I think back to some of the best decisions of my life and really at the time they were not the best decision according to logical thinking.
When I graduated from college and did not have a "real job" I decided to take out a business loan and purchase a commercial tent rental company. Many people thought this was a horrible idea to go further into debt (on top of student loans). "Get a real job and pay down your debt" they said.
Through that business I met a man who owned a software startup. I took him out to coffee and he decided to hire me for a "real job" as a marketing specialist. I later sold the tent business for a profit that allowed me to pay off my student loans completely.
My life is filled with examples of situations where if I had followed my logical mind I would have missed out on the greatest opportunities I have had.
It is ok to fail and take a step back because when you succeed you are taking an exponential step forward.
A perfect example of this is deciding on a whim to move to Buenos Aires, Argentina for a month with my girlfriend. Logically we should save our money and work harder at our jobs back home. But who knows what the potential upside will be. That chapter is yet to be written.
As they say the greatest risk is taking none at all.