367 - Choosing From the Wreckage: The Stoic Guide to Impossible Decisions

How do you make a decision when all the choices in front of you feel like bad ones? Today I want talk about how Stoicism can help us take action when faced with impossible choices. 

“What should we have ready at hand in a situation like this? The knowledge of what is mine and what is not mine, what I can and cannot do.”

— Epictetus, Discourses I, 1.21

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Transcript

Erick Cloward 0:00

How do you make a decision when all the choices in front of you feel like bad ones? So today I want to talk about how stoicism can help us take action when faced with impossible choices. Hello, friends. My name is Eric Cloward and welcome to the Stoic Coffee Break. The Stoic Coffee Break is a weekly podcast where I take aspects of Stoicism and do my best to break them down to the most important points. I share my thoughts on Stoic philosophy and pull from ancient and modern wisdom as well as psychology, neuroscience, anything that I can find that can help you to think better, because I believe if you think better, you can live better. This week's episode is called Choosing from the Wreckage: The Stoic Guide to Impossible Decisions. What should we have ready at hand in a situation like this? The knowledge of what is mine and what is not mine and what I can and cannot do. Epictetus. I had a coaching call this week that I haven't been able to stop thinking about. So my client, a business owner who has built something real over the past few years, came to me in a little bit of a panic. And that's what struck me first was that there was some panic and some resignation. She was in that quieter, heavier place where someone who's already done all the math and doesn't like any of the answers. The economy is shifting beneath her feet, AI is reshaping her industry, and every option in front of her feels like she's choosing which bone to break. And she said something that I think a lot of people are feeling right now, but haven't really found the words for it. And it's that she's not stuck because she doesn't know what options are available. She's stuck because every path forward requires giving up something that I worked incredibly hard to build. And that's what real overwhelm sounds like. It's not traumatic, it's grinding. And it's exactly the kind of moment that Stoics were built for. So there's a specific psychological phenomenon that was making her situation worse. And it has a name: sunk cost fallacy. And it's the tendency to keep investing in something, whether that's time, money, identity, effort, because of what you've already put in rather than what the future actually holds. I mean, she's built something and she's sacrificed for it, and walking away from any version of it feels like saying that all of it didn't matter. But here's the cruel irony. The more you're invested, the harder it is to see clearly. The past becomes a lens that distorts to the present. And I could see that happening in real time on that call. And she's not alone in this. Entire industries are facing this right now. AI isn't coming, it's already here. Political and economic instability isn't just a blip, it's a condition. Millions of people are sitting with exactly the same kind of decision. Not how do I succeed, but which version of loss can I live with? The Stoics would recognize this moment immediately. They lived inside collapse, and they left us a roadmap. So the Stoics knew all about disruption. So Marcus Aurelius didn't rule Rome during the Golden Age. He ruled during plague and war and economic strain and constant political betrayal. Epictetus was a slave, and every single decision he made happened inside a life where the external circumstances were largely terrible. Seneca watched Nero's reign destabilize everything he'd built. And these weren't philosophers writing from comfort. They were practitioners of clarity inside of chaos. What they developed wasn't optimism. It was something more useful, a framework for making good decisions when all the conditions are bad. So Epictetus opens the Incritian with perhaps the most important sentence in Stoic philosophy. He said, Some things are in our control and others not. Things in our control are opinion, pursuit, desire, aversion, and in one word, whatever is of our own doing. Things not in our control are body, reputation, command, and in one word, whatever are not of our own actions. Now, as I listened to my client, I kept coming back to this. AI disruption is not in her control. The economy, not in her control. Whatever her competitors do, not in her control. Her response, her character, her next deliberate action, entirely in her control. Now this isn't dismissive of the difficulty. It's clarifying about where her energy should actually go. So Marcus Aurelius wrote in Meditations, confine yourself to the present. And elsewhere he wrote, never let the future disturb you. You will meet it if you have to, with the same weapons of reason which today arm you against the present. Now the sunk cost fallacy is, at its root, a refusal to let the past be the past. Every hour she spent calculating what she'd already lost was an hour she was living in something that no longer exists. Now the Stoics weren't cold about this. They understood lost, but they were clear that the past has no vote in what happens next. Now this is where I think the standard reading of Stoicism falls short, and where I had to gently push back with my client, because traditional readings would say, acknowledge the dichotomy of control, release the sunk cost, move forward. And that's not wrong, but it's incomplete. What she was experiencing wasn't a logic problem, it was grief. She was grieving the business that she believed she was building. She was grieving a future that she had planned for. And I can see that until that grief is acknowledged, not suppressed or bypassed, she isn't going to be able to think clearly about any of it. So Brene Brown has done a lot of research on this. And she writes