Story

Odysseus finds himself on the island of Phaecia, at a banquet. He hears the song of the fall of Troy and weeps. King Alcinous asks him who he is and his story begins.

He starts at the moment of victory. He and his men leave Troy and finally sail home after 10 years of war.

A storm pushes his fleet of men towards the coast of the Cicones, allies of the Trojans whom they had fought against. Odysseus and his men sack and plunder their city, Ismarus. Killing the men and taking the women. This is the kind of journey home that Greek soldiers expected after winning a war.

It’s one thing to win a victory, its another to become a barbarian. Odysseus decides that enough is enough and tells his men to load the ships and leave before reinforcements arrive for the Cicones. They refuse. They want to feast, drink and celebrate the victory they had just spent a decade fighting for. Overnight, some Cicones who had escaped come back with an army. At dawn they attack. Over seventy of Odysseus’ men are killed. Six men from every ship. All because they didn’t know when to stop.

They barely make it to the ships, and almost as soon as they sail, they find themselves in a storm. The storm lasts for nine days and blows them wildly off course. They find themselves in completely uncharted waters. Odysseus and his men happen upon an island. Odysseus sends three men to scout it. They discover a peaceful people who offer them a strange flowering plant to eat called the lotus.

The scouts eat the lotus and they are completely satisfied. They weren’t poisoned, they weren’t sick. Almost as soon as they had eaten the lotus they forgot food, their wives, their homes and even their names. Their only desire became to sit on the island and eat lotus forever.

Odysseus finds these men, and drags them back to his ships kicking and screaming. As he takes them back, they weep and fight him the entire way. Odysseus and his crew tie them under the rowing benches like cargo. He then orders the rest of his men to stay clear of the plan and gets every ship off the island before anyone else is tempted.

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Truth

As soon as they leave Troy, Odysseus’ men fail. They fail twice within the same 10 days. This failure looks like two different problems:

• Hubris / At Ismarus, they can’t stop.

  They had won and continued to celebrate their victory to excess. Too much wasn’t enough. It costs them greatly.

• Apathy / At the island of the Lotus Eaters, they can’t start.

  They are satisfied to the point of not wanting anything at all. Their lives become easy and comfortable and their entire reason for going home disappears.

ὕβρις (hubris) is excessive pride that oversteps its rightful limit. Apathy, or ἀκρασία (akrasía) in Greek is literally a lack of strength. It is doing what you know you shouldn’t do, or failing to do what you know you should do. Even while you continue to observe yourself do it.

Hubris and apathy look like opposites. They share a root, a lack of discipline.

It takes discipline to not push beyond what is appropriate. It also takes discipline to do what you know you must do, even when you don’t want to.

Solomon said this about hubris:

“If you find honey, eat just what you need, lest you have too much and vomit it up.”

/ Proverbs 25:16

He said this about apathy:

“He dies for lack of discipline, led astray by his own great folly.” / Proverbs 5:23

A lack of discipline will lead us to both excess and apathy. And the compound effect of either, or both will lead to our downfall.

Discipline was the only thing that could have stopped Odysseus’ men from being killed or being stuck.

Practice

Discipline is simply the application of what you already know.

If you want to fail in life, it’s easy. Simply don’t do what you know to do every day. And over time, you will accumulate failure.

If you want to win in life, it’s also easy. Simply do what you know to do every day. And, over time, you will accumulate success.

“Here’s my formula for success: A few simple disciplines practiced everyday. Success is accumulated discipline.” / Jim Rohn

Myron Golden says that success or failure are automatic. You will automatically be a success or failure. How? Based on the decisions you make. If you make good decisions every day, you will become automatically successful. If you make bad decisions every day, you will become an automatic failure.

So, here’s the question:

What do you know that you need to do every day that you just aren’t doing?

When are you going to start doing it?

Story

Surviving Poseidon’s wrath with Ino’s help, Odysseus makes it to shore and collapses beneath two olive trees. He’s naked, half dead and buries himself in a pile of leaves for warmth and falls asleep out of exhaustion.

He awakes to the sound of girls laughing.

Nausicaa, the princess of the island was visited by Athena in a dream and guided to wash her clothes in the river that morning with her maids. After washing their clothes, they began to throw a ball to each other on the beach while their linens dried. One wild throw landed in the river and the girls screamed, waking Odysseus.

He crawled out from the underbrush, filthy, salt-crusted, naked and holding a leafy branch in front of himself for modesty. Every maiden except for Nausicaa ran away. Odysseus asked her kindly for directions to the city and if she had anything to spare so he could cover himself.

She asked her maids to bring him olive oil to wash the salt off his skin and clean clothes from her brother’s chests. She asked him to follow her wagon into town, and gave him instructions on what to do as soon as he reached the palace: walk past everyone in the courtyard and go directly to her mother - Queen Arete. The only problem was that town was full of people and the Phaecians were hostile to strangers and outsiders. How would Odysseus make it that far? Athena shows up disguised as a young girl carrying a water pitcher. She begins to pour a thick mist all around him, wrapping him in it so he becomes invisible to everyone he passes. She then guides him through the streets to the palace and tells him about the layout of the palace and tells him how to approach Queen Arete.

Odysseus takes this journey and finds himself in an extravagant hall with walls made of bronze and a silver threshold. At the end of the threshold were bronze watchdogs that Hephaestus - the god of fire - had forged. He sees the queen and falls at her knees to tell her his story. As soon as he hits his knees, his cloud of invisibility disappears.

Odysseus did more than tell her his story, he took a ritual posture in ancient Greece called ἱκεσία (hikesia). The English translation for this word is supplication.

This wasn’t begging, this was an ancient unwritten law. The Greeks believed it was a tradition handed down by the gods. A sacred plea for protection and refuge from a person who had no ability to care for or protect themselves.

Odysseus had nothing. He had no men, no ship, and no plan. He didn’t even have any clothes. He was stuck on this island and his only chance was the mercy of the king and queen. However, this wasn’t improvised desperation, this was the official way to ask for mercy and protection. Odysseus implored Queen Arete for help to get home.

At this moment, her husband, King Alcinous heard him speak, lifted him up, set him by the fire and promised him a ship home.

