A few months ago I was contacted by the Freelancers Union, an organization based out of Brooklyn, NY. They were planning on setting up a satellite here and wanted to get a lay of the land. This week a small group of them arrived in town to host a couple of events (including one tonight, 11/21). It also provided me with an opportunity to meet with a couple of them to continue our conversation.
Last night they held a small cocktail party, which gave me an opportunity to further connect with the group from New York. I also had some really interesting conversations with other Portland freelancers that I had not managed to cross paths with before. Most of the conversations were some permutation of the joys and challenges that come with being one’s own boss.
This morning I woke up with Missing Person’s “Destination Unknown” running through my head. That combined with yesterday’s numerous conversations reminded me of something else I had been thinking about lately.
A week or so ago, I being interviewed for a gig, and was asked how I felt about working in an environment where there is rapid change and the uncertainty that comes with it. I explained that having been self-employed for as long as I have, I am very comfortable with uncertainty and have a high tolerance for ambiguity.
One of the greatest lessons I have learned is that there is nothing linear about running a business. Sustainability comes from a continuous ability to adjust services to the market. It is a precarious proposition, akin to walking on a tightrope above a pool of hungry alligators. Every time a potential client asks me to do something, I have to both weigh their timeline against my other projects and assess my ability to successfully achieve their goals. And even when my plate is completely full (as gratefully, it has been recently), I need to still build in time for both marketing and ongoing education.
And when the going isn’t as good, I am responsible for buoying my own spirits and finding ways to fill my time. That is a challenge in and of itself, because whatever project I take on needs to be something I can drop at a moment’s notice when work reappears.
It is a crazy way to make a living, but apparently I thrive on it. But it can also be lonely and isolating at times. Most of my close friends have “typical” day jobs. They try to understand the ups and downs, but it is a different experience to have the same conversations with someone who also works for themselves. That is why I so enjoyed the opportunity to converse with a room full of people whose lives look like mine. Where from day to day, you don’t know your destination.