Let me preface this by saying, if you ask 20 stage managers for advice, you may get 21 opinions on this.
1. As I posed above, am I too old/too inexperienced to pursue this dream?
No, you are not. I will say there is ageism in this career, but the life experience you are going to bring to the table, and previous work experience in managing people is going to pay off in the long run. It's about how you will start. One of the things you didn't list is where are you currently located? Do you want to start part time in theater and then transition full time? That will factor into some advice. It's never too late to pursue your dream . . . but let's add a dose of reality.
You are going to face some prejudice . . . “Why is this 30 year old applying for jobs that usually go to a 22 year old?” Be prepared for those answers. Be prepared to upsell yourself . . . why are you better then the 22 year old? I know that all things being equal, bringing someone onto a team with life experience can bring a nice balance.
2. How do I get a foot in the 'theater' door?
My first recommendation is try to arrange shadowing opportunities with professional theaters in your area. A quick letter of introduction may get your foot in the door to see a professional show being called, or in rehearsal or in tech. Try also volunteering to be a tech runner during tech - filling in the gaps, being on book, or just watching. Anything to get your foot in the door and start sensing out what this life is professionally. Also, don't under estimate volunteer options in other areas of theater . . . since stage management is often a hub of so many things, getting to know various shops, devo, marketing, box office, front of house, etc . . . all will help you get a sense of the big picture. What I want for you to understand is not only the job, but the entire lifestyle that comes with doing this job. It’s not the job that kills us, it’s the lifestyle surrounding the job that wears us down – networking, freelancing, unemployment, long, long hours, high stress – all of these things lead to burn out.
If you are in a financial position to do an internship, start looking around at places you want to live and work. I highly recommend doing an internship with a professional theater in the city you wish to live in . . . . hate the idea of living in Chicago, then maybe don't do an internship there (although if you can’t get a dream internship in your dream city, then weigh the options – a good internship, is a good internship). You will be making contacts in the city you are working your butt off in . . . so make the contacts count. Work on the killer cover letter, and don't hide the fact your transitioning, play it up - find the skill sets from your current life that can cross over. (Here's a little secret - a lot of stage managers are stage managers as a second career . . . . even me)
If you are not in a financial position to take an internship, then look for theater opportunities that would you to keep your current job - run crew? PA positions? Aim for a professional theater in your area . . . it will only help when you make the transition into full time. If it's non-pro theater, then so be it . . . but limit yourself there. (But, who knows, you may find the magic middle ground of keeping your current job, but being wildly fulfilled doing non-pro theater . . . many people I know would have been much happier.
3. Should I pursue a BFA?
Maybe. If you can find a good program, that will not put you into too much debt, it might be the best way to build up a lot of experience. Do you already have a BA? You might want to look into getting a MFA. Build upon the experience you already have. Some of the MFA programs are very competitive, but some are looking for bright, intelligent people to step in and learn. And if you spend the next year getting ready for a program, you will put yourself in a better position.
You don’t need the degree, you need the experience. And the educational program might be the best way for you to get your experience. c
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4. How would I get an internship?
Go to any theatre’s web site and look up the internship programs (usually under education). Contact them.
Final words . . .
If you want to talk more in detail, drop me a line. But, just remember, this job market is flooded right now, and you need to asses yourself and see if your life can be sustained by this career. Too many people competing for too few jobs. It sucks. And it continues to suck (just in bigger ways) as you move up the career ladder. Shadow. Talk to Pro SMs. Observe. Get to know what this world is. See if this career can sustain the lifestyle you want to live. Don’t make a business decision based on your heart.