Coffee Break

156 – What Could Possibly Go Wrong?

What Could Possibly Go Wrong?


What could possibly go wrong?

What could possibly go wrong? I think one of the biggest mistakes that we as humans make is that we are far too optimistic about how something we’re planning might go. In doing so we often fool ourselves into believing that it will work as planned, and overlook what could go wrong. In this weeks episode, we’ll discuss how we can take steps to avoid the blind spots that can easily derail us.

How many times have you started a project, or tried to start a new habit, only to run into all kinds of unexpected resistance? Maybe you want to start going running each morning or maybe you have a project at work and despite your best-laid plans, things start heading off the rails in ways that you never expected. The optimism and energy you had starts to wane as you deal with one setback after another. I run into this all the time. I think that I have things well planned out only to find that what I thought were conservative estimates and plans were far too optimistic.

When we make overly optimistic plans, we act as if it were a simple mathematical formula that we can plug in the right variables and have things turn out exactly as expected. But as we all well know, the best plans don’t mean anything if they can’t stand up to the reality of a situation. We fall into overly optimistic thinking because our brains are trying to be efficient. It takes time and effort to dig into a planning process and go deeper than our initial optimistic plans. It takes exploring uncomfortable thoughts and ideas and being willing to throw away any ideas that don’t stand up to reality, even if we’re very attached to them.

So why is it so hard to get things nailed down and complete the things we want? First, we’ll look at two of the most common mental traps that we fall into. Then we’ll look at some ways we can work around own limitations, and help mitigate the challenges that surprise us along the way.

Confirmation Bias

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

—Richard Feynman

Probably the most pernicious enemy of trying to plan for something is confirmation bias. Confirmation bias is when we seek out evidence which supports our decision and ignore evidence that conflicts with our preconceptions. It is the clearest example of overly optimistic thinking, and we are all guilty of it. Confirmation bias blinds us to all kinds of other possible solutions. When are too attached to an idea, when we want to prove that we already have the solution, we miss out on finding better solutions. The more that we can approach something with an attitude of seeing where we could be wrong, the more likely it is that our plan will stand up to scrutiny and be more successful. Take the time to examine your own bias and to ask yourself, “Am I defending this idea simply because it’s mine? Am I ignoring contradictory information because I’m too in love with my own idea?”

We saw this happen in the second Iraq war where, because the decision makers had the idea that there had to be illegal weapons in the country, even the smallest bit of data that could bolster the argument was held up as definitive proof. Anything showing the opposite was simply dismissed and ignored because it didn’t support the idea. Once the country was invaded, it became evident that there were no such weapons and it became clear that the evidence was flimsy at best.


Belief Bias is a concept similar to Confirmation Bias. Whereas Confirmation Bias seeks out information to confirm the decision we want, Belief Bias is when we use an existing belief to support a conclusion that lines up with that belief. When we don’t allow our belief to be challenged, and to be open to the idea that we might be wrong, we don’t allow reality to influence our decisions. We may make bad decisions because they are based upon a faulty belief. Circumstances change, discoveries happen, and being open to new evidence is critical to making progress in ourselves, as well as successfully completing projects that we embark on.

For example, if we believe that women are not as smart as men, then we may dismiss a great idea because we believe that only good ideas can come from men. I’ve heard from a few women about how their ideas were dismissed at work, simply because they were a woman. Once the same idea was presented by a male colleague, it would be given the consideration it deserved. Because of this belief, it’s taken centuries for women to be treated as equals, to be paid the same as men, to be able to vote. As we progress as a society we often ask ourselves how could we ever have held such a ridiculous belief?

So how do we avoid these traps? What are some steps that we can take to be sure that we aren’t fooling ourselves?

Open to Criticism

“If any man is able to convince me and show me that I do not think or act right, I will gladly change; for I seek the truth by which no man was ever injured. But he is injured who abides in his error and ignorance.”

— Marcus Aurelius

One of the most important areas of making better decisions is to be open to criticism. One are where we can see that thrives on criticism is the are of science. One of the reasons why we have made so much scientific progress over the last 100 years is because science is open to the idea that a discovery or an idea is only valid for now. That it is based upon the best evidence available and should only stand as long as withstands review and stands up to criticism.

