The Wisdom of the Trickster

broken image

A few months ago, I couldn’t get myself to do any work. I was in a really rough place. I was broke. The company I had been working for had gone under. I was a consultant so was being paid below market rate and was banking on the company raise Series A funding. The CEO called me one day and told me that user growth wasn’t strong enough and that the funding wouldn’t come through and they would be shutting the company down.

The weird thing is I knew this was a likely outcome. When I had come on board, the CEO (who is a friend of mine) had been pretty honest and transparent about how much runway we had and that the plan was to to see if this idea worked or not. I had been consulting at this company for about 5-6 months and I couldn’t find the motivation to look for other jobs. I would just not feel like doing work. Even doing the consulting work was de-motivating. And this boggled my mind. Why was I feeling this way? I had a shot to enter a new industry and I was blowing it. I had worked really hard to get this consulting job and now I got it. Isn’t this what I wanted? I wanted to enter crypto currency because it was going to be the next big thing.

In Jungian psychology there is this idea that we are made of sub-personalities that are vying for dominance. And that unbeknown to our awareness the sub personalities drive our actions leading to the phrase: “you are not the master of your house”. These sub personalities can often be given common names and themes as they recur as motifs throughout history. The trickster, also called the joker, is one such character.

In its benign manifestations, the trickster plays tricks and make jokes. Among a group of guys its usually the dude who is playing pranks. A more refined trickster is also a truth teller. It is Feste the fool in Twelfth Night that in jest tells Olivia that she is the fool for wasting her youth mourning her dead brother if she believes he is in heaven, and to Orsino that his love for Olivia is fickle. The auto-biography “Surely you must be joking Mr. Feynman” shows Richard Feynman embodying this role. Famous for being a merry prankster, we also know Feynman as someone who was able to tell profound truths about the physical laws of the universe.

The Trickser’s darker parts can also be used to manipulate and sabotage other people. In the Marvel movie series Thor’s brother Loki is an example of this. He is deceptive, shapeshifting, manipulating and sabotaging plans.

The trickery of the trickster can be directed outwards but your trickster can also sabotage you. It shows up when you are working on an important project and your attention is swayed towards something else. Perhaps you are at a sales job and you keep messing up and sabotaging your very important sales calls, or you feel fucking demotivated doing an important assignment in your marketing job.

Robert Johonson, a Jungian psychologist, relates:

When I first became an analytic psychocologist, I often had to work in the evening. Many of my patients worked during the day and could only come in the evening or on weekends. It was not a bad schedule since I had my days free, but for some reason I resented it bitterly. Some inner part of me was used to having my evenings free for me – for visiting friends, socializing, music, personal life.

The childish part of me was furious. And the unconscious, irrational resentment found its way into my practical life. I was irritable to my patients. I almost forgot appointments. These are the kinds of things that happen when someone in the unconscious is absolutely opposed to what the ego has set up.

I took this problem to Active Imagination [a Jungian technique]. I looked for that part of me that was angry at my work schedule. The image that came up was a spoiled adolescent. He said: “No! I will not work in the evening. That is feeling time. That is fun time. That is human being time. That is not work time, and that is final!”


I found this passage towards the end of a year where felt unproductive and inefficient. Through the year, I could see the money dwindle in my bank account. I knew I needed to apply for jobs but I just didn’t feel like it. I didn’t feel like doing anything. I went on long walks and took long hot showers. I felt a little depressed by the fact that I couldn’t do anything. It is easy to be hard on yourself. Especially when you compare yourself to other people who are getting so much more done. The whole situation sucked. And the fact that I couldn’t do anything about it sucked.

