How to Build Your Self-Esteem by Deschooling Yourself

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Self-esteem is at the core of living a happy life. By “self-esteem” I don’t mean the stuff of cheesy motivational posters or overpriced workshops with goofball speakers. I don’t mean books written by Malcolm Gladwell-types that are read by depressed office workers or pill-popping upper-middle-class housewives.

By self-esteem, I mean the ability for an individual to look at what they do and who they have become and be happy with what they see. I mean a person who has integrity by knowing their values and sticking to them. I mean a person who has esteem for themselves.

The person of self-esteem knows what they stand for and doesn’t compromise on their values. They know what they stand for and can set down plans and paths to build their future according to those values. Self-esteem is at the core of living a happy life because it is so important for figuring out what happiness means to the individual and having the confidence to analyze, build, and execute on a plan for building a life that reflects that state of happiness.

Schooling is notoriously good at crushing self-esteem. From age-grouped peers who mock their fellow-travelers to cliques of the high school and college scene; from assigning Sallie as a “Failure” because she learns to read two years later than Johnnie, who is labelled as “excellent” because he learned to read a year before everybody else; from making children and young adults who learn differently than others feel like outcasts for their learning-styles to discouraging play as “something that happens outside of work, schooling is the perfect institution for driving down the individual’s self-esteem.

Even when somebody gets through 12-16+ years of schooling without having their self-esteem beaten down through a number of processes and doesn’t have to resort to putting on a show to just get through their days — like too many young people must — schooling still has negative effects on self-esteem when compared to alternative ways of building one’s view of oneself. When we go through years of schooling as success stories, we begin to identify with our success in school. We see ourselves as being able to create plans and follow through on them, even though these plans are more-or-less created by necessity in the institution of schooling. Once we get out of schooling, the likelihood that we see how limited our ability to create our lives really is increases. Maybe we hide away in a highly-structured job somewhere, go to graduate school, join Teach For America, or something. Eventually, the bottom falls out somehow. We are confronted with the fact that we don’t actually know as much as we thought, we can’t control our lives as well as we thought, and that our credentials and schooling telling us that we know something doesn’t actually mean that we know it.

How do we protect against this?

Deschooling and Self-Esteem

School drives us to identify our self-esteem with our performance in the institution. A young adult isn’t weak-willed or lesser if they fall victim to this — it’s to be expected after more than a decade of 5 our of 7 days of every week being consumed by schooling. What we must confront is how to parse apart self-esteem and schooling. How can we help an individual see themselves as separate from their school experience and anything that extends directly from that?

Deschooling offers an answer. By deschooling ourselves, we are forced to step back and ask if we must take control and create the structure of our lives. We must cultivate the focus, creativity, and play in order to learn the knowledge necessary to follow these paths and to discover what we actually value. Maybe we thought we valued fame and wealth, but in reality we value family and solitude — we only thought the former because that’s what our peers in our competitive schools valued. Once we remove ourselves from those schools and reflect critically on what we want, we may find that what we want and what we thought we wanted are totally different.

Saying that deschooling offers an answer is great and fine, but how  does it offer an answer? What, exactly, can we do to build up our self-esteem?

First, we must totally disassociate our identity with our schooling. If this means dropping out, then drop out. If this means not seeing oneself as a med school graduate in medicine but as a doctor who did what he had to do to become a doctor, do that. If this means contemplating a career change from one that we only thought was great for us because it extended from the classes we were good at, contemplate that career change.

Second, we must discover those things which we hate doing. This is easier than figuring out what we love doing. When we see that we hate doing A, B, and C, maybe we can get a better idea of what our values are. Maybe you hate doing rule-oriented, detail-demanding work. You hate doing your taxes, doing the books for your business, and filling out paperwork. Now you know you should not be an accountant and that you shouldn’t feel bad for not being good at these things. You are moving a step further down the path of parsing your identity apart from your career choices and your education.

Third, we must understand that failure is not an identity. This is more abstract than the above. Many self-help authors would encourage you to go fail. I don’t. Failure sucks. Avoid it as much as you can. But here’s the paradoxical secret to knowing that failure doesn’t make you a failure: go work with successful people. The likelihood that one or more of their major projects failed is incredibly high — yet they are successful. They are seen as successful. They see themselves as successful. They don’t identify with their failure. In this sense, they’ve deschooled themselves.

Fourth, and finally, cultivate an attitude and habit of intense focus. Start small. Create a personal development project to go the gym 3 days-a-week and to write every day. Set a 3-month goal. Set a year-goal. Keep moving up. Doing this not only helps you cultivate habits and stick to them, it helps you prove to yourself that you can build plans and goals and execute on them yourself without the instruction of a teacher.


The connection between schooling and self-esteem is not explored enough, despite the fact that nearly everybody knows that going to school can crush a child’s self-esteem. We just tell people to swallow their pride and know it will be over soon. But this isn’t always the case. Young children who come to have low self-esteem from schooling grow into adults with low self-esteem. They grow into parents with low self-esteem and raise children with low self-esteem. The cycle continues. Doing what we can, as individuals, to move outside of the schooling that does this is the first step. Deschooling ourselves and forcing ourselves to create the paths we want is not only a good idea, it’s necessary.

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