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Is Stoicism Good or Bad? A Quick Look at The Pros and Cons

Part of me loves Stoicism. Part of me hates Stoicism.

In this post, I’ll share my love / hate relationship with Stoicism and how it can both help and hurt you as a young man transitioning through different phases of life.

Let’s explore the pros and cons of Stoicism:

Stoicism as an Asset, aka The Good Parts

When life is flying at you like a 100-mph fastball, ready to hit you square in the ribs, you need something that helps you get out of the way.

Or, if you can’t get out of the way, at least you know you’re going to take the pitch hard on the ribs, you’ll be bruised for weeks, but you’ll barely grimace as you jog to first base and give a hard-line stare back at the pitcher.

You need David Goggin’s mentality that “you can’t hurt me.” The Marcus Aurelius quotes. The RedFrost Motivation on YouTube.

The trivial things of life won’t affect me.

Respond, don’t react.

I won’t be worried, anxious, scared at whatever comes my way. I’ll handle conflict and obstacles with an even-keel demeanor. Challenges will roll off my back like water off a duck’s back.

I love it!

I lived into that mentality during my teenage years and early adult years.

It helped me get through a number of tough transitions, tough situations, and tough relationships. (More on those another time.)

Stoicism allowed me to get married at 22 to a 19 year old, both of us being jobless for our first two months of marriage, dealing with a miscarriage, moving across the country, handling life with 3 kids under 4 years old, a failed foster parenting attempt, and living below poverty line for a handful of years.

Stoicism helped me muscle through 4 years of doing jobs I hated just to put food on the table and try to improve our lot in life.

As I got older though, maybe around 30, I started to realize that some of the Stoic philosophy wasn’t serving me.

It was great in theory and it had helped me through a lot, but it was starting to cause trouble in practice. In fact, Stoicism was transitioning into more of a liability than an asset.

Here’s what I mean by that:

Stoicism as a Liability, aka The Bad Parts

In real life, my wife was trying to navigate healing from trauma and abuse of various forms. She was trying to figure out how to draw the right boundaries with a toxic family. She was trying to get herself healthy and raise healthy kids – physically, emotionally, mentally, and spiritually.

She wanted a man who could feel, who could empathize, who could show that he actually cared about what she was experiencing. I had suppressed my own feelings for so long, I could hardly feel anything myself, let alone feel for someone else.

My wife might ask how I feel about something and I’d just shrug or dismiss the question.

“Omer, there’s more than a ‘meh’ dismissive feeling about everything in life. You need to learn how to feel.”

Hannah Redden

Honestly, I needed one of those emotion charts they use for kids in counseling, where you point to the emotion you’re feeling based on the face the little icon is making. There are 30 options to choose from.

I actually remember referencing it a few times in discussions. “Well, I guess a little of this (frustration), with this (sadness), with a tinge of this (anger).”

We even had a joke amongst my work colleagues that I only had two emotions: bad and even. They made a shirt for me that had the straight-faced, expressionless emoji. That was me, to a tee / T. No pun intended, but definitely appreciated.

So, my wife wanted someone who could feel, empathize, and care. I couldn’t do any of it.

Pros and Cons List

Let’s take the stories above and make a quick, clear list of this, so you can easily apply it for yourself. Here are the pros and cons:

Disclaimer: these pros and cons come from personal experience. Any fault in applying the full Stoic philosophy correctly is my own.

Questions a Stoic Must Ask… Eventually

As my kids got into preschool and early grade school, I learned they were experiencing and displaying a whole slew of emotions that I had no idea how to handle. My wife was helping them emotionally, but I wasn’t. I certainly couldn’t help them talk through it, think through it, learn to manage it, because frankly, I hadn’t talked through, thought through, or learned to manage my own emotions.

This forced me to look even harder in the mirror. I had to decide, for the sake of my wife and my kids, for the sake of growing a healthy marriage and raising healthy kids, if I was going to learn how to handle my own emotions.

Was I going to acknowledge that I actually had emotions, more than one or two?

Was I going to delve into the real issues that were bothering me deep down?

Was I going to acknowledge and accept past hurts, as well as past accomplishments? So I could feel both the hurt and the joy in those experiences?

