One of the best reasons to quit your job or drop out of school to work on your startup is that there is no longer an easy retreat. Cortez, according to legend, burned his ships while invading Mexico so that his men would fight to the death knowing that there was no way to retreat from the attack.
Of course, startups are likely to fail and removing the stigma of failure is important for a country’s entrepreneurial sprit. However, there are many people who will never succeed because as soon as things get tough, they will go back on their boat and leave lands unconquered.
It is important to do some analysis and see if your startup is an opportunity that you’re passionate about and to sanity check that it is achievable. However, nobody will bring you series A money or large customers. At some point, you just have torch your ship and say you will get them because you have no choice.
If you are having trouble getting something done, email someone saying that task is done and you will send it to her/him in a few hours. Personally, I like to pre-program emails to go out in the morning saying I have finished something. Hello, insanely productive all-nighter.
I left school to build and sell a product for a semester. I recently changed my computer background to the flaming ship pictured to remind myself. My business is not scalable with a large enough total addressable market (TAM) to become a multi-year pursuit. However, I can build it all by myself, without outside money or contracting any engineers. It should allow me to pay off some of my student loans before I move on to my next pursuit.
Using Coursera and several other MOOC’s I am still taking technology focused classes, so leaving school was not so that I would have more free time. (In fact, I think that not having enough free time as a student is a cop out for not building a proof of concept.) However, I needed to leave school so I have no easy retreat. It might take me a while to get through this jungle, but I will try my damn hardest to leave it with less debt; I have no choice.
P.S. Sorry for a business post that uses a war metaphor. I know that many people, myself included, are Sun Tzu-ed out.