Why Outcome Optimism Fails

Are you motivated by fear? What if that fear is actually at the root of why you’re not getting the results you’re going after? In this week’s episode I want to talk about how to stop fear from sabotaging your best work.

“What I advise you to do is, not to be unhappy before the crisis comes; since it may be that the dangers before which you paled as if they were threatening you, will never come upon you; they certainly have not yet come." — Seneca

The Problem

Let me ask you something that might sound strange.

What if the thing pushing you forward — the thing that gets you out of bed, that makes you open the laptop, that keeps you grinding when you'd rather quit — what if that thing is also the thing quietly sabotaging you?

I'm talking about fear.

And before you push back on me, hear me out. Because fear is sneaky. It dresses up as motivation. It feels like drive or even responsibility. You tell yourself you're being realistic, you're being prepared, you're staying sharp. But underneath the productivity, there's this low hum — what if it doesn't work, what if I can't make it, what if I'm not enough. And you keep moving, partly because you love what you're doing, but partly because the alternative is to sit still with that fear, and that feels unbearable.

So we keep moving. And it kind of works. For a while.

Look around. The world right now is loud. Politics, economics, AI, climate, the news cycle that won't stop screaming at you. Fear is in the culture. It seeps in whether you want it to or not. And on top of that ambient hum, most of us are carrying our own private version of it. The fear of failing at something we care about. The fear of not being able to pay the bills. The fear of looking foolish. The fear of falling behind.

I'll be honest with you. I know this one personally. I run a coaching practice. And there are days when the work I do isn't really driven by let me build something I'm proud of. It's driven by what happens if this doesn't work? How am I going to cover the bills? And I notice it, because the work I do from that place feels different. It feels tighter. more desperate, and less like me.

I bring that up not because this episode is about me, but because if you're listening and you recognize that pattern in yourself, the fear that hides behind the hustle, you're not alone, and you're not broken. You're just human, doing what humans do.

But here's what I want you to sit with for this episode. Here's the thing the Stoics understood that I think most of us miss.

Fear-driven work tends to produce the very failure it's afraid of.

When you work from fear, you work small. You hedge and play it safe. You don't take the creative risk, you don't make the bold offer, you don't say the true thing. You optimize for not losing instead of for actually creating. And the work suffers. People can feel it, and it shows in your work.

So fear isn't just unpleasant to live with. It's actively undermining the thing you're trying to protect.

Which raises a question. If fear is such a bad driver, what do we replace it with? A lot of people would say optimism. Just be more positive. Believe it'll work out. Visualize success!

I don't think that's quite right either. And in a minute I want to tell you why optimism, in the way most people use the word, is just fear wearing a different costume. And what the Stoics offer instead, is sturdier than both.

The Philosophy

The Stories We Tell Ourselves

So let's go back about two thousand years.

Epictetus was a Stoic philosopher who started his life as a slave in Rome. Eventually freed, he went on to become one of the most influential teachers of his era. And in his handbook, the Enchiridion, he spoke a line that I think is one of the most useful sentences ever written about the human mind.

He said: "People are disturbed not by things, but by their judgments about things."

Think about that.

We are not disturbed by things. We are disturbed by our judgments about things. It’s the stories in our head that create the fear.

The economy isn't making you afraid. Your judgment about what the economy means for you is making you afraid. The empty calendar isn't making you anxious. Your story about what the empty calendar predicts is making you anxious. The chaotic news cycle isn't making you tense. Your interpretation of what it all means for your life is making you tense.

This is a description of how the mind actually works. Something happens — an event, a piece of news, a number in your bank account — and before you even notice, your mind hands down a opinion, a verdict. This is bad. This means I'm in danger. This means I'll fail. And then you feel the fear, and you assume the fear is about the thing.

But the fear isn't about the thing. The fear is about the verdict.

And here's why that matters: the thing isn't yours to control. The verdict is.

