Being in business
Running my own, albeit extremely small, business provides new opportunities and experiences regularly. But you know you're really a designer when you use Adobe Illustrator to combine the 1099 form and the 1099 content output by QuickBooks to get the printing to align properly. ;-)
Note: You will be fined $50 if you were to do this for the form you have to send to the IRS since you apparently have to use their official red version (you cannot print 1099 employer forms from the web--unlike pretty much every other form). However, the copy you send to your subcontractors isn't subject to these limitations since it's never sent to the IRS.