We should take this same idea and apply it in our own lives. We should only hold onto an idea or a habit as long as it serves us and helps moves us the direction we want to go. When we seek out contradictory opinions, we are taking steps to counter our own bias. When we come upon new information or receive criticism, we should be willing to review it and change direction if need be.


“How ridiculous and how strange to be surprised at anything which happens in life.”

— Marcus Aurelius

One of the things that sets us apart from other animals is our imagination. The ability to tell ourselves fictional stories, to think about what-if scenarios is a powerful tool in creating our future. Without imagination, we would not have the ability to create ideas about what we think the future will be like. We would have no way to plan for the future. This singular ability is what helps us to move from being reactionary beings to creators and designers of our future. But far too often we suffer from a failure of imagination and end up surprised that things don’t turn out as we expect.

Because we have the gift of imagination we need to consider the unlikely, to think of the impossible, and be open to ideas that we may not like. This also opens us to a larger pool of possible solutions.


“Nothing happens to the wise man contrary to his expectations.

— Seneca

One of the most important practices that the Stoics have is Premeditatio Malorum, which is to imagine all that possible ways that things could go wrong. I’ve talked about it before on the podcast, and it’s a very useful practice. This is not the same thing as being pessimistic. I like to think of it as a way to test your ideas and plans against reality, by using your imagination. This is not an easy exercise. It takes effort to let go of your wish to have the right solution and to think of all the things that could go wrong.

I came across a similar exercise that psychologist Gary Klein calls a “premortem”, that illustrates this idea rather nicely. As Dr. Klein explains, “Our exercise, is to ask planners to imagine that it is months into the future and that their plan has been carried out. And it has failed. That is all they know; they have to explain why they think it failed.” Just as doctors do a postmortem to understand what happened after the fact, a premortem is a way to truly imagine the most likely ways that a plan could fail.

Being Wrong

A lot of the topics I’ve discussed today revolve around the fact that we don’t like to be wrong. We get attached to an idea and want that idea to be right, and thereby validating ourselves. But the thing is the more try to avoid failure, rather than facing it head on, the more failure we’re going to have. Being able to let go of needing to be right, of validating ourselves, the more we can get out of our own way and make better decisions.

Hey friends, thanks for listening to the podcast. If you like what you hear, I would really appreciate it if you could help support me by making a pledge on Patreon. You can find me at Even just a small amount helps in keeping this podcast going. Also, head on over to my website at and sign up for our weekly newsletter. And lastly, if you know of someone that might like or could benefit from this podcast, please share it with them. Word of mouth is one of the best ways to help this podcast grow. Thanks again for listening.

Coffee Break

155 – Interview with Jeff Emtman of Here Be Monsters

Interview with Jeff Emtman of Here Be Monsters


This weeks episode is an interview with Jeff Emtman from the Here Be Monsters podcast. This is my first time interviewing someone, and Jeff is a very interesting and thoughtful guest. We talk about life challenges, creative challenges, and what it’s like to drag main.

You can find Jeff’s podcast at It is strange, mysterious, and at times very touching.


Hey friends, thanks for listening to the podcast. If you like what you hear, I would really appreciate it if you could help support me by making a pledge on Patreon. You can find me at Even just a small amount helps in keeping this podcast going. Also, head on over to my website at and sign up for our weekly newsletter. And lastly, if you know of someone that might like or could benefit from this podcast, please share it with them. Word of mouth is one of the best ways to help this podcast grow. Thanks again for listening.

Challenges Coffee Break Fate

154 – The Paradox of Change

The Paradox of Change


The only way is through!

One of the weirdest things about being a human is how we get comfortable with our habits, and resist change, while at the same time we get bored when things stay the same. In this weeks episode, we’ll talk about how to deal with the paradox of change.

When one day is pretty much the same as the next, we crave variety. If something is too easy, we get bored and quickly lose interest in it. But when life throws a challenge our way we often complain and whine about how life isn’t fair.

