Guest Post: What does it mean to have a plan — or not? (Risk and Plans, part 2)

This is one of my most treasured wedding presents, a painting from Uncle Tom. There is a sloth that burns inside us all. I’m sure they think about the roses and thorns of self-employment as much as we do.

A contribution from my friend and writing mentor, Jackie Wong.

Second in a series on risk and plans (part 1).

If you make a living that involves a whiff of ambiguity, precariousness, or unknowns, it’s likely that people often ask you questions like “So, what are you working on these days?” or, “What are you doing for work?”

It can be frustrating, particularly the implication that you are just a special kind of unemployed, or you’re always scavenging for more work, or that if you were just able to land that dreamy full-time job with health benefits, everything in your life would be fine. In other words, if you had more of a linear plan in place for your life, you and the people around you could breathe easier.

I’m not sure if this is true. It’s human to seek comfort through categorization and linear, cause-and-effect thinking. But human life is also messy, unpredictable, and complicated, so I’ve never found that making a structured, year-over-year plan for my own professional life has been particularly helpful. At the same time, it’s not been in the cards for me to float breezily through my days, either; I’ve neither had the gumption nor the cash to pursue a graduate degree; the wages I earn don’t allow me to travel internationally or on a plane very often; and as a young person, I was always working — I couldn’t and didn’t take a gap year or long stretches of months away backpacking or volunteering.

I love structure, and to me, that’s the foundation that lets flexibility in. I feel like much of my life consists of thinking slowly, then galvanizing quickly. While I like to take time to think through the stuff of my life thoroughly and methodically, I’m quick to make decisions and quick to act on them. Should we move in together? Yes! Should I quit my job? Yes! Should we get married? Absolutely! Should I throw myself back into the feral wilds of self-employment after a few years in steady gigs while also trying to have a family? Which brings us to present day.

These can seem like big decisions, but then again, maybe they’re not; they’re just the stuff of life, after all. But it’s through experiencing the tension of new changes that we start to practice being uncomfortable — that practice goes a long way in helping us experiment with ourselves and decode habitual patterns that can leave us feeling trapped and stuck. I used to describe myself as a highly indecisive, anxious person; I would often find myself overwhelmed by all the possibilities and paralyzed by choice, whether it was buying a pair of jeans, staying in a difficult relationship, or deciding whether or not to apply for a job. Fearful that I would make the wrong decision, it would be near impossible for me to step forward at all.

Over the years, though, and through the course of a working life that often demands fast acting (faster than I would like) and fast decision-making (also faster than I would like), I have learned (by necessity and somewhat reluctantly, because I am shy and comfort-seeking and I love nothing more than a do-nothing evening at home) to move more quickly and to act more decisively. The process has been liberating.

If we let the most dire, if real, consequences of our decisions guide us — if I leave this relationship, everyone will hate me; if I quit this job, I’ll have no money — it can be paralyzing, particularly if we are likely to accept the black-and-white thinking that is so ingrained in our culture.

But learning to step forward into the unknown, without a clear plan, and practicing that in safe, supported, sometimes very small ways, can be helpful practice for the bigger, scarier stuff. For me, this process of practicing being present in the unknown has helped me trust my intuition and to be more spontaneous in many areas of my life.

My experiences with practicing mindful meditation, yoga, and in therapeutic counselling have helped me become more aware of my thought patterns, my habitual ways of thinking, and my feelings — this awareness has helped me understand myself better and has also heightened my interest in exploring what happens if I go against the grain of my usual ways.

Risk is inherent in all of this. There are unknowns everywhere in life, and the more I learn, the more I realize that I’ll never know everything, and neither will anybody. Over the past few months since leaving my last steady part-time job, I’ve found that I have started to let go of my fear of the unknown and my fear of instability. I have previously spent a lot of emotional energy worried that whatever I was doing was unsustainable and wouldn’t work out. I have also spent a lot of emotional energy worried about the lack of guaranteed monthly income in my life, the lack of foundational stability that is part of being self-employed and part of being a full-time freelancer.

I still have doubts and I still worry, but those fears are less prominent now than they have been in the past. I feel more committed to my current work than I have in the previous years of what felt like a more free-floating freelance life where I knew myself less well and thus felt less confident with the work I was both seeking and doing.

I have never been one to make a five-year plan, but I have often planned my life on a season-to-season, year-by-year basis. Smaller-scale planning seems more doable to me and also more sustainable, given that life is changing all the time, and many of those changes are facilitated by forces far outside ourselves. Rather than having a plan for how exactly things are going to go, I like to set intentions and loose goals built around what I’m hoping for in my life, big and small.

But those intentions and goals aren’t feet-to-the-fire commitments; if something else comes up or something doesn’t work out, that’s part of the plan, too — for things to change, for me to change, and for all of us to allow, expect, and support that in each other.

Check out Jackie’s recent talk on gentleness and vulnerability in writing. Jackie Wong is a journalist in Vancouver writing about race, addiction, mental health, and equality, publishing in magazines online and in print. She facilitates workshops on writing and media for young adults, is a workshop facilitator for a long-running low-barrier journalism program for inner-city adults at SFU Woodward’s, and facilitates a weekly creative writing workshop at Onsite, a detox and transitional housing program above Vancouver’s supervised injection facility. She loves watching comedy and reading fiction, and she’s so glad it’s spring.