maintain a balance between chaos and order. But my crowbar could not dislodge the following assumptions.

If you don’t routinely strip bare your beliefs, you can end up making poor choices. Dig down to uncover your foundational beliefs. Consider how your beliefs shape your perspective and influence your decisions.

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Taming emotion

Your emotions influence your decisions. Learning to read and regulate your emotions will help you make better choices and build better relationships.

When I was nineteen, I spent four months traveling in India to learn meditation. Given the opportunity to experiment with dozens of different meditation techniques, I learned how to witness my thoughts and emotions and not react to them. Surprisingly, this is one of the most practical and useful skills I’ve learned, and I use it every day in my interactions with people.

Our emotions evolved to help us survive and reproduce. Fear, anger, sadness, joy, and disgust are names we give to describe different states of our nervous system. Fear is experienced as contraction in your belly or chest. Joy brings a feeling of expansion. Your reactions to these types of physical sensations influence your decisions and behaviors.

Babies express raw unregulated emotion. Discomfort due to hunger or pain causes them to cry. Babies have not yet been taught how to regulate their emotions. Imagine the reaction you would get at work if you started crying because you were hungry. Although I don’t cry when I’m hungry, I do have similar strong emotional reactions to situations that would be just as ridiculous if expressed.

As we mature, we are taught what is an acceptable display of emotion and behavior by the people around us. Breaking these social norms brings consequences. In ancient times, if you were kicked out of the tribe due to your behavior, you would likely not survive. This primal fear persists today, and strongly influences our behavior at work and in our personal lives.

Emotions are powerful but they are short lived unless you continue to feed them. If you are willing to sit in the emotion fully, instead of struggling to ignore or repress it, you will find the emotion is very short and lasts only moments—not minutes. It amazes me how if I’m cut off while driving, I can go from a calm state to full-on rage in less than a second. And then return to a calm state a few minutes later. My brain interpreted the car cutting me off as a threat and reacted. In that moment of rage, I felt capable of physical violence toward the driver who cut me off. Most likely the person did not wish me harm. They probably did not even see my car. If you pay attention to the physical sensations in your body, it’s hard to stay angry for more than a few moments unless you continue to feed the anger with additional mental chatter.

Emotional intelligence is the ability to separate your emotion from your behavior. The better you get at reading, regulating, and expressing your emotions, the better your relationships will be.

People with high emotional intelligence perform better at work. It’s not surprising that surveys of employers showed that 71% of them valued emotional intelligence over IQ in an employee. For managers and leaders this is an essential skill.

Emotional intelligence allows you to stay calm in times of stress, conflict, and challenge. This helps you resolve conflict effectively and quickly. By practicing active listening and taking an interest in understanding other people’s perspectives, you gain empathy, which creates the opportunity to cooperate. All of this allows you to form and develop better relationships with others.

Your ability to manage stress and build better relationships also increases your physical and mental health, preventing the onset and progression of heart problems, anxiety, and depression.

Emotional intelligence can be learned. But just like any skill, it requires consistent practice. You don’t get a healthy body by going to the gym once a week. And you don’t learn a new language by just attending a few classes. Building your emotional intelligence requires consistent practice over a long time-frame. But you can do it in small steps.

Here are a few useful ways to improve your emotional intelligence.

  1. Practice meditation at least 10 minutes every day. Meditation is an effective tool to build self-awareness. I use the Waking Up app by Sam Harris because the instructions Sam provides are useful and the app tracks the time. A common misconception about meditation is that you are detached and not feeling your emotions. The opposite is true. You are not distancing yourself from your emotions. You willingly feel emotions and physical sensations more intensely to fully experience them in your body. But you experience them without judgment. Meditation is practicing being fully aware without reacting. For example, you can’t close your ears and stop sound from entering. But you can listen to sound without it triggering an emotional reaction. Imagine if you are trying to concentrate at work and someone is speaking loudly near you and its distracting. You’ve a choice in how you respond. You may feel anger or frustration but it will not likely serve you to act out of anger in your response. 
  2. Ask for feedback. Ask people with diverse perspectives to give you feedback frequently. Be vulnerable and open to receiving what you hear. Monitor your emotions so that you are not defensive. Feedback gives you an opportunity to gain empathy by seeing different points of view, and it shines a bright light on your blind spots. Feedback also helps you correct mistakes quickly and improve your performance.
  3. Be curious about your emotions. Practice curiosity by becoming interested in the patterns of energy in your body in different situations. Approach this exercise as an experiment. Notice when you’re angry or frustrated. Are there certain people or situations that trigger these responses? Look for patterns.

Your emotions are a natural part of being human, but you can learn to regulate them in order to be happier, healthier, and more productive.

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Write to think better

Nothing is more important or more valuable than thinking and communicating clearly. Thinking before acting helps you minimize expensive and painful mistakes. Clear thinking allows you to prioritize effectively, produce more, and make better decisions. Good communication starts with good ideas. So, your ability to deconstruct ideas and think critically enables you to communicate effectively. Expressing your ideas effectively empowers you to influence people and have an impact on their thoughts and actions.

The best way I’ve found to improve my thinking is learning how to write. Writing helps you formulate and organize your ideas into a clear and persuasive form before you act on them. You can write down more facts, ideas, and stray thoughts than you can remember at any one time. Putting your ideas in writing allows you to organize and edit them. Writing also exposes gaps in your knowledge while allowing you to see the interactive effects of ideas.

Writing instead of meeting

Replacing work meetings with long-form memos is one way you can practice writing to help you think and communicate more clearly while also saving time. Most meetings are an inefficient waste of time and resources. When I walk into a meeting, the first thing that comes to mind is how much it costs to have all these people sitting in one room instead of getting work done. Communication based on long-form writing forces an exchange based on complete thoughts and ideas whereas meetings encourage participants to react in the moment and shoot from the hip.

Communicating through comprehensive written memos also frees you from the constraint of aligning schedules and allows people who could not be in the room to understand the issues, assumptions, and decisions. I’m not suggesting you do away with meetings altogether because there can be value in getting people together to discuss ideas. However, meetings should be a last resort and not the first option.

Writing to gain leverage

Writing also gives you leverage and the ability to scale your ideas. Sharing your written ideas offers opportunities to find peers, collaborators, and business opportunities. Paul Graham, cofounder of Y Combinator, wrote online essays to share his ideas and lessons about how to build a start-up. This strategy attracted start-up founders from around the world and has contributed to Y Combinator’s massive impact and success.

Writing to learn

Writing also helps you learn faster as it forces you to internalize learning at a deeper level. My mind is terrible at retaining what I read. I bet I only retain 10% to 15% of a book’s content. However, when I write an essay that synthesizes ideas I have been reading, the act of writing helps me internalize knowledge and remember it.

Useful tips to improve your writing

I’m always looking for ways to improve my writing. Here are some tips I’ve found useful.

Use writing as a tool to help you think and communicate more clearly. Invest time to improve your writing to achieve your potential.

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How do you generate new business ideas?

The best way to develop ideas for new services or products is to consider your own problems. What do you find tedious, annoying, or inconvenient? How could you solve that problem or minimize the irritation?

Solving your own problem will ensure the problem actually exists. It’s much harder to create a solution for a problem you don’t have. If you don’t experience the pain yourself, you will have to depend on customer feedback to determine if you have solved the problem.

Even worse: You may find a great solution to a problem that doesn’t actually exist or that doesn’t cause a lot of pain. Many new businesses fail because they start with a made-up idea.  

I’ve made this mistake myself. I started a software company that calculated estimates for electricity, natural gas, and water bills based on property data, local utility rates, and climate data. Because utility costs are 20%-40% of housing expenses in most of the U.S., we expected that homebuyers would be eager to have such information. We contracted with Zillow and other real estate websites to give buyers a good picture of the total cost of ownership before they made a purchase. Contractors could also use our data to show potential customers how much they could save by installing solar or upgrading their air conditioner or heater.

