T-shirt orders tend to be the most entertaining as they often need an original graphic component to make them work best. Sometimes I can get the point across with just a some simple font manipulation, but usually I tend to lean towards adding some graphic image to make the design shine. Granted, sometimes those designs can get a little carried away and I have had a few screen printers who swear that my design is absolutely unprintable, but then they go ahead and print it anyway and it looks great. Having been in the industry for so many years I know how far you can push the limits of the medium as well as the people running the machines, and when a difficult print works everyone is happy.
Back when I first began freelancing for other people in the early 80's it was always a challenge to figure out how my artwork was going to be best represented for their use. Technology has changed a lot of how we do things, but in the end I still tend to keep in mind how the image will be used and in how many variations it will be required. I've seen a lot of designers that jump right in with all sorts of fancy colours and effects that look great, but when it comes time to actually print those designs and the customer only wants to pay for a three color imprint, those designers need to go back to the drawing board and simplify their design and sometimes it's not quite as good a design when you break it down. I like to start with something simple, preferably in black and white, and then work up to all the bells and whistles. If my client knows he needs a two color left chest imprint for his uniforms I'm not going to be designing in Photoshop in process colours.
Back to my point though . . . as a full time freelancer this is it. This is how I make my money to pay my bills and feed my family. I don't have another source of income as I found that the other source of income always took away from my time as a freelancer, a husband and a father, and those are the things I love. There have been some really good years, and there have been some really rough years. This is not a get rich quick idea for anyone, but it does allow for peace of mind and the knowledge that you are responsible from start to finish for every design you come up with.
I've had many friends who have seen the "free time" they believe me to have who have then decided this is the life for them . . . only to realize it's not. It's not for everybody, it requires dedication of your time and your talent and it requires you not to get sidetracked watching endless episodes of television and youtube videos while putting off your next project. Your customers expect you to get the job done on time and hopefully those same customers understand that they need to pay their invoices on time if they intend to get more work done. Most of them do and I appreciate those customers dearly, but there are always a few who think you're their bank and will come up with endless excuses why the cheque has yet to be issued. Sometimes you can allow for that for a short period of time but eventually you may need to cut that customer loose and move on because at the end of the day they're messing with your finances and there's no profit in that.