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How to Stop Overthinking for Every Thing

How to Stop Overthinking for Every Thing

Take a second to imagine an alternate version of your life, one where you always knew the right choice to make given any decision. And this version of your life would be pretty awesome, right? Not only would you always make the right choice, which would mean that you’re probably a billionaire at this point, but you also wouldn’t spend a whole lot of time deliberating over your choices. You would always see the right one and instantly pick it.

Now, provided that you are not Dr. Strange, that you can’t simply look forward into the future and see which path you should take, you’re probably like the rest of us. You don’t always know the best decision to make, and if you’re anything like me, that means you overthink your decisions more often than you would like. You get caught up in analysis paralysis, and that’s the problem that I want to tackle in this article because overthinking can be a huge detriment to our lives.

It can cause us to procrastinate more than we want, it can cause us to completely set decisions aside because they’re too stressful. And most importantly, it can cause us to miss out on fleeting windows of opportunity that don’t stay open forever. In our pursuit of finding the best option, we often lose out on that best option because we hesitate too much. And as I see it, overthinking is actually underpinned by a few more fundamental problems related to decision-making.

Three of the biggest are fear in the decision-making process and abundance of choice which can paralyze us. And a lack of proper prioritization, which doesn’t give us clear direction.

So, what I want to do in this article is share some strategies, and mindset shifts, and mental tactics that you can use to maybe not fix these problems entirely, but reduce their influence in your life. And the first one that I want to talk about is a mindset shift that I think is the most important one you can make for becoming more comfortable making decisions and being able to make them more quickly, and more confidently.

I. The Set-Path and Experimental Outlooks

And that is making a mental shift from what I call the set-path outlook to the experimental outlook. The set-path outlook is the thought that whatever decision you make right now is going to lock you onto a path for the rest of your life. It’s kind of like choosing to get on a roller coaster, you make the choice to sit in the seat, you bring the bar down at ratchets, stick you in the seat, and then you’re on a track.

It’s gonna take you somewhere you cannot deviate from the set-path, but most of the decisions we make in life are not like that. There are a few, yes. If you are standing at the very edge of the Grand Canyon, then the cardinal direction of your very next step has the potential to be pretty life-altering. But for the most part, the decisions we make in our lives, don’t set us upon a completely fixed set-path.

We have the ability to pivot and iterate upon our decisions at the next junction point. That’s the crux of the experimental outlook, viewing decisions as experiments, being like a scientist, realizing the choices we make are going to get us consequences or rewards in the short term, maybe both. They’re also going to get us data, They’re gonna get us information that we could not have gotten otherwise, which will allow us to pivot and go onto a new path if we don’t like the one that we see ourselves on. And this applies not only to small choices but also to big ones, ones that feel monumental in the moment.

I remember when I was a freshman in college, I thought my choice of major was gonna set me on a path for life, and I felt that I had to pick the right one the first time, otherwise I would screw up my entire life. Well, the major I picked, MIS, was really intended to get me into a corporate job, running their computer networks and now I’m making articles. And data even shows that a third, a full third of college students change their major within the first three years of enrolling.

I didn’t change my major, but I still pivoted nonetheless. So, if something that monumental could be pivoted and iterated upon, most of the decisions that you are faced with on a day-to-day basis can be as well. To go back to our analogy, most decisions are not like getting on a rollercoaster with a set track, but more like getting onto a ski slope.

Yes, once you have picked her out to go down, gravity makes it pretty tough to crawl back to the starting point. But as you’re going down you have agency. You have the ability to turn and pivot and choose where you’re going to end up making small adjustments in the middle. But, how do you adopt this mindset into your life in the first place? How do you get comfortable with it? Because it’s not like an on/off switch in your head, right?

II. Incomplete Information: The Poker Mindset

One of the first steps in becoming comfortable with the fact that almost every decision in your life involves incomplete information.

Or to put it as. Annie Duke does in her book, “Thinking in Bets.” “Life is more like poker than it is like chess.”

See, in chess, you almost have perfect information when you’re playing, you can see every possible move on the board that you could make and that your opponent could make. There is almost no hidden information in the game, which means that there’s almost no luck. But poker and life are very different, in poker, you can never be 100% certain of the cards that your opponents are holding. And only a couple of circumstances can you be confident that you have the best hand at the table.

In most cases, you’re gonna have a losing hand. So, successful poker players have to, number one, become okay with the fact that they are going to lose more hands than they win. They have to work against the natural loss aversion that all humans experience, but they also have to become okay and comfortable working with incomplete information.

They can do certain things to get more information, they can be very observant about the way their opponents bet, they can try to read tells and body language, but they’re never gonna be 100% certain. And that is how we need to look at our decisions as well because that’s how pretty much the entire world works.

Richard Feynman once said of science, “Statements of science are not of what is true and what is not true, but statements of what is known to different degrees of certainty… every one of the concepts of science is on a scale graduated somewhere between but at neither end of, absolute falsity or absolute truth.”

And if we can become comfortable with that fact in our decision-making process, and with the fact that the results of our decisions may not always be optimal even if our decision-making process was sound, then we’re going to be more confident and able to make decisions in the first place.