So how do we deal with the challenges that life throws our way? How can we learn to cultivate and attitude of gratefulness for the hard things in our lives, and use them to grow and become better people?

“A setback has often cleared the way for greater prosperity. Many things have fallen only to rise to more exalted heights.”

— Seneca

I want you to think about the last movie you watched or book that you read. Can you remember the challenges the hero had to face? The obstacles they had to overcome? Maybe the hero got knocked down and had to struggle over and over to get back on her feet, and eventually through hard work and determination, overcame a great challenge. This is something that we as humans crave in our stories. I mean how interesting would it be if the story started with, “Our hero had everything her heart desired, and lived happily ever after”? Not much of a story, and certainly not one I would be interested in.

So why do we love this in our stories, yet complain about it in our lives? This is what I call the paradox of change. Life is continually changing and bringing new challenges our way, but we get comfortable and feel distressed when our comfort is disturbed, forgetting it’s the challenges that make us who we are, that help strengthen us into being the kind of people we want to be.

Say that you wanted to start your own company. If you want to succeed, then you have to learn how to deal with difficult people and situations. Because it is impossible to never face a tough situation or to have everyone you deal with simply follow and agree with everything you say. You have to expect setbacks and failures because you are going to have to learn how to navigate difficult situations if you want to succeed. In fact, the more you can anticipate and plan for setbacks, the better off you will be. If you only plan for rosy scenarios, then you will have a much harder time when challenges come your way.

“The greater the difficulty, the more glory in surmounting it. Skillful pilots gain their reputation from storms and tempests. ”

― Epictetus

When challenges come our way, one of the most important things that we can do it learn how to face them, and not shy away. If we make a habit of turning away from difficult situations and challenges, we’ll never get stronger. We’ll never reach our full potential. When we make a habit of leaning into the hard things, even if it scares us, then open the door to greater growth and opportunities. If we only take on the easy challenges, then our skills will never improve. If a pilot only sails their ship on the calmest of waters, they’ll never leave port because they can’t count on always having great weather. If a singer only sticks to nursery rhymes, they’ll never develop the skills to tackle the aria they want to master.

How can we look at something in a way that helps us see it as a tool for growth? I think the biggest thing, and this is something that I struggle with, is to let go of the outcome. When we get so tied to the desired outcome, we often just want to skip the hard stuff and get to the end result. When we’re stuck thinking that we want a situation to be a certain way, we can begin to feel like that’s what we’re entitled to. The problem with this kind of thinking is that we can’t control the outcome of any situation. Life has too many random things that happen that are simply out of our control.

When we develop a love of change, an acceptance that everything and everyone is always in a constant state of change. No one in life is static. Too often we get stuck thinking of ourselves as being a certain way, and what our lives should be. When something comes along and disturbs that, we often resist those changes and ignore the reality of the situation. We do this with other people as well. We decide that a person is a certain way and hold to our judgment of them, we find it difficult to accept that they may have changed.

“The impediment to action advances action. What stands in the way becomes the way.”

― Marcus Aurelius

When we can look at a challenge, we need to see it as a teacher, as the thing that will actually train us how to overcome it. We need to look at something and ask, “What can I learn? What skills do I need to develop to over this?” When a musician starts a new piece, she doesn’t simply try to play it start to finish and then give up when she can’t play it perfectly. She starts working at a very basic level. She’ll break it down into smaller workable parts. Each passage presenting its own challenges. She will probably run into things that she’s never done before or isn’t very good at. Working on these passages are the very things that will help her to become better. Maybe she struggles with triplets, and rather than wishing they weren’t in there, she doubles her practice on them. Working on the challenges of the piece is the very thing that trains her in the skills to be able to master it.

“Win or learn, then you never lose.”

— Anonymous

It’s been said that those who don’t learn from history are bound to repeat it. And while this was said more as a critique of society, I think that it’s very true for each of us individually, as well as the places we work. If we label our failures as such rather than as something to learn from, we risk repeating them. A client of mine once made a mistake that brought down some of his companies computer systems. The company fired him missing an opportunity to work with that him to figure out how to prevent it in the future, as well as improving their employee training.