Was I going to face my childhood and the moments that shaped me the most? Good, bad, and ugly?

Was I going to acknowledge that I, too, had a heart and not just a head? That I was an emotional being as well as an intellectual being? I was not just the Tin Man, R2D2, or the Grinch?

Was I going to start working through this on my own, or with help, or both?

Was I going to shed Stoicism entirely or keep the good parts of it?

A More Nuanced View of Stoicism

Ultimately, I couldn’t just throw out Stoicism. It had served me so well through so many tough situations in life. And I knew there would certainly be more tough things to come.

But I also knew I had to face the hurt, scared, and displaced little boy who was hidden behind this tough exterior. I knew I had to shed this coat of armor because I had a chink in it, where my heart had been pierced.

I was wounded, and I couldn’t fight any more battles until I got healed up and healthy.

So, I started working through all the hurt, the pain, the moments of good, bad, and ugly. I admitted I had a heart and a head. I acknowledged that I had a lot more than one or two emotions and I started naming them.

I did this on my own, I did this with my wife, I did this with my children, and I did this with counseling.

For the deep, inner work: I went to counseling and received some tips. I wrote and journaled, more than usual. I used prompts to get clear on how I felt. I listened to emotional and mental health books. I also listened to podcasts on similar topics. I took a few solo trips, some close to home, one across the ocean to Ireland.

Basically, I went hard in the paint to learn what emotions were, how to acknowledge them, and how to manage them. And I did the solo trips because I needed full separation and space to get clear on who I was, where I was doing well, where I was falling short, and who I needed to become. (See the One Page Life Plan review I wrote for an in-depth look at those self-improvement goals.)

While I know I’ve made a ton of progress from where I was 5 years ago, and leaps and bounds in the last 2 years, I know there is still so much further to go.

Next Steps

I’ll be continuing to work on this more balanced view of Stoicism, growing into an emotionally healthy man, husband, and father.

I hope you’ll be doing the same.

If you need any help along the way, please reach out on social. And this resource may help you out as well.

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Climb The Hill

There are 5 things that will slow you down:

  • Climbing with too much weight
  • Climbing with ice on the hill
  • Climbing with an injury
  • Climbing with too little energy
  • Climbing while exposed to the elements

I’ve done all of these at some point. 

Recently, I was driving up a hill and had too much weight in the vehicle. Tough climb.

Earlier this winter, I was trying to climb up a hill that had ice on it. Slip and fall.

Last summer, I was trying to climb a hill with an injury. Painful.

Another summer, I climbed without sunscreen and without a shirt, exposed to the elements. Sunburnt.

I remember trying to climb a hill once when I was hungry and thirsty, too little energy. Miserable.

But these same principles apply whether you’re climbing a literal hill or trying to accomplish a new goal.

Single guys can launch a business faster and easier than a husband / dad with a full house. They aren’t carrying as much weight. They only have one mouth to feed.

Are you trying to break into a super crowded market? Are you trying to do something in a space that’s extremely difficult to get into? Are you doing something you’ve never done in your life? I’d consider that ice on the hill.

If you don’t have a good example to follow, are starting from an unhealthy place financially, mentally, emotionally, or maybe you’ve never had the support from others in your corner, you’re climbing with an injury, a handicap of sorts.

If you’re working 12-hour days already, chances are it’s going to be tougher to accomplish a new goal. Too little energy.

Are you struggling to make ends meet or already living in substantial debt? You might be too exposed to the elements. Don’t get burnt.

But hear me out before you throw in the towel and give up…

I’m not saying you can’t do it. You can climb a hill with too much weight, with too little energy, with exposure to the elements, with ice on the hill, with an injury. You can do it. But it’s going to be slower, tougher, harder, longer, more painful, more miserable, etc.

What I’m saying is that when you’re trying to climb a hill, you want to put yourself in the best position possible. You want to get support from others, learn from examples, get your crap straightened out, get healthy, and get the right gear. 

There are many ways to climb a hill, some easier than others.

But you can do it.

Whatever the case, easy or hard, climb the hill. The exercise and the view will be worth it.

Confessions of a Workaholic: The Wake-Up Call

When I was working for a fast-growing company a few years back, I was placed in a position of leading a large team. 