Unfortunately, this service did not create enough value to justify the cost. I was too far away from the problem to accurately assess the value of our solution. And my desire to help reduce energy use in homes contributed to my blindness. You can avoid this type of mistake by identifying a painful problem that frustrates you personally. It’s likely you are not the only person dealing with that problem, so focus on solving your problem or looking for ways to ease your frustrations.

Is there a missing element that could fix your problem? Often, the best solutions fill gaps between existing products or services rather than creating a completely new way of doing things. Seek out ideas that are unsexy but make weekly tasks easier.

And make sure your idea passes the dog food test: Will the dog eat the dog food? In this case, you are the dog. How much would you be willing to pay for a product to solve the problem? If you would not be inclined to pay to solve this problem, then why would anyone else?

Cultivating ideas to solve your own problem at least ensures you are creating something you want. And if you want it, it’s likely some other people will too. 

Create constraints

If I gave you a blank piece of paper and told you to start writing, you might have a hard time knowing where to start. But if I gave you a blank piece of paper and asked you to list your favorite foods, you likely would have no trouble. When thinking about new business ideas, don’t get paralyzed or overwhelmed by the abundance of choices. Instead, create constraints to help you narrow your focus.

Zoom in. Focus on problems you can solve with minimal outside help and support. Your goals and the constraints you set will determine what types of ideas you pursue. I’m currently in the process of creating a new online business, and I imposed the following constraints on my ideas:

My constraints limit the type of ideas I can pursue.

Consider your own constraints. Do you want to create a lifestyle business that optimizes freedom, flexibility, and time for your family and interests? Do you want to build a company that requires investors and employees? Maybe you should constrain ideas to a specific industry or product type. 

Here’s an idea I decided not to pursue. I listen to a lot of podcasts and audiobooks. Often, I hear an idea I want to capture, but I’m doing the dishes or driving and can’t stop and take out my phone and record a note. Even though I’m experiencing this problem myself, solving it would not align with my constraints. A solution to this problem would likely require building a new software application, raising money from investors, and hiring a development team. But please let me know if you build a frictionless, hands-free solution for taking audio notes from Audible and podcasts that integrates into Notion (my preferred note taking app.) I’ll happily pay you a $10/month subscription fee.

Practice noticing problems 

Notice friction throughout your day. Look for it. The friction will often lead you to good ideas hiding in plain sight. Think about the last time you purchased a car. If you’re like me, after you narrow down your choices to a specific make and model, you start seeing the model everywhere as you drive around town. You spot the car because you are now tuned to look for it. When you pay attention, you will notice a lot of friction as you go about your day.

Identify what you don’t want

Often it’s easier to identify what you don’t want than what you do. Imagine you and I are going to dinner, and I ask you what you want to eat. Your brain thinks through all the potential options of food you like, and you find it hard to narrow down your choices. However, if I ask what type of food you don’t like, it’s likely you would give me a quick answer.

So, make a list of things you don’t want to do. Maybe you don’t want to travel for work, talk on the phone, or manage people. Then screen out new business ideas that would require you to invest a lot of time in these activities.

Find your niche

Don’t chase the latest hot trends. Avoid competition. What are you good at? What have you done that gives you a unique perspective? Where can you build a personal monopoly because of your specific knowledge? Start with the smallest niche possible and expand out only after you gain traction. Even the biggest successful companies started by focusing on a niche. Amazon started with books. Facebook targeted students at Harvard. Airbnb rented out blow-up mattresses for conference attendees who could not find hotel rooms. Try to find the smallest viable audience that shares your painful problem.

Build your idea muscle

Become an idea machine. After you have identified a problem, then start generating creative ideas for solutions. Build your creativity muscle. Muscles get weak and flabby unless you put them to work. Exercise your creativity muscle to generate more and better ideas. Creativity requires practice. 

Create an idea habit. Invest 10 minutes a day generating new ideas. Hat tip to James Altucher for sharing his daily practice of writing down 10 new ideas every day. Yes, I said 10. Make your brain sweat. Let your imagination run wild and write down all of your ideas. Don’t worry if most of the ideas are terrible, and don’t limit yourself to business-related ideas. This daily practice will help strengthen your idea muscle. You may be surprised to discover how creative you become when you stop limiting yourself to only good ideas.

Describe your idea in 50 characters or fewer

Complex ideas are a sign of muddled thinking or a made-up problem. Ideas need to be clear to spread. Use clear and concise language to describe your idea. Entrepreneurs who think and communicate clearly have a big advantage because your idea must be clearly defined in order to sell, recruit, and raise money. Creating a 50-character limit forces you to distill your idea down to its simplest form. 

Examples

Surround yourself with optimistic people

New ideas are fragile. And good ideas usually don’t sound good in the beginning. Ideas need to be nurtured, so don’t keep them secret. It’s rare for anyone to steal your idea. And 99% of the work is in the execution, not the idea.

Surround yourself with smart, creative people and share your ideas freely. Explain your projects to help you refine them and get feedback to improve them. Don’t waste your time hanging around people who make you feel stupid for sharing bad or silly ideas. 

Combining ideas creates innovation.

In biology, male and female genes combine to form the embryo. The re-combination principle also applies to ideas and technology. Every new idea is a combination of other ideas, and new technology is a combination of other technologies. Apple did not invent silicon chips, the touchscreen, batteries, GPS, or any of the dozens of other technologies that combine to create the iPhone. It just combined existing technologies in a new and novel way.

Mix and match ideas and experiment with new combinations. Be playful with this exercise. Some of the combinations may not make sense. But you may be surprised when you create a combination you had not previously envisioned.

Size matters

If you can’t identify the immediate next step to test your idea, then it may be too big or too far out of your circle of competence. Try to break the idea down into smaller pieces. 

Sell before you build

Talk to potential customers about your idea. Don’t build a minimum viable product (MVP) or invest significant time in an idea without trying to sell the value to your target customer. Start by crafting your message. The exact language you choose to describe your product and the value of your offer will help you and your customer understand what you are selling. Test your idea by trying to sell it to a customer before you write a line of code or build anything.

Be creative. Create a landing page with your offer and try to sell the product. You don’t need to fulfill the order. Put customers who click the call-to-action button on a waiting list. Call customers or meet them in-person and speak with them one on one. Beware—they will lie to you unless you are presenting a specific offer and price. If they bite, get a letter of intent to purchase your product when it’s ready.

Test lots of ideas

Experiment a lot. Don’t be attached to the outcome. Most of your ideas will fail, so you need to develop the correct mindset to learn fast and move on. Edison tested 6,000 plant materials to find the right type of bamboo for the filament of a light bulb. Mozart was a prolific composer and wrote over 600 compositions across multiple genres, but only a select few of those compositions are known by most people today. 

Let ideas evolve slowly

Let ideas simmer. Don’t rush to create a company. If you get good feedback from customers on an idea, consider turning it into a project, but keep expectations low. Iterate on your idea and build momentum. Work on the project as long as possible before turning it into a company. The moment you create a company, expectations change and financial commitment increases. 

Now it’s your turn

Notice friction throughout your day. If you approach this task in the right mindset, it can be addictive and fun. Flex your idea muscle to generate lots of creative solutions. Combine ideas and identify ways to test them quickly with minimal time investment. Start with language to sell the value and gauge interest. Enjoy the creative process and, most importantly, have fun.

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Slow-burning questions

Questions guide your attention toward a destination. Imagine you could look at a map depicting every important decision you’ve made. You would see that at every fork in the road you had faced a question. Your answer to that question determined your next step, which determined your path forward. 

Questions are tools for self-reflection that can shift your mindset and reframe your thinking. Just as Michelangelo carved his masterpiece David from a single block of stone, cutting away pieces of marble to reveal an awe-inspiring image, use questions to chip away your assumptions and motivations to reveal your fears and desires. 

Make a list of important questions, but don’t try to answer them right away. Let them stew in the back of your mind as you gather new experiences and additional information. Every time you learn something new, take note of that new knowledge and test to see whether it applies to any of your questions. 