When we can learn to be grateful for the challenges that we face, we can approach them more readily, and humbly. We don’t try to avoid them, but rather welcome the challenge and become excited for the skills and the growth that they will bring. Then when things don’t go as planned, we are able to quickly regroup and learn what we can from the experience, and push forward and do better the next time.

Hey friends, thanks for listening to the podcast. If you like what you hear, I would really appreciate it if you could help support me by making a pledge on Patreon. You can find me at Even just a small amount helps in keeping this podcast going. Also, head on over to my website at and sign up for our weekly newsletter. And lastly, if you know of someone that might like or could benefit from this podcast, please share it with them. Word of mouth is one of the best ways to help this podcast grow. Thanks again for listening.

Coffee Break

153 – Hatred of Others

Hatred of Others


Don’t be a dick!

Are you disturbed by the political landscape that has changed so rapidly over the last 4 years? As more and more authoritarian parties come into power around the world, we see that hatred towards others – immigrants, refugees, women, minorities – seems to be at an all-time high. In these troubled times, we need to take a look at ourselves and be sure that we don’t fall into the trap of hatred and blaming others for the disappointments in our lives.

When we look at today’s news, we can see that there seems to be an uptick in political violence. We see leaders being elected that openly advocate violence towards others. Why is this? Why do people feel the need to hate other groups?

I think it comes from people feeling disappointed with not getting what they think they deserve in life. And when that disappointment happens, people look for someone or something to blame. Rather than taking the time to think about why they didn’t get what they wanted like most of us, we find it’s easier to blame something outside of ourselves because our egos don’t want the uncomfortable reality that we are in charge of our lives and that there are things that we did or didn’t do.

When reality doesn’t live up to our dreams, when we don’t get the things that we think we deserve, we look to someone to tell us why. Politicians and leader exploit this need and provide us with easy targets as to why we didn’t get what we wanted. They give people someone to blame, and usually, it’s those that even less fortunate than the ones that they’re appealing to, such as getting the declining middle class to turn against the poor by taking away

Is there ever a time when it’s okay to hate another group based on race, nationality, gender, sex?

“Never in reply to the question, to what country you belong, say that you are an Athenian or a Corinthian, but that you are a citizen of the world.”

— Epictetus, Discourses

The Stoics held that we are all part of the same human family, that we are all very much like each other and that we are here as to help each other. When others try to act as though their group, their culture, their skin color is so much better than someone else’s, they’re really quite delusional. The thing is, we are all basically the same with some minor variations. And it’s this mix of difference, the variety that helps us all as human beings. How many of us have been touched by inventions and ideas that came from other cultures? Science and math had strong origins from the Arab world and from India as well as Europe.

I know I used this quote a few episodes ago, but I really think it’s work repeating.

“One cannot pursue one’s own highest good without at the same time necessarily promoting the good of others. A life based on narrow self-interest cannot be esteemed by any honorable measurement. Seeking the very best in ourselves means actively caring for the welfare of other human beings. Our human contract is not with the few people with whom our affairs are most immediately intertwined, nor to the prominent, rich, or well educated, but to all our human brethren.”

— Epictetus

When we fail to help our fellow humans, when we think only of our group, our tribe, we are not contributing to the world. We are making the world a worse place.

One of the first things that I ever read from Epictetus was the first chapter of the Enchiridion. :

“To achieve freedom and happiness, you need to grasp this basic truth: some things in life are under your control, and others are not. What things are under your total control? What you believe, what you desire or hate, and what you are attracted to or avoid. You have complete control over these, so they are free, not subject to restraint or hindrance. They concern you because they are under your control. What things are not under your total control? Your body, property, reputation, status, and the like. Because they are not under your total control they are weak, slavish, subject to restraint, and in the power of others. They do not concern you because they are outside your control. If you think you can control things over which you have no control, then you will be hindered and disturbed. You will start complaining and become a fault-finding person.”

