How to Stop Obsessing Over "What If"?

Here's what's happening in your head, and how to finally move on.

Have you ever done something, and it didn’t go as well as you hoped, and then you started obsessing over it?

Like, you went through every detail over and over, imagining all the ways you could have done better?

I did this recently. It got bad. Eventually, I started to research what was happening to me, and discovered the scientific term for it:

Counterfactual thinking.

Then I wondered: How do I make it stop?

So I called around, spoke to some psychologists who specialize in this area, and got answers.

In this newsletter, I want to share what I learned — because it helped me feel better, and I think it can help you feel better too.

My trip into Counterfactual Crazyland

About a month ago, I went on Gary Vaynerchuk’s podcast to promote my book.

Gary was nice as always. He asked good questions. We spoke for 30 minutes. But the whole time, I felt like my answers were flat. My points were disjointed. I just couldn’t find my footing. I don’t know why — it just wasn’t my day.

We taped it remotely, so when it was over, I was just alone in my bedroom. I started pacing. Then I started talking out loud. “It was fine,” I started to tell myself. “It was fine, it was fine.” But I didn’t believe it was fine. I kept thinking about all the things I could have done better. The smarter answers I could have given. The opportunities I missed.

I felt empty. Obsessed. I could not let it go. It went on like this for a week.

“What is happening to me,” I wondered? That’s when I Googled around and discovered the term: counterfactual thinking.

What’s that?

“Negative events prompt us to think about what could have been different,” says Amy Summerville, Ph.D., a social psychologist who studies decision-making and regret. “We want to reinvent—how could I have avoided this bad thing?

There are a couple major things that trigger counterfactual thinking, she says. They are:

  • Proximity. The closer you feel to success, the more you’ll obsess over how you didn’t succeed.

  • Routine. If you usually have a routine, and then you fail after deviating from that routine, you’ll believe the deviation was to blame.

  • Control. If you’re a person who usually feels in control, you’ll be kicking yourself for how you could have done something different.

I can relate to all of that. Amy says that checks out:

“So this sense that, ‘Oh, this is controllable’ certainly seems like something that entrepreneurs think a lot of the time,” she says. “That would therefore lead you to say, ‘Oh, I should have controlled this thing and I could have acted differently to change this.’”

So what can we do to stop obsessing?

Unfortunately, there are no perfect answers. Amy said we know a lot more about why it happens than how to stop it.

But she had a compelling way to reframe the experience in your mind.

“If it was not important, you would just get over it,” Amy says. “So I think you need to accept—that's just the price of caring.”

I really like that phrase: That’s just the price of caring.

To care about something is to ride its ups and downs. I’d rather feel attached to the thing I care about, than to feel detached about something I don’t care about.

But of course, that’s cold comfort in the moment of a counterfactual freakout. So here’s something else:

“The trick is — and this is going to sound a little funny — but the trick is to consider additional alternatives. Consider other counterfactuals,” says John Petrocelli, Ph.D., a social psychologist and professor at Wake Forest University, who studies this subject.

Here's why, John says: Our counterfactuals are built on faulty premises.

For example, I was recently talking to a founder who had a high-stakes call with an investor. The investor ultimately passed on the deal, and the founder has been obsessing over how he answered one of the investor’s questions wrong. If only I'd given a better answer, he kept telling me.

But is that true? Would the founder have gotten the deal, if only he’d answered that one question correctly? There is no way to know. Maybe that founder’s answer was actually perfectly fine, but the investor just didn’t like the company. Or was feeling grumpy that day. Who knows! We cannot know.

That’s the thing — we’re often so sure about how we could have made a situation better, but we’re only guessing.

We've obsessing over a guess. We're obsessing over something we might be very wrong about.

That’s why John’s advice is so smart. Instead of fixating on one counterfactual that has no basis in reality, drown it out with more counterfactuals. Consider many more outcomes. Other ways it could have gone wrong. Other things you could have done. Prove to yourself that, hey, you did your best, and there’s no way to control for every outcome.

After all, that’s just the price of caring.

Want to know more about this? I dig much deeper — including more solutions, and why our brains engage in counterfactuals in the first place — in the latest episode of my podcast.

Can I Ask You A Favor?

How to Stop Obsessing Over "What If"?

Here it is: Would you review my book on Amazon?

It doesn't matter if you bought it on Amazon. If you've read or listened to it (or intend to!), please go to my listing page here, then scroll down until you see the "Customer reviews" section, and then click "Write a customer review."

Why? I will be straight-up honest with you...

Reviews help a book become more visible on Amazon. That's why every author seeks them out. In fact, when my book launched, my PR team told me to round up 50 reviews within the first few weeks. But guys, real talk: I was so completely overwhelmed with everything I had to do (and am still doing!) to launch this book, that the whole Amazon review thing just fell by the wayside.

A lot fell by the wayside, actually. When people ask me what I wish I knew before launching a book, I'd have said: I wish I fully understood how quickly I'd run out of bandwidth. I'm not exactly sure how I'd have solved that problem. But it would have been good to know! I will surely write more about this later.

Anyway, point is: If you review the book on Amazon, I owe you one. Thanks! 😁

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Cover credit: Getty Images / Klaus Vedfelt