Here are some questions I added into in my note tacking app. Whenever I learn something that applies to a question, I add a quick note so I don’t forget it.  

The question effect

Can asking a question really be that powerful in shaping your life? Let’s explore this one: “How much money do you want to earn?” Have you thought deeply about this question? Do you want $100K, $500K, $1M, $10M, or $50M? Before you say, “the more the better,” invest the time to think through the benefits and tradeoffs of your choice. 

There’s not a right or wrong answer, but your response will impact where you live, how much free time you have, the quality of your relationships with friends and family, your health, what type of house you buy, and who you marry. Your answer maps to your aspirations, abilities, values, and interests. And your answer will likely change and evolve over time. 

There are many perks and benefits to earning lots of money. But earning more money also comes with tradeoffs. Before you set your sights on earning $50M, recognize that your primary relationship will be your career. You will need to work many nights and weekends, and 12- to 14-hour work days will be standard. You will shoulder immense responsibility and stress. 

You won’t likely have the time to watch your kids play sports, perform in a play, or teach them how to ride a bike. You won’t have free time to pursue hobbies or spend much quality time with your partner.  Envy and expectations may strain relationships with friends and family. It may be harder to make new friends because in the back of your mind you will be wondering whether someone wants to be your friend just because of your money.

Your family may face security threats. Criminals target wealthy people for robbery, kidnapping, extortion. Criminals buy airline flight manifests and target wealthy people when they travel, which explains why many of them will use a different name when traveling out of the U.S.

Earning more money may bring increased status but only marginal utility after you have acquired enough to be comfortable and take care of your family. The entertainment you consume, trips you take, health care you receive, food you eat, or technology you use will not be significantly better at $50M compared to $1M.

Your answer to the question of how much money you want ripples throughout your life. Important life decisions start with good questions. Make a list of important questions. Let them burn slowly in the back of your mind, and beware of your initial answers.

Use questions as a tool to guide your decisions and ensure you are heading toward your desired destination.

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Blind certainty

Our interpretations of the world can often be wrong due to bias, optimism, pessimism, or bad information. Yet most of us think we are right and other people are wrong. This can cause us to overlook or dismiss crucial information and lead to bad decisions.

In 1847, Ignaz Semmelweis proposed doctors wash their hands before delivering babies in obstetric clinics to reduce the spread of “childbed fever,”  a common and often fatal disease in hospitals in the mid-19th century. A doctor and a scientist, Semmelweis had noticed that two clinics had a significant difference in mortality rates for women giving birth. The two facilities used similar techniques, but one clinic taught medical students, who also performed autopsies, and those students did not wash their hands before going to the maternity ward to help a woman give birth.

 The second clinic taught midwives and did not engage in autopsies, so the students  had no contact with corpses. The clinic educating doctors had a mortality rate of 10%, and the clinic educating midwives had a mortality rate of 4%. Women begged to give birth in the clinic with the midwives and would even give birth in the streets to avoid the clinic with the  student doctors.

Although Semmelweis published results showing that the mortality rate for mothers dropped below 1% when medical staff engaged in proper handwashing, his observations conflicted with what the scientific and medical establishment believed at the time. Doctors were offended by the idea that they should wash their hands and mocked him. Semmelweis ended up having a nervous breakdown because no one would accept his findings. He was committed to a mental asylum and died 14 days later, at the age of 47. Cause of death was gangrene from a wound he received when he was beaten by the guards. 

The blind certainty of the doctors in Semmelweis’s day caused people to die. It took us 150,000 years to figure out that washing our hands prevents the spread of disease. In evolutionary timescale, this is the equivalent of yesterday, and a lot of lives were needlessly lost in those years. 

Our veil of ignorance prevents us from seeing reality accurately. I’ve noticed that the top experts in a field often admit  that there is a lot they don’t  know or understand. The more you know about something, the more likely you are to see how much you don’t know. We don’t even understand consciousness or how our own brains work, and we have barely begun exploring the oceans or outer space. To say we have blind spots is a big understatement.

Fooling Ourselves

The easiest person to fool is yourself. As you get older, you realize how  wrong you  were in the past. Most of the  beliefs I held most deeply in my twenties and thirties were wrong. In fact, it would be an easier exercise to identify what I was right about than to try to count all the ways I was wrong. I see the error of my past ways more clearly now because I’ve learned more, seen more, and thought more. Exposing yourself to different viewpoints and engaging in a little bit of self-reflection can reveal how easy it is to trick yourself. 

It’s very difficult to convince yourself of a new idea when a contradictory idea is already anchored in your thinking. When you understand that this blind spot is our normal state, you can  design decision-making processes to overcome it — which can help you avoid painful mistakes and give you an unfair advantage. But this effort takes humility and can be difficult. 

Here are a few ways I’ve found to improve my judgment and be wrong less often.

Don’t fool yourself. Apply these ideas to see reality more clearly, improve your judgement, and be wrong less often. 

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The company’s most valuable asset

People are the most valuable asset of most companies. Your strategy to attract, hire, and retain talent will have a big impact on the success or failure of your business. To solve hard problems, you need to assemble a team with diverse skills, personality traits, and viewpoints. Bringing together individuals with different mental models, experiences, and worldviews creates an opportunity for a competition of ideas that reduces blind spots and spurs innovation.

The people you hire will determine your ability to innovate, and you must create the right incentives to accelerate innovation. At Google X, the company’s research and innovation lab, bonuses are given to teams that kill their own projects by disproving their hypotheses.

Successful teams can be characterized by their rate of learning and ability to implement new insights quickly. This is why venture capitalists often focus more on the quality of the founding team than on the business idea, which is likely to evolve and change, while the team will remain.

You will build a competitive advantage if you attract people who are smart, motivated by learning, and want to work at your company. Zappos, an online shoe and clothing retailer, filters out less-than committed employees by paying them to leave. After four weeks of training and a week on the job, new hires are offered a $3,000 bonus to leave if they think the company is not right for them.

Recruiting and retaining talent is the largest expense for most businesses. Building effective hiring practices to attract the right people and investing in professional development to retain those people saves a company money in the long run as it will reduce turnover and facilitate high-performance teams.

You must be a good detective and a good salesperson to hire the best employees. Your detective skills allow you to look for patterns and signals in a candidate’s work history to find a good match. Your sales skills allow you to promote the company’s vision and highlight opportunities for the candidate’s professional advancement.

The current approach to hiring is broken. Résumés are not an effective way to assess talent, and most companies fail to effectively run a structured interview process well enough to minimize bias. Whenever possible, it’s more useful to use assessment tests and in-person working sessions with members of your team to assess a candidate’s potential. In interviews, make sure you create a structured process to reduce bias by asking predefined questions that are mapped to the job description, which should detail the position’s clearly defined roles, responsibilities, and required skills.

To ensure consistency, the same interviewers should ask the same questions in the same order of all candidates. This helps minimize bias. You are detective looking for clues, patterns, and signals. Don’t ask how potential employees would solve a problem in the future role. Ask how they solved a specific problem in a past role.

Avoid these common mistakes

  1. Prioritizing customers over employees. This may sound counterintuitive, but employees are the ambassadors of every interaction your company has with customers, partners, and vendors. Happy and engaged employees will drive high customer satisfaction.
  2. Rushing the hiring process to fill a position due to high workload. Although it is tempting to hire quickly to get help with a crushing workload, hiring the wrong person creates more work and stress and problems in the long run.
  3. Not prioritizing professional development and mentoring. Growing talent from within not only increases retention but can also help attract high-quality candidates because happy employees offer the best referrals.
  4. Hiring only people who think and act like you. Seek out people with different experiences and worldviews who can challenge your thinking.

My Talent Checklist

In addition to screening for relevant job skills, I prioritize these traits and ask myself these questions about a candidate.

Attract and retain smart, curious, and motivated people who want to work at your company. And you will be unstoppable.

