In a recent article, I wrote:

“Should” is a moral concept. When you say you “should” do something, you are saying it is the moral thing to do. If you, as I, ascribe to the moral code of rational egoism, “I should” means:

Based on everything I know, including all of the values I hold most dear, plus my thoughtful observation of the present circumstances, the following action is in my best interest, and as a consequence, taking this action now rather than delaying or doing something else is the most likely option to leave me both satisfied at the end of today and happy over my lifetime.

I mentioned in that article that some people would need to automatize a new meaning of “should.” In the meantime, “should” is likely to keep coming up in confusing ways, especially in the realm of self-improvement. 

For example, a Thinking Lab member asked me, “Should I spend time fixing the fact that I overthink things?” Let’s call her Amabel. The short version of my answer is that I don’t believe you ever should set a goal to “fix” yourself. Rather, you should set a goal to create something in the world that matters to you. Along the way you will gain the knowledge, skills, and values that, as a side effect, eliminate problems that might be described as “I overthink things.”

And yes, I am using the word “should” in the moral way I explained above. 

My advice is counterintuitive to most people. So let me concretize how and why this approach would help you sidestep many, many problems that arise if you hold the issue as, “I need to be fixed.”

First of all, I would assume there is a real issue that is bothering Amabel, which she has conceptualized as “overthinking.” But I wouldn’t assume I know just what that is. I would ask her to come up with a specific case in which this alleged “overthinking” is getting in the way of some real result.

People often reach general conclusions about their strengths and weaknesses that are based on false assumptions and mistaken theories. This is an innocent error, which they may very well remain unaware of, until they find themselves in a concrete situation where the contradictions become apparent. 

That’s why the most effective way to grow psychologically is to focus on acting in reality. When you take action based on your assumptions, you get a reality-check with every step you take. 

In Amabel’s case, I saw a mistake. The question “Should I be fixing the fact that I overthink things?” implies that “overthinking” is some kind of personality trait or settled fact about onself.

This makes no sense to me. I don’t believe that “overthinking” is a valid concept, much less that it can be a personality trait.

Thinking is a highly purposeful, reality-focused process. Part of thinking is keeping it on track in an effective way. 

This woozy term, “overthinking,” likely refers to such things as compulsive ruminating, fear of making a decision, or wallowing in confusion. Amabel was likely seeing a pattern of wasted time in mental activity. That activity might superficially resemble thinking, but “thinking” should be reserved for the purposeful process that these are not.

Indeed, all of these problems are best addressed through actual thinking, especially thinking with the goal of identifying your feelings and why you feel them, i.e., introspection. If you conceptualize these problems as overthinking, you confuse the issue. 

But obviously Amabel didn’t see that, or she wouldn’t have phrased her concern as she did. 

Proper advice on self-improvement should accommodate the possibility that what you think you should do is based on a mistaken idea. Amabel can’t be expected to recognize the logical error in her analysis or sort out a theory of “overthinking” in order to move forward. Fortunately, in order to grow, all she needs to do is to identify some real, concrete situation in which “overthinking” appears to be the problem, and sort that out. 

I’ll switch to my own real example now, so you can see how the right method enables you to move forward effectively.

I cast my mind back to an example of “overthinking” in my life, and “reviewing the week” popped right into mind. When I first attempted planning my week, 20 years ago, I had a lot of difficulty. I tried to follow the method recommended by David Allen for a weekly review, and it was overwhelming. I would get bogged down in the details for hours. Literally eight hours on more than one occasion. Either I’d give up without finishing, or I’d be demoralized by the huge lists I created. 

Once you have a concrete case, you need to identify the values at stake, i.e., the positive result you want to create. 

In this case, the problem I saw was that I was wasting my time. But that is not a positive. That is a negative. 

In a similar situation, Amabel saw the problem as “overthinking,” also a negative.

When your goal involves removing a negative, it focuses your attention on your flaws, weaknesses, and areas of ignorance. That pretty much guarantees you’ll feel helpless and hopeless, not a good foundation for making life-serving changes. It also leaves open what would count as a solution. You can stop wasting that time by just stopping the weekly review, but where would that leave you? You can stop overthinking by stopping thinking, but where would that leave you? 

As an engineer, you learn it’s not enough to solve a problem. You need to solve the right problem, and you need to do that without creating new problems for the manufacturing department, the budget keepers, or the end users.

You do this by identifying the positive result you want to create. In this case, I wanted to use the weekly review to make my whole week more productive than if I hadn’t done it. 

When I held my overall productivity as a goal, I came up with a simple heuristic: spend no more than 10% of my time reviewing/planning. I gave myself 30 minutes a day for daily reviewing/planning, and an extra 30 minutes once a week for my weekly review. Just by knowing the positive goal, I could find a way forward that I knew would be likely to pay off. 

In other words, I set a goal that I could adapt to my current level of knowledge and skill. What I do during my half-hour has evolved over time as I have developed more skill at working on a schedule:

1. Just review the task list and calendar and note any special considerations
2. #1 plus identify the top 3-6 tasks to get done in the upcoming week
3. #1 and #2 plus compare the top tasks with the calendar and verify there is time for each of them
4. #1, #2 and #3 plus assign tentative goals for each day of the week

Someday I expect to get to the next level:

5. #1, #2, #3 and #4 plus schedule when I will do the top tasks

By keeping my eye on the positive result I wanted to create, I was not tempted to wallow in confusion for eight hours trying to review my week according to some process that someone with very different skills and priorities found useful. I was not tempted to chastise myself for “overthinking.” I was able to come up with a simple way forward that was consistent with my current abilities. 

That is the way to self-improvement. Pursue positive goals that you care about, then adjust the way you pursue them to take advantage of your existing knowledge and skills.