Prepare for the worst, then forget you did
A pessimist and an optimist walk into a bar... err, office. They need each other. They also drive each other insane.
A Slack notification came in last week. Potential new project. Exciting, ambitious, not totally aligned with what we’re doing but not crazy either. The kind of thing that doesn’t come along often.
My brain was three steps ahead before I’d finished reading the message. Not in the good way. I had a list of problems forming. Integration complexity. Scope creep. Dependencies nobody had mapped yet. Who inherits the maintenance when the excitement wears off. I know this movie.
I got to about seven reasons before I caught myself.
Counted to ten. Closed Slack. Said to myself: not today, Satan.
Let it play out. Don’t shut it down before it starts. I’ve done this before. Walked into a conversation already holding a verdict I formed in the time it took to read a subject line.
I deliberately caught myself. A couple of weeks earlier, my superior called me a pessimist. Not the first time. Most likely not the last. But this time it sent me down a rabbit hole: why does he see me that way when I know I’m not? I did some research. What I found made me pause this time with the Slack notification.
If I’m the pessimist in this story, he’s the opposite. The endless optimist. The visionary. Almost every time I raise potential problems, it triggers him. Every time he doesn’t acknowledge what I’m seeing, it triggers me. Two people who genuinely want the same thing, unable to hear each other.
The remark made me defensive in a way I hadn’t expected. I’m not a pessimist. I believe in the projects we’re doing. When I raise issues, I’m not trying to kill the idea. I’m trying to catch what will hurt us before it does, approach things from a better angle, think them through before the problems become crises.
That’s not pessimism. Is it?
The label stuck with me. Why does he see it that way? While doing the research, a different question started forming: when do we need the dark side and when do we need the bright side? In ourselves, in the people around us. When is the pessimist’s checklist the right tool, and when is it the thing getting in our way?
I came across a piece by Rishikesh Ranjan that pushed me further into it.
When not knowing is the superpower (and its tab)
Ranjan writes about George Dantzig, a PhD student who showed up late to a statistics lecture at Berkeley in 1939. Two problems were on the board. He assumed they were homework, copied them down, and handed in solutions a few days later with an apology that they had seemed a little harder than usual.
They weren’t homework. They were unsolved theorems that had stumped the field for years.
Ranjan puts it well: “Naivety is the amplifier. Optimism or pessimism is the signal it amplifies.” An unskilled person who doesn’t know what they don’t know produces noise. A skilled person who temporarily sets aside what they know about why something shouldn’t work? That’s where breakthroughs come from.
I hadn’t heard the story before. And I wish it were always that clean.
You build it, it works, it ships. Then real life happens. Problems surface. Edge cases multiply. The thing that seemed impossible to break starts breaking. The other mode kicks in: safety, not making it worse, keeping the lights on. The people doing that work are rarely the ones who built the thing.
Someone pays that tab eventually. Usually not the optimists who ran it up.
Nothing wrong with either side. You need both. If you’re a leader, the job is making sure they don’t end up hating each other.
There’s a concept in Zen Buddhism called shoshin, beginner’s mind. It gets romanticized. Usually interpreted as: act like you know nothing. That’s not it. Shoshin is a deliberate choice to re-enter a familiar domain with openness and curiosity. Not the ignorance of a beginner. The humility of someone who knows enough to realize they might be wrong.
Marc Benioff does a version of this at Salesforce. Each year he runs a blank-slate exercise, questioning every assumption about the business as if seeing it for the first time. He’s learned that expertise, left unchecked, calcifies.
Benioff does it deliberately. Dantzig did it by accident. Shoshin is what it looks like when you choose it.
Two camps, and why they need each other but drive each other insane
A pessimist and an optimist walk into a bar. Err... an office. They have to deliver a project. This is where the joke ends and real life starts. They’re representatives of two types involved in every project. I’ll exaggerate.
Camp one: “Everything’s possible. Let’s not think about problems. Let’s just do it.”
Camp two: “Okay, what can go wrong? What trapped us last time? Which problems will we inherit from doing this new thing?”
These two groups often can’t understand each other. Camp one reads camp two as pessimists, people who think everything will fall apart, who find a problem in every direction. Camp two reads camp one as reckless, or worse: they can afford to be optimistic because they won’t be the ones fixing what breaks.
Both reads are wrong. Each camp is right about itself and wrong about the other. Camp one isn’t reckless. Camp two isn’t obstructive. They’re built for different phases of the same project.
Writing this reminded me of Good Omens, Terry Pratchett and Neil Gaiman’s book (and TV series, both worth your time). An angel who isn’t all good and a demon who isn’t all bad. The end of the world is looming and they have to stop it together. Neither could do it alone.
Pessimists vs optimists? Same thing. Slightly lower stakes than the apocalypse.
I’m usually in the second camp. Btw. the pessimist label wasn’t the only one I’ve heard in the past. I’ve also been told I’m looking for excuses not to build. That one stung. Because it was so untrue. From the inside, I was asking the right questions: do we need this, what problems will this create, are we solving the right thing? From the outside, it looked like putting obstacles in the way. The same question sounds like rigor or obstruction depending entirely on who’s hearing it and what phase the project is in.
No, I’m not a pessimist. But I do have an operational mind. I’ve built things from scratch, probably more than people assume. But I’ve also been part of the team that gets called when something someone else built starts leaking, needs maintaining, or breaks in ways nobody planned for. Years of that will do something for you.
