The Next Edit - Issue #031
Confession of a worst case scenario planner....
đ§ ONE BIG IDEA
Iâm sure you have heard of a âpostmortemâ.
The common practice of looking backwards in time at something that didnât 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 darkâbut 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 surpriseâand sufferingâwhen life refuses to follow the plan.
Today, we call this a premortem.
Instead of asking, âWhat if everything works out?â
You ask: âIf this went sideways⌠what likely caused it?â
Businesses do this all the time.
Retirement planning? Almost never.
Which is ironicâbecause retirement may be the biggest lifestyle and identity transition of your life.
Iâm a Professional Worst-Case Scenario Planner
Hereâs the part that still makes me laugh.
I am exceptionally good at planning for things going wrong. Iâm the person who lies awake at night building contingency plans.
Multiple airline reservations âjust in case.â
Backup plans for the backup plan.
Iâve done premortems for jobs, teams, relocations, travel, major decisionsâyou name it.
This is not new behavior.
And yetâŚ
When it came to retiring?
I didnât do one. I assumed the rest would sort itself out.
I hadnât 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 ironicâbecause if anyone should have seen this coming, it was me.
Stoic philosophers like Marcus Aurelius and Seneca believed clarity comes from confronting reality earlyâespecially the parts weâd 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 donât knock you off balance when they arrive.
The Stoics understood something we tend to forget:
Suffering isnât caused by events.
Itâs caused by unmet expectations.
And retirement is full of expectations.
Where Retirement Often Goes Wrong (Quietly)
Most people plan retirement like this:
âIâll finally relax.â
âIâll figure it out once I stop working.â
âOther people struggle, but I wonât.â
A Stoic premortem asks a different question:
Imagine itâs two years into retirementâand youâre unhappy. Why?
Common answers:
You lost daily structure and didnât replace it.
You underestimated how much identity came from work.
Your social circle shrank faster than expected.
Your partner retired with youâbut not like you.
You mistook burnout for readiness.
You assumed purpose would simply appear.
None of these are personal failures.
Theyâre predictable.
Which meansâtheyâre preventable.
đ§ TRY THISâŚ.
Fast-forward three years.
Youâre saying, âThis isnât what I hoped retirement would feel like.â Why?
Answer theseâhonestly, not optimistically:
What am I missing most from work?
(Structure? Status? Belonging? Momentum?)Where do my days feel empty instead of open?
What surprised meâin a bad way?
What did I assume would âjust happenâ that didnât?
What warning signs did I ignore before retiring?
Now the Stoic move:
đ What could I put in place now to reduce these risks later?
Thatâs not fear.
Thatâs foresight.
đŹ THE LAST EDIT
Hope is not a plan.
Optimism is not a strategy.
If youâre 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 youâno backup flight required.
See you in the next edit,
Andrea



This post was so good! I always enjoy the Try This section, and "What did I assume would âjust happenâ that didnât?" stood out for me. It's the kind of reflective question I love asking clients. Thank you
Whoa. This one is deep! In a good way, of course. Keep it coming!!