Imagination vs. Reality

Seneca, writing letters to his friend Lucilius, said something that pairs with this perfectly. He wrote:

“There are more things, Lucilius, likely to frighten us than there are to crush us; we suffer more often in imagination than in reality." — Seneca

Think about how true that is. Most of the fear you've felt in your life was about something that never actually happened. The presentation that went fine. The conversation that didn't blow up. The bill that got paid somehow. The client that did sign. We rehearse catastrophes that almost never arrive. And meanwhile, the fear itself is real and it costs us sleep, it costs us peace, it costs us the quality of the work we do today, even though the catastrophe stays imaginary.

Seneca's point isn't to shame you for worrying. It's to point out that imagination and reality are different countries, and most of our suffering happens in the wrong one.

As Michel de Montaigne later wrote:

"My life has been full of terrible misfortunes, most of which never happened." — Michel de Montaigne

Our minds are constantly on the lookout for the worst case scenario, yet most of those never happen.

Okay. So if fear is largely a product of our judgments, and our judgments are ours to change, what's the alternative? What do we put in fear's place?

A lot of people would say optimism.

But I want to be careful here, because I think there are two very different things people mean by that word, and one of them is a trap.

Optimism

The first kind of optimism, the kind I want you to be suspicious of, is outcome optimism. It's the belief that things will work out. That you’ll succeed. That the bills will get paid. That the future will be what you want it to be.

Here's the problem with that kind of optimism: it's just fear with the polarity reversed.

Think about it. Fear says the outcome will be bad. Outcome optimism says the outcome will be good. But both of them are doing the exact same thing — pinning your peace of mind to a prediction about something you don't control. When the prediction is wrong, and predictions about the future are wrong all the time, the optimist crashes just as hard as the pessimist. Maybe even harder because they didn't see it coming.

The Stoics would say both of these are unstable foundations. Anything built on a forecast about externals is going to wobble, because externals wobble. You can’t control the outcome of anything.

Since you can’t control the outcome, what's the alternative?

The alternative is what I'd call fortitude optimism. It's not a prediction about what will happen. It's a confidence about who you'll be when it does.

This is why courage is one of the four cardinal virtues of Stoicism. The four cardinal virtues are all about character, and courage is key to building strong character. Courage doesn’t mean that you won’t have fear. It means that you’re willing to stand up and take action even when you feel that fear. It means believing in yourself and your ability to keep going, regardless of the outcome.

It sounds like this: I don't know how this is going to go. The work I’m putting in might succeed. It might not. The economy might cooperate. It might not. But whatever shows up, I trust that I can meet it. I trust that I'll keep showing up with integrity. I trust that I'll learn what I need to learn. I trust that my worth isn't riding on the outcome.

That kind of confidence isn't aimed at the future. It's aimed at yourself. And unlike the future, yourself is something you actually have a hand in shaping.

That's the optimism the Stoics would recognize. Not things will be good, but I can meet what comes.

The Hidden Cost

Now I want to come back to something I planted at the top of the episode, because I don't want it to slide by.

I said fear-driven work tends to produce the failure it's afraid of, and I want to tell you why.

When you're afraid, your nervous system narrows. That's its job. Fear is supposed to focus you on a threat so you can survive it. The problem is, that same narrowing is poison for creative, generous, courageous work.

Fear makes you defensive. You stop taking risks. You stop making bold offers. You stop saying the true thing because the true thing might cost you something. You hedge every sentence and water down every pitch. You play not to lose instead of playing to create.

And here's the thing about work that comes from that place — people can feel it. They can feel when something was made from fear, even if they can't name what they're feeling. It feels tight. It feels needy. It doesn't move them.

So the fear of failing at your coaching practice, your business, your art, whatever — that fear is often the very thing making the practice mediocre. The fear is creating the conditions for the failure that you’re afraid of.

You can't outwork that. You can't out-hustle it. The only way out is to change the fuel. To stop running on fear and start running on something steadier.

So here's where we land at the end of this section.

Reality isn't yours. Outcomes aren't yours. The economy, the market, the news cycle, whether someone signs up to work with you next month — none of that is yours to control.

