'What-if' Thoughts and How to Deal with Them

Hey there,

Picture this: You’re sprinting across a train platform, weaving through a crowd, coffee sloshing around in a half-closed to-go cup. 

Just as the doors slide shut, you hurl yourself inside.

Heart pounding, adrenaline spiking, but—congrats—you made it! 

You plop down next to a random stranger. 

Plot twist: you don’t know this yet, but that stranger becomes your future business partner. 

Even bigger plot twist: catching that train gets you home early, where you find your partner tangled up in a romantic situation.

… definitely not what you had in mind when you craved something spicy for dinner.

Now hit rewind. 

Same day. Same train. But this time, you miss it by half a second.

No new business partner.

No heartbreak discovery.

And no chain of events that spirals your life into a late-night Google search of “can stress cause actual organ failure?”

If this sounds suspiciously cinematic, you’re not wrong.

It’s the plot of the Sliding Doors movie.

But it’s also a perfect example of our human tendency to ask: “What if?”

The Psychology of “What If”

Whether it’s the big stuff—like your career choice, taking that dream job across the country, or saying “I do.”

Or the little stuff like missing your bus stop, getting a bad grade on an exam, or speeding when you shouldn’t have been.

We’ve all wondered how things could’ve turned out differently in an alternate reality.

Psychologists call this counterfactual thinking (Latin for “contrary to the facts”)—aka your brain playing director, obsessively replaying past events under different circumstances than what actually happened.

Kinda like a toxic ex—constantly bringing up old stuff you swore you moved on from. 🤦🏻‍♀️

Sometimes, these mental reruns help you improve. Other times, they trap you in exhausting what-if spirals of anxiety, mental fatigue, and overthinking.

Where It All Begins

Counterfactual thinking lives in your brain’s prefrontal cortex—the place for decision-making. Every time you run a What if? scenario, your brain is test-driving an alternate timeline:

— What if I’d taken a different route? Or moved in with my ex?

— What if I’d swallowed my nerves and asked for a promotion?

— What if I hadn’t sent that snarky email reply that started with “Per my last message”?"

Or, if you’re more a big picture overthinker like me: “What if Elon Musk used his billions to fix world hunger instead of naming his kid a CAPTCHA code?”

A little reflection is healthy. But if you’re stuck in a coulda-shoulda-woulda loop, it can wreak havoc on your mindset.

Upward vs. Downward: The Two Modes of “What If”

Psychologists break counterfactual thinking into two types:

• Upward counterfactuals – imagining how things could have been better (this is our default setting).

• Downward counterfactuals – when we imagine how things could have been worse.

Scientific studies have proven this theory on Olympic medalists to see how happy they were with their wins. The result? Silver medalists are the least happy.

Why? Because their brains do the worst kind of thinking.

It looks like this:

— Gold medalist: “Is it just me or does this medal really bring out my eyes?”

— Silver medalist: “I was this close to gold… now I’m blinking like a malfunctioning robot, praying my deodorant can mask the scent of failure, and wondering if this anthem is 4 mins. long just to torture me.”

— Bronze medalist: Third place, baby! …which is basically first place in ‘Winning Just Enough to Brag, But Not Enough to Get Drug Tested.’

It’s counterintuitive—second place should feel better than third. But they don’t.

Because silver medalists spiral over what they lost, while bronze medalists celebrate what they avoided.

Looks like the silver medalists are basically the middle children of the podium—ignored, bitter, and one bad mood away from flipping the medal stand.

The Double-Edged Sword

So, is counterfactual thinking good or bad? Both.

On the upside, it helps us:

• Learn from mistakes – “Next time, I’ll start studying earlier than the night of the exam.”

• Make better decisions – “Maybe I won’t answer cryptic late-night texts from my ex.”

• Foster growth – “I can do better—I see how close I got. I’ll adjust.”

On the downside, it can:

• Trigger regret – “Why didn’t I do it differently?”

• Keep you stuck – Overthinking and rumination cycles halt progress.

• Distort emotions – Too much “What if?” fuels anxiety, depression, shame, and guilt.

READER POLL

The Fix: Flip the Script

So, how do you break free?

The thing is you can’t just shut off counterfactual thinking because your brain has been rehearsing counterpoints since birth.

So instead of fighting it, use it against itself.

If you’re stuck imagining how things could have been better, flip it—start imagining how they could have been worse.

This isn’t toxic positivity or pretending mistakes don’t exist. It’s balance.

If your brain insists on rewriting the past, at least give it both versions of the script.

Next time you’re rummaging through regrets like a hoarder in the attic, try this: shift to a downward scenario.

• Missed that dream job? …maybe you lucked out and dodged a workplace with mandatory trust falls.

• Got a bad grade? …at least you didn’t accidentally write your name in the professor’s “Comments” section when you told them off. 

• Still thinking about the ex? … now you don’t have to put up with a lifetime of them “forgetting” to take the trash out and you pretending to care about their fantasy football team.

Perspective is everything. Shifting it is priceless.

Use The Past, Don’t Live There

The takeaway: The past is a place to learn, not a place to live. 

Whenever you feel that “What if?” spiral tightening around your thoughts, pause and breathe. 

It’s normal. You’re human. It’s hard wired into our brains. 

But your life is happening here, not in some parallel universe of missed trains and alternative job offers.

So next time your mind drifts to “What if I’d done it differently?”—remember the train platform: sometimes missing it changes everything, and sometimes catching it does.

Either way, the only track that matters is the one you’re on right now.

Shift your focus to that.

Because at the end of the day, yesterday’s “what if” fantasies shouldn’t steal from today’s reality. 

Although, I’m still convinced there’s an alternate universe where there’s a version of me that ALWAYS chooses peace instead of texting back “K” just to start a fight…

See you next week,

Shakila

p.s. Here’s the results of last week’s poll.