in Daring Greatly, when we deny our emotion, it owns us. When we own our emotion, we can rebuild and find our way through the pain. And her research aligns directly here. Unprocessed emotion doesn't disappear, it goes underground and it starts making decisions for you. This uncost fallacy is often grief in disguise. We can't let go because we haven't actually mourned what we're losing. So real stoic strength isn't powering through the feeling, it's having the courage to actually feel it, name it, and then, only then, think from a clearer place. So let's talk about virtue over outcome. So here the Stoics reframe what I think changes everything about the least worst options. So Marcus Raelius writes, You have power over your mind, not outside events. Realize this and you will find strength. The Stoics didn't measure a good decision by whether it produced a good outcome. They measured it by whether it was made virtuously, with wisdom, with courage, with justice, with temperance. A decision made with clarity and integrity, even if the result is painful, is a good decision. A decision made from panic, attachment, or avoidance, even if it accidentally succeeds, is a poor decision. So let's talk about some things you can do to work through making impossible decisions. So step one is to name the grief. The first thing to do in a situation like this, before any strategic thinking, is to honestly name what is being lost. Not catastrophizing, but just an honest accounting. In her case, it would be I built this for years. I believed in this future. That future is no longer available, and that is genuinely painful. You can't think clearly from inside unacknowledged grief. And this step isn't weakness, it's seeing things as they actually are, including the painful things rather than turning away. Now, step two is what I call draw the circle. When you're in a situation like this, you can take out a piece of paper and draw two circles, one inside the other. In the outer circle, write everything about your situation that is outside of your control. The economy, AI, competitors, policy changes, what has already happened. Get it all out. Now, in the inner circle, write only what you can actually influence your response, your next action, how you show up, what you choose to prioritize, the values that you bring to the decision. Then only work on the things from the inner circle. Because everything in that outer circle just needs to be acknowledged, and then it needs to be set down because it's something that is outside of your control. Now, step three, think about the present moment. So Marcus Aurelius was managing simultaneously empire scale crises, and he didn't solve everything at once. He returned again and again to one question: what is the right action available to me right now? Not next year, not the five-year plan, right now, this week. What is the one decision, not all the decisions, just the right one, that can be made with clarity and integrity? The Stoics call this cathakon, the appropriate action in this moment given these circumstances. Not the perfect action, but the appropriate one for where you are. Now, step four is redefine what a good decision looks like. Stop measuring your decision against the outcome you wanted before things changed. The outcome is no longer the benchmark. It's part of what you're grieving. Instead, ask, can I make this decision with honesty about the situation as it actually is? Can I make it from my values rather than my fear? Can I look back in a year and say, I chose with integrity, even though the circumstances were painful? If the answer is yes, then that's probably a good decision, regardless of how it turns out. Step five, act small, act now. So Seneca writes, we suffer more in imagination than in reality. So overwhelm thrives in abstraction. The antidote is a small, specific, concrete next action, not figure out the whole business model. Maybe it's have one honest conversation with my most important client this week. Not decide whether to pivot, but rather spend two hours researching what the pivot would actually require. Momentum is built by motion, not by certainty. And what you need is to find that next action, just one, and that's enough. So my client dealing with this isn't weak. She's not failing. She's experienced what the Stoics would recognize as a genuinely hard moment, the kind that has always existed and that has always asked something of us that feels like more than what we have. But here's what I kept coming back to on that call. The difficulty of the decision is not evidence that she's doing something wrong. It's evidence that she's someone who's built something and who cares deeply about it, and who is now being asked to demonstrate a different kind of strength than the one that got her where she is today. The strength that builds a business is vision, drive, and commitment. The strength that navigates a crisis is clarity, honesty, and the willingness to grieve what was while choosing well about what comes next. So Marcus Aurelius wrote: the impediment to action advances action. What stands in the way becomes the way. She doesn't need the wreckage to clear before she can move. She needs to find the virtuous path through the wreckage. And I think that's true for anyone sitting with an impossible decision right now. That path, as it has always been, runs directly through what you can control, what you value, and the single next action available to you today. And that's not the least worst option. That's stoic strength. And that's the end of this week's stoic coffee break. As always, be kind to yourself, be kind to others, and thanks for listening. Also, if you haven't purchased my book Stoicism 101, I would appreciate it if you would. You can find out more about that on my podcast on my podcast website at stoic.coffee. Also, if you're following me on social media, you can do so as well. You can find me on threads and Instagram at stoic.coffee. And you can find me on YouTube, LinkedIn, and Facebook at stoiccoffee all one word. Thanks again for listening.