Short answer: Never. When I was little I always wanted to be a "secretary" who sat at a desk, typed on a computer, and wore power suits (it was the 80's). It wasn't until I became an adult that I realized that was actually the description of a manager, executive, leader, or even an entrepreneur. So this is something I've always wanted to do and I'm happy I made that happen. I am truly living my dream and doing what that little girl always wanted to do. Except for the power suit part. Those went out of style a long time ago. Pajamas, a sweat suit, or a robe will suffice just as good. However, when I am out conducting business or errands, I am dressed professionally. As far as actual reasons why I would never go back to a day job. Those would be: 1. Never having to sit in traffic ever again. 2. Never having to say, "Good Morning" every single day to every single person who walks in the office ever again. I don't know why I hated that so much. I am not a morning person and I hate talking while I am still getting adjusted to the daylight. 3. Never having to use an alarm clock. 4. Never having to leave my warm bed/home during the cold months. I endured some years of crazy winter weather during college in San Francisco and longed for the days I no longer had to walk up steep concrete hills in the fog, drizzle, wind, and cold. What about you?