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Be like Ike: Make better decisions, get more done

Dwight Eisenhower was a productive person who is best remembered today as a military leader and two-term U.S. president. In World War II, Eisenhower served as a five-star general in the U.S. Army and supervised the invasion of Normandy as the commander of the Allied Expeditionary force in Europe.

After the war, Eisenhower served as president of Columbia University and as the first Supreme Commander of the North Atlantic Treaty Organization (which may be better known as NATO) before running for president in 1952. He was elected twice in landslide votes (with the help of his famous “I Like Ike” slogan), serving as president from 1953 till 1961.

As president, Eisenhower signed the Civil Rights Act of 1957, championed the interstate highway system, and authorized the creation of the space program while containing the spread of Communism across the world. He still found time to golf frequently during his presidency, even having his golf balls painted black so he could play when there was snow on the ground. He also found oil painting relaxing, creating about 260 paintings in the final 20 years of his life.

Eisenhower Decision Matrix

Success in so many endeavors required Eisenhower to be a master of prioritizing tasks and making decisions. To optimize productivity, he employed a simple decision-making tool that has become known as the Eisenhower Decision Matrix. The tool helps you discern between urgent and important tasks and is built on the idea that what is important is seldom urgent and what is urgent is seldom important.

The two-by-two matrix helps prioritize your actions into four possibilities. Start by drawing a four-square grid and label the quadrants according to the following categories.

  1. Urgent and Important. In this square, list the tasks you will do immediately. These are time sensitive  and important tasks that help achieve your goals. Examples include meeting a customer deadline, resolving a key employee issue, or fixing a web server problem.
  2. Important But Not Urgent. Aim to invest most of your time working on tasks that fall into this quadrant. These tasks are important but do not need immediate attention. Examples include developing a strategic plan, creating a budget, building relationships, or solving an important engineering problem.
  3. Urgent But Not Important. Here, you should list the tasks you will try to outsource or delegate to someone else. The items in this quadrant will be issues that make you feel like you need to react immediately, but they likely don’t have long-term consequences. This list may include responses to last minute meeting requests, most events, text messages, emails, or a timely news story.
  4. Neither Urgent Nor Important. These are the tasks to avoid. This is the most important category. The best and most underutilized productivity tool is saying, “No,” and removing a task from your list. Ask yourself, “Do I really need to do this?” Examples include attending most conferences and most things that distract from focus on customers and product.

Effective Productivity Tool

Don’t waste time and mental energy keeping your tasks in your head or spread across emails, meeting notes, and pieces of paper. I use the Eisenhower Decision Matrix every day to prioritize my “to-do” list. When I arrive at my desk, the first thing I do is spend five to ten minutes slotting my tasks for the day into these four categories. I use a free version of a note-taking app called Notion and organize my to-do list under these four headings. I can then access my list on my mobile phone or computer whenever I need it.

I find it useful to identify my top priority for the day and then order my tasks to follow. This practice better organizes my day, prevents unnecessary task switching, and allows me to stay focused on my number-one priority. After completing a task, I don’t need to think about what to do next, conserving mental energy and reducing distraction.

Don’t risk getting jerked like a puppet by the conditions around you. Use the Eisenhower Decision Matrix to focus the majority of your time on important non urgent tasks.

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The advantage of going first

Have you ever had the experience of walking down the street and found yourself smiling at a stranger who smiled at you first? You were practicing mirrored reciprocity, a universal social norm. For the last 20,000 years of recorded human history, mirrored reciprocity has been foundational in human relationships, culture, and economic exchange. By choosing to go first, you can employ this ancient and powerful principle to build stronger relationships and gain an unfair advantage in business and in life.

Long-lasting, healthy relationships in your professional and personal life make a huge impact on your happiness and success. However, we often hesitate to cultivate those relationships. We don’t reach out and share our true thoughts and feelings with people around us because we fear rejection or judgment. Learning how mirrored reciprocity works and choosing to go first can radically change your life and relationships.

Mirrored reciprocity is imbedded in the blueprint of life. The evidence is overwhelming and all around us. In physics, Sir Isaac Newton’s third law of motion states that every action has an equal and opposite reaction. This has been true for over 13.5 billion years — since the beginning of our universe. The pattern of mirrored reciprocity has also been evident in almost all biological life on earth for the last 3.5 billion years.

You don’t have to be a scientist to observe mirrored reciprocity. Aggression is usually met with aggression, whereas playfulness or affection is met in kind. You can witness reciprocity even in the simplest of human interactions. If you walk into an elevator and smile and say good morning, the people in the elevator will almost always return your positive greeting.

However, mirrored reciprocity works for both positive and negative behaviors, so think carefully about your attitude and actions. If you display aggressiveness or treat other people badly, expect that other people will treat you poorly. I’ve watched calm, normal people escalate into full-on road rage in less than a second after a rude or aggressive driver cut them off in traffic. I bet you have seen that happen, too. Or maybe you’ve been that driver!

If you strive to be trustworthy, courageous, competent, and kind, you will attract people into your life with similar aspirations.

Choosing to go first, bringing authenticity, and engaging people will yield a positive result the vast majority of the time. Of course, there is always a small chance you will be rejected or judged. But the rewards and benefits far outweigh the risks.

Don’t wait for other people to reach out or take the first step. Default to action and go first. Apply this principle to important relationships in your life. Don’t worry if people do not initially invest an equivalent amount of time or energy in the relationship. Hold a long-term mindset. Over time, you will benefit from your investment in these relationships.

Bring your “go-first” mindset to your work. Express your ideas. Start a blog or podcast to connect with people who share your interests. Initiate conversations with people you don’t know. Everyone you meet has something to teach you. You never know what opportunities are around the corner. Go first and you will build stronger relationships and gain an unfair advantage in business and in life.

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Find the root cause

To build something new requires you get good at solving problems, and you need every advantage to solve them. Clearly defining the problem is always the first step in the process. Tease apart the problem and break it down into smaller pieces to recognize the type of problem you are facing. We frequently do not recognize exactly what problem we are trying to solve until we dig deeper.

Breaking a complex problem down to its foundation and generating original solutions from the ground up is called thinking from “first principles.” Write down your assumptions, then ask “why?” and keep asking “why” until you have exhausted your ability to answer. There you will find the root cause of your problem.

Often our assumptions, biases, and blind spots hold us back from identifying the best solution. To overcome those hurdles, use first principles thinking to reveal the underlying truth.

Here’s an example. I worked on a business that sold leads for home improvement projects to the best contractors in San Diego CA. But we were struggling to get ahold of contractors even though we were generating quality leads. 

They are in the field working and too busy to reply.

Most contractors are small businesses and don’t have administrative support.

They are doing the work themselves and not able to scale their businesses to hire more employees to support them.

Most small contractors enjoy working with their hands more than the administrative office work. Also they struggle to find employees to do the quality work in the field without their constant direct supervision.

Most of their business is from referrals from homeowners who were happy with the quality of their work.

The contractors did most of the work themselves to ensure a high quality job. Therefore the best contractors had too much work and were not interested in buying new leads.

You can see once you break down the problem and tease it apart, the problem becomes clearer. Use this same approach to solve problems at work or to learn a new skill. Once the problem is clearly defined, you can develop an effective strategy to solve it. Next time you are wrestling with a problem, break it down to find the root cause and develop the solution from the ground up.

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Solving problems backward

I want to share one of my favorite mental models called inversion. Mental models provide shortcuts to higher-level thinking, forcing your brain to think about a problem or decision from different perspectives. Inversion helps you flip a problem around and approach it from the opposite end of the natural starting point. Instead of starting at the beginning and thinking forward, start at the end and think backward.

It’s a lot easier to identity something that is likely to fail versus something that will likely succeed. Therefore removing an obstacle is often easier than creating a new solution. To see this process in action, try doing a pre-mortem with key members of your work team at the beginning of your next important project. Imagine the end of the project and think backward to identify all of the ways the project could fail.

