How To Trick Yourself Better

The magic of a dream often collapses during the day because even the aptest dreamer cares more about the outer world than he should when he is awake. The insane are much better at this: They declare themselves emperors and their cells as their castles, and everything is wonderful. Being able to magically transform the outer world without going crazy, that is our goal. It’s not easy but, on the flipside, there’s little competition. –Hermann Hesse

We have been tricked into this. We have been tricked into putting on these fine jackets and pantsuits. We have been tricked into spending our most precious hours of warm and wondrous daylight in neon-lit rooms. We have been tricked into showing up at 9 in the morning and staying until the early evening.

We have been tricked into looking at screens everyday, in order to fill out spreadsheets we don’t care about, attend meetings we don’t care about, work on projects we don’t care about that produce results… we do not care about.

We have been tricked into accepting a 30-minute lunch break as if it was even akin to a fair deal.


There are probably two main reasons for ending up bored at a job: A lack of guts and a lack of vision.

The former is getting more attention in the blogosphere, but I guess the latter might be more common. The lack of vision is revealed when people automatically choose certain careers without really considering their options. There are many reasons for this, but I think two are of specific importance:

  1. Many get tricked by the money: You need it to fix your expensive lifestyle, and so you work. You need it to improve your expensive lifestyle, so you work more. You work more until the lifestyle you aimed for becomes a workstyle.
  2. The rest gets tricked by a more subtle promise: If you take the safe way, you might have a hard time when starting out. But wait for it. Pay your dues. Be patient at the bottom of the ladder. In the long run, you’ll get promoted. You’ll get responsibility. You’ll get more powerful and influential. And then you’ll receive the reward of working on stuff that matters.

Honestly: Does that ever really happen? Do you ever get to that point? More importantly: Once you get there, are you still the same person? Can you still relate to the ideas and the ideals that made you enter the rat race in the first place? Or will you fall into overconformity and operate in the spirit of the bureaucracy you were raised in, without reflecting on your former dreams anymore?

If you become the average of the five people you spend the most time with, where are you going to end up? The hippie wave in the 60s was probably caused by the same phenomenon as the yuppie wave in the 80s. Choose your allies wisely. ((And your enemies, of course.))

You want to be fooled

So how do you counter this situation? Waiting for your midlife crisis to change the world is risky. “Follow your passion” may not be enough. ((It may even be dangerous. Not all of us can be writers and singer-songwriters. Not all of us even want to be writers and singer-songwriters, if we think about it.)) Cal Newport calls the lack of vision “a stunted vocabulary when it comes to discussing career aspirations”. He advocates building a deeper career vocabulary that allows you make better choices.

For Newport, this involves considering the value of craftmanship, your lifestyle preferences, and also your personal ethics. These are good starting points and part of what I call a broader understanding of costs and resources. ((I’ll first cover higher-level considerations (mindset and strategy), but more on this topic later in this series.)) But what about the other tricks we fall for?


In magic, the best tricks work even when you know you’re being tricked. Take Apollo Robbins, the master pickpocket: Even when you’re aware that you’re about to get cheated – even when he explains to you what he’s doing – you still fall for it.

As John Cutter says in the magician movie The Prestige:

Now you’re looking for the secret. But you won’t find it because, of course, you’re not really looking. You don’t really want to work it out. You want to be fooled.

You want to be fooled. The most successful tricks in life work exactly this way. You want to be fooled into believing them, just as you fool your kids into believing in the tooth fairy. You want to be fooled because it makes life easier. Fighting against convention costs a lot of energy that could be used for other things. Is it even worth it?

The Case for Dropout Counselors

Moxie Marlinspike has it right when he analyzes how we plan our careers within conservative support structures that always lead to the same place, just as a funnel:

Highschools have “college counselors” (not “dropout counselors”), scholarships and financial aid packages lead in a single direction, and university overlaps with internships — which then culminates largely in a series of “career fairs.”

There is a tremendous amount of support for these decisions, and very little support for making any deviating choices.

When we arrive at the ends of these funnels, it’s possible that the direction we’re facing is more a reflection of those structures than it is a reflection of ourselves.

At some point in our lives, we need dropout counselors, not college counselors. Is there any chance we can become one on our own?


As a first step, what if you started to play better tricks? What if, instead of letting societal expectations and personal anxieties trick you, you would trick yourself from a position of sovereignty and empowerment? What if you followed Hesse’s advice to “magically transform the outer world without going crazy”?

Here’s how I see it: If we understand that we’re tricking ourselves no matter what, we may as well trick us into living a better life. We may trick ourselves into doing fulfilling work, despite the societal smoke and mirrors. We’re free to invent new tricks that serve us better.

Don’t care about what they say, as long as they don’t lock you up. Become consciously self-delusional and see what happens. That sounds weird, I know. But it’s a good first step in the transition, whatever it is that you’re aiming for. If you know about tricks, you can use them to your advantage and live a better story.

More on that next week.

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