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"What-If" Thinking Can Be Harmful

we can't change the past
❝We cannot change the cards we are dealt, just how we play the hand.❞ -Randy Pausch

It's raining out as we sit outside underneath our awning. The rain prevents us from having a campfire, but we're grateful that this awning is keeping us dry. We're talking about our day. We are in southern Indiana, and earlier today, we visited a couple of wineries.

There are more wineries in Indiana than I thought there were. It's nowhere near California's level, of course, but there are a lot more than we have back in Minnesota. After researching the wineries that were a reasonable drive away that also allowed our dog Bingo, we settled on three wineries that we could check out.

After such a great experience at the first winery we went to, we decided it probably made more sense to spend more time at two wineries instead of a little bit of time at three wineries. So we chose to skip the middle one and go straight to the third.

The second winery we went to - the third on our list - wasn't as fun. It was right on the highway, and their patio was more crowded. The tasting felt more rushed even though it was free, and there was more of a salesy vibe.

As we're talking, we thought that we probably screwed up. We should have gone to the second winery and skipped the third one. The first one was so great, and the third one was a drag. If only we had done things differently, we would be happier with our decision.

A little bit of regret showed up as we're talking. Then it hit us. We can only know this because we made the decisions we did. We only know this because of hindsight. Had we went to the first and second winery only, we would be back here wondering what it would have been like had we gone to the third.

What-ifs rarely do us any good.


Thinking about what could have been or what never was is so common that it has a name. Counterfactual thinking refers to thinking about these alternate realities.

This can be healthy if we are using downward counterfactual thinking. In other words, if we are comparing where we are now to various scenarios where we would have been worse off than we are now, then we can appreciate where we are. This is what gratitude is all about.

As good as gratitude is, that's not how most of us engage with counterfactual thinkin