Self-Doubt and Discouragement

How to Work With Them Instead of Against Them

This is a note that I wrote to myself:

Discourage (August 21, 2023 at 10:35 PM)

I think one of the biggest hindrances to my life and my work has been that I can be easily discouraged. It is a habit that I formed long ago, probably as a way to protect myself from embarrassment or whatever. I need to learn to not get discouraged, for example I am writing an article about Joe Rogan, and there are about 1 million reasons I think of everyday that I shouldn’t write it and that it will be bad and a joke and no one will like it. It doesn’t matter. I want to do it. That’s all that matters. 

The Joe Rogan article that I mention ended up being the first edition of this very newsletter on 12/10/2023. I don’t remember exactly what was going on when I wrote this, but I suspect it went something like this - I felt I had something to say - started writing it - worked on it for a day or two - started thinking about how it would be received by the world - it began to feel like a chore to work on - I hit a wall. A wall that consists of all the reasons I should not write this thing. This is a process that has repeated itself many times before I finally broke through and hit publish on the Rogan essay. Although for me, it was not hitting publish that was the hard part. It was getting through that initial wall of self-doubt and discouragement. Instead of trying to overcome self-doubt, I have found it helpful to accept it and work through it, because as I mentioned last week, we’re all going to die, so we might as well do the things that we feel called to do. Furthermore, many of the common reasons for discouragement and self-doubt do not make sense outside of one's own head. This one piece of writing is not going to define the rest of your life. In general there is little to no downside in sharing an idea. This can apply to many aspects of life outside of writing and creative pursuits, but today I will be looking at self doubt-through the lens of writing.

Any time I start writing something, it's much easier to come up with reasons why I should not write it, then why I should.

Some of the usual reasons I come up with are:

• Parts of this will make my friends or family upset with me for expressing a view I have that they do not agree with. I will become alienated.

• Why should I bother publishing something to an audience of five people? 

• This has probably already been said one hundred times.

• I have no authority or credibility to speak on this topic.

• Maybe I’m the only one who thinks this.

• This is not a good idea, I’m not a good writer, no one will take this seriously.

Again, this applies to many aspects of life. Why should I not give this person a compliment? Why should I not tell my manager this idea I have? Why should I not start this business? Are often easier questions to answer than why should I?

In general, my experience with self-doubt as it relates to writing is equal parts - fear of my ideas being negatively received by people, and the fact that I am kind of lazy and would rather sit on the couch and watch tv than write something (this isn’t as true as it one was). I think it is possible that sometimes self-doubt is just an excuse for us to not have to do any work. Effort can be a scary thing, especially when the end result can be failure. But as I mentioned before, oftentimes there is no downside in sharing an idea, and “failure” is usually not so bad.

The best way that I’ve found to get through the self-doubt discouragement wall is to create momentum in the direction you want to go and maintain it. This can be applied to diet, exercise, work, anything. There is a great metaphor for this that I first heard via Noam Chomsky, which he calls “the bicycle theory.”

Interviewer: How do you account for your amazing stamina and energy level at age 87?

Noam Chomsky: The bicycle theory. As long as you keep riding, you don’t fall.

With the Rogan essay, I made a deal with myself based on an idea I picked up from “Atomic Habits” by James Clear. In one part of the book he talks about how the best way to create a new habit is to make it convenient and easy. If you want to meditate, start by meditating for just one minute, instead of trying to start with fifteen minutes. At first I thought this sounded dumb. Why would anyone bother meditating for just one minute? When I was stalled with the Rogan essay however, I saw the potential of this idea. My deal with myself was that I would work on the essay for ten minutes, three times a week. It usually ended up being longer than ten minutes, but occasionally if I really wasn’t feeling it, I would stop after ten minutes and not feel bad at all, I had still showed up.

Rick Rubin has some useful thoughts on self-doubt in his recent book:

Ultimately, your desire to create must be greater than your fear of it.

By accepting self-doubt, rather than trying to eliminate or repress it, we lessen its energy and interference.

He says that when creating something, if we get stuck, we need to lower the stakes, and realize that this piece of work will not define us for all of eternity; it is just a stepping stone.

As I’ve been trying to learn how to write a newsletter, I get discouraged all the time. However, after thirty-four years of life I’ve realized that my desire to write is greater than my fear of “failure,” so I’m going to keep pedaling, and hope that my words can be helpful to at least a few people.