Just before the holidays, I ordered a tablet for a work project. There was a seasonal promotion running at the time: buy the tablet, get a free wireless keyboard.
In my multitasking, list-checking, end-of-year rush, I forgot to add the keyboard to my order.
A couple of weeks later, after the tablet arrived, I went online, navigated past the relentlessly cheerful chatbot, found a real human customer service agent, and politely asked about the keyboard.
“Not to worry,” he said. “I’ll raise a case, and you should get an email within 48 hours with a special promotional link so you can buy it for free.” The email never came.
After multiple follow-ups, long holds, sincere apologies, and escalating case numbers, I finally received an email informing me that I could, in essence, go pound sand. The free keyboard offer was only applicable if it had been part of the original order.
It’s been two weeks since that final answer. I am still thinking about that keyboard. Engaged in a what-if trap.
Here’s the thing: I don’t need the keyboard. I have no use for it. I don’t even want it. But I have now fallen into the far more dangerous trap of standing up for principle.
If the first agent had told me I didn’t qualify, I would have walked away. Case closed. Sure, I might have spent a few minutes berating myself for not adding the accessory in the first place, but I would have gotten over it. Instead, the idea was introduced, encouraged, and briefly made to feel possible, then withdrawn.
And that’s where things went sideways.
“The pain of losing is psychologically about twice as powerful as the pleasure of gaining.” Daniel Kahneman
Psychology explains this rather inconveniently well. If something is completely out of reach, we tend not to care. But when we think it could be ours, especially when someone reaches out to offer it, then reneges, the loss hits harder than logic would suggest.
This is loss aversion at work. Once something feels possible, or briefly ours, the brain treats its removal as a loss rather than a neutral outcome. Losses hurt more than gains feel good.
But even more than loss aversion, what keeps this ridiculous keyboard alive in my head is another familiar psychological culprit: what-ifs.
Behavioral scientists call this counterfactual thinking—mentally constructing alternatives to events that have already happened. What if I had clicked one more checkbox? If only I hadn’t rushed. What if that first agent had been right?
These thoughts show up most intensely when an outcome was close, personally relevant, and contingent on a tiny change. Missing a flight by five minutes hurts more than missing it by an hour. Being offered something and having it withdrawn hurts more than never being offered at all.
This isn’t a character flaw. It’s how the brain learns. Counterfactuals evolved to help us refine future behavior by simulating alternate paths. The problem is that the same mechanism that helps us learn can also trap us in regret.
It’s like watching a replay of a game your favorite sports team lost, convinced that this time, something pivotal might change.
Psychologists distinguish between two kinds of what-ifs:
- Upward counterfactuals (“If only…”), which are linked to regret, sadness, and rumination.
- Downward counterfactuals (“At least…”), which can increase gratitude and emotional resilience.
Like most of my what-ifs driving regret and rumination, my keyboard saga is clearly an upward one.
I’m learning to recognize when I’m in what-if mode and trying my best to replace the “What if?” with “I’m here now.” I hope that would drag my reluctant brain to the present, since rehearsing the past has, in my extensive experience, never fixed anything.
My Plan B, if my mind refuses to acknowledge the futility of spiraling in what-if cycles, is to consciously postpone the rumination. I tell myself: Between 5:00 and 5:15 pm today, we’ll deal with this. Not now. Treating my brain like a pesky relative—not never, but later—has proven surprisingly effective.
And by the time later arrives, there are usually newer, shinier what-ifs waiting for attention, often about things that matter far more than a free keyboard I never needed in the first place.