There was a banquet that night and Odysseus was invited. A blind singer played the lyre and sang of of the wooden horse, the fall of Troy and ten years of war. Odysseus heard his own life story told to him and it made him weep.

King Alcinous was the only one who noticed. He stopped the music and asked”

Who are you?

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Truth

Odysseus didn’t improvise his request out of desperation. He knew the ancient way to ask for help and he followed it.

ἱκεσία wasn’t an emotional breakdown. It wasn’t getting emotional and distraught and throwing yourself at a person’s feet. Everyone knew the process. Kneel, touch the person’s knees, and state your need. If a person was asked for help in this way, it obligated them to respond positively to the request. It wasn’t about returning favors or reciprocation. Even though Odysseus had nothing, he still had the ability to practice ἱκεσία. Asking for help wasn’t his last resort, it was a part of the normal process.

In the Western world, we can’t fathom this. We’ve turned asking for help into something we do at the bottom. Something we only stoop to when we are desperate. We white-knuckle as long as we can, and only once we’re completely broken do we ask for help. Our request for help isn’t composed at that point, it’s chaotic.

That’s not the way God prefers for us to ask for help. Hebrews 4:16 says it this way /

Let us then approach the throne of grace with confidence, so that we may receive mercy and find grace to help us in our time of need.

When the writer of Hebrews says the word confidence, they use the Greek word παρρησία (parrēsía). This word means “freedom in speaking all one thinks or pleases.”

To approach with confidence doesn’t mean to crawl once we’ve exhausted every other option. It means to live our lives in a way that asking for help is a normal part of our experience.

Practice

Paul says in Philippians 4:6

“…do not be anxious about anything, but in everything by prayer and supplication with thanksgiving let your requests be made known to God.”

God gives us our own ἱκεσία. An ancient way of asking for help. Prayer.

This isn’t just something that we do in times of desperation. This is supposed to be our normal approach to everything. The way to avoid anxiety is to stay in this posture at all times and as much as possible.

Odysseus got help because he followed the ancient way of asking for help.

The same thing can happen for us.

Don’t just ask God for help once you’ve exhausted every other option. Make it your first move.

Where do you need to approach God with confidence? What “anything” are you anxious about? What “everything” have you not asked God for help in yet?

Stop white-knuckling and start asking for help. It’s what you’re supposed to do about anything and everything.

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We last saw Odysseus sailing away from Ogygia. He’d left Calypso, the island, and immortality behind in a raft she helped him build.

Athena had taught him to steer by the stars and for 17 days he sailed alone. On the eighteenth day, he saw the dark outline of the mountains of Phaeacia - a magical island kingdom - on the horizon. He wasn’t home yet, but he was well on his way.

Unfortunately, Poisedon saw him too. He still hated Odysseus for blinding his son, the Cyclops Polyphemus, years before. Seeing his enemy this close to land, this close to freedom, Poseidon raised his trident and called every wind at once. Black clouds swallowed the sky. Waves rose like walls. The mast snapped. The raft that had carried Odysseus for seventeen days came apart in an instant.

His death was certain now. He’d escaped Poisedon 9 times before, but this time there was no way out. He should have just died at Troy with honor instead of dying alone in the middle of the sea. He clung to a single plank and waited to go under. Breathing more water than air with every breath.

That was right when a sea goddess named Ino saw him. She had once been mortal herself, and was caught in an abusive marriage with an insane king named Athamas. She had thrown herself off a cliff into the ocean to escape him in death. The gods showed her pity by transforming her into a goddess. When she saw Odysseus, she rose out of the water in the form of a seagull and landed on the wreckage beside him.

She gave him a veil and told him to wear it and remove the clothes Calypso had given him. After changing his clothes, Ino told Odysseus to let the plank go. Her veil would protect him from drowning. He could take her veil with one condition, that he throw it back into the sea when he found himself on land.

The only issue was that Odysseus was still alive because of this plank. The raft might have been gone, but he was still floating. Letting go of it felt like giving up his only chance to survive. He was also well acquainted with the gods’ trickery, and was not sure that Ino was actually there to help him.

He did it anyway. He tied Ino’s veil across his chest, and started swimming with nothing else to hold onto.

The sea threw him wherever it wanted. Yet the veil protected him from drowning. After two days and nights of struggle he finally saw the shore. However, this wasn’t a gentle beach. It was a wall of jagged rock. The waves now hurled him towards the rocks. As he hit up against the rocks, he reached out and grabbed them. Then the undertow tore him backward. Ripping the skin from his hands. He found a way to swim parallel to short until he found a river mouth where he could crawl onto land. More dead than alive, he collapsed beneath two olive trees that grew together into one.

He dug himself into a pile of dry leaves to keep warm. He had made it through the storm, but now he was on a strange island with no raft, no clothes, no men and no plan.

Truth

Odysseus did the right thing. And he was nearly killed for it.

We often make assumptions about “right” decisions. We think that the proof that we made the right decision is that our lives get easier, happier or at least we feel some relief. Many times, it seems to be the opposite.

Right decisions cost a lot more than wrong ones.

For some people, making the decision is hard enough. But what they don’t realize is that the decision isn’t the hard part. It’s what comes after the decision.

What saved Odysseus?

It wasn’t him charting a course and sailing for 17 days on a raft he built himself. Sure, that got him close, but then all that progress was destroyed in an afternoon.

What saved him was letting go of his plan to get home.

He had to have a realization that if he was ever going to get home, it wouldn’t be under his own power. He couldn’t do it on his own and would have to have help. And this help would come from sources he’d never had to trust before.

Think about that in relation to the decisions you’re making right now. You’re making the decisions, but the outcomes aren’t up to you. You’re having to trust.

That’s a hard bargain. We are taught to build rafts our whole lives. Common wisdom says that our knowledge, competence and planning is what will keep us afloat. So when the storms come, we develop the instinct to hold on tighter to what we’ve been told is supposed to be our way to the dream, vision, or goal.

Ino told Odysseus to let go.

God tells us the same thing.

“Trust in the LORD with all your heart, and lean not on your own understanding; in all your ways acknowledge Him, and He will make your paths straight.” (Proverbs 3:5-6)

Sometimes…well, maybe most of the time, making the right decision means letting go of what you understand; what’s rational, comfortable and safe.