One of the main reasons was because we needed to build out new courses /products and I had the mind of a teacher. I also had a great understanding of the audience we were serving and what they needed to succeed. I could project manage, I could work with designers, I could create collaborative teaching arrangements. If I didn’t know something, I had a few great people to lean on who knew even more. Together, we’d release 12 products over 12 quarters together.

A great fit on so many levels!

The only problem with being in the position was that I would also be the direct manager of approximately 12 people. That’s 12 one-on-ones every week (as an introvert). Leadership experts say the right number of people for a single person to manage is 5, if you have creative or complex roles. I was managing 2.5x that and releasing a product every quarter. 

Manage isn’t quite the best word here either. These people were absolutely amazing. They needed very little oversight. They coached or supported people, day in and day out. If they ran into a crazy situation, or needed a sounding board, they could vent to me. I could ask our team what the clients were experiencing as challenges. If that was all it was, it would have been simple.

But…I was also supposed to add all this extra structure and expectations around their role. Frankly, it made me cringe. It felt restrictive and prohibitive. I didn’t like it.

But…the person paying my paycheck wanted these standards, expectations, and the structure in place, so I felt the responsibility to make it happen. Obligated. I felt obligated to make it happen.

We didn’t have middle managers fully installed yet, so I had to lead that charge. I felt so uncomfortable.

These were people I respected, people I admired and saw their brilliance. I felt like we should let them do their thing. Hire great people, get them the tools they need, then get the heck out of the way. That was my philosophy. But that wasn’t my boss’s philosophy. He wanted a replicable system that anyone could be plugged into and do that role.

I can articulate that now; I couldn’t articulate that then.

So I lived in this terrible, gut-wrenching discomfort. I worked pretty much every waking moment of a day. I neglected my family 90% of the time. My wife handled everything. I threw myself into this work. I wasn’t emotionally healthy enough to see the problems arising. Or maybe I saw all the problems, heard all the problems, dealt with all the problems — all day, every day — and just thought I could plow through them. I was strong. If I just weathered the storm, handled the next person leaving, getting the next person hired and trained, getting the next product released, it would all be ok. That’s what I told myself.

Looking back, I felt caught in the middle of a terrible circumstance. Sure, I weathered the storm. But the collateral damage was significant.

Family damage at home. Lost great people at work. Lost friendships for a time. My respect for my boss dropped a notch.

The company was “winning!” We were “growing!” Growth! Growth! More growth! We were launching new courses and products every quarter to help more people. Boss was happy because he had a replicable system that anyone could be plugged into and do that role.

But I couldn’t feel the excitement. I couldn’t celebrate the wins. Because I was stuck. Emotionally depleted. Relationally bankrupt. I didn’t feel like I was actually helping the people on my team I knew and cared about. And I certainly wasn’t helping my own wife and kids at home.

After we “turned around that team”, meaning 75% of the people on the team left the company and we hired all new, I was given badges of honor (awards and a small raise). I was then moved over to another role to improve another area of the company. The stakes were even higher. But that’s another story for another time.

Let me stop this one here. If the lessons haven’t been explicit yet, let me state some: 

  1. Never sacrifice your family for work. You’ll have a lot to apologize for and a lot to fix. Much of that damage is irreversible.
  2. You’ll also live with that remorse for the rest of your life (missing parts of your children’s childhood, losing friends), so the sooner you catch it, the better.
  3. If something feels like it’s going against your conscience, if something isn’t settling well, get curious about it. Ask why and do the work to get clear on why.
  4. If your management philosophy doesn’t align with your boss’s, work to sort that out early, find a new position within where you’re not managing, or find a way to exit graciously.
  5. Embrace the times when work feels fun, when coworkers are great, when you’re doing things in your wheelhouse. It is a great joy! At the same time, remember it’s work and that’s one piece of the puzzle that is life.

This is also part of the Failure series, Entry 2. You can read Failure, Entry 1 for a more humorous account.

When You Don’t Hit Goals

This was the background on my phone for the last two months of 2025:

“Last [expletive] lap of the year. Run it hard.

