The Bright Side of "What If Everything Goes Wrong?"

for the beautifully unhinged minds who find comfort in contingency plans

Why Play

Imagine your brain is a smoke alarm. It’s designed to go off at the faintest whiff of trouble—not because something is burning, but because something might.

Imagine the smug satisfaction of having a backup umbrella on a day everyone else gets drenched. That tiny victory, that quiet "I told you so" to the universe—that's the allure of our mental gymnastics. It’s not about wanting things to go wrong; it’s about the profound comfort of knowing you’ve got a plan B, C, and possibly even a Z tucked away. While the relentlessly optimistic might see this as pessimism, we know better. We're not dwelling on doom; we're simply… prepared.

Enter: negative thinking. Often dismissed as pessimism, it’s actually one of the brain’s oldest survival features. Turns out, negative visualization isn’t self-sabotage. It’s self-preservation—and when done right, it’s self-liberation.

Welcome, fellow contingency connoisseurs. This is an invitation to play with your inner skeptic and explore the illuminated corners of "what if", where anticipating the worst could possibly illuminate your path to the best.

Who’s Playing

This game isn't for:

• The truly paralyzed by their anxieties (we're aiming for proactive, not petrified)

• Those who genuinely believe the sky is always falling (we're pragmatists, not prophets of doom)

• Anyone who uses "what ifs" as an excuse for inaction (we're all about planning and doing)

It's perfect for:

• Anyone who sleeps soundly knowing they have an emergency kit for every eventuality

• Anyone who secretly enjoys the intellectual puzzle of problem-solving before the problem even exists

About the Game

Defensive Pessimism

Psychologists Julie Norem and Nancy Cantor coined this term in the 1980s after observing a curious pattern: some high-achievers worried excessively before important tasks—but used that anxiety to prepare meticulously. Instead of pretending everything would be fine, they visualized what could go wrong—then created solutions in advance. The result? Better performance, less regret, more control.

This mental jiu-jitsu turns anxiety into action.

Pre-Mortem

Developed by cognitive psychologist Gary Klein, the pre-mortem flips traditional planning on its head. Instead of asking, “How will this succeed?”, you ask, “It’s one year later, and this totally failed—why?”. Teams that ran pre-mortems made more realistic plans, spotted weak spots early, and avoided wishful thinking traps.

It’s like future-you whispering warnings back through time.

Stoicism

2,000 years before modern psych labs, Stoics like Seneca practiced premeditatio malorum—imagining worst-case scenarios, not to wallow, but to disarm them. Paradoxically, contemplating negative possibilities can actually enhance our appreciation for the present.

The contrast between the imagined negative and the current reality can amplify feelings of gratitude and contentment.

Control

Uncertainty breeds anxiety, but our brains crave control, and so the feeling of preparedness, even for negative outcomes, can be remarkably soothing. When we mentally play out "what if," we're essentially running simulations, giving our brains a sense of familiarity and potential mastery over those scenarios. This imagined control can significantly reduce actual anxiety when facing the real deal.

Think of packing for a trip. The "what if I need a sweater?" or "what if it rains?" thoughts might seem like minor inconveniences, but the act of packing those items provides a tangible sense of control over potential discomfort. Our brains apply this same logic to larger life events.

Problem-Solving

The "what if everything goes wrong?" scenario is, at its core, a problem-solving exercise. The mental workout of considering potential roadblocks, brainstorming solutions, and developing contingency plans strengthens our problem-solving muscles, making us more adaptable and resilient when unexpected challenges inevitably arise.

It's like a mental fire drill. You don't want a fire, but practicing the escape route makes you far more likely to navigate it successfully if one occurs.

The Rules

Rule 1: Give Your Anxiety a Job

Don’t silence your dark voice—assign it a role. Treat it like a paranoid intern: annoying, but sometimes right. Let it audit your plan, poke holes, run drills. Your optimism makes the plan. Your anxiety pressure-tests it.

Rule 2: Fail on Paper First

Before you take the leap, simulate the fall. Use the pre-mortem. Ask, “How could this fail catastrophically?” Write it out. Not to scare yourself—to spare yourself. This is fireproofing, not fear-mongering.

Rule 3: Visualize the Suck, Then Shrug

Use negative visualization intentionally. Close your eyes and imagine the pitch bombing, the date ghosting, the rain ruining your wedding. Then notice: you're still here. Still breathing. Still sipping overpriced coffee. It didn't kill you — it just built calluses.

The Science

Cognitive Reappraisal

According to Stanford researchers, when we mentally rehearse bad outcomes, we weaken their emotional punch. This rewires the brain to handle stress with more calm and less cortisol. It's exposure therapy for the soul.

Anticipatory Dopamine Release

Neuroscientist Tali Sharot found that anticipating both good and bad outcomes stimulates the brain’s reward system, since the act of formulating a solid contingency plan triggers a small release of dopamine, reinforcing the feeling of safety. When we plan for worst-case scenarios, we’re not depressing ourselves—we’re giving our brains closure loops.

Locus of Control

Psychologist Julian Rotter’s research showed that people with an internal locus of control—those who believe they can influence outcomes—report higher wellbeing. Constructive pessimism tricks the brain into shifting from helpless to helpful. You’re not spiraling, you’re steering.

Power Ups

If-Then

For key goals or potential challenges, create a series of "if [negative event happens], then [my action will be]" statements. This turns abstract worries into concrete action plans.

Reverse Brainstorm

Instead of brainstorming ways to succeed, brainstorm all the ways you could possibly fail. Then, develop strategies to prevent each of those failure points.

Feedback

Share your "what if" scenarios and contingency plans with others. A new set of eyes always helps gather valuable perspectives and identify blind spots.

TL;DR

Negativity isn’t always noise. Sometimes, it’s the prelude to clarity.

• Visualizing failure makes you more prepared — and paradoxically, more calm

• Defensive pessimism isn’t giving up — it’s gearing up

• Mental rehearsals of disaster build emotional resilience

• Planning for the worst opens the door to actually hope for the best

So go ahead. Ask, “What if everything goes wrong?”. Just don’t stop there.

See you for our next playdate.