This exercise is opposite of the way most teams begin a project. Normally, you discuss goals, roles and responsibilities, tasks, and the timeline, but you rarely spend time identifying potential problems. Inversion helps you identify obstacles and develop strategies to avoid or overcome those obstacles.

Inversion also works to help you achieve goals. Instead of focusing on what actions or processes to add, focus on what should be removed. For example, I’ve wanted to invest more time writing on the weekends, so I set a weekly goal and allotted a specific time to write. Even so, I continued to struggle to meet my goal.

I decided to run an experiment. I cut out drinking alcohol. Removing this one behavior made a huge difference. Not consuming alcohol allowed me to sleep better, think more clearly, and increased my energy and motivation. I ended up doubling the amount of time spent writing. What’s the number one behavior you can cut to help you achieve your goals. Experiment with removing it and see what happens.

Next time you are facing a tough problem, try thinking about it forward and backward. You may find that it will be easier to reduce errors or remove obstacles than to create new solutions.

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The advantages of thinking gray

Black-and-white thinking distorts your ability to see reality objectively. Jumping to conclusions too quickly when making important decisions does not serve you well. The stakes are high because your decisions will play a large part in determining whether you succeed or fail.

The world is complex. To efficiently navigate life, we make instant judgments. We categorize information as true or false. We label people as friends or enemies. Making quick decisions had its evolutionary advantages in helping us avoid predators and poisonous snakes. However, relying on quick judgments is not the most effective way to make important decisions at work and in your personal life.

We make instant judgments and quick decisions because uncertainty is both uncomfortable and mentally demanding. Our brains use lots of energy to process conflicting information, which is what we get when we engage in nuanced thinking or look at a problem from multiple points of view.

We want to resolve conflicts as quickly as possible to restore our physical and mental comfort. Think back to the last time you had a disagreement with a friend or co-worker. If you are like me, you wanted to either avoid the issue or resolve it as soon as possible. That’s how our brain feels when it’s conflicted.

Thinking gray is a mental model that forces you to delay forming an opinion until you have reviewed all the important facts and heard from all key stakeholders. This technique forces you to be patient. Thinking gray helps us overcome confirmation bias, which is our tendency to search for, interpret, and favor information that confirms our pre-existing beliefs and desired outcomes.

Important questions rarely have black-and-white answers, and important decisions require self-reflection and input from others. In business, you make dozens of decisions every day.

Can you think of anything that will have a bigger impact on your success than the decisions you make? Luck may play a part, but your decisions can overcome bad luck or squander good luck.

Here are a few ways you can apply thinking gray to improve your judgement.

  1. Have fewer opinions. We are not experts on most things, so why do we need to have an opinion on so many issues?
  2. Hold your opinions loosely. Be open to new information and seek out diverse points of view.
  3. Change your vocabulary and learn to say, “I don’t know.”
  4. When you are in conflict with others, invest the time to understand other sides of an argument better than you understand your own.
  5. Write down and apply decision-making criteria to think through a problem.
  6. Create scenarios and use probability weighting. Are you 50%, 70% or 90% certain your decision is correct?

The best way to improve your thinking and the quality of your decisions is to refine your decision-making process. Not all decisions are important enough to require a process. But employing a process to avoid bias and blind spots when you are making an important decision will give you the best chance to be successful. Next time you’re making an important decision, avoid black-and-white thinking and remember to think in shades of gray to improve your judgement.

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How’s the water?

Two young fish are contentedly swimming along when they happen to meet an older fish swimming the other way. He nods at them and says, “Morning, boys. How’s the water?” The two young fish swim on for a bit, until one of them looks at the other and asks, “What the hell is water?”

Like a fish in water, we are swimming in our cognitive biases, which are errors in thinking caused by our brain distorting reality. Our biases are pervasive, highly resistant to feedback, and can cause us to overlook or dismiss crucial information.

Biases and blind spots

To save time, our brain creates shortcuts called judgment heuristics, which allow us to think faster and to conserve energy. These mental shortcuts are usually helpful, but can also create blind spots when you are trying to make important decisions.

“The first principle is that you must not fool yourself—and you are the easiest person to fool.”

Richard Feynman (Nobel-prize-winning physicist)

Self-deception and ignorance can harm you. Not seeing reality accurately can often lead to unnecessary painful mistakes. Too often, we make decisions without recognizing our own biases.

Here are examples of common biases that can get in the way.

Availability bias. This leads you to believe that what you see is all there is. It can cause you to give priority to info and events that immediately come to mind, usually because they were recent, memorable, or personal.

Example. Most people overestimate the number of people killed by terrorism and underestimate risks associated with driving a car. More people die in car crashes every six days than die from global terrorist attacks in a year.[1] Yet, people are often more worried about terrorism than driving.

Representative bias. When two things look or seem similar, you may assume the two things will be the same or will lead to the same outcome. Representative bias is at the heart of stereotyping.

Example. Imagine you have a friend who grew up playing chess and video games. She was president of the computer science club in high school and loved to build things. You might predict, based on her interests and activities, that she would be likely to major in engineering at college. However, numbers show she is more likely to major in business as there are almost four times more business degrees given annually than engineering degrees.[2]

Confirmation bias. We tend to search for, interpret, and favor information that confirms our preexisting beliefs and desired outcomes rather than viewing information with objectivity.

Example. Confirmation bias is prevalent in politics and can be seen when people consider emotionally charged issues such as immigration and abortion. Deeply held beliefs can cause people from varying political viewpoints not only to see the same event in radically different ways, but also to reject alternative explanations.

Affect bias. Beware of making decisions based on a strong positive or negative emotional state—a “gut” feeling—without consulting all the evidence.

Example. Attitudes toward nuclear power and climate change are commonly influenced by affect bias. I’ve been guilty of this bias. I worked for twenty years promoting renewable energy and energy efficiency. Due to my strong beliefs, I did not fully consider the benefits of nuclear power and fossil fuels. I was wrong.

Here’s a more extensive list of cognitive biases.

To avoid fooling yourself, stress test your ideas by trying to disprove your assumptions, get feedback from people with different perspectives, hold your opinions loosely, and follow a structured decision-making process. It’s unlikely you can eliminate bias but you can be wrong less often.


[1] According to a report created by the U.S. Department of Homeland Security, in 2017 18,753 people were killed globally by terrorists. According to Safer America, every year, roughly 1.3 million people die in car accidents worldwide—an average of 3,287 deaths per day.

[2] According to a report by the National Center for Educational Statistics, in the academic year 2014–15, 364,000 degrees in business and 98,000 engineering degrees were awarded.

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Sin

“To sin” means “to miss the mark.” And you have missed it.

Weak-willed. Timid. Malleable. You are mediocre.

How did you let this happen? Why do you continue to let this happen?

Your dreams of greatness lie wet and soggy, like a loaf of bread left out in the rain.

You can’t stay on course. Your plans are uprooted like a sapling pushed over by a weak gust of wind.

You live as if you have no power to resist. No will. No agency. No strength. Your moments of resolve break like the weakest link in a chain.

You feel sorry for yourself because you think you deserve better. Have you earned it? Do you deserve more when you are so easily distracted?

A few drops of water extinguish your burning desire to achieve. You recoil at the slightest pain. You’re always seeking comfort. Greatness cannot be found there.

You must push through your weakness of will. Pick up and shoulder the weight of responsibility and do not drop it.

Your weakness is rooted in fear. Afraid of judgement, you contort yourself like a circus performer. Your lack of courage is repulsive.

Fear wraps around you like boa constrictor—squeezing your voice and crushing your creativity. You even fear the judgment of strangers walking near you on the street or sitting next to you in a restaurant. Why? Why do you care more about their opinions than your own?

Why are you so afraid? How long will you allow your fear to rule your decisions?

Was it fear that allowed mediocre people to sculpt your beliefs? You failed to question, probe, and puncture the assumptions and instead accepted and believed out of laziness. Is it really a surprise you were so wrong?

Like a sponge, you soaked up the ideas in your environment without caution or thoughtful consideration. Distorting, bending, and forcing reality to fit your limited ability has disfigured your mind.