III. Dealing with Too Much Choice

So, now let’s talk about the second problem we listed at the beginning of the article, the abundance of choice. Now, having a lot of choices seems like a good thing sometimes, but when you have too many choices, it can become a bad thing as anybody who’s ever played with a Reliquary Tower and Magic Gathering knows.

And that’s because the more choice you have, the longer it often takes you to make a decision. In fact, there is a psychological principle called Hicks Law that describes this. As more and more stimuli are added to a pool of choices, the longer and longer it takes the subject to actually make a choice. And this hesitation isn’t the only problem associated with the abundance of choice.

As Sheena Iyengar wrote in one of her research papers on the paradox of choice and analysis paralysis, “The presence of more choices has been associated with lower chooser confidence and greater experiences of negative effect; that is, people choosing for more extensive choice sets are less satisfied with their decision outcomes and pay more for purchases that make them less happy.”

She’s also noted that the abundance of choice can often push people to never make a decision at all. With her biggest example, being retirement savings options, people are often so inundated with so many different investment choices that they never choose anything, and they never save for retirement. The worst possible decision, barring putting it all on black in Vegas or something.

So, this abundance of choice that we often think is a good thing, can not only cause us to hesitate and put off important decisions, sometimes indefinitely. But it leads to us being less satisfied overall with our decisions, and it can cause us to spend more money on things that ultimately don’t matter. And this leads to a conclusion if you want to overthink less often, and if you want to be more satisfied with your decisions, you should restrict your choice pool, do it deliberately.

For example, say you want to buy a new TV. What do you do? Well, most people are probably gonna go on the internet and start reading TV reviews, but that exposes you to pretty much every TV you could buy, and it exposes you to hundreds, or thousands or millions of different opinions, spec sheets, fact listings, and you could spend the rest of your life if you wanted to go through and comparing side-by-side all of these TVs with their different specs. And maybe you’re going to get the best overall TV at the end of the day if you do that.

But again, the research shows we’re gonna spend a lot of time hesitating, we’re going to waste a lot of time comparing things that ultimately don’t matter. And we’re probably gonna convince ourselves to buy a TV that’s more expensive than we really need. So, maybe what you should do instead is just walk into Target or your local electronics store and buy whatever TV looks good on the wall. Are you going to get the TV with the absolute best contrast ratio, and lag time, and all that kind of stuff?

Probably not, but ask yourself this, six months down the line when you’re watching a movie on your TV that you’ve had for a while, it’s up on the wall, you’ve gotten rid of the box and all that. Do you care about those features? Cause personally I don’t, the TV I have today is much, much better on a technological level than what I had when I was a kid watching TV at my grandma’s house. But, if I really asked myself, honestly, I’m no happier watching TV on that big, fancy flat-screen than I was watching TV on the gigantic furniture box my grandma had.

The overall happiness level is really the same at the end of the day. So, restricting my choice pool in this example would save me a lot of time, and probably save me a lot of money, and my overall satisfaction would be higher. Now, the third major problem that we talked about in the intro was the lack of prioritization. This can cause overthinking just as much as the abundance of choice, and fear, in the decision-making process.

How many times have you woken up with a task list that has five or 10 items on it, and you’re not really sure of which one to start with. None of them have a hard deadline, so you spend a bunch of time procrastinating, just trying to figure out where you should start. That’s a lack of priorities in action. And actually, the last example we just went through has an application of the tip that I’m gonna share with you,

IV. The Regret Exercise

Which is to go through what’s called the regret exercise. This is a great way to set your priorities, even if they are not clear in the present moment. And this involves mentally fast-forwarding to the end of the day, or the end of a specific time period, and asking yourself, what choice would I regret the most here? So, in the case of having a to-do list, if you’ve got 10 items on the list, mentally fast forward to the end of the day and ask yourself, which of these things would I regret most not getting done?

And once you have your answer, you know what you should start working on right away. But the regret exercise works for longer time periods as well. Personally, I always wanted to take vocal lessons, but I was always really scared to do it. I was scared to embarrass myself, and I also had this little feeling in the back of my head. Like, I don’t have a good voice, it’s not even worth going to try to develop it because I’m not naturally a good singer.

But then I asked myself, you know, I mentally fast-forwarded to myself at 80 years old and asked would I regret never taking vocal lessons? Never trying. And the answer was an absolute yes, which is something that I wanted to do. And by mentally fast-forwarding out of my present moment, I was able to get clarity on that question, the answer to it was so much stronger. So, that pushed me to go and take my first lesson, and I’m really glad that I did. And going back to that TV example, I mentally fast-forward it to a period six months after I bought the TV in my head and asked, do I really care about the contrast ratio?

Do I really care if the TV is 70 inches or 65 inches? No, I don’t. So, I should just go to Best Buy and buy whatever looks good. The regret exercise is very powerful and it’s a great prioritization tool. Now, we have gone through some pretty powerful decision-making tools in this article, we talked about the experimental outlook, versus the set-path outlook.

We talked about getting more comfortable with incomplete information like a poker player versus a chess player, we talked about the abundance of choice and purposely limiting your choice pools. You hesitate less and you’re more satisfied with your decisions. And we also talked about getting more clear on your priorities utilizing the regret exercise. And these tools, while powerful, are not the only decision-making tools out there. This is a lifelong pursuit, becoming better at decision-making.

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