The very awesome Nate Baumgart invited me to be on the comedy filmmaking panel at his first annual Inside Joke: Chicago Comedy Symposium a few weeks back, and he prompted me to think about five things I wish I'd known before I started comedy and filmmaking. Here's what I came up with.
#1. The quality of your equipment matters very little. Don't wait until you can afford the perfect camera, the best editing software, classes or workshops. You probably already have what you need to get started and the most important thing is simply DOING this thing you want to do. If you have a computer, you have editing software. If you have a digital camera made in the last ten years, you (almost certainly) have video-shooting capability. Writing is writing and editing is editing, no matter how elaborate or simple your technical setup. (I shot the following short with a $100 digital camera, and I still think it's still one of the funniest things I've done so far.)
#2. It doesn't matter how much schooling\training\experience you have or don't have. Of all the filmmakers I know, two went to school to study filmmaking. The (many, many) others, who are also dazzlingly skilled and talented, are self-taught. There are a million tutorials on YouTube that can teach you anything you can't figure out on your own about iMovie, Final Cut, Photoshop, you name it. Libraries are bursting with books about film theory and editing, and a surprisingly large percentage of creative people on Twitter and elsewhere online are willing to help newbies with questions.
#3. Creativity is a group thing (even in the "solo arts" like stand-up comedy). Find (or make) your group and forge strong bonds. You need each other. The more you can keep yourself open to people and ideas and experiences, the better an artist you'll be, and - bonus - the happier a human being you'll be. Find each other, and stick together.
This can be tough for some people, but the rewards are rich for those willing to push themselves out of their comfort zones. I'm a lifelong introvert\quiet person who is most comfortable behind the camera and more than happy to shine the spotlight on those who bask in it. Making friends and being social was a little tough for me when I first moved to Chicago, after ten very quiet years as a dog-walker and housesitter, a job that had me interacting with animals more than people. I accommodated my social difficulties by entering the comedy world gradually in different capacities I felt comfortable in - as a writing student at Second City, then a blogger covering the Chicago comedy scene with The Bastion, briefly as a stand-up comic, and eventually a stand-up producer (at Chicago Underground Comedy, see clip below) and filmmaker.
#4. Stabilize yourself financially so you can be creative. It's hard to transcend daily existence enough to create art when you're scrambling to pay rent and feed yourself. Panic and stress do not soothe the muses. Hang on to that dull but bill-paying day job as long as you can. Definitely explore avenues of getting paid for what you love to do but be ready for some overlap.
If you live in Chicago, sell your car and ride your bike everywhere - you'll save money and be fitter and more energetic too. Shop at thrift stores and neighborhood grocery stores, cook for yourself, have roommates to help cut down on expenses, whatever it takes.
If you can keep your expenses low, you can probably get by with almost any kind of job, and, minding that, try to find something enjoyable and low stress. Work at a fun coffee shop. Be a nanny. (Seriously, parents, stand-ups are the best nannies ever. Imaginative, loving, and very playful. Hire them!) Find a day job that is minimally draining and doesn't hurt your soul every time you punch in.
#5. Do it. Do it, do it, do it. Don't talk about it, think about it, dream about it, and keep it locked up in your head. You don't know what it's really like until you DO IT. Are you scared? Do it anyway. Are you insecure? Join the club, buddy! If you weren't nervous about getting onstage/putting yourself out there, something would be wrong.
Don't sit in your hometown for ten years after college, wishing and hoping and dreaming (oops, was that a little too specific?). Get yourself together, boldly proclaim your desire to be a filmmaker\actor\musician\whatever, and DO IT.
You can stifle a desire like that for as long as you like, but #1 it's not going to go away, #2 the suppression of that desire will cause you a lot of pain and turmoil and #3 the world needs what you have to offer.
That last bit is very important but somewhat difficult for self-critical brainy types to absorb. It's key, so work on it. Realize that it's not selfish for you to want to develop and share your creativity, you actually have a contribution to make to the world with your gift, and your talents are needed. Truly, the selfish thing would be not sharing your gifts with the world.
At whatever level you can start, start doing the thing you want to do, and keep doing it. Volunteer to help with other people's projects, reach out for advice and support, watch people who are further along in your art do their thing. It takes time and just plain hard work, but don't be afraid. Plop yourself on an exercise ball and bounce around while you write/edit/whatever on your computer, make writing/creative dates with friends to work together, read a book about ADD management strategies - whatever it takes for you to develop the habits of a productive creative. DO IT. And keep doing it. You have no idea what opportunities might open up to you, but one thing is for sure - if you do nothing, nothing will happen.