
It has been a busy first month of the new year, and in my typical fashion I’ve been working on so many different things it can be hard to keep track of what’s what, even for me. I’m constantly working on projects that I really enjoy, and/or tasks I need to get done, but as a self-employed person with a very small (but awesome) team of helpers, I often find myself in a tunnel of “doing” and sometimes suffer temporary blindness to the bigger picture of what I’m working towards.
I know this is happening when I see friends for lunch or beers or whatever, and they ask what I’ve been up to, and I seriously just blank out. I can’t think of one thing. Even though I was just doing a million things. All the things! Depending on my mood that day, it can be a jarring sense of overwhelm and sometimes unnerving and sometimes it turns to dread that I’m just spinning my wheels, delusional that I’m actually going anywhere.
The good news is that after being an independent worker for so long, I now know this is just a feeling, and I am actually working towards things and accomplishing many of them. I know this because I now (after many years of self-employment) have solid, simple systems in place for planning, goal-setting and project management. But at any given moment I might not be able to articulate a concise summary, a bird’s eye description of what’s going on in my work life — and in part, this is because my weird work life doesn’t fit into any common model of what “work” or a “career” should be.
At the moment I’m juggling work roles of author, coach, podcaster, blogger, online course instructor, community organizer, property manager and musician, and fuck if I know how that’s supposed to fit together into a recognizable package.

I guess I’ve always been okay with this, since it is the life I’ve chosen for myself, but in the last couple years I’ve grappled a bit with getting reeeeally okay with it in a deeper sense. At some point in recent years I realized that since I’m not following any real career model, I don’t exactly know how it’s all going to turn out, and I’d better be okay with that.
In general, I totally am. But in certain moments, when I’m extra busy and working a lot, I can feel disoriented and confused. What sometimes follows is a sheepish feeling, like “What the hell am I doing?”
Thankfully this interior monologue has become familiar, and I now simply continue the conversation with myself with some version of a shrug and chuckle and a “Fuck if I know!” answer. And I carry on.
Or I pat myself on the head in a slightly condescending way and tell myself in an inexplicable accent, “Don’t worry, it’s all going according to plan.” Then I laugh an evil “MUAHAHAHA” laugh and move on to the next task.
If this sounds a bit koo-koo, well, welcome to my world. It’s the best way I can describe the attitude I have cultivated to make sense of my self-defined reality and to keep moving forward. It works for me, for now at least, most of the time.
What works for you?