Two months. That’s all that’s left. Sixty days that’ll decide whether this year was growth or just another blur. This isn’t the time to slow down; it’s the time to lock in. You’ve been through the distractions, the self-doubt, the lazy phases; now finish what you started. Forget perfect plans, just show up every damn day. The world won’t remember the times you almost tried, it’ll remember the stretch where you refused to quit. So cut the noise, tighten your focus, and give the last weeks everything you’ve got. Because how you end the year says a lot about how you’ll start the next. So give it everything. No breaks, no pity, no bull. Two months. One mission. Run it hard.” 

– The Key for Success Mind

I read this every day for the last two months. Why? Because many of my goals for the year went to total crap in Q1 of 2025.

Usually, I set them, track toward them, and hit 80% plus of my goals. This year, I started super strong, on track for every goal, all 6.

Then, I got injured at the beginning of March and felt like it took my legs right out from under me. Which is what literally happened. Completely tore my MCL and PCL. But I didn’t realize how much it would affect the next 5-6 months. Physically, I could not walk. But emotionally, psychologically, even relationally with my family, the injury messed with me.

I had a couple injuries in the past. But nothing that affected daily mobility. Nothing that affected my entire lifestyle.

Now, I have sympathy for people with real injuries. I’ve told a couple people that recently. In the past, I’d just say, “Man, that sucks,” and sort of move on. Now, I hear the injury or see the brace and I have deep sympathy. Sympathy and empathy. Been there, experienced that. I’m so sorry, I know HOW MUCH it sucks.

The countenance changes. The lifestyle is being recalibrated. The pain you live in. But also the pain your loved ones are living in. Because you can’t pick up the baby. Because you can’t wrestle with the boys. Because you can’t jump on the trampoline with the girls or play in the yard with everyone.

I get it.

But this whole post started about goals. Hitting them, not hitting them.

Considering how bad the middle of the year went, I actually finished the year in decent shape on my goals. How? I pushed so hard in the last two months.

  • Goal 1 (Family goal) was 80% hit.
  • Goal 2 (Learning goal) was 70%.
  • Goal 3 (Physical goal) was 100%.
  • Goal 4 (Author goal) was a miss.
  • Goal 5 (Personal goal) was a miss, but many valiant efforts.
  • Goal 6 (Personal goal) was 100%.

If I wouldn’t have pushed hard in the last two months of the year, it would have been 1 for 6 on goals, with 3 full misses.

Here’s one small lesson I learned: Injuries aren’t just for pity parties. They aren’t just distractions. They aren’t just detours. They are invitations. 

Invitations to slow down.

Invitations to re-evaluate.

Invitations to feel more deeply.

Invitations to grow in sympathy, empathy, resilience.

Goals are meant to be guides. You should absolutely strive to hit them.

But it’s less about hitting them and more about who you become as you work toward them.

Thank You God for 2025

A baby became a toddler, learning how to talk, how to jump, how to ice skate, and how to snowboard.

A boy was offered a spot on two separate hockey teams after a week of grueling tryouts. He sharpened his skills in multiple summer camps and he’s now playing at a whole new level.

A girl made a big impact on her competitive cheer team, learned how to use AI, and became an avid reader. She also attended her first concert.

A girl started high school and is about to get her first varsity letter. She sharpened her skills with gymnastics lessons and became a key member of her team.

A mom did house projects to make her home feel warm and cozy. She organized more calendar events, practices, camps, gatherings, visits, rides, and trips than she can count.

A young buck tore 2 ligaments in his knee and spent 5 months rehabbing it, learning how to walk again. He started a new writing endeavor, drove more miles than he can count to more kid activities than he can count, and learned a few new skills for life.

Some wanna-be ranchers put in more fences and more accommodations for their animals.

A family worked through some big issues to become stronger, more understanding of one another, more resilient, and more united.

There’s a belief that big things are possible, that healing is always worth the work it takes, and that the universe is a generous place.

The Quiet Week

Between Christmas and New Years sits a beautiful 7-day period.

(If you want to get technical, it just depends on what day you include in your counting. The point isn’t the math here.)

During this period of time, many businesses are still open. Many people still report to work.

But, many businesses also run skeleton crews. Many people go on vacation or don’t work at all.

🤫 Factories run a little quieter.
🤫 Offices run a little quieter.
🤫 Homes run a little quieter.

Schools are closed. Universities are closed.

