I've been at this for over 10 years now. Started with coins and macro, then to landscapes, then to dogs and pets, back to landscapes. Now I'm into people. Lighting and imaging people and capturing emotions is becoming more satisfying than the idea of grand landscapes.
I'd love to do this full time, but I've crossed the mid-40s mark, and it seems ridiculous to put myself in competition with established photographers in a limited market at this point in life. Years ago, I actually thought that once I reached this point, I would find success. As it is now, I do one wedding a year, two or three senior photo shoots a year and the odd engagement shoot or pregnancy shoot. That's about all I drum up with a full day job. The take away lesson, which is almost useless now, is the working full time and trying to work on the dream(s) part time. If I could do it over, it would be all or nothing. Part timing it always yields part time results.
My frustration is that I'm good at this now. No more fumbling and guessing, no more nervousness, no more lacking equipment when I go to the field. I now have a good workflow, and have worked through situations to have a good knowledge base.
Every 6-8 weeks I hire a model for a few hours and practice lighting or whatever creative things I've jotted down that I can pull off on the cheap, in a relaxed environment. Is this where it ends for the middle age photographer? Did I simply start too late, and will forever remain on the outskirts and have to pay to play?
I want to shoot more. Lot's more. I have skill and resources to do much more with photography at this point in my life. I'm even pondering a studio with spaces to rent, events and educational resources. Not sure on the profit angle, but I can now seed something if I decided to. I talk with the models I hire about where the money is at, and they all tell me it's mostly ego stroking and not much for real end product. At least in Michigan.
So what do do? I know it will be hard to take photos with a cane and walker in one hand as the years pass, so I really need to step this up soon, or let it die.
After doing about 20 weddings, events, etc I decided I just didn't like posing people. To some it comes naturally and to others it is an acquired skill. For it to be an acquired skill you need to, like any other profession do it often and gain experience. Friday night I would study all the required and money shots - I was lucky if I remembered 20%. We always got the family shots. etc. I gained a whole new respect for pros and wedding pros. 