In the gospels of Matthew, Mark and Luke there’s a similar story to Odysseus. Jesus is in a boat with his disciples, and he falls asleep. A storm showed up that was dangerous enough that these lifelong sailors were scared for their lives. Jesus was still asleep. They wake him up, he gets up, stops the storm and asks them where their faith was. Why would Jesus ask this question? They had forgotten who was in their boat.

We will try to build our lives on our plans, competencies and what we understand. None of these things are wrong. However, in all our personal growth, empowerment and development, we can often miss something. Our plan for our life ≠ God’s plan for our life.

God’s plan is better than our plan, but it’s also not within the realm of our understanding. Therefore, we must learn to place our trust in something outside of us that we cannot control.

We will all do the right thing and find ourselves in the water, clinging to a plank of our understanding at times.

The right thing to do is let go.

Practice

What are you holding on to that’s keeping you afloat in the midst of what you don’t understand?

Is this helping you, or are you just afraid to let go of it?

God wants to use everything in your life to bring about his plan. Which is good, pleasing, perfect and better than yours. You’re not going to understand it right now. So instead of thinking about what makes sense, start to think about where you can place your trust in God.

What does it practically look like for you to trust Him right now?

Feeling stuck doesn’t just happen in failed situations we are desperate to escape. It can happen when things are working too.

Story

We pick up our story right after Telemachus sails to Sparta.

While he goes to Sparta, Odysseus is on an island.

This isolated island — Ogygia — belonged to the nymph Calypso. It was, by every measure, paradise. Lush forests. Perfect weather. Springs flowing with crystal water.

Odysseus had been on this island for seven years, and Calypso had fallen in love with him. Out of her love, she had offered him the one thing no human had ever been offered: immortality. Stay here with me, she told him, and you will never grow old. You will never die. You will live forever in complete paradise.

Odysseus should have said yes. He had been at war for ten years. He had lost every single man he sailed with. He was exhausted. His wife, son and kingdom were twenty years behind him. His son had grown up without him and his wife surely had moved on. Besides, the odds of making it home — across open ocean, with gods working against him — seemed impossible. Staying was the logical choice. In fact, it was really the only choice if he wanted to live.

But every morning, Odysseus walked to the edge of the island, sat on the rocks and wept. Staring out at the sea in the direction of home.

He wasn’t weeping because he was suffering, or the island was perilous. He was aware of how great his life was on Ogygia. The problem was that this island wasn’t his home and Calypso wasn’t his wife. He was comfortable and content. But there was a deep dissatisfaction. These things were great, but they also weren’t his. This wasn’t supposed to be his story. He knew this in his bones.

The gods knew it too, and they intervened. Although Calypso’s island wasn’t a prison, it had turned into one for Odysseus. Calypso didn’t understand why he would want to leave and didn’t allow him to. Hermes arrives with a message from Zeus demanding that Odysseus be allowed to leave. When Calypso tells Odysseus, he doesn’t believe her. He makes her swear an oath that she’s not deceiving him to go out to sea so she can drown him. She helps him build a raft, gives him provisions, and watches him sail away from paradise. Choosing uncertainty over immortality. A hard sea over a soft island.

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Truth

We will all face the choice of Odysseus on Ogygia.

There is a kind of comfort that is both comfortable and wrong. A career that pays you well, but consistently drains your energy. The friends that you love that also help maintain your inertia. Who you are today that is in something that seems good, even though you feel deeply unsettled at the same time. You’re not settled, but you’re trying to talk yourself into it. Everyone else around you might be too.

That’s exactly what makes these types of situations hard to leave. They aren’t bad. If the situation was bad, of course you would leave. It’s not that the situation is bad. It’s just not supposed to be yours.

Odysseus wept every day and still didn’t leave. He knew he didn’t belong on the island, but he still didn’t try to leave. Knowing the truth about your situation doesn’t give you the will to act on it. It just makes staying more painful. It can also make you feel guilty about feeling pain in the middle of something that’s supposed to be good.

What finally moved Odysseus wasn’t his own courage. It was an outside intervention. Our clarity comes from an external conviction. We know something to be true in ourselves, but then a conversation happens that shifts everything. We get fired, experience a loss or a moment that cuts through our comfort. In this story, Odysseus didn’t need to change himself, he needed to change his environment. Home was not where the heart is. Home was a real place, and he was not there. The gods reminded him that he didn’t belong there. His intuition was correct. He needed to leave a good situation for the right situation.

Hebrews 12 describes it plainly: let us throw off everything that hinders, and the sin that so easily entangles (12:1). The writer doesn’t say throw off the bad things. It says throw off the things that hinder, which sometimes includes things that look and feel good.

The prison of comfort is often the hardest to escape. Because when you walk out, it seems like you’re leaving paradise.

Practice

Trying to change yourself without changing your environment will make change almost impossible.

We get a choice when it comes to this prison. Do we change our inner reality to match our outer reality? Or do we change our outer reality to match our inner reality?

Yes, you’re comfortable. Things are good. But are you settled? Do you really believe this is the right situation for you to be in? Are these the right friends? Is this the right environment for your growth and the realization of your highest potential?

It’s not about just leaving the thing and going into the unknown. Odysseus knew where he wanted to go, and he built a raft.

If you don’t know where you need to go, that’s the first thing. How do you know where you need to go? What environment resonates with you, makes you feel alive, or is filled with people who are producing great fruit?

If you know where you need to go, there’s still a step to take. Odysseus knew where he needed to go, but he sat on the rocks for seven years before he started building a raft.

If you know where you need to go, it’s time to start building the raft. What does that look like? You don’t have to completely leave the old thing to start the new thing. But, you do need to start the new thing if you’re ever going to leave the old thing.

Where do you want to go? How will you get there?

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If you haven’t seen this movie yet, you should. It might be the greatest film Christopher Nolan has ever made. It’s a 10/10.

The only problem I have with it is that it isn’t really The Odyssey. It’s definitely his interpretation of the Odyssey. There are not just missing parts to the story, Nolan’s Odysseus is quite different from Homer’s. I love movies (most people with a film degree - like me - say film). I love them because I love stories. Christopher Nolan’s take on Odysseus is in line with the kind of protagonists he often portrays. Odysseus is portrayed as ashamed of himself and conflicted about what he had done to the Trojans.