Errors of overconfidence and misplaced certainty litter your life with failure. How many times do you need to fail before you learn?

Beliefs were not all you sponged up from the people around you. Constantly seeking affirmation, you began to model their vices: drowning your sense of purpose in alcohol. Desiring, wanting, consuming. Never satisfied. Never content.

The fat on your body testifies to bad decisions. Fuzzy black mold rots your brain as you scroll through useless information, hour after hour.

You don’t have time to waste. You don’t have to live this way; get up and get going.

The antidote to sin.

Don’t act like a victim. Victim mentality will rob you of your agency and power. Take action to improve your situation and be grateful you’re not rotting in the ground.

Embrace responsibility. Own your strengths, weaknesses, and position in life. Take responsibility for your actions and own the outcomes. 

Follow your interests. Build specific knowledge around your interests and find something you love to do. You will gain unfair competitive advantage because your passion will push you to work harder than other people and spur you to be creative and innovative in your field.

Create meaning. Find meaning by shouldering as much responsibility as you can manage, building competence, and contributing value.

Aim with purpose. Identify what you want in the long term and aim for that.

Update your identity. The most important step in building the life you want is to embrace the identity of who you want to become. Identity is shaped by your beliefs, behavior, and worldview. Self-development requires continually learning and upgrading your identity. The stories you tell yourself about your experiences shape your identity and mental state. Your mental state is your reality.

Build daily habits. You need goals to know where you are going and daily habits to help you get there. Get a little better every day. Consistency develops ability. Few things impact the quality of your life more than daily habits. Good habits help you become the person you want to be, whereas bad habits lead to pain, suffering, and self-loathing.

Upgrade your friends. Don’t underestimate the power of the people around you to influence your behavior. The social norms of your group shape your behavior. Surround yourself with people who push you to be better and give you feedback. Direct, honest feedback is hard to find because very few people are willing to tell you the truth. Most people want to avoid conflict, and they don’t want to jeopardize their relationship with you. 

Nobody’s going to do the work for you. You can do better. Dare to be great. Define your future. Take aim, shoot, calibrate, and repeat until you hit the mark. The worst sin of all is to quit trying.

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DO IT

Following a process helps you improve the quality of your decisions. Too often we let thoughts bang around in our heads and never apply a process to structure our thinking.

I created the acronym DO IT (Define Observe Imagine Test) to help me remember the steps. With a little practice, applying this process becomes automatic and you can use it daily for different type of decisions.

Not all decisions are important enough to require all four steps, but I recommend engaging in at least the first two steps for most decisions. Use no more steps or complexity than needed. Calibrate your time investment to the importance of the decision and how urgently it needs to be made. An effective process requires thinking deeply and writing down answers to each step.

Consider these four steps when you are in the process of making a decision.

DO IT (Define, Observe, Imagine, Test)

Step 1. Define

Define the problem or opportunity. Recognize the type of decision you are facing. You may think you do this now, but I bet you don’t. Following your fuzzy intuition without consciously thinking about the nature of the decision does not count. Write down the problem or opportunity using clear and precise language. Clarify the importance. What’s the magnitude? Is it reversible? How much time do you have to make the decision? Do other people need to be involved? Who are they? If you are the only decision-maker, then it’s easier, but multiple parties may need to be involved for a complex decision.

In addition to defining the problem, you also need to define who is responsible for the outcome. Every decision needs an owner who is held accountable and bears the consequences (good or bad) of the decision. No two people are alike in their knowledge, values, and experience. Therefore it makes sense to have different levels and kinds of decision rights. Decision rights should not be based on the rank of the person in the company hierarchy but should be given to the person closest to the problem who demonstrates good judgment and a comparable advantage to make the decision.

This first process step can be accomplished in a few minutes of focused thinking, but you must slow down enough to determine what you are facing before you move on. The time invested in this step depends on the complexity of the decision. Straightforward decisions may take only a few minutes while more important and more complicated decisions will require more time.

Step 2. Observe

After you’ve clearly defined the problem or opportunity, pause again and consider this question: Why do you need or want to solve this problem? Is making a decision about this issue the most important thing you can do now? What are your motivations? How does this decision or opportunity map to your goals? Make sure you are solving the right problem. Before you start digging in to seek solutions, ask yourself, “Am I focused on the right problem? Is this problem even worth solving?” Your time and attention are valuable, and you could be working on many problems.

To determine if this problem deserves your attention now, quickly review your list of priorities. Pausing and asking why forces you to prioritize your time before you blindly stumble into action. This only takes a few moments, but we rarely do it. Practice this process after you complete each task during the day and are preparing to move to the next item on your to-do list.

When you determine a problem is worth your time investment, start breaking down the problem into smaller pieces. Tease it apart. We frequently do not recognize exactly what problem we are trying to solve until we dig deeper. Breaking a complex problem down to its foundation and generating original solutions is a way of thinking from “first principles.” Write down your assumptions, then ask “why?” and keep asking “why” until you have exhausted your ability to answer. There you will find the root cause of your problem.

Step 3. Imagine

Engage in mental time travel and create multiple scenarios of the future. Scenario analysis helps you evaluate your choices. Don’t be lazy. Invest the time and energy to think through and evaluate your options. Before you write a line of code or change a single piece of hardware, make sure you have probed and punctured your best ideas from every angle. Nothing saves time and money more effectively than a well-run evaluation process to vet scenarios. Not every decision needs scenario analysis, but all important decisions do.

Step 4. Test

Test your ideas by getting feedback from customers, partners, or other appropriate stakeholders. Try to disprove each scenario. Without feedback, we are blind and stupid, and we will make the same mistakes repeatedly. Feedback helps you better see the reality of the world and allows you to correct mistakes and learn faster. Feedback provides an opportunity to gain empathy by seeing different perspectives, and it shines a bright light on your blind spots, which can improve your decision-making ability.

Direct, honest feedback is hard to find because very few people are willing to tell you the truth. Most people want to avoid conflict and are reluctant to jeopardize relationships. Thus, you will need to actively seek feedback from people with diverse perspectives and experience. Seek out people who have truly different skills, experiences, and worldviews to expose your blind spots. Challenge yourself to accept feedback from someone you dislike. I admit this is hard to do, but we can learn from everyone.

Make the decision

After you engage in the four DO IT steps, then do it—make the decision. For important decisions, think slowly. Be less impulsive and more deliberate. Your first reaction is usually not the best one. Take time for careful and considered reasoning. Take a break. Set aside time to review and think about scenarios. Grapple with tradeoffs, uncertainties, and risk. Sleep on it to allow your mind to consider your options. Your subconscious mind does more thinking than you realize. Frequently, a better solution will occur to you the next morning.

Don’t let thoughts bang around in your head. Apply the DO IT steps to structure your thinking and improve the quality of your decisions.

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How to beat robots and build wealth

Career decisions determine where you invest the majority of your time. These important life decisions have a huge impact on your well-being and quality of life—and your risk of being replaced by a robot.

In the industrialized economy of the 20th century, most people learned a skill and then worked the majority of their careers at one or two companies. That industrialized economy required scale and specialization, so large companies were organized around manufacturing and office jobs. Hierarchies were created to manage large groups of people while creating incentives for advancement.

The information economy of the 21st century is decentralized and global. Widespread access to personal computers and the internet has democratized knowledge so that anyone in the world with an internet connection and a desire to learn can build skills and contribute value to the global economy. The advancement of new technology will require workers to continuously learn new skills. Working as an independent contractor and / or working for many different employers is becoming the norm.

Skills needed in the job market are changing rapidly. Artificial intelligence (AI) and automation is accelerating and will replace most jobs that are repetitive or don’t require creativity. Many doctors, lawyers, investment advisors, taxi and truck drivers, accountants, cashiers and most service workers will be replaced by robots and software. Any job that is not creative or complicated is at risk.

