The best time to start a web comic is when you don't need or want to start a web comic. When you really have something to say or really need that money you THINK a web comic will earn you then you're probably not going to think things through as much as you should. One of the many problems that I had with my motion comic is that I was trying to learn the process artistically and technically at the same time and that was, in the end, my downfall. It became too much, I got burned out and eventually lost interest. That is NOT what I wanted to happen with Robot Friday, so I decided to approach things a bit differently.
My goal was to develop my concept and characters and then create an entire year's worth of comic strips before I ever posted anything online and I spent an entire year doing just that before my impatience got the best of me. To my credit I did noodle out a lot of concept art for Thomas, Gary and Michele. I even did some world building and thought about what I wanted to achieve with the comic and how I might go about doing that. I worked out business plans, tactics for marketing and who my ideal audience might be. I did all of the things they tell you to do in Business Class 101 and about 95% of that did not matter at all.

The 5% that did matter, though, was comedy. I did a bit of research into being funny and found that I had a natural wit and humor that most people lack and that, if I were to make a difference in the world, I would need to annoint as many people as I could with my natural gift. Of course all of what I just typed is nonsense, the only thing that makes stuff funny is ending a story with something the audience won't expect. That's it. All those seminars and lectures on comedy can be summed up in two words, "surprise people". What I just gave you in about 2 minutes of reading (one and a half if you were a gold star kid) is what I learned in about a year of trying to figure out how to succeed in web comics. The thing I did next was the key to my success above all else. I promptly ignored all that I'd learned in that year and just started making comics.
The thing that actually does matter in making comics is ACTUALLY MAKING COMICS! All the research, all the gurus, all the perfectly crafted scripts and jokes mean jack squat unless you draw a picture and attach a word balloon to it. Draw three and you have a comic. Draw four and a fart joke and you have Robot Friday!

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