— Epictetus, Enchiridion

Here we see clearly that one of the things that are outside of our control is our bodies. That means that we and everyone else has no control over where they were born, what color their skin is, what gender or sex they are. When we hate someone for something that is outside of their control, there is nothing that they can do about it. If someone hated me because I was born in Salt Lake, there’s nothing that I can do to change that. I can’t change that I have light skin, that I have blue eyes, that I don’t have much hair.

But the thing is, that when we hate, we do more damage to ourselves.

“Whoever does wrong, wrongs himself; whoever does injustice, does it to himself, making himself evil.”

― Marcus Aurelius, Meditations

When we give into blame, hate, and violence, then we damage ourselves. We become just as bad, if not worse than what we accuse others of being. We are no longer people that we strive to be. We become the monsters.

“Events don’t disturb people; the way they think about events does. Even death is not frightening by itself. But our view of death, that it is something we should be afraid of, frightens us. So when we are frustrated, angry or unhappy, let’s hold ourselves responsible for these emotions because they are the result of our judgments. No one else is responsible for them. When you blame others for your negative feelings, you are being ignorant. When you blame yourself for your negative feelings, you are making progress. You are being wise when you stop blaming yourself or others.”

— Epictetus, Enchiridion

Why is this so hard for us to do? It really comes down to our egos. We like to think of ourselves as being smart, hardworking, kind, gracious, etc. and when we do things that might contradict this, we will gloss over and even ignore some pretty bad behaviors. We try to fool ourselves because we don’t want to see that we’re not as great as we think we are. Our ego, our identity may also feel threatened as well. When we have an idea of ourselves that we present to the outside world when we do things that are out of character, we will ignore them because we want to maintain this identity.

So how can combat this hatred and violence? This is always a tough question. The person that can work on most is ourselves. We need to exemplify the kind of people we want to see in the world. Gandhi talked about this when he said, “Be the change you wish to see in the world.” Because we can’t change other people, we can only change ourselves, we need to act like the kind of people that we think should be in the world.

So what can we do to inoculate ourselves against this kind of thinking?

“No soul is willingly deprived of the truth; and the same applies to justice too, and temperance, and benevolence, and everything of the kind.  It is most necessary that you should constantly keep this in mind, for you will then be gentler towards everyone.”

— Marcus Aurelius

When we can recognize that people are acting out of what they think is their best interest, we can be compassionate towards those that think differently than us. And this includes people who may have different political views than we do. And it’s not easy. We may see them as irrational and intolerant, and they may be. But if we counter that with irrationality and intolerance, then we are just the same as them. We may be on the opposite side, but we need to set the example of how to be inclusive.

One of the best ways to do this is developing a sense of empathy. Each of us likes to think that our way of living is well thought out, well-reasoned, and the best way of living. The person on the other side probably thinks the same thing. When you can put yourself in someone else’s shoes and see the world through their eyes, even as distasteful as we might find their worldview, it helps us to understand why they think as they do and helps us to possibly find ways to help them see their own irrational behavior. When we try to understand the influences that they had in their lives – their culture, family, education – we can begin to see why they hold their worldview.

This is not easy and it takes much more effort. Anger is easy. Hate is intoxicating.

“Convince your enemy, convince him that he’s wrong

To win a bloodless battle, the victory is long

A simple act of faith, of reason over might

To blow up his children will only prove him right”

— Sting

There’s a lot of hate going on in the world, and it’s easy to be angry at those advocating violence. But that’s all the more reason to do our best to take the high road. We need to make sure that we create a culture where violence and bigotry and misogyny are not acceptable. Where people see every other person as just another person with their own thoughts, opinions, and ideas about how to live their lives, but to do so in peace.

Hey friends, thanks for listening to the podcast. If you like what you hear, I would really appreciate it if you could help support me by making a pledge on Patreon. You can find me at Even just a small amount helps in keeping this podcast going. Also, head on over to my website at and sign up for our weekly newsletter. And lastly, if you know of someone that might like or could benefit from this podcast, please share it with them. Word of mouth is one of the best ways to help this podcast grow. Thanks again for listening.