Around the same time I watched myself procrastinate. What would I do when I was procrastinating? I found that I got more and more interested in Jungian psychology and would read up on it anytime I was procrastinating. I learned about Jungian archetypes and the trickster. And I began to wonder if there was a trickster in my psyche that was sabotaging me. I came across the above Robert Johonson passage. In it he continues on how he resolved it:


So I set up a long conversation with him. I explained and explained: “Look: We have to make a living; we have to earn money or both of us will be out on the street and hungry – you included. Since we are just starting in the profession the only patients we have at this time are those who come in the evening or on weekends. That is the practical necessity. It has to be done.”

At first he wouldn’t budge. I said: “Look, we have to pay the rent.”

And he said: “I don’t give a damn about the rent. I just want to have fun. And that’s what I’m going to do.”

I said: “But I do care about the rent.”

And he said: “That’s tough. You go worry about that.”

I said: “I can’t work and earn a living if you are going to sabotage everything and make me moody and resentful all the time. It affects the patients. I forget things. I put appointments in the wrong places.” All of this was true. There was general chaos because such a large part of me was in rebellion against my work.

Finally I got this fellow by the throat–- in my imagination of course — and up against the wall, and I said: “You’ve got to listen, or we are in bad trouble. Now, what kind of deal, can we make?”

So the following horse-trade developed: He agreed that if I would go to a drive at 10:00 every night and have a nice meal and take him to a movie a couple of times a week after the patients were gone, then he would keep off my back the rest of the time and let me work in peace with my patients. For many months it worked that way. As long as I gave him his meal out, and an occasional movie, he was happy and he let me work. But if I missed one of our meals out, this juvenile would be irritable the next day. He would make me resentful and forgetful in my work. It was incredible to me that this character had so much power over my moods and my functioning. But he did.


There are two interesting parts of this story. First that the childish part who was playing tricks had some wisdom to convey. The second was that once it was heard, it could be negotiated with.

Reading this story made me ask myself, if there is a part of me that’s sabotaging me, what is it trying to get me to pay attention to?

I asked this question for a few days, until the answer came to me.

I’ve always wanted to write. But I’ve always made it a second priority in my life. I think part of what stopped me from writing was that putting constraints on my writing killed my soul. In my head I made a pact with myself that I would only write safe things like business and not touch on things like masculinity or religious topics or inner work. Fuck that. I am going to write whatever I feel like writing about. Now there is a pragmatic part of me that’s made this deal, that I will write about whatever I want to write about for myself, but before I hit publish I give the pragmatic part of my personality leeway to say ‘not now’. Or if I do publish something controversial I’ll be razor sharp in my arguments so that I have the conviction to stand by them. Writing also gives me the freedom to have experiences and learn new things and write about them. My current pact is to write for 15 mins a day at least on anything I want to.

And then, I fucking love talking to interesting and people and their stories. I want to broadcast them. I have a knack for finding interesting stories and angles. I want to interview people and broadcast their stories.

This realization also means that I’ll have to give up a few things. Part of me in my 20s fantasized about starting a venture backed startup, going to Ycombinator and growing it into a multi-million dollar business. I want to be the in-it guy whose doing a crypto currency company. I’m going to give that up in order to pursue this goal of being a writer and broadcaster. Even more, what I’m realizing is that I don’t want a lot of uncertainty in my day job. I don’t want to work for a company that could go under in a few months. I want structure and a company that provides mentorship so that I can have the freedom to have interesting experiences outside of work and write about them.

Once I accepted this fact, a huge weight lifted off my shoulders. My productivity went up again. Not only was I writing again but I was thinking of new ways to apply for jobs as well. Since I don’t want to get paid for writing because that will stop me from being creative, all of a sudden having a career where I did well was extremely important. It would allow me to focus on writing, and the discipline of doing well in a career would transfer over to my writing. Yeah I still have the occasional day where I’m scattered. But I have focus and motivation that were previously only present when I had extrinsic accountability. There was wisdom in the trickster sabotaging me, and in a weird way I’m grateful for it.

[1] Inner Work by Robert Johonson

[2] There is nuance here because you will never be 100% into your work at all times but tracking this over many months is helpful