The Next Edit - Issue #031

Confession of a worst case scenario planner....

🧠 ONE BIG IDEA

I’m sure you have heard of a “postmortem”.

The common practice of looking backwards in time at something that didn’t go as expected to figure out what happened. We all know that hind site is 20/20.

The Stoics had a practice that sounds a little dark—but turns out to be incredibly practical.

They called it premeditatio malorum: imagining what could go wrong before it does.

Not to be pessimistic.
Not to spiral.
But to reduce surprise—and suffering—when life refuses to follow the plan.

Today, we call this a premortem.

Instead of asking, “What if everything works out?”
You ask: “If this went sideways… what likely caused it?”

Businesses do this all the time.
Retirement planning? Almost never.

Which is ironic—because retirement may be the biggest lifestyle and identity transition of your life.

I’m a Professional Worst-Case Scenario Planner

Here’s the part that still makes me laugh.

I am exceptionally good at planning for things going wrong. I’m the person who lies awake at night building contingency plans.

• Multiple airline reservations “just in case.”

• Backup plans for the backup plan.

• I’ve done premortems for jobs, teams, relocations, travel, major decisions—you name it.

This is not new behavior.

And yet…
When it came to retiring?

I didn’t do one. I assumed the rest would sort itself out.

I hadn’t anticipated how much structure work gave me.
Or how much of my sense of value came from being needed.
Or how much I would miss the conversations and connections that came from being in the office everyday.

Which is especially ironic—because if anyone should have seen this coming, it was me.

Stoic philosophers like Marcus Aurelius and Seneca believed clarity comes from confronting reality early—especially the parts we’d rather avoid.

More recently, Ryan Holiday, through The Daily Stoic, has helped modern audiences rediscover this idea: you can try to anticipate obstacles so they don’t knock you off balance when they arrive.

The Stoics understood something we tend to forget:

Suffering isn’t caused by events.
It’s caused by unmet expectations.

And retirement is full of expectations.

Where Retirement Often Goes Wrong (Quietly)

Most people plan retirement like this:

• “I’ll finally relax.”

• “I’ll figure it out once I stop working.”

• “Other people struggle, but I won’t.”

A Stoic premortem asks a different question:

Imagine it’s two years into retirement—and you’re unhappy. Why?

Common answers:

• You lost daily structure and didn’t replace it.

• You underestimated how much identity came from work.

• Your social circle shrank faster than expected.

• Your partner retired with you—but not like you.

• You mistook burnout for readiness.

• You assumed purpose would simply appear.

None of these are personal failures.

They’re predictable.

Which means—they’re preventable.

🔧 TRY THIS….

Fast-forward three years.

You’re saying, “This isn’t what I hoped retirement would feel like.” Why?

Answer these—honestly, not optimistically:

1. What am I missing most from work?
   (Structure? Status? Belonging? Momentum?)

2. Where do my days feel empty instead of open?

3. What surprised me—in a bad way?

4. What did I assume would ‘just happen’ that didn’t?

5. What warning signs did I ignore before retiring?

Now the Stoic move:

👉 What could I put in place now to reduce these risks later?

That’s not fear.
That’s foresight.

💬 THE LAST EDIT

Hope is not a plan.
Optimism is not a strategy.

If you’re someone who plans for worst-case scenarios everywhere else in life, ask yourself why retirement should be the exception.

Do the premortem.

Your future self will thank you—no backup flight required.

See you in the next edit,

Andrea

Photo by Tzenik on Unsplash