In my opinion, there’s a slight problem with this. In the story, that’s not really Odysseus. He also has a lot more of a sense of humor and is much smarter than the movie makes him seem. Nolan’s Odysseus is more like Virgil’s Aneas in The Aeneid. I’d love to see that film too.

So, for this and many reasons not listed. It’s a 5/10 adaptation. It gets the rough outlines right, but doesn’t strike all the notes for me. But everyone should see this movie. What makes these stories so timeless is that they have been reinterpreted and given perspective for thousands of years. See O Brother Where Art Thou for another interpretation. This is what I love about movies - and stories of all kinds - is that we all can watch the same movie and read the same book and have completely different takeaways.

I’m the furthest thing from a purist. I hope that Nolan’s film inspires people to read Homer, Virgil and everyone else. And that they also are drawn to the culture and philosophy that built these myths.

If you want to read the Odyssey, I like these two translations /

Daniel Mendelsohn’s 2025 Translation

This translation strikes a great balance between being poetic and readable. I haven’t read much of this one, but I like what I have read.

E.V Rieu’s Translation

I read this one in high school. Less like a poem and more like a story. It has its own charm.

If you don’t want to read the Odyssey at all, but want to be familiar with it. YOU ARE IN LUCK. That’s what we’re going to do over the next few weeks. This (and the Iliad) are some of my favorite things I’ve ever read. So now it’s time for our version of the Odyssey.

Story

Odysseus has been gone twenty years — ten fighting at Troy, ten lost somewhere at sea trying to get home. His son, Telemachus, has grown up without him. He is a young man now, technically the master of his father’s house. But everyone around him treats him like a boy.

His house has been overrun. More than a hundred men who want to marry his mother and become the next king of Ithaca have moved in. They are there day and night courting his mother Penelope, eating through the family’s food and wine. 100% certain that Odysseus is dead and the estate is theirs for the taking. It’s just a matter of time.

Telemachus hates it. He knows it’s wrong. He says this quietly, to himself. And he does nothing. He has no proof his father is dead, no confirmation he’s alive, no clear next move, so he waits. This feels like what he’s supposed to do. After all, isn’t patience a virtue?

Then a stranger arrives at the door, asking for hospitality. Telemachus welcomes him in and the two talk. The stranger is Athena - the goddess of wisdom, strategy and warfare - in disguise, and she challenges him. She tells him plainly that sitting here doing nothing is not what a man in his position should be doing. She tells him he isn’t a child anymore, that people can see plainly whose son he is, and that it’s time to act like he is the son of a great man. She tells him to stop waiting for news of his father to arrive on its own — to go and find it himself. Go to Sparta, ask the men who fought alongside Odysseus what they know about him.

After this conversation, something changes in Telemachus. The next morning, for the first time in his life, he calls a public assembly - the first since his father left - and stands up in front of the entire island to confront the suitors openly. He tells them that they are shameful. They are destroying his home and calls on Zeus to hold them accountable. However, it doesn’t go how he planned. The suitors blame Penelope and the assembly breaks up with nothing resolves.

The situation doesn’t change. But Telemachus does. He’s never spoken in public before, never confronted the suitors in all these years. He loses the fight. But he learns that being mature isn’t always about winning. It’s about being willing to take a stand even if you lose. Then he does something even bolder. Against his mother’s wishes, with no guarantee of what he’ll find, he outfits a ship and sails out to look for the truth himself.

His father was still missing. The suitors were still in his house. Circumstances had not changed. But Telemachus had. He stopped waiting for the situation to resolve itself and started acting like the man he was already supposed to be.

Truth

We assume maturity, wisdom, greatness or success are things that happen to us — that one day we’ll simply experience these things if we wait long enough.

We wait for these things the way that Telemachus waited for news of Odysseus. Passively telling ourselves that waiting is probably the right thing to do. After all, we don’t have the skills, resources, or relationships. We could fail, badly. In fact, it seems like if we try to do anything it will probably fail. We’ve hit a wall. It’s too uncomfortable and challenging to climb. We should just wait for the right opportunity, the right situation, or the storm to pass.

Days, weeks, and years go by. Nothing changes. Maybe God will come take care of it for us?

Telemachus learned an open secret. It’s not really a secret, but it feels hidden. It feels hidden because it’s actually really hard to do.

Just do it.

He acts first. He gets the failure out of the way. But somehow the failure gives him a sense of confidence. He gets on the ship and sails away. After all, nothing changes if nothing changes. Courage is not the absence of fear. Nor is it the presence of certainty. It is the ability to do what needs to be done when you’re afraid and uncertain.

In 1 Timothy, Paul tells Timothy not to let anyone look down on him for his youth, but to set an example now . (1 Timothy 4:12).

We’re not supposed to wait until we feel ready. We’re supposed to take the step, and let the qualification catch up to the action. Qualification is not proof we are ready. It’s proof that we already did it.

Practice

Stop waiting for a feeling that will never come.

My dad has always said “It’s better to act your way into a feeling than to feel your way into an action.” Waiting to feel like you are ready, capable or even desire to do it will only come once you actually move.

The feeling will not come until you act. So move first.

What’s the one thing you know you need to do that you have been waiting for?

“Opinions are like armpits, everybody has them and most of the time they stink.”

The quote I have always heard is a little different than this one, but this is a PG rated letter, so we’ll keep it that way.

It seems like when we make decisions about anything, there’s always someone around us who wants to share their opinion with us about their decision that we’ve made. This happens so often that we often make decisions and then spend the next three days, monitoring, observing, and digesting how everyone around us - even strangers on the internet - are responding to it.

Story

Aesop tells us a fable about a miller, his son and a donkey. A miller was one of the most common trades in the ancient world. They would take the crops from a city and crush them into flour with heavy millstones. They were highly skilled laborers and were integral to their local economy.

This particular miller live with his son just outside of his town. One morning they set off to sell a donkey.

They hadn’t gone far when a group of women at a well called out: “Look at those fools. They have a perfectly good donkey and they’re walking.”

The miller thought it over. Then he lifted his son onto the donkey.

A little further on, old men in the shade shook their heads. “Shameful. That lazy boy rides while his father walks.” So the miller switched. He rode, his son walked.

