Hire a DP based on this
1 - How well can they run a crew and do they have the people skills to delegate tasks and work through problems. Also, are they actually nice people who you want to work with for an extended period of time.
2 - A really good DP does their homework and planning on the front end, aka pre-production. Showing up and hoping it works out because you have camera X is a terrible plan. It's kinda like building a house without the blueprints. A good DP selects the right crew, camera, gear, etc based on the job in the prep. They need to be practical while at the same time holding true to a creative vision.
3 - People make movies, not equipment. Sounds cliche, but i'll take a skilled team of experienced people over equipment any day. A skilled gaffer and key grip can make your movie better then any camera. I don't just mean the actual image, I mean the process. When things roll along smoothly, on time and on budget, everyone is happier. That is a real tangible thing. Put the money into people, not equipment.
10 Years of production on TV shows, commercials and documentaries here's my approach:
Personally I flip the concept of fear and failure around. I want to fail fast, I want to know what doesn't work and I want to figure that out fast. If i'm wrong about a lighting set up or camera move, I don't fear the sense of failure from it, I want to know quickly so I can move on and try something else. I'd rather have rolled on something bad then rolled on nothing because I was afraid of failure.
Failure is good, it lets you know what doesn't work and I personally want to know that sooner then later. You just need to see it as a tool not a mental block.
Want some examples of good and bad failure and a new approach to it? Read this great freakanomics transcript of "Failure is your friend"
Maybe the conversation should be around the right gear that is going to last you years and has serious ROI. Having worked at a production company for 10 years, we look at purchases that have lasting value. Our most recent purchase where some Kino Flo LED Celeb 200's. Amazing lights with many uses. They can last 5-10 years and be relevant. Throwing money at every new camera is sure fire way to lose money fast. We have a few work horse cameras that get upgrade every 2-3 years. Need a speciality camera for a shoot, rent it! 95% of clients don't care about the camera you are using.
You should also factor in the massive amount of marketing and advertising these companies tailor to the "indie market". This gear obsessive gear syndrome is similar to why people are always buy the new iPhone. You're programmed to think it's better and you must have it to complete your life. The camera companies tap into the same part of your brain to take your cash and leave your wanting more.
Hey Jason, i'd recommend starting at a film coop and trying out all the different roles. Narrow down what you really like and be open to the ones you didn't expect. Also, if you have project management experience, why not leverage that in your transition? The role of a producer / production coordinator would easily overlap with that.
Having worked in docs and TV for 10 years here is what I find what makes people sink or swim. 1- Having a desire to learn. 2) Having great communication skills. 3) Working smart.
It's really that simple, after you find what you really want to do, focus on that and go to a production company, take internships and make your indispensable. People, not equipment, make everything spin around in this business. Be one of the good ones and you'll be fine.