How Would Stoics View Org Transformation?

“When the number of options available are limited, it is foolish to fuss and fret. We should instead simply choose the best of them and move on with life. To behave otherwise is to waste precious time and energy.”

William B. Irvine, The Stoic Challenge

On my best days, I feel like these words personify the work of organizational transformation. A problem is presented, and then a review of the available options. Consensus is garnered for the best, and then communication flows through direct reports as to how we will all respond.

As if there’s an aisle in the store labeled “quick and easy answers.” Simple, right?

I also wish I had a full head of hair and had the chance to play college basketball. Also, it would just be easier if you let me win every time to avoid the confusion.

When I open the fridge to decide what I’m making for dinner, I am by nature presented with limited options. Even if I had just gone to the store, I have at max 5-7 options for meals to make my family. Making the choice is infinitely easier because all I have to do is say, “hey do you all want roast chicken or pork tenderloin for dinner?”

Deciding the best framework, consultancy, terminology, success metrics, and everything else in a transformation each have more than a few available options. Each of these decision points presents an infinite number of outcomes. Multiplied by the number of departments, lines of business, and teams created, and we’re talking Dr. Strange level of madness in the multiverse of transformation.

The quote above is part of an experiment I’m running for my leadership journey at the moment. To learn and appreciate the traits of stoicism in an effort to learn if it would affect how I approach the work I have devoted this part of my career.

Stoic — a person who can endure pain or hardship without showing their feelings or complaining.


The early stoics led a life they desired to have in harmony with nature. To seek virtue in its purest forms: wisdom, justice, courage, and moderation. To take this purely logical perspective on the world, it removes a sense of the lowest of low feelings.

A virtuous life should keep you from feelings of anger, hatred, jealousy, and more.

If you’ve read the last few years of my writing, you can imagine how challenging this topic is for me to address. I spent four decades learning how to appreciate the high emotional energy I bring to my work. Therapy time accepting this is who I am. Collaborating with like-minded peers on their work through masculinity and emotion.

When the current marketplace encourages higher amounts of emotional learning in organizations, why would stoicism be of need? Is it even possible to be a stoic and still embrace the emotions I believe elevate my efforts?

Thankfully, I believe it is.

Resilient organizations respond better to change.

One of the main tenets of stoicism is being more resilient to the frequent setbacks of life. That can be difficult with orgs identified as “fragile”.

When the environment is fragile, extra protection is put in place. Not in the best way, either. Eggshells are laid out to ensure everyone tiptoes around the office. People feel unable to say no, but fortunately it’s also balanced by never being held accountable for commitments. It also creates a culture of fire fighting, but not for the right reasons.

These are orgs who constantly complain of change fatigue. When moving any of my cheese makes me feel like layoffs are coming, I’m gonna rock the boat little and say any change is too difficult to handle. A sense of helplessness grips us all to varying extents.

Irvine argues that these groups of people use a word that has become very charged in our current vernacular: victim.

Transformation was inflicted upon them. Leaders decided they knew better and that their directs should get on board. They were never asked how they felt things were going, or at least to collaborate on options they would want to try.

I’ve learned you can’t step your way to resilience. That trait is the result of repeated small, successful, and transparent experiments to discover better ways of working. Removing victim hood is a person-by-person journey of helping everyone see setbacks don’t mean hand slaps. They are chances to show we have improved.

Setbacks are to be encouraged, not avoided.

Stoics have a history of welcoming any of the many disappointments in life. When you carve a sense of resilience, you learn to frame expectations for every situation in advance. Their mental preparation can harden an ability to withstand “failure”.

Musonius Rufus was banished from his homeland not once, but twice (banishment was a common punishment for people considered to be heretics). Even after the second, it did not take on the feelings of depression or disappointment. He merely chose to see his circumstances for what they were: just a setback.

The virtuous life he had created had not been taken from him. Just his home and material possessions. In fact, some of his greatest speeches were created while in exile. He argues that he profited from his setback.

Imagine trying to sell that on a pitch deck to C-suites.

Parents of the late 20th century (trust me, I was raised then) sought to remove setbacks from environments for children (in the US at least). Those parents are now in charge of many organizations, and attempt to do the very same thing at work.

Failure simply isn’t an option for most teams in most lines of work. No matter how many times you hear leaders reference a desire to fail fast, their following actions rarely demonstrate this being true.

The key seems to hover around seeing setbacks differently. It requires different metrics, behaviors, and leaders willing to praise colleagues for their willingness to learn. Frame things in a new light.

How are we supposed to reframe all of this?

It all starts with the subconscious, which governs our mind more than we realize. Want proof?

Lay down on the ground and tell yourself to not think about anything. Actively attempt to not think of anything, and watch the flood of thoughts that never ceases.

The stoic doesn’t master the subconscious, because that’s impossible. They simply spend more time training their conscious self to see the subconscious coming from a mile away and use it to further embrace the four aspects of virtue.

Our subconscious form is the origin of intelligence such as the emotional quotient. Reading body language and tone of voice can mean the difference between a conversation of healthy conflict or heated fights. Taking away that ability would be disastrous, for it holds the greatest aspect of our creativity.

Can the anchors of our organization be seen as opportunities? It certainly seems that can be the beginning of larger problems being reframed.

Instead of seeing WIP limits as constraints meant to punish teams, being able to appreciate being saved from doing too much at once as a team is a feeling of safety.

Introducing test-driven development to every team has often created a sense of not trusting team members to create defect-free code. Wouldn’t it be easier to reframe it as a framework for writing the least amount of code to pass acceptance?

Understanding the customer’s impact on our requirements is definitely extra steps towards validation. It’s certainly easier to just ask our boss what to do and write down just that. You can’t be fired for copy and pasting into Jira. Reframing customer interaction as a chance to celebrate success sooner and reducing rework is certainly a situation I would enjoy!

It’s not a challenge to broadcast these ideas and get some head nods. The real struggle with getting a large group of people all rowing in the same direction is going person by person.

Walking together through seeing these setbacks sooner and crafting the best expectations to frame setbacks as successes. They see there’s no such thing as failure.

The result can be game-changing, but we’re not done yet. We have to remember luck plays a part.

Even when you do everything right it still might not work. Some of the experiments I’ve attempted have been solid approaches, just resulted in an unintended outcome. And yet, resilience for some can end in the sublime.

Zen and the Art of Motorcycle Maintenance was rejected 121 times by publishers. Van Gough only sold one of his 860 canvases before his death. James Dyson went through over five thousand iterations of his vacuum design before success.

Does that mean resilience comes from organizations being willing to labor at the bottom of the change curve and stay the course? Perhaps the bravery to go from individual to individual and walking each of them through their own change curve is the way. Or teams that are willing to do it as a group of single-digit contributors as a group that’s against the world can begin removing eggshells from the floors.

I’m currently evaluating the tiny part of the world I have a say in to see the anchors and see a way to reframe them. Reading this book has shown me I don’t prepare for the setbacks of every conversation and bring the meta-skills (thanks Bob Galen) necessary to reframe those expectations.

It’s exciting to consider the possibilities of a more stoic life. One filled with plenty of highs, just less of the lows.


One thought on “How Would Stoics View Org Transformation?

  1. Got here via the weekly newsletter of Stefan Wolpers. Love the point of view. I am convinced the workplace should become more stoic, factual, less emotional. That context would allow agile teams to not be jerked around by emotional or panicky decisions of others. Anyways, keep up the good work!

    Liked by 1 person

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