They hadn’t gone much further before a woman passing the other direction scowled, “How can you ride in comfort while your poor child stumbles in the dust?” The miller decided that he and his son would both ride the donkey.

Once they entered the town, people began to stare and whisper, “how cruel. Two riders on that poor beast.” The miller, desperate to finally do right by everyone, did the only thing left to do. They would carry the donkey. They bound its legs to a pole and hoisted it on their shoulders.

On the bridge into the market, the donkey panicked, broke free from the pole, and fell into the river.

It drowned.

They had come to sell the donkey. They went home with nothing.

Truth

Every critic along the road wasn’t entirely wrong. It wasn’t bad advice that killed the donkey. It wasn’t too much advice either. It was the application of all the advice to please outsiders.

In my twenties, I worked for our church as a Creative Director. One of the dynamics of working in this kind of position in a larger organization is that everyone is mad at you at one time or another. There’s a Lead Pastor who serves as the CEO of the church, but then also, there are all kinds of different leaders and ministry directors who think that they have taste. From a leadership perspective, of course the CEO makes the ultimate decisions, but each leader also sees themselves as the CEO of whatever area they are over. Add to this your own personal creative taste and making creative progress in this type of environment can be difficult if you care about pleasing people.

I wouldn’t call myself a people pleaser. However, all of us should care about what people think on a level, most of our jobs depend on it. As much as I don’t care about pleasing people, I do care about providing for myself. And a significant aspect of providing for ourselves requires that certain people are happy with us. This felt like a dilemma that I didn’t know how to fix. I ended up having a conversation with my mom about it and she said something very simple that changed my life: “You just have to choose who you are willing to disappoint.”

That thought changed my life.

In the story of the miller, the problem was not that his plan was bad. It was that he allowed his plan to be altered so much by the desire to make people who weren’t a part of the plan happy. He actually ended up sacrificing his plan for the sake of making random people happy. These people were not invested in his success, didn’t care about his plan, and were just spouting their opinions. Like most of the people around us.

Proverbs 15:22 tells us that there is “wisdom in a multitude of counselors.” When we get other people’s perspective on a problem or plan, we are given the gift of a vantage point that we didn’t have before. That’s a great gift, however, it’s one thing to get someone’s perspective, its another thing to change your plan based on the perspective.

There’s a difference between getting people’s perspective and applying it. You can get a lot of people’s perspective, but you can’t apply all of it. Their perspectives will often oppose each other and pull you in opposite directions.

Maybe we can, and should get as many perspectives as possible. However, it seems that we should also be intentional about whether or not we apply those things to our life.

Practice

How do we know who to listen to? Ask yourself these types of questions:

• Does this person have good fruit in the area of their life they are giving me their opinion in?

• Is this person valuable to me?

• Does this perspective help me to get to where I need to go?

• What happens if I disappoint this person?

• Did I believe this decision was right before they said anything? Why?

• Does this person want what’s best for me?

• Am I afraid of being wrong? Or of being judged?

Most importantly, decide who you are unwilling to disappoint.

That list is usually a lot shorter than the people who are giving you their perspective. I only have three people on my list:

1. God - Ultimately, I am not trying to “win the approval of human beings…” (Galatians 1:10) I want to live by conviction.

2. My parents - I both work with them/for them and they are my chief mentors, I respect their voice the most in my life.

3. My wife - I will do everything I can to make sure the life we live and what I do honors her and keeps her happy.

Finally, before you change a decision because of someone’s reaction, stop and ask:

Am I changing this because they’re right — or because I’m uncomfortable with their disapproval?

Most people live their lives by committee instead of conviction. They don’t do the right thing, they do the thing that the greatest amount of people approve of. That’s the road to a failed life. Don’t kill your donkey trying to please people who don’t care.

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Story

Athens. 4th century BC. The greatest city in the ancient world. The birthplace of democracy, of philosophy, and of the most valuable form of power in Greek civilization, rhetoric.

In Athens, there were no lawyers. And no courts as we know them today. If you had a grievance, a claim, an accusation, you stood up in front of a jury 500 or more citizens and made it yourself. The people who heard your case would vote based almost entirely on who was more persuasive. You had to argue your case yourself. And it ultimately didn’t matter who was right, it mattered who was most persuasive.

When Demosthenes was seven years old, his father - a wealthy sword-maker - died. His appointed guardians did what corrupt people do with other people’s money, they spent it. By the time Demosthenes came of age, his inheritance (land, money and even a working factory) was nearly gone.

His guardians were not concerned or afraid of him. They had watched him grow up. He was physically frail, had a speech disorder and was a poor speaker. And in Athens, if you could not speak, you could not win, regardless of whether you were right. Enforcement of the law was not a matter of facts. It was a matter of whoever stood before five hundred men and persuaded them. These guardians had the confidence to steal from Demosthenes because they knew he couldn’t fight back.

He tried anyway. His first attempt at speaking publicly before the Athenian assembly ended in humiliation. The crowd didn’t just ignore him, or disagree with him. They jeered and mocked him. He had a weak voice, a stammer, short breath, and poor delivery. He was laughed off the platform. He tried to speak again another time and they refused to hear him. He was taunted and insulted publicly by his guardians.

This is where most people’s story ends. Their failure confirms what they already believe about themselves. Their setbacks become permanent verdicts. Demosthenes knew he was a poor speaker, but he resolved not to remain one.

He went to see one of the greatest actors and speakers in Athens, Satyrus. He told him about his father’s death, the stolen inheritance and his failure to defend himself. Satyrus asked Demosthenes to recite a passage from a Greek tragedy. Demosthenes did. Then Satyrus performed the same passage back to him.

The difference was immediate and clear to Demosthenes. What he had delivered was flat, lifeless, and unconvincing. Satyrus spoke in such a way that the passage came alive. What was the difference between him and Satyrus? Satyrus saw himself as a great communicator. Demosthenes saw himself as frail, strange, uncultured and uneducated. It wasn’t the speech impairment, or the crowd, it was how he saw himself.

