Why Your Projects Fail Before They Start: The Stoic Pre-Mortem

How Negative Visualization Turns Anxiety Into Preparation

The Disaster You Could Have Seen Coming

Every project manager has that one project. (Some of us have had many such projects.)

The one where, months later, you look back and say, “Seriously, none of that should have surprised us.”

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The vendor delay. The requirements that were never really agreed upon. The key resource who was “50% allocated” but actually had no time. The dependency on another team that was already underwater.

If you’re honest, the red flags were there. The team even mentioned some of them in passing. But everyone was optimistic, the kickoff energy was high, and the schedule was already tight.

So you pushed ahead.

I, we, know this overture intimately.

Hurricane Harvey: When You Have 48 Hours to Launch an Untested System

In August 2017, Hurricane Harvey hit slammed into Texas.

The Coast Guard and our federal partners stood up crisis action teams. We were coordinating search and rescue operations across multiple states, managing resources that had never been centralized before, and dealing with a humanitarian situation that was evolving minute by minute. Oh, and Hurricane Irma and later Maria were inbound to the southeast.

The month before, in July 2017, I had authored and obtained approval for a new Coast Guard team for emergent search and rescue (part of ESF #9): the Federal Search and Rescue Coordinator (FSARC) position. It was innovative, necessary, and had never been tested. This was a perfect time to do so! 🤔

And by “the perfect time,” I meant now. We had to deploy the first person into that role, to College Park, Texas, into the chaos of Harvey, almost immediately.

This was about as real as it gets. Not a PowerPoint project with a go-live date. Real people in danger. Real lives on the line.

When we stood up that coordination cell, we could have said:

• “The policy is solid; let’s hope it works.”
• “We’ll learn as we go.”
• “The new coordinator will figure it out when they get there.” (I think I actually did say this at one point…)

Instead, the best people in that room did something different. They, we, I, imagined failure.

In those first hours, we asked hard questions:

• What if the federal coordinator arrives and no one knows they have the authority to make decisions?
• What if the state teams have been operating independently for 12 hours already and don’t want to share information?
• What if Texas says no to federal help? (They had in the recent past up to that point.)
• What if the communication systems are down and we can’t actually coordinate?
• What if our newly written policy conflicts with something in the field?
• What if the coordinator doesn’t have the resources they need to actually do anything?

We didn’t ask these questions to scare ourselves. We asked them because we had 48 hours to get it right, and people’s lives depended on us not failing.

So we took action:

• We briefed the state commanders personally, in advance, explaining the coordinator role and why it mattered.
• We ensured the coordinator had direct phone lines and clear escalation paths.
• We built in redundant communication systems.
• We gave the policy teeth: explicit authority, budget authority, and decision-making delegated in advance. The three-star gave his blessing.
• We pre-positioned resources so the coordinator wouldn’t have to start from zero.

When that coordinator hit the ground in Texas, it wasn’t perfect. But it worked. The system held. The coordination happened. People were rescued who wouldn’t have been without that function.

We didn’t imagine every problem. But by asking “What could go catastrophically wrong?” and then preparing for it, we avoided the disasters that would have been fatal.

That’s the power of pre-mortem thinking in a real crisis. And it’s the same power we need to bring to our projects every single day.

From Post-Mortem to Pre-Mortem (and we can thank Seneca for this)

Most organizations are good at post-mortems.

Something fails. We gather in a room. We ask, “What went wrong?” We document lessons learned. Sometimes we actually read them later.

The Stoics, especially Seneca, recommended something far more powerful: negative visualization… deliberately imagining worst-case scenarios ahead of time so you can prepare.

In your Stoic Project Management Journal, Week 3 is titled “The Pre-Mortem – Negative Visualization.” The scenario prompt is stark:

“Imagine it is 6 months from now, and your project has failed spectacularly. It was a total disaster. Write the story of how it happened. What went wrong? Who dropped the ball? What risk exploded?”

That is a pre-mortem.

You don’t wait for failure. You rehearse it in your mind while you still have time to act.

Seneca put it this way:

“Rehearse them in your mind—exile, torture, war, shipwreck. All the terms of our human lot should be before our eyes.”

He wasn’t trying to make you anxious. He was trying to prepare you.

In your role as a Stoic project manager, that’s exactly what you do: you rehearse the failure before it happens. You imagine the disaster. And then you ask, “What do I control here? What can I do right now to prevent this?”

How to Run a Stoic Pre-Mortem With Your Team

Here’s a simple, 30-minute way to turn Seneca’s advice into a practical, repeatable project tool.

You can run this in a kickoff, a major phase gate, or anytime things “feel too smooth.”

