I quit my job about two years ago and now make a decent living coaching chess, teaching photography, and guiding kids to practice imagination and socialization through playing Dungeons & Dragons.
I am literally a professional Dungeon Master.
As awesome as it is to be able to say that, there’s an inherent difficulty in finding boundaries between my professional work and my hobbies. Because when your job is doing something you love, then there is a tremendous risk that anything you love could start to feel like it is your job. Worse, it becomes easy to justify almost anything you want to do as “part of my job”, leading to days or even weeks long distractions.
I’ve always been bad about finding that line.
It’s less a problem of starting projects and never finishing them. I do that. I need only look at my office desk to see: A pinhole camera. A light diffuser. Prisms for photography. Paper for book binding. A broken digital picture frame. Memory cards and external hard drives filled with recordings from several projects that failed to yield a good build video. Camera mounts placed in the best spot for game streaming. Books (fiction, nonfiction, and curriculum) in various stages of writing, editing, and graphic design. Scraps of code from various video games and AI art projects.
Incomplete or failed projects are not the problem. Experimentation is essential in making, photography, and content creation. I’m not even especially bothered by having seven different projects running at the same time, because it just means that when I finish one project I’m already through the conceptualizing stage of several others.
The challenge is that I don’ know what to focus on and call work.
I love what I do, but I dislike being dependent on one online learning platform. Moreover, I really want to get myself into a position where my work is primarily asynchronous, where people pay to be in my classes because they really want to be live, but they could also watch my videos and read my writing… and maybe play my games.
Even writing this blog is a gray area: Am I blogging because I want to be a professional “content producer” (pause as the author swallows bile)? Is this a mildly exhibitionist act of journaling to sort out my emotions in a forum where, perhaps, other people will benefit from my rambling or give me advice? Am I just avoiding “real work” by clattering at my keyboard while Walker does homework beside me?
There’s a lot to love about working for myself, but the greatest challenge is that I often feel like I need… not a boss, but a producer. An editor. A creative partners. Somebody who looks at all of the ideas I have and says, for example, “I like your writing, but you should focus on producing photography guides” or “I know you think it’s dumb, but you really should make a video series about binding books.” Or even tells me that this whole asynchronous urge is a dream and I should focus on making the best live classes I can.
That’s difficult to admit and even harder to find. Internally, I know it’s true and I have said it about other creators. George Lucas is a mess without Steven Spielberg or Lawrence Kasdan to rein him in. Lady Gaga is best when she limits herself to an EP or short album. A certain British author is best when she sticks to children’s fantasy, rather than going off on politics.
Creatives do their best work when they have constraints. Limits make us angry. They frustrate us. The cause creative angst and make us stay up late fuming over how to best stick it to the man.
That’s a lot to ask of someone and has the potential to create tension, unless both of the participants in the arrangement benefit from it. Ironically, I’ve created tension in my own mind and in some relationships by trying for years to find this sort of dynamic. I’ve tried to ask parents, partners, friends, and co-workers for their opinion on my work and frequently found frustration when they either ignore my work (I love my friends, but they don’t always care about the same things I do) or give blanket affirmations (I love my family, but I’m not as good as they think).
The best answer would be for me to develop my internal critic to the point that I know what is worth focusing on as “work” and what I should just dabble in as a hobby, but that is damn hard to do.