But your perspective? Your judgments? The story you're telling yourself about what any of this means? That's yours. Completely. And the Stoics would say that's the only territory where freedom actually lives.

So the question isn't how do I make the future safer. The future will be what it will be. The question is what verdict am I handing down right now, and is it true?

That's where we go next — into the practice of catching those verdicts, examining them, and building the kind of fortitude that doesn't need a forecast.

Act 3 — The Practice

If perspective is the territory where freedom lives, the question becomes, how do we actually work that territory? How do we move from understanding this intellectually to using it when it counts, which is usually three in the morning when the fear has its hands around your throat and Epictetus is nowhere to be found?

I want to give you four practices. Some of them are reflective — things you do on the page. Some of them are behavioral — things you do with your body in the actual moment. Different practices land for different people, so try them all and keep what works.

Practice 1: Name the Fear

The first practice is to name the fear out loud.

A few episodes back I talked about akrasia — that ancient Greek word for the gap between knowing what you should do and actually doing it. And one of the things I want to add today is that fear is one of the main engines of that gap.

You know what to do. You know the email to send, the offer to make, the conversation to have, the project to start. But something keeps you from doing it. And if you look closely at that something, it's almost always fear wearing a costume — fear dressed up as perfectionism, fear dressed up as research, fear dressed up as "the timing isn't right yet."

The move here is just to name it. Out loud, ideally. I'm not doing this because I'm scared. Scared of what? Scared it won't work. Scared of what people will think. Scared I'll look like I don't know what I'm doing.

That's it. That's the whole practice.

Naming the fear doesn't make it go away. But it does something almost as good — it separates you from the fear. You stop being someone who is afraid and start being someone who notices they're afraid. And that little gap, that tiny bit of space between you and the feeling, is where choice lives.

The Stoics would say that gap is everything. Everything important happens there.

Practice 2: Premeditatio Malorum

The next practice is to follow that path of fear all the way down.

This is Seneca's premeditatio malorum, the premeditation of evils. It sounds dark but it's actually one of the most liberating exercises in the whole Stoic toolkit. I think of it a jujitsu move against our mind’s willingness to catastrophize.

Here's how it works. Most of our fears are vague. They live in this fog of "what if it all falls apart." And as long as they stay vague, they stay powerful, because the imagination keeps inventing horrors faster than you can fight them.

So you bring the fear into the light. You name it, specifically, and then you walk it down step by step.

I'm afraid my business will fail. Okay, what does fail mean? It means I won't have enough clients. Okay, then what? Then I won't be able to pay my bills. Then what? Then I'd have to find other work, or move, or ask for help. Then what? Then I'd be embarrassed. People would see me struggling.

And there, usually, is where the actual fear lives. Not in the catastrophe, but in the shame about the catastrophe. Not in being unable to pay, but in being seen as someone who couldn't pay.

Most fears die at step three or four. Not because the situation isn't serious, but because the version we imagined is almost always worse than the real one. When you actually look at what would happen, you discover something the fear was hiding from you: you'd handle it. You'd figure something out. People do. You would.

The fog is what gives fear its power. Specificity, clarity, is what takes it back.

Practice 3: Perspective Audit

The third practice is what I'd call the perspective audit.

This one's short, and you can do it in thirty seconds, but I'd argue it's the most important Stoic move there is.

When you notice fear or anxiety rising, you stop and ask one question: Is this a fact, or is this a verdict?

Something happened, and your mind handed down a ruling about what it means. The empty inbox, a slow month, a tough market — those are facts. Nobody wants what I'm offering, I’m a failure — those are verdicts.

The facts are usually neutral. The verdicts are doing all the emotional damage.

So you separate them. You write them in two columns if you have to. Here's what actually happened. Here's the story I'm telling about what it means. And then you ask the harder question: Is the story actually true? Do I actually know that? Or is my mind just filling in the worst-case version because that's what minds do?

Nine times out of ten, the verdict is doing more work than the evidence supports. And once you see that, the verdict loses its grip.

