OK, I'll bite. It depends on your individual situation and which aspect of the business you want to enter. If you are talking about becoming a driver, entering the business during a slow time can be good because you may not feel as pushed to hurry and learn everything. You can have a little more time to learn some of the basics. If you are talking about becoming an owner operator, a slow down could be good if you are flush with cash. If you have the money or decent credit, you can probably get a good buy in a good used truck. A slow time is not necessarily a good time to buy a new truck. You don't want high payments or debt when the economy is slow. If you can find a good deal in a good used truck, it can work to your advantage to get into this business during a slow down. When things pick up, you will be ready to run.