There’s a name for what most of us are actually doing every day: defensive pessimism. Not a personality trait. A deliberate coping strategy: you set low expectations, run through scenarios of what could go wrong, and prepare for the outcomes you’re dreading. The fire you’ll need to fight. The dependency nobody mapped. The scope that will quietly double.
Done right, it lowers your anxiety, helps you handle what actually breaks, and builds acceptance of whatever the outcome is. Taken too far, it increases anxiety, convinces you the failure is so inevitable there’s no point trying, and (this one hits close to home) creates friction with people who find it hard to be around someone always bracing for impact.
The last one sounds familiar. Not a personality clash. A strategy clash.
Julie Norem’s research gave me something I hadn’t expected: evidence that the mode works. She studied two groups: strategic optimists, who prepared by imagining success and staying positive; and defensive pessimists, who prepared by mentally rehearsing everything that could go wrong.
Both groups performed at roughly the same level.
The 30% gap in their predictions (pessimists expected worse, optimists expected better) collapsed to near-zero at the point of actual performance. More striking: when researchers gave defensive pessimists cheerful, encouraging feedback before the task (”You’re going to do great! Don’t worry!”), their performance dropped by 29%. The cheerful coaching didn’t help them. It sabotaged them. Their anxiety wasn’t a bug. It was the mechanism they used to prepare.
The problem isn’t optimism or pessimism. Early planning needs the bright side to get started. Deeper planning needs the dark side, but not all of it. Execution needs both.
The anxiety tax on expertise
There’s a cost to knowing things. The more you understand about how a system can fail, the higher the threshold for action. Sometimes so high you never actually start.
I’ve seen this with experienced engineers. They know the edge cases. They’ve been burned by the migration that corrupted production data, and the API that changed without warning. Every scar makes the next decision heavier. They can see all the ways it might go wrong.
Startup mythology loves to celebrate the opposite. Evan Spiegel at 21. Zuckerberg at 19. The Collison brothers in their early twenties. The narrative: youth and inexperience are advantages. And sometimes they are, not because young founders know less, but because they haven’t accumulated enough failure patterns to trigger the anxiety tax.
The data tells a different story. The NBER’s 2018 study found the average age of top-performing founders is 45. Experience predicts higher success rates on average. The teenage prodigies are survivorship-bias highlights (we only hear about the ones who made it), not the pattern. Both deserve airtime. Although only one gets the magazine covers.
Whenever someone has a brain fart (an idea that’s arrived before it’s been thought through), I go quiet. The checklist starts. Have we thought about this angle? What problems are we creating three projects from now? Who inherits this? I hate repeating mistakes. What I hate more is when other people repeat theirs and I have to clean up after them. I’ve become (and no leadership book has ever put it this way) a professional shit shoveler. Someone whose job has repeatedly involved dealing with what other people’s enthusiasm left behind. One of my previous teams made it official: they called it “General of Shit Shoveling” mode, gave me a badge, and stood by my side as a small shit shoveling army. It was funny. Gallows humor, but also accurate.
How does shit shoveling start? Usually with a project that has real potential and not enough hard questions asked upfront.
A project gets proposed. The people behind it dismiss the complexity, wave off the timeline, treat the hard parts as solvable later. Not afraid. Collaborative. Creative. Those are real strengths, and I mean that sincerely.
Then the project starts. Reality shows up. What was manageable becomes the most critical thing in the building. People get pulled in without context. Another thing breaks. The pressure compounds because the runway was shorter than anyone admitted. Nobody likes solving shitty problems with artificial urgency created by ignoring reality for too long. Hence the badge.
I can see it coming from a mile away. I’ll say something. I’ll nudge, warn, coordinate. Sometimes it doesn’t matter. The shit arrives on schedule regardless. At some point you just put the badge on.
Seeing it coming isn’t intuition. It’s systems thinking.
Systems thinking is what gives you the map. Once you understand how a system works, every new proposal arrives with ripples attached. Some good. Some less good. Some neutral until they become someone’s problem two projects later. The system will have to change anyway. Not the issue. The question is whether you’re changing it with your eyes open. Not pessimism. It’s seeing things as they are: complex and intertwined.
You can’t just turn this mode off. It doesn’t respond to “just be more positive.” It took years to build and it exists for real reasons. Putting it down, even temporarily, even when you need to, takes actual energy. Not a mindset shift. It’s a skill. But a skill worth learning.
Not today, Satan (reprise)
Dantzig solved those theorems because he didn’t know they were impossible. He was a PhD mathematician working at the edge of the field and the accidental ignorance just removed the ceiling. A good example of how not knowing a constraint can sometimes be exactly what solves the problem. And a note for those of us with more scars than average: maybe stop whispering “this can’t be done” before someone else has had a chance to find out for themselves. Who knows, maybe they’ll find a way nobody has before them.
You can’t reproduce that accident. You can’t unknow what you know. But you can choose when to use it.
Back to that Slack notification. This is why I set it down. I still saw the problems. I’ll probably still be right about most of them. But I recognized that wasn’t the moment for that particular skill. The problems will get their turn. The checklist will come out. Just not before the thing has had a chance to breathe.
There’s a time and a place for the pessimist, and a time and a place for the optimist. Most people know which camp they’re in. Fewer know when to step aside.
The visionary will probably still get triggered the next time I raise a problem. So will I when he doesn’t acknowledge what I’m seeing. But now I understand what we’re actually arguing about. And that changes what I can do about it.