There’s a beautiful exhale of sorts.

If you need to catch up on some work and projects, you can often focus better and knock things out quicker because so many people are gone.

If you need to reconnect with friends and family, you often have more margin to relax and spend time together.

If you need time to reflect and re-evaluate where things are at in your life, you often have space to do that.

Maybe you need all three of those things. Maybe you need something else entirely.

Take advantage of this quiet week and do what you need to do.

The one thing I can tell you for certain is that it goes by quickly.

Carpe diem! Enjoy!

Does It Make A Sound?

If I didn’t take a picture of it and post it on social media, did it even happen?

The answer is yes.

My family and I do dozens of cool things every year that I don’t post on social media.

  • Sometimes, for the sake of savoring the moment instead of trying to “document” it.
  • Sometimes, because I’m exhausted after the fun trip and don’t want to post it.
  • Sometimes, because I prefer my privacy.
  • Sometimes, because it’s a form of silent protest.

I protest the idea that you have to share your whole life on social media for everyone else’s consumption.

🧔‍♂️I can be a good dad without having to broadcast it to everyone.

🧔‍♂️I can be a good husband without having to brag about it.

🧔‍♂️I can be a good person without having to “show” everyone all the good deeds I do.

Does that make sense?

There are thousands of people out here trying to prove something by what they post. Trying to put up a facade that they have things together, that they are “being good” or “doing good,” but inwardly, it’s an absolute mess. They’re trying to convince themselves and/or convince everyone else of a certain narrative.

I post The Daily Omer because I want to share something worthwhile, something that will benefit you as a reader. I don’t need to “prove” anything by the things I post.

My family and I had a great Christmas. My wife, kids, and I have had a ton of fun. Lots of great family time. And I hope you’ve had an awesome Christmas and great family time as well. Soak it up! Enjoy it!

And if you don’t post about how awesome it’s been, just know I’ll be worrying, making all kinds of assumptions, judging, and criticizing from afar. 😜

Failure (1)

What a flat title.

But that’s how failure feels, right?

FLAT.

“You fell flat on your face” – the common expression.

I’ll share an easy failure first, so I can warm up to the topic. Perhaps it’s an outer layer.

We’ll peel back the onion over the coming weeks and months. The onion is scary. It smells so strong. It has so much power. Too much of it can ruin a dish. Ruin your tastebuds. Even ruin your stomach. But just the right amount can season a meal to perfection.

“Let me cook!” as the kids say.

Failure 1 goes back to high school. A lot of people know I played college football. But almost no one knows how my football career actually started.

QB Is Not For Me

Growing up, I was an athletic kid. Practiced hard, played hard, won a lot of trophies, even had a couple MVPs. The trophies were in soccer, basketball, and most of all, baseball.

In middle school, I switched from soccer to start playing football. Honestly, I don’t remember if I wanted to, or if my dad wanted me to. Our school district didn’t have football for young kids. You couldn’t start until 7th grade.

But here I was, playing football competitively for the first-time ever. Tried quarterback and frankly wasn’t good. I was smart. I was kind of fast. But I was not a big kid. Barely over 5 foot. Hadn’t touched 100lbs yet. One practice, I tried to scramble out of the pocket and got chased down and tackled by a kid who had already hit puberty. He had chin hair in 7th grade for goodness sake!

He hit me so hard that I ended up in the cornfield next to the field. I had dirt and small rocks embedded into my elbow. My knees hurt. My back hurt. Everything hurt.

Literally ate dirt that day.

After that tackle, I didn’t want to play QB anymore. No more scrambling and running for my life with a massive target on my back.

I preferred wide receiver, safety, or cornerback. The more I could avoid contact, the better.

Play football the rest of 7th grade, and play again in 8th grade, but it still wasn’t my thing.

Scout Team Defense

Now, I’m a freshman. I’ve started to grow a little bit, but still a scrawny kid. Probably 5’6″, 125lb soaking wet. Freckled, no muscles, no chin hair.

Coach is trying to put together the good ol’ scout team defense. I know I don’t want to be a benchwarmer forever. I also know there’s not a chance I’ll be on varsity as a freshman. But I need to start to make a name for myself.

I’m a willing, but timid participant.