Demosthenes resolved to do everything he could to become a great orator. He created a disciplined program to work on his diction, voice, delivery and gestures. Demosthenes built an underground study to practice speaking. He would also shave half his head to force himself to stay inside and practice instead of going out in public. He ran uphill while reciting speeches to build breath control. He would speak loudly at the seashore over crashing waves to learn to project above noise. He placed small stones in his mouth to train his tongue to form words clearly, and practiced in front of a large mirror for hours.

Eventually, he prosecuted his guardians and won. Demosthenes became the greatest communicator in the ancient world. He made his living as a rhetorician, wrote speeches for wealthy and powerful men, and became a teacher of rhetoric.

Truth

Think about this: your performance is a reflection of your self-esteem, not a measurement of it.

Most people think the opposite. They think when they do well, they are worth something. And when they don’t, they aren’t. These people are constantly at the mercy of their results - or lack thereof. Every setback makes them want to quit. Every critical statement is like a stab in the heart. The gap between where they are and where they want to be becomes the reason for them to believe they will never get there.

Think about driving a car. Very few people get behind the wheel thinking they will wreck. It’s not arrogance for you to get in your car everyday, believing you will make it to your destination safely. Your confidence in your driving ability is not fake or manufactured. It is the accumulation of your training and experience. When you first started driving, you may have been afraid, but over time, there is none. This is what people miss most often about self-esteem. You aren’t comfortable because you tell yourself you’re a good driver. You’re comfortable because you have driven enough times to know you have become a good driver. You have evidence.

Alex Hormozi said it this way: “You don’t become confident by shouting affirmations in the mirror, but by having a stack of undeniable proof that you are who you say you are. Outwork your self doubt.”

If you want to win, you need self-esteem. If you want self-esteem, you need to build it. To build self-esteem, you need to work to build it. Your outer success - or lack thereof - is a reflection if the inner price you have been willing to pay to cultivate confidence in yourself.

This is why nothing is more important than how you see yourself.

And there is no greater work than the work you do on yourself.

Practice

Demosthenes developed a training program to develop himself and is self-esteem. Denis Waitley was a naval aviator who became a motivational speaker, writer and consultant. He spent a lot of his life studying the psychology of success and described 10 daily action steps for self-esteem:

1. Greet everyone you meet with a smile.

   Smiling is the first, and easiest thing you can do to add value to any room you are in.

2. Answer the phone pleasantly.

   Small moments are where you train yourself to act like a winner.

3. When you are driving, listen to something that helps you grow.

   Turn your car into a classroom.

4. Invest in coaching.

   Winners always have people in their life who correct, direct and encourage them in their greatness journey.

5. When someone compliments you, say thank you.

   Do not play it down. Deflecting a compliment is not humility — it is a small act of self-deprecation.

6. Do not brag.

   Only the insecure need to talk about their achievements. The confident let the results speak for themselves.

7. Do not share your problems with people who are not part of the solution.

   Venting teaches you to tell the wrong story. Anyone who can hear your problems and not be a part of the solution will not help you see yourself better. They will only agree with your negativity.

8. Find a “master mind” and become a “master mime.”

   Find someone you see as a master, and do everything you can to imitate their greatness.

9. Look at your mistakes as the tuition you pay for greatness.

   My dad has always said “you never lose if you learn.” The only true failure is a failure to learn. You are not failing. You are paying the price of an education that cannot be found in any classroom.

10. Spend one day a week doing something you really love.

    It’s hard to enjoy yourself when you don’t enjoy your life.

Pick 1, 3, 5 or even all 10 and start applying them to your life. I bet you’ll be pleasantly surprised by the results.

We all want more.
Money, followers, influence, achievement, peace, rest, friends, meaning, purpose.

Why do we want more of these things. Simply, we want to be happy, and we want more happiness. And we think these things will bring happiness to us^.

We have an assumption: the problem is that we just don’t have enough of “X” yet. Once we get more, we’ll finally be able to be happy.

I’m not sure that’s ever really happened for anybody.

Story

Alexander the Great (326-323BC) became the king of Macedon (an ancient kingdom north of Greece) at the age of 20 when his father Philip II was assassinated. He immediately set out to do what his father was planning before his death: conquer the Persian Empire.

He marched through Asia Minor (modern day Turkey) defeating Persian forces, taking major cities, and winning countless battles. He eventually took control of all Persian land, wealth and prestige. He eventually made his way to India. In his twenties, he had conquered most of the known world. His empire stretched over 3000 miles from Greece to Egypt to India. The only problem was that it wasn’t the entire world.

Once Alexander reached India, his army refused to go any further and he decided he wouldn’t compel them to march by force. He had heard a philosopher named Anaxarchus talk about the possibility of an infinite number of worlds, and he began to weep. When he was asked why, he answered, “I am not yet lord of one.” (Source) Or, as Hans Gruber put it in Die Hard; “And when Alexander saw the breadth of his domain, he wept, for there were no more worlds to conquer.”

Everyone had hit their limit except Alexander. His success didn’t end his striving, it only increased it. His appetites could not be satisfied. The world was not enough for him. In the years that followed he drank heavily, executed close friends out of rage and spiraled out of control. He would die in Babylon at the age of 32 without an heir and his empire fell apart.

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Truth

Fundamentally, we all want happiness. This is the core pursuit of humanity. No one told us we should want to be happy. We never stop to even consider whether or not happiness is a worthwhile goal. The United States Declaration of Independence shares this idea that the right to pursue happiness is a God-given right endowed to all people.

I think we should do everything that we can to pursue happiness. Being happy is a good thing, and it is a worthwhile goal.

The problem is not the pursuit of happiness. It is our definition.

Like Alexander, we can easily assume happiness arrives from some external source. Conquest, validation, achievement, status, wealth. If we can just get “more” then we’ll be happy. More money, more friends, more enlightenment, more peace, more approval from the right crowd…

It’s like climbing a mountain, believing that the peak is going to be worth it. Steven Covey thought about it like climbing a ladder. In Seven Habits of Highly Effective People, he wrote that we can spend our whole lives climbing the ladder of success only to discover it is leaning against the wrong wall.

The tragedy of Alexander is not that he failed. He achieved total victory. The problem was his definition of success.

Aristotle — Alexander’s own tutor — divided the things we pursue into two categories: limited goods and unlimited goods.

