I had an interesting interaction with my 3-year old over the weekend that reminded me that most of us are faced with whether to be naughty or nice throughout our entire lives. Sometimes its just worth being naughty — even considering the consequences.

Sunday my youngest turned 1, and we had a birthday party for him. My 3-year old helped me frost cupcakes before the party and decorate them with sprinkles. He had plenty of licks of icing while we did this, and partook in the sprinkles as well. As you may imagine 30 minutes later he was jumping out of his skin, running around like crazy. He must have asked me 30 times whether he could have a cupcake. I must have answered at least 30 times that he could, but he had to wait until the party and until we sang happy birthday to his brother.

The doorbell rang. I went to answer it, looked back, and there he was shoving a cupcake in his face. So off we went to time out. After the required 3 minute time out, I asked him whether he knew why he was in time out. He said “yes mommy, I ate the cupcake.” I said “Ok, so please remember next time you have to listen to mommy.” To which he replied with a devilish twinkle in his eye “But mommy, the cupcake was so good!”

I had a hard time holding a straight face. I couldn’t believe he was telling me that the cupcake was worth the punishment. But at the end of the day — we have all been faced with choices where we have to think about whether the consequence is worth “breaking the rules.”

Entrepreneurs are faced with these types of decisions all the time. Do you rack up huge credit card bills, take on a second mortgage, and boot strap your dream at the risk of losing it all? Many entrepreneurs have decided that it is just worth the risk.

Mommy CEO

AvatarSabrina Parsons

Sabrina has served as CEO of Palo Alto Software since 2007.