Step 1: Set the Scene

Tell your team:

“Imagine it’s six months from now. This project has failed—publicly, painfully, undeniably. It’s a mess. Nothing shipped on time. Stakeholders are angry. The team is burned out. Our names are attached to it.”

Yes, it feels uncomfortable. That’s the point. The discomfort is a signal that you’re touching something real.

Step 2: Ask Them to Write the Failure Story

Give everyone 5-7 minutes in silence.

Prompt them with these questions (write them on the board):

• What went wrong?
• Which risks exploded?
• Who dropped the ball—and why?
• What assumptions turned out to be false?
• Which dependencies hurt us?
• Where did leadership fail to decide or support?
• What did we think would be easy that turned out to be hard?
• What did we ignore until it was too late?

Let them write individually first. This matters. When you ask for silent reflection, quieter voices get heard. The introverts, the people who think before they speak, the team members who’ve been holding their concerns—they get to articulate them without being talked over.

Step 3: Collect and Cluster the Risks

Have people share their “failure causes” one by one. Capture them on a whiteboard or digital board. Don’t edit them. Don’t debate them. Just collect them.

Then group them into themes:

• Vendors and external dependencies
• Requirements and scope
• People and capacity
• Environment, tools, and infrastructure
• Stakeholder clarity and governance
• Communication and knowledge
• Quality and testing

You’ll see patterns quickly. The same few root causes will show up in multiple people’s stories. The team already knows what could go wrong. They just haven’t said it out loud in an organized way.

That’s why this exercise is powerful. You’re surfacing what everyone already senses.

Step 4: Ask the Stoic Question: What’s In Our Control?

For each cluster of risks, ask your team:

• What parts of this are in our control?
• What can we influence?
• What is outside our control, but we must acknowledge?

This ties back directly to Week 1 of this Substack—the Dichotomy of Control. You’re not just catastrophizing; you’re sorting the fear into controllable vs. uncontrollable and then acting on your side.

For example:

Risk: “Vendor will delay.”

• What you control: When you engage them, what contract terms you lock in, how closely you monitor progress, whether you find a backup vendor now, and when you escalate if they slip.
• What you don’t control: Their internal capacity, whether their own vendors fail, and whether they change priorities.
• What you do: Start vendor engagement early. Build in a buffer. Have contingency plans in place now, not when they slip.

Risk: “Requirements will keep changing.”

• What you control: When you lock the requirements, how rigorous your change-control process is, and how you communicate scope limits to stakeholders.
• What you don’t control: Whether the market shifts, whether the customer changes their mind, whether their leadership overrides their own team.
• What you do: Get stakeholder sign-off early. Set explicit change-control gates. Communicate the cost of changes before they happen.

Step 5: Choose 1-3 Actions to Take This Week

This is where the exercise becomes real and stops being theoretical.

For each major failure mode, pick one concrete mitigation action:

• If vendor delay is a significant risk, engage them now. Clarify expectations. Add a backup vendor option. Or accelerate your own contingency work.
• If requirements churn is likely, mandate a requirements-freeze date and a formal change-control process. Get sponsor buy-in in advance.
• If environment readiness is shaky: Agree on minimum go/no-go criteria now, with dates. Start building early.
• If key people might leave: Identify cross-training needs. Document critical knowledge. Reduce single-points-of-failure.

The journal’s Weekly Practice for Week 3 is clear:

“Pick the one most likely cause of failure you identified. Take one concrete action this week to mitigate it.”

Do that at the team level. Don’t let the exercise end in the meeting. Action kills anxiety. Preparation kills panic.

Why Negative Visualization Reduces Anxiety (Not Increases It)

Many people resist pre-mortem exercises because they think it will make them more anxious.

If all you do is imagine catastrophe and then do nothing, they’re right. That would be torture.

But when you pair negative visualization with targeted action, the effect is the opposite. Anxiety plummets because:

• You have named the fear explicitly. Secrets cause anxiety. Open conversations relieve it.
• You’ve separated out what you can and can’t control. Worry without clarity is just noise.
• You’ve taken concrete steps on what you can control. You’ve moved from victim to agent.
• You’ve accepted that the rest is fate. And strangely, acceptance is peaceful.

In Stoic terms, you’ve done your duty as a rational agent. You’ve prepared. You’ve planned. You’ve acted. After that, you can sleep.

Harvey taught me this concretely. Standing up that coordination team under time pressure would have been nightmarish if we’d just improvised (well, maybe not). Instead, because we asked hard questions and prepared answers, I slept well those nights. Not because nothing could go wrong, but because we’d done everything within our power to handle what might go wrong.

Your journal’s Reflective Prompt asks:

“How does visualizing this worst case make you feel? Anxious? Or prepared? How can you use this ‘history of the future’ to change what you do today?”