However, I’m not yet convinced that our main problem will be robots and software taking jobs from humans. Historically, we do a poor job of imagining the jobs of the future because we are blind to the new industries, technologies, and services that will be created. In a very short period of time, we have seen personal computers, the internet, cable tv, mobile phones, and cloud computing go from science projects to mainstream, essential infrastructure. The largest tech companies in the world, including Amazon, Google, Facebook, Apple, and Alibaba, did not even exist when I was born. And I’m not that old!

Our main problem is that our educational system was not designed for a global information economy, and our broken system is not equipped to handle the massive retraining effort needed. Most colleges today don’t prepare graduates with the necessary skills for our current economy. As highlighted in this article in The Atlantic, companies have been complaining for years about the lack of skilled workers, even though millions of people are unemployed or looking for full-time work in the U.S. New models of education are needed.

Although our current system is not yet designed to address the scale of the problem, access to knowledge and training has never been more available to anyone who is self-motivated enough to pursue it. Also, low-cost computing power and the internet provide a path to go around the traditional gatekeepers in many industries, such as media, music, art, publishing, and technology. Here are a few ways to build wealth while pursuing the career you want and ensuring robots will never replace you.

Constructing Your Future

Follow your interests. Build specific knowledge around your interests and find something you love to do. You will gain unfair competitive advantage because your passion will push you to work harder than other people and spur you to be creative and innovative in your field.

Pursue highly technical or creative work. Creative work equals job security. Anything not creative can be replicated and replaced by AI. Specific technical knowledge cannot easily be duplicated.

Invest in continuous learning. Technology advancement will impact every industry. If you are not constantly learning, you will be left behind. Seek out roles and opportunities that accelerate learning. Gain an advantage by building a personalized learning system that keeps you on the cutting edge of knowledge in your field.

Get equity to ensure financial freedom. You will not gain wealth by getting a paycheck. Start your own business or get stock options or restrictive stock units in the company you join.

Move to a hub where your industry is centered. Leverage network effects by building relationships and living in a location where your industry ecosystem is strongest. For example, if you are in tech, move to San Francisco. New York is the best place if you’re interested in fashion or finance. If you want to pursue acting or music, go to Los Angeles.

Seek leverage and compounding value. The information economy has dropped the cost of entry to almost zero. Software and the internet provide a multitude of opportunities to help you make money while you sleep. Find ways to contribute value to the world that do not require you to work by the hour.

Work for people who will help you grow. You work for a person not a company, and your boss will likely determine your growth and satisfaction. Don’t work for people who are not invested in helping you grow, even if the company is great.

Create a decision-making process. Career decisions require identifying and weighting decision criteria. List up to five criteria to evaluate and test potential scenarios. Weight the decision criteria based on importance. For example, if I were evaluating new job opportunities, I would use the following five criteria.

After writing down your decision criteria, assign weights to each criteria on a 0–100 scale based on importance. Maybe the most important is interest level and you assign 30 points, while the least important is location that gets 10. The sum total of the weights should equal 100. After establishing your weighted decision-making criteria, apply a score between -10 to 10 to each criteria for each job. For example, if one job opportunity had a short 20-minute commute I would give it a score of 8. Compared to another job that a  one hour commute I would give a score of -9. This process will help you determine a total score for each job, but don’t get caught up in being too precise. Remember, it’s a tool to help you grapple with tradeoffs and think better.

We live in an unprecedented time of opportunity and prosperity. However, you need to work hard and make smart decisions if you want to participate in this abundance. No one is going to look out for your interests or care about your future more than you do. Find something you love to do that is creative or highly technical and then invest lots of time learning to be the best in the field. Prioritize learning over short term financial gain and find ways to create leverage and compounding value over time. Use criteria and a structured decision-making process for important career decisions to ensure you are on the path to financial freedom. Build specific knowledge in highly technical or creative work and you will not be replaced by a robot.

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Culture of envy

Envy causes pain and unhappiness and can even lead to emotional or physical violence. We slip into envy when we resent others for their achievement or good fortune. There are two types of envy. Malicious envy wants the person who has found good fortune to suffer and to be stripped of their achievement, status, or possession. Benign envy can be a motivational force to push you to work harder to succeed.

Natural-born talent is not equally distributed. No matter how hard I work, I’ll never beat LeBron James at basketball or world champion Magnus Carlsen at chess. I’ll never be able to sing and entertain a crowd like Bruno Mars or solve complex physics problems like Nobel laureate Donna Strickland.

But talent is not all that is involved. The effort people invest in pursuing their interests or passion is not equal. In the early days of Microsoft, Bill Gates worked almost around the clock and sometimes would not leave the office for days at a time. Lebron James invested thousands of hours practicing basketball, developing his body, and studying the game. Donna Strickland spent decades studying the physics of lasers.

The birth lottery plays a significant role in your health, intelligence, physical ability, family support, and the opportunities that are available to you. All these factors can lead to different levels of value people contribute to society and to different levels of rewards for their contributions. The result is lots of opportunity for envy.

Humans have struggled with envy for a long time. It’s one of the seven deadly sins in Christian teachings. In the Hebrew Bible, envy is the motivation behind Cain killing his brother Abel. Hinduism, Buddhism, and Islam all feature prominent warnings about the dangers of envy.

Today we are seeing a backlash against competent, educated, wealthy, and successful people. Billionaires such as Jeff Bezos, Warren Buffet, and Bill Gates are frequently vilified on mainstream and social media. This trend is disturbing. Their businesses have created massive value to society, and their companies employ over a million people. In addition, Gates and Buffett are voluntarily giving away almost all their wealth to help solve the world’s biggest problems. Bezos is investing billions in space exploration, which will convey massive benefits for society and the development of new technology.

There’s not a fixed pot of money. Unfortunately, there are people who hold a wrong assumption that those who have more have taken it from those who have less. Accumulation of wealth is not zero sum. Poker is a zero-sum game because the amount of money in the pot is fixed. Therefore, the person that wins the game is taking money from the players that lose. Life and business do not work this way. Businesses such as Amazon, Berkshire Hathaway, and Microsoft contribute to lower prices for consumers, employ people, and contribute value to society. Microsoft sells software that supports the growth and success of thousands of businesses, nonprofits, and government agencies.

The vast majority of millionaires in the United States earned their wealth. They did not inherit it. An article in U.S. News titled 7 Myths About Millionaires highlights “a 2017 survey found that 88 percent of millionaires are self-made. Only 12 percent inherited significant money (at least 10 percent of their wealth), and most did not grow up in exclusive country club neighborhoods.”

Don’t allow envy to breed discontent, resentment, and bitterness. Here are a few questions I ask myself to overcome envy when it arises.

  • Do I want to switch places with this person?

We don’t get to pick and choose parts of someone’s life. You can’t pick the NBA success and skip the hours of physical training or the relentless media attention. You get the good with the bad. I have yet to meet someone who I would be willing to trade places with.

  • Has this person worked harder or contributed more value to the world than me?

My honest answer is usually “yes.” Once I acknowledge the contribution and effort of a highly successful person, I am motivated to work harder.

  • What am I grateful for?

Answering this question immediately reframes my perspective and allows me to feel gratitude for all the prosperity I enjoy.

Use benign envy to push yourself to work harder to succeed. But let’s stop malicious envy. In addition to helping lower the temperature in our public conversations that decide how we govern our communities; we will help ourselves by reducing our emotional pain and resentment.

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Treat mental fitness like physical fitness

Do you dedicate time to improving your mental fitness? Most of us believe we should take active steps to improve our physical health, dedicating time to exercise and making an effort to eat healthier food. However, many of us don’t think much about enhancing our mental fitness.

Go to bed smarter than you woke up.

Mental fitness requires exposing yourself to new ideas, considering opposing viewpoints, and learning new skills. Interest and inspiration sparks learning and motivates us to act. It awakens our inner creativity, shaking us from our apathy and triggering our desire to grow. Curiosity and a desire to gain understanding activates learning.

Learning takes effort.