An assistant coach is looking at a group of us scrawny freshman. He looks at me directly.

“Are you fast?”

“Yes, Coach. What do you need?”

“Well, we’re lining up against first team offense. They run the ball 95% of the time, and only have one wide receiver.”

“Do you want me to be a backup receiver?”

“No, no. That receiver doesn’t do anything anyway. I need defense. I need guys who can stop the run.”

He looks at the 4 other guys standing next to me and just shakes his head. They’re as small and scrawny as I am. All the big kids, who love to tackle are already on the field.

He looks at me again, “Do you play defense?”

“Yes, sir.”

“What position?”

“Corner or safety.”

“We have a safety. Ah hell, go be a corner. Don’t let that guy catch anything and don’t get caught picking dandelions.”

“Yes, sir.”

I strap up my helmet, put in my mouthpiece, and hustle out to the far side of the field. Out on an island, guarding the senior wide receiver, knowing that they’ll probably throw the ball to him one time the entire practice.

I think to myself “Good! I got this. I’m probably only a half step slower than him, and I’ll stop him from catching anything. Otherwise, I get to stand here and not have to hit anyone.”

Five plays go by, no action. The offensive coordinator hollers at the O-line that they aren’t doing their jobs. They’re missing assignments and the offense isn’t looking like it should.

I hear it, but I dismiss it. I’m on defense. It’s kind of fun to hear them get hollered at. I’m out on my island, guarding this scarecrow of a wide receiver. He doesn’t even block me. I just backpedal, then the whistle blows, repeat. Nothing.

Ten plays go by, still no action.

But now, the Head Coach is yelling at the O-line, because they’re still missing assignments and not blocking like they should. He ups the ante. He gives everyone on offense some up-downs.

“You should be scoring a touchdown EVERY SINGLE TIME! You guys are juniors and seniors. You’re going against the scout team. Get your asses in gear! I want to see some blocks! Let’s see some hits!”

I laugh to myself. What a great day to be on defense!

The scarecrow wide receiver runs back to the huddle and gets the play. He comes out to his post, shaking his head. I smirk. He’s probably mad he got up-downs.

QB calls out his cadence, ball is snapped, and my receiver runs diagonally in toward the line.

“What the heck?!” I’m processing as I watch him run in toward the linebackers. He hasn’t done this before. “What’s going on?” I wonder.

By the way he is running, he’s not running a route. And I know, as scout team defense, on this play, we’re supposed to imitate a zone defense.

I recognize something strange is happening. Two linebackers are turned and starting to run my way.

Oh shoot! The receiver is doing a crack block!

“Crack, crack!” I holler. I’m putting the pieces together in my head, micro seconds.

That means the play is coming toward me. It’s a run.

Just as the realization hits, I turn my head.

Suddenly, this huge offensive lineman is facemask to facemask with me. His hands are under my pads. My feet are coming off the ground. My head goes backward. I’m weightless.

“Oh no! He’s the pulling guard. He’s got me!” It clicks in my brain.

Then, just like that, boom, crash, my ass hits the grass.

But it’s not grass. It’s more like concrete.

Butt, then back, then head. They hit the ground in sequence. Feet still in air.

The offensive lineman runs over my limp body. Then, the running back hurdles over my limp body.

A few seconds later, I hear the varsity guys celebrating in the distance. They had scored a touchdown. I hear the offensive coordinator clapping. I hear the head coach shouting, “There you go boys! Now, that’s what I want to see.”

I’m laying there, still limp, gasping for air.

The offensive lineman comes back by me, bouncing and laughing.

“Yeah! Yeah! Hey little boy, how’d you like that pancake?!”

Pancake.

I had just been pancaked.

My second time ever having the wind knocked out of me.

Bumps and Bruises

Honestly, I don’t remember how I got up that day. Did the receiver come back and help me up? Did a fellow defensive player help me up? Did the assistant coach help me up? Did I just peel myself off the ground like Wylie Coyote?

Who knows?

What I do remember is that I left that practice and it hurt to sit in class for over a week.

Bruised tailbone.

Bruised ego.

Got to hear about it from that lineman the whole week.

Never again would I get lulled to sleep at the cornerback position.

And best believe, I’m still always on the lookout for that crack block.