School and corporate life have this in common: that they encourage people to fit in and punish those who stick out.
Both of those environments punish efforts to reach towards individuality, particularly when those efforts aren't succeeding. It's better to be nobody than to be someone who's trying to be somebody but failing. Someone who publishes science fiction books while working for MegaCorp Inc will get penalised for it (they're obviously not committed to their long-term career there, so they won't be promoted as easily), but someone who is trying to get published and failing will get both that, and a good serving of pity and condescension. You're trying and failing? How pathetic. Get back in the ranks!
Another thing both environments try to do is take possession of your life, and declare themselves owners of your means of self-expression. If you're working for Company X, then any comment you make in public could reflect on The Corporation, and so you should shut the fuck up and stay in your cubicle, not go and write blogs about what life is like inside the asylum. This can last for years after leaving. It took me a long time before I felt truly comfortable writing a post like My life in Accenture before startups. Even today, I sometimes feel "maybe I shouldn't talk about client X or project Y, because someone might get in trouble".
Both of these forces make it very difficult to find your voice, your individuality, and to become someone who is likely to build successful ventures.
Getting over it
One of the things that really drew me to the startup crowd, initially, was that this was an environment that accepted individuality. It's ok to be a technologist who likes to run a productised services business and has published some blogs and likes to write short fiction (I'll try and publish some of that sometime!), and posts crazy amounts of stuff to HN. Most of those things would not be compatible with corporate life. In the startup world, they are not only compatible, but encouraged, useful, and in some cases necessary.
Being someone recognisable, having a platform to express yourself, having connections to people in the industry, all those things are very valuable in the startup world. And at the same time, as we've seen, they are things that are strongly discouraged by the corporate environment many people operate in.
This is why some of the steps to getting out of the corporate world that I mention in the startup escape path are to start publishing a blog and then write something interesting enough for people to vote it up on HN. This helps to get over the fear of being someone, of sticking out. They force you to realise that it's not only ok to be trying to do something different (even if you suck at it), but that it's good, that people will look up at you for it, even if you fail.
At a recent London HN meetup, Harj Taggar was invited, and he highlighted one of the presentations that had occurred that night as particularly worthy of praise. Which one did he pick? Not the slick ones that showed cool, successful, profitable startup products. No, it was probably the most basic presentation of the lot. A guy called Hrishi Mittal shared an extremely simple project called Share What You Make.
Harj picked out that presentation and said, "this is what we need more of": people willing to take their early projects, put them out there, and see what people think, without being afraid of failure. And he's right, because exposure to useful feedback is one of the most important factors to getting from a crazy idea to something actually useful to someone. Paul Graham also expressed this thought when he recently wrote that:
In most places, if you start a startup, people treat you as if you're unemployed. People in the Valley aren't automatically impressed with you just because you're starting a company, but they pay attention. Anyone who's been here any amount of time knows not to default to skepticism, no matter how inexperienced you seem or how unpromising your idea sounds at first, because they've all seen inexperienced founders with unpromising sounding ideas who a few years later were billionaires.
Going back to our initial topic, we all have the potential to be different and unique within us, and unlocking this potential is an essential step towards being a successful startup founder. However, this potential is strangled and extinguished during the long years of school and corporate life that many of us endure. In order to regain that potential and make the most of it, we have to be willing to try and fail, at least a few times, before we can expect to succeed.
Being someone, being extraordinary, being different, standing out - these are part of the promise and the demand of the startup world. So if you're currently stuck in an environment where this is not possible, you will need to take deliberate, calculated steps to make sure you get over it as part of your learning process.
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