Muscles grow stronger when you stress them until they fatigue. Your brain grows stronger through practice, repetition, and exposure to new ideas. Making the effort to learn leads to knowledge.

When you pursue a goal or explore an interesting topic, you are emotionally invested in the outcome — no one has to force you to learn. The emotional investment helps motivate you to do the hard work of gaining proficiency and competence.

I love learning but hated school. I felt like I was being told to memorize a lot of information but had no idea how it applied to me. My teachers did not show me how I could apply concepts I was learning in algebra and geometry classes to help solve problems in my life.

Unfortunately, few people actively pursue learning after their formal schooling ends. They may learn as a consequence of performing their jobs or being in relationships with people, but they are not seeking out methods and practices to improve performance.

You can’t just wait for inspiration to strike. You must seek it out. Expose yourself to inspiring people and place yourself in challenging situations. Look for books, podcasts, blogs, lectures, videos, and performances that will inspire you and help you learn. A lot of people in the world are doing amazing, inspiring things — actively search for them.

Be selective.

Time is your most valuable resource. We are drowning in social media and 24-hour news. Don’t waste your time consuming information that you will not care about next year. Focus your attention on topics you are interested in and want to master.

Read a lot.

According to a 2015 article by Kathleen Elkins on the Business Insider website, a study of 1,200 highly successful people showed that reading was a common pastime and a practice they use to educate themselves. Successful people would rather be educated than entertained.

If you don’t like to read, then listen to audiobooks and podcasts. Choose quality over quantity. You don’t have to finish a book or podcast that does not capture your interest. Move on and start reading or listening to something else.

Read or listen actively when you are alert and focused. If I try to read in bed before going to sleep, I rarely finish more than two pages before the book smacks me in the face. Reading while sitting in a chair in the morning works better for me.

Schedule time for reading. You won’t finish many books if you prioritize other activities and think you will just fit reading in when you have time. I read for 30 minutes as a part of my morning routine.

Compound your knowledge.

Compounding interest works in economics because you earn “interest on your interest” and your money compounds over a long-time frame. You can get a similar exponential return on learning by investing a small amount of time every day to add new knowledge. The more you read, the better you get at it. You will start to read faster, and your knowledge will compound.

For example, if you read 30 minutes a day you will read 183 hours over a year. The only way I’m able to dedicate that much time for reading is by building it into my morning routine. Reading the book Waking Up, by Sam Harris, and practicing meditation inspired my morning routine and has reduced my tendency to react to challenging situations, improved my focus, and given me a more relaxed start to my day.

Take notes.

You don’t get a lot of benefit from reading if you forget what you read. Write down important ideas and key insights as you read, and you will learn more and remember more about what you read.

I tend to forget things, so I take notes as I read instead of waiting until the end of the chapter or my allotted reading time. I prefer to use the Notion app because it is searchable and organizes my notes. However, using pen and paper helps reinforce learning, so use a notebook if you prefer. Notes provide a nice summary of all the ideas and insights you have learned.

Create a schedule to review your notes.

Reviewing your notes will maximize retention. Spaced repetition, as explained in this article on the Farnam Street website, is a learning technique built on reviewing previously learned material at increasing intervals of time. It has been proven to significantly improve learning.

You don’t have to spend a lot of time to practice spaced repetition. A typical schedule to review your notes may be one day after reading, then one week, then two weeks, then one month, then six months, then one year. Invest a few minutes per session to review notes. After I started taking notes and reviewing them, I noticed that I retain a lot more information than in the past.

Share your knowledge with other people.

Teaching other people forces you to internalize learning at a deeper level. Test your knowledge by first writing down your concept in a way that you could explain it to an eight-year-old child. This article on the Farnam Street website labels this technique the Feynman technique, named after the brilliant Nobel-prize-winning physicist, Richard Feynman. This process will help identify gaps in your existing knowledge and help you learn faster with better understanding.

My recommended books and podcasts

I go out of my way to listen to people and ideas that challenge me. If I’m learning about a new topic or want to achieve a greater depth of knowledge, I seek out experts in the field that hold opposing opinions — especially controversial ones. Ideas rooted in truth always hold up to deep skepticism and scrutiny. Here are a few book recommendations, and the podcasts I listen to on a weekly basis.

Books

One of many insights I am learning from reading these books is that the most effective intervention point to impact change in the world is at the level of the individual.

The Gulag Archipelago by Aleksandr Solzhenitsyn (new abridged version with volumes 1, 2, 3)

Notes from Underground by Fyodor Dostoevsky

Blitzscaling by Reid Hoffman

Meditations by Marcus Aurelius

On Writing Well by William Zinsser

How to Change Your Mind by Michael Pollan

What You Do Is Who You Are by Ben Horowitz

Beyond Good And Evil by Friedrich Nietzsche

Enlightenment Now by Steven Pinker

12 Rules for Life by Jordan Peterson

Good Profit by Charles G. Koch

Podcasts:

I spend a lot of time (1 to 2 hours/day) listening to podcasts. I listen at the gym, while walking my dogs, commuting, doing dishes, and waiting in line. If I’m not working or talking with someone I’m most likely listening to a podcast. I take notes while listening, typically I use use voice-to-text to record my notes quickly using the Notion app because I’m usually not in a position to write them down.

Personal Development, Psychology, Improving Society

Naval

Making Sense (Sam Harris)

The Jordan B Peterson Podcast

Conversations with Tyler (Tyler Cowen)

The Tim Ferriss Show

The Knowledge Project (Shane Parrish)

The Portal (Eric Weinstein)

Derek Sivers

The Arthur Brooks Show

Akimbo (Seth Godin)

TED Radio Hour

Hidden Brain

Freakonomics Radio

Technology & Startups

Y Combinator

a16z

Greymatter (Greylock Partners)

Masters of Scale (Reid Hoffman)

This Week In Startups (Jason Calacanis)

AGI Podcast

How I Built This (Guy Raz)

Political

Quillette

The Ben Shapiro Show

Miscellaneous

The Joe Rogan Experience  includes lots of diverse, interesting guests but I usually don’t listen to interviews with comedians/entertainers or the mixed martial art (MMA) show episodes.

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Have fewer opinions

We are not experts on most things, so why does everyone need to have an opinion on so many issues? It’s very difficult to convince yourself of a new idea if a contradictory idea is already anchored in your thinking. We are too frequently blinded by our own opinions, but we can design decision-making processes to overcome this bias. Such a process can help you avoid painful mistakes and gain an advantage, but this effort takes humility and can be difficult.

As you get older, you realize how much you got wrong in the past. Most of the beliefs and opinions I held most deeply in my twenties and thirties were wrong. In fact, it would be an easier exercise to identify what I was right about than to try to count all the ways I was wrong. I see the error of my past ways more clearly now because I’ve learned more, seen more, and thought more. Exposing yourself to different viewpoints and engaging in a little bit of self-reflection can reveal how easy it is to trick yourself.

Cultivate nuance

It’s highly unlikely you’ve studied most issues or problems enough to have an informed opinion, but jumping to conclusions too quickly can be the path of least resistance. We make instant judgments and quick decisions because uncertainty is both uncomfortable and mentally demanding. Our brains use lots of energy to process conflicting information, which is what we get when we engage in nuanced thinking or look at a problem from multiple points of view.

To efficiently navigate life, we like to make instant judgments. We categorize information as true or false. We label people as friends or enemies. Making quick decisions had evolutionary advantages in helping humans avoid predators and poisonous snakes. However, relying on quick judgments and opinions is not the most effective way to make important decisions. Delay forming an opinion until you have reviewed all the important facts and heard from all key stakeholders. This process forces you to be patient. Important questions rarely have black-and-white answers, and important decisions require self-reflection and input from others.

Here are a few ways to stop yourself from being too rigid in your thinking.

Good ideas survive deep skepticism and intense competition. Stress-testing ideas exposes their weaknesses and highlights their strengths. You gain confidence in the truth of an idea by trying to disprove it.

Be humble, expose yourself to diverse viewpoints, and have fewer opinions.