Quitting your job to pursue your passion is a privilege

Passion without genuine skill and knowledge is useless. You can be passionate about many things, for example cars, but unless you put in the hours, your passion doesn't mean you will be a great car engineer, or automotive company executive.

[EDIT] Also want to add that people grossly underestimate the responsibility of being their own boss. There are a lot of tasks you have to handle outside of your usual work like finances, scheduling, client outreach, etc...

The OP seemed to understand this, but a lot of people will create a start-up for the sake of being on the creating end of something without really knowing how practical their venture really is.

Paul Grahm may disagree though.

I think of this every time I come across one of those motivation videos on youtube. It'll have like twenty million views, how many of those people actually took it to heart?

I agree with your summary, that's what the author is stating, though I don't think the conclusion is true.

The best way to start becoming an entrepreneur is to start small. The mantra 'fail early, fail often' is useful, but only if you have the resources to apply it more than once, which means that assuming you're not rich you should start small. Start a side project, do consulting work in your spare time, etc... It's not rocket science.

That being said, I understand the desire to quit a job you don't enjoy. I know that desire can override doing things rationally. I have that desire often.

> We praise people that are “courageous” enough to quit their 9-to-5 and dive into the deep end of the exciting unknown. We idealize and romanticize the idea of being our own boss and being in charge of our own schedule. To take a risk and reap the bountiful benefits. Yet no one talks about the real sustainability or self-sufficiency of this formula when the playing field is never even.

There are risks and then there are calculated risks. In other words, you should always know what you're getting yourself into ahead of time. A simple understanding of evidential probability will yield you the proper decision making tools in that regard.

I agree with the sentiment that privileged people have a softer landing if they fail, but there are many examples of working class or even penniless entrepreneurs becoming successful. Jan Koum comes to mind.