Limited goods are things that run out (hence the term “limited”) . Money, power, fame, status. They are real and they matter, but they are means, not ends. “Money is evidently not the good we are seeking,” Aristotle wrote, “for it is merely useful for the sake of something else.” Limited goods aren’t just limited in their supply, they are also limited in how much they will actually contribute to your happiness.

Unlimited goods work differently. Wisdom, courage, justice, love. These do not run out. They are also unlimited in how much they help you be happy. The more you pursue them, the better your life becomes. They cannot be taken away from you by anything you can’t control.

We have placed the ladder on the wrong wall when we think that having more limited goods will make us happy.

We have placed the ladder on the right wall when we know that having more unlimited goods will lead to our happiness.

The Stoics built their entire philosophy on this distinction. Happiness is not something that comes to you as a result of external validation. It is something you cultivate — through living a life of virtue. Culture changes. Circumstances change. Feelings change. Definitions of success can change based on many factors. Virtue doesn’t change. Virtues are things that are always right, always good and always true.

In other words, we should pursue happiness. But we should also be intentional about happiness’ definition. Happiness isn’t about having more, it’s about being more.

We won’t gain happiness by conquest. Happiness comes as a result of building our character.

Practice

Marcus Aurelius wrote in Meditations: “You must have these principles at hand both night and day; you must write them down; you must read them.”

Our life is filled with decisions. The decisions we make are a result of a criteria we have internally. Those are called our values.

When we make a decision, of course we are attempting to make a good one. What causes the distinction between a good and bad decision? The criteria we use.

You and I have values, but not every value is a virtue. In other words, we all have criteria for making decisions. Not all our criteria are always right, always good and always true. Some of my criteria are limited goods.

In order to be happy, as much of my criteria as possible should be virtuous (unlimited good).

So, this week /

1. Think about the kind of unlimited goods you’d like to pursue. What thing that is always right, good and true would make you truly happy (make you a better person)?

2. Consider the decisions you have to make.

3. Assess their goodness. Which option leads you more towards an unlimited good?

Story

When Hercules was a young man, he came to a fork in the road on an unfamiliar path and sat down to think.

He didn’t just think of which path to take. He began to think about his future. He was at a crossroads - figuratively and literally.

As he sat there, two women appeared — one on each road.

The first was beautiful, dressed in fine clothes, smiling. Her name was Kakia. She told him her road was easy. On this road there was no suffering, no adversity, no struggle. In fact, the whole road was basically a shortcut. Everything he needed would be given to him, his dreams would simply come true and he would live like a king.

The second woman was plainly dressed and her face was serious. Her name was Arete. She told Hercules her path was quite different. She warned him her road would be long and sometimes painful. He would have to learn courage. He would have to learn discipline. He would face things that hurt. Nothing truly good, she said, could be bought without effort.

Hercules chose Arete.

The women’s names give away what the choice really is. Kakia meant vice, wickedness and depravity. Arete meant excellence and virtue — the full expression of what a person was made to be. The choice we have in common is what we choose at the crossroads. A life of vice or virtue.

The Greeks used the term arete for everything. It illustrates excellence of any kind. A knife had arete when it cut well. A horse had arete when it ran fast. A person had arete when they became the best version of themselves.

The whole story is asking one question: how do you become your best?

Truth

Aristotle said: “It is impossible to be wise without being good.” The Bible puts the same idea in Proverbs 9, where wisdom and folly are personified as two women calling out from the streets — presenting the same choice Hercules faced.

But what is wisdom? Wisdom isn’t what you know. It’s what you do with what you know.

You can read every book ever written and still live like a fool. You can quote Socrates and Solomon and never become either. Information isn’t transformation. The proof of wisdom is never in how you think — no one can see how you think. The proof is in how you act, and what your life produces.

So how do you become wise? Not the way most people assume.

Solomon wrote a whole book (Proverbs) about this, and the answer he keeps returning to is:

Whoever loves discipline loves knowledge, but he who hates correction is stupid. (Proverbs 12:1)

Wisdom starts with how you respond to correction.

Most of us hate it. Someone points out our blind spot and our first move is defense — they don’t know the whole story, they don’t understand my situation, they’re being unfair. Or even I already know what they are trying to teach me.

But why does correction happen? It’s not because we don’t know something. It’s because we aren’t doing something. And what then is the goal of correction?

To get us to do what needs to happen without having to be told.

In other words, if you don’t want to be corrected, accept the correction and fix it. And then don’t need correction next time.

That’s our simple definition of wisdom for today.

Wisdom is learning to correct yourself.

When you learn to correct yourself, you will seldom need correction from others. That’s the path of Arete - of being your best. Wisdom is not the absence of mistakes, it is the willingness to see them, own them, and change. The person who can do that grows. The person who can’t, doesn’t, no matter how smart they are or how much they claim to have learned.

So either we can learn to love correction, or we can be stupid. We can be our best, or we can be our worst.

We’re choosing between them every day, in a hundred small ways. Mostly without noticing.

Practice

This week, pay attention to the next time someone corrects you or gives you feedback.

It can be your spouse, your boss, your child, a stranger, or a one-star review.

Whatever it is, notice your first reaction. Most of us go straight to defense before we’ve even considered whether the feedback is valid.

Before you respond, ask yourself one question:

What if this is true?

Not is it fair? Not do they understand my situation? Don’t justify with statements like I’m trying my best or negative self talk.

Just / what if it’s true.

Think about it for ten seconds before you say anything.

Be careful, considering this question this might change your life.

Because the goal of every correction — from a boss, a friend, a stranger, or God himself — is to get you to the place where you can correct yourself. And once you can do that, you’ve stepped into being your best.

One story, one truth, one practice. Every week.

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It’s been about a month since I last wrote here. That break has most definitely not been intentional. Although I have been writing quite a bit /

I finished ghost writing a book that’s going to release soon this year.

Completed a book that may not come out anytime soon.

Completed a book proposal for a book that should release in 2027.

One of my biggest lessons as a communicator in the last 12 months has been: There’s a difference between what I want to say and what people need to hear.

This seems like a small distinction. But it’s not. There are many great thinkers out there whose thoughts could change the world. The problem is not the quality of their thinking, it is the quality of their presentation. It’s one thing to think well about an issue, it’s another thing entirely to be able to communicate your thinking well.