This isn't denial. This isn't pretending the situation is fine. It's just refusing to confuse the situation with the story you're telling about the situation. Because Epictetus was right — the situation isn't what's disturbing you. The story is.

Practice 4: Optimize for Action

The last practice is to stop optimizing for the outcome and start optimizing for action.

This is where the Stoic dichotomy of control becomes a tool you can actually use, not just a concept you nod along to.

Outcomes aren't yours to control. Whether the launch works, whether the client signs, whether the post takes off, whether the bills get covered this month — none of that is in your hands. You can influence those things, but you can't determine them.

But what action you take is yours. The next email you write. The next session you prepare for. The next conversation you have. The quality of attention you bring. The quality of the offer. Those are yours, completely.

So when fear shows up, and it will, the redirect is to stop asking will this work and start asking what's the next right move, and how do I do it the best I can?

That's a smaller question. It's also a question you can actually answer. And here's what's strange about it — when you stop white-knuckling trying to control the outcome and pour that energy into the quality of you actions, the outcomes tend to improve. Not because you forced them, but because work that comes from that place is just better work.

Virtue is in the doing, not the result. The Stoics were emphatic about that. And it turns out to be practical advice, not just philosophical.

Four practices: Name the fear out loud. Walk the fear down. Audit the perspective. Optimize for action, not the outcome.

You don't need all four. You need one or two that fit your wiring, used consistently, when it actually matters.

Conclusion

I want to leave you with this.

There's a line you've probably heard before — that courage isn't the absence of fear, it's acting in spite of it. It's almost a cliché at this point. But I want you to hear it again, because I think most of us read it once, nodded, and missed what it actually means.

It means the fear isn't the problem.

The fear is going to be there. As long as you care about something — your work, your people, your life — there's going to be fear. That's not a flaw in you. That's not something to fix. The fear is just the price of caring about anything in a world where you don't get to control how it goes.

What you can control is whether the fear gets to drive.

That's the entire shift this episode has been pointing at. You don't have to stop being afraid. You couldn't if you tried. What you can do is refuse to hand fear the steering wheel. You can let it ride along, you can let it have its opinion, you can even thank it for trying to keep you safe — and then you can keep your hands on the wheel and drive the car yourself.

That's fortitude. That's the thing that's sturdier than optimism, sturdier than positive thinking, sturdier than any forecast about how the future is going to go. It's not a prediction. It's a posture. It's the quiet confidence that whatever shows up, you can meet it — not because you know what's coming, but because you trust who you are.

And here's the thing I want you to hold onto.

The Stoics weren't trying to make you indifferent. They weren't trying to turn you into a stone. The whole point of doing this work — the perspective audits, the premeditation of evils, the catching your fear-driven choices — the whole point isn't to feel less. It's to clear the obstacles between you and the life you actually want to live.

As Marcus Aurelius reminds us:

"If you are distressed by anything external, the pain is not due to the thing itself, but to your estimate of it; and this you have the power to revoke at any moment." — Marcus Aurelius

Fear is one of the biggest obstacles. It eats your energy. It shrinks your work. It keeps you small in a world that needs you to show up at your biggest and best. When you stop letting it drive, what you get back isn't numbness. It's the opposite. You get back the space to actually create something, to actually love something, to actually do the work you came here to do.

That's not optimism. That's not pessimism. It’s just being free.

So here's what I'd ask you to take with you.

This week, just notice. When you make a choice — about your work, about a conversation, about whether to send the thing or not send the thing — notice what's driving. Is it the version of you that's creating something? Or is it the version of you that's defending against something?

If it's the second one, pause. Walk the fear down. Audit your perspective. Then ask what you'd do if you trusted yourself to handle whatever came next.

Then do that.

Not because you're sure it'll work. You won't ever be sure. But because you know that you can handle it. If you fail, then you’ll learn from that failure, and keep moving forward.

Fortitude over forecast.

Trust yourself. Not the outcome.

That's where the freedom is.

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