That phrase—”history of the future”—is powerful. You’re not fantasizing. You’re running a rehearsal. You’re writing the history in advance so that when reality deviates from the plan (and it will), you’ve already seen the scene once in your mind.

A Quieter Kind of Pre-Mortem: Home and Family

Crisis work and large-scale projects aren’t the only places I use this thinking.

With five kids and an active household, you learn to pre-mortem fast, or you learn patience the hard way.

Before a family road trip, my wife and I do a quiet version of this exercise:

• “OK, if the toddler melts down at hour 2… what’s our plan?” (Snacks. Walk break. Leeway on schedule.)
• “If the older kids start fighting… how will we separate them?” (Audiobooks, tablets with downloaded shows, individual snack bags so they’re not competing.)
• “If traffic adds two hours… what do we have?” (Extra snacks. Bathroom stops planned. Flexibility in hotel arrival.)

We don’t sit down with sticky notes and call it a pre-mortem. But that’s exactly what it is: negative visualization in service of a calmer, saner experience.

The key is this: Preparing for failure doesn’t make you pessimistic; it makes you responsible.

And responsibility, paradoxically, is less stressful than hope.

Hope says, “Maybe it will all work out.”

Responsibility says, “I’ve prepared for what might not work out, so I can stop worrying and enjoy the drive.”

That’s true on projects, too.

Turning the Pre-Mortem Into a Habit

Make this more than a one-off workshop:

Add it to your kickoff checklist:
Make “Run 30-minute pre-mortem” a standard agenda item whenever you charter a significant project. Make it non-negotiable.

Use it at phase gates:
Before moving into execution, ask, “If this phase fails, what will have done us in?” Then adjust your plan accordingly.

Combine with your risk register:
Translate the pre-mortem outputs into formal risks with owners and mitigation steps. The exercise surfaces what the team already knows but hasn’t said out loud. Make it official.

Model calm leadership:
Stay unemotional during the exercise. You’re not looking for drama; you’re looking for clarity. That tone—calm, curious, rational—tells your team it’s safe to talk about what could go wrong. It signals that you value realism over optimism.

Use it for your own semester/quarter/week planning:
In a life where you’re a Boeing PM, an MPA student, and a parent of five, the pre-mortem is also a personal tool. “What could make this quarter fail?” is a powerful planning question.

Your Assignment This Week

Here’s your action, straight from Week 3 of the journal:

1. Pick one live project.

Preferably something important, visible, or fragile. Something you care about getting right.

2. Schedule a 30-minute pre-mortem with your core team.

Call it exactly that. Use the term. Put it on the calendar. Don’t overcomplicate it—the title can simply be “Pre-Mortem: How This Project Fails.”

3. Run the exercise:

• Read the scenario: “Imagine it’s 6 months from now and this project has failed spectacularly.”
• Have each person write silently (5-7 minutes): Write the failure story. What went wrong?
• Share and cluster: Collect all the root causes and group them.
• Ask the control question: What’s in our control here? What can we actually do?
• Choose one action: Pick the #1 risk and identify one thing you’ll do this week to mitigate it.

4. After the meeting, journal for 5 minutes.

• What did your team already know but had never said plainly?
• How did you feel running the exercise? More anxious or more grounded? Why?
• What surprised you?

That’s it. 30 minutes in the meeting, 5 minutes of reflection. That’s how you build the Stoic discipline of preparation.

A Challenge and An Invitation

The hardest part of pre-mortem thinking isn’t imagining failure. It’s accepting that you might not be able to prevent it.

The Stoic response? Do your duty. Prepare. Plan. Act. Then release attachment to the outcome.

You cannot control whether the project succeeds perfectly. Too many variables, too much outside your control, too much that depends on others.

But you absolutely control whether you walk in blind—or with your eyes open.

Choose the second. That’s the Stoic way to manage projects. That’s how I got through Harvey without panic. That’s how you’ll get through whatever crisis or crunch your project faces.

Call to Action

When you run your pre-mortem this week, what’s the #1 risk your team surfaces that you hadn’t fully acknowledged before?

Share it (anonymized, of course) in the comments:

• Don’t name the company, product, or confidential details.
• Just describe the risk and what you decided to do about it.
• One or two sentences are enough.

You’ll help other project managers see patterns in their own work. And you’ll reinforce your learning by articulating it.

Plus, I read and respond to every comment in the first 48 hours. Let’s build this community of project managers who lead with preparation, clarity, and calm.

Next week: The Optimism Bias. Why we all underestimate timelines (and how to stop).

Ryan Erickson
PMP, veteran, student, father
Learning to lead with wisdom, courage, justice, and temperance—one project at a time.

P.S. If you’ve ever run a pre-mortem (formal or informal) that caught something important, I’d love to hear about it. Drop a comment. Those real stories are how we all get smarter.