It seems like every communicator has a strength on one side of the spectrum and has to learn how to work on the other side. There are many charismatic communicators whose thoughts are not well thought out. There are also many great thinkers whose communication style turns us off completely from their thinking. I’m not sure if this strength is natural or acquired. For me personally, I have spent much of my life learning about how to think. I have also spent a lot of time learning to communicate. However, there’s a gap. What I have realized that I learned is how to communicate what I want to say. On one hand that’s important, on the other hand, that doesn’t really help people.

When you spend a lot of time thinking about what you want to say, an interesting phenomenon happens. In Psychology, it’s called the Curse of Knowledge. People that have a lot of information tend to overestimate how much other people know. In other words, once you know something really well, it becomes difficult for you to remember what it was like to not know it. As a result, an expert on a subject will often explain things at a level that beginners can’t follow. There’s a danger to becoming an expert in anything. When a person becomes an expert, it is easy for them to forget what it’s like to be a beginner. Which can then make them unable to help beginners. This has potential to be a significant problem. Who do beginners need the most help from? Experts.

One of the most famous examples of the curse of knowledge came from Stanford researcher Elizabeth Newton. She performed a simple study where she asked people to tap the rhythm of a song on a table for someone who didn’t know which song they were tapping. She asked the tappers what the likelihood would be that the listeners would identify the song. They thought they would ~50% of the time. The actually success rate was ~2-3%.

Why? Because the tapper hears the entire song in their head. The listener just hears tapping. This is the curse of knowledge. The expert hears music, the beginner hears tapping.

Experts in every field can often forget how hard it was to learn things that have become simple for them. In fact, all the research points to the fact that the more of an expert someone becomes in any field; parenting, leadership, communication, medicine, etc. the harder it is for them to actually be an effective teacher.

For much of my life, until my late teens, I played multiple musical instruments. Piano, guitar and the saxophone. One of my guitar teachers was a legitimate genius-level guitar prodigy. I remember the day he tried to teach me chord inversions. They are incredibly useful, and a significant part of mastering the guitar. Inverted chords can be played faster, since you don’t have to move your hands up and down the fretboard as much. They add a lot of depth to the music you are playing, and they help a guitar player master the fretboard. Using inverted chords is a simple concept, but can be difficult to master because you are playing chords completely differently than your muscle memory. I remember asking him how he was able to contort his fingers so easily and his answer was: “I don’t know, I just do it.” I’m pretty sure that was my last lesson with him. The truth is, even if he is a prodigy, there was a day where inversions were hard for him. He had just forgotten it.

Think about when you try to teach your kids something that you are familiar with. How hard is it for them to follow the most basic instructions? It can be hard for an adult to control their attitude, even if they have a lifetime of experience and training. How much harder is it for a five-year old who doesn’t?

Ultimately, the question is not “how good is my content?” It’s “can someone who doesn’t know what I know understand what I am saying?” This is the battle that every teacher, writer, leader, and parent faces. The better we become at something, the easier it is to forget what it was like when we started.

So, how am I learning to fix it?

1. Starting with the question - “What do they need to hear?” Instead of “What do I want to say?”

There’s still plenty of room for what I want to say, but only after I’ve considered what people need to hear. What I want to say is the endpoint, what they need to hear is the starting point. Great leaders/communicators understand how to take the journey from what people need to hear, to what they want to say.

2. Storytelling

Abstract information is rarely helpful. Jesus taught through story and metaphor for a reason. Truth is easier to grasp through stories than simple information

3. Think like a beginner

“In the end, people are not looking for a better idea, they are looking to do life better.” // Erwin McManus

Better ideas help people do life better. But only once they’ve been shown how the idea can practically help them right now. There are so many great ideas out there, so why aren’t they helping more people? Because the people who have these great ideas are not connecting the dots for their audience. People don’t need more information, they need more helpful information. Our lives are filled with real, practical, daily challenges. If the information I’m being presented with right now doesn’t help me right now then I don’t care about the information.

It is not the responsibility of the listener to understand the practicality of a message, it’s the responsibility of the communicator. It is not my children’s job to understand what I am saying, it is my job to make myself understandable.

This, like much of life is not a binary issue. This is a tension between two ends of a spectrum, and we should always be working to find the balance. And the balance will be different in each relationship and room we happen to be in. This lesson is visceral for me right now. I just spent most of last year writing a book that I wanted to write, but when I showed it to my agent, the biggest feedback I got was “I’m not sure this is a message people need/want to hear.” You might say, “well, that’s just one person, publish the book anyway.” And cite JK Rowling, Mark Victor Hansen and various other authors who were rejected by publishers many times before writing a bestseller. That is certainly one path.

However, it really wasn’t just one person’s feedback. My book was shown to multiple publishing people and they had the same feedback. In addition, this is in line with the same kind of feedback I have gotten over the past few years as a speaker from my audiences. So, maybe I’m supposed to listen to it. Just maybe.

Ken Blanchard said “feedback is the breakfast of champions.” And I trust experts in my life who actually want to help me succeed. The first book I wrote was great practice. That writing may see the light of day. The good news is that I think we’ve hit on an idea that I’m excited about, my agent and publishers will be excited about too. Overall, I write this much about this lesson for me, because hopefully my lesson will be yours too. Remember your own curse of knowledge and mitigate it.

Letters

This week I am launching a new short-form email simply called Letters.

For most of human history, the best ideas in the world weren’t in books. They were in letters.

The New Testament is mostly a collection of letters. Many of Paul’s writings were letters to specific people and churches dealing with specific problems.

Seneca wrote letters to his friend Lucilius near the end of his life. They were practical reflections on friendship, anger, death, suffering and virtue written to a younger friend. Two thousand years later, Letters from a Stoic is one of the most accessible introductions to Stoicism.

A letter is more thoughtful than a conversation, more personal than an essay and often more practical than a book.

So, you’ll be getting a letter from me weekly containing timeless lessons for living better right now. Each letter contains a story, truth and practice to help you master the art of living. The first one goes out this Friday, June 5.

If you could, forward that email to your friends. Read it to your kids and show it to your coworkers.

I’ll still be writing a lot of longer-form stuff. But considering all that I just wrote above, it’s time for me to think a little better about the practicality of what I am communicating.