The risk of taking no risks
On independent work in the age of AI.
At the beginning of this year I was at a portfolio career crossroads.
It was January and I’d just sent my final invoice to a beauty brand I’d been working with, on and off, for almost 2 years. I’d known for some time that my contract was winding up and found myself deliberating my next move. I had two main options: do the responsible thing and tap my network on the shoulder to land another fractional gig, or take a risk and dedicate time to growing my scalable income streams.
Intuitively I knew that pausing client work to focus on digital products, mentoring and writing was the right move and I secretly hoped I could click my heels and everything would work out great, but I’d by lying if I said the worst case scenarios didn’t run through my mind.
What if, without reliable retainers, everything fell apart? What if my mentoring work dried up? What if my digital products tanked? What if my Substack got hacked and I was left out in the digital cold? What if I became financially destitute, creatively vacant and motivationally comatose? What if the world I’d worked so hard to colour suddenly turned grey?
Interestingly, if I were faced with this situation 6 years ago when I first quit my job, I’d have chosen to find a new client immediately because I doggedly believed that avoiding risk was “fiscally smart” and made me a “responsible business owner”. Back then when it came to matters of the hip pocket, I stuck to what I knew, played it safe and kept my cool.
These days, however, I’m more bullish on taking risks because I believe in my ability to enact the backup plan if/when everything falls apart. If my product sales fell off a cliff, I could whip up 10 new ideas to market them. If money dried up, I could ping 30 founder friends who might need my help. If I lost all momentum and motivation for writing, I could pivot and try something else. Even in the most dire of straights there’s always a contingency, meaning I have no reason not to take calculated risks. And when you work independently (like moi) pushing yourself, testing new paths, trying new things and expanding your brain is almost a requirement. In a world where AI is gobbling up everything, there’s risk in being overly cautious. There’s risk in being dependent on a single income stream, skillset or employer. There’s risk in taking no risks. In a twisted turn of events, playing it safe is no longer safe.
We’re not in Kansas anymore, Toto.
Work is changing and so are we. Society. Technology. Culture. It’s all being turned on its head.
At a time where up is down, left is right, ChatGPT is my daily therapist and Donald Trump is President, here are a few ways I’m preparing to take bigger and smarter risks:
I’m increasing my emergency fund from 3-6 months to 6-12 months. A solid slush fund is an absolute must in my opinion because the more buffer you have, the more leeway you have, the more options you have.
I’m releasing 1-2 new digital products before Christmas and launching a portfolio career cohort early next year (more on this soon).
I’m surrounding myself with experienced founders, solopreneurs and mentors who’ve taken bigger risks and dealt with far harder things than I have. Hearing their stories puts everything in perspective.
My boyfriend and I constantly communicate about the risk we’re happy to take in his job, my work and our life, weighed up against the potential reward.
I’m betting on myself. Every time. There is no other way.
It’s an interesting time to be a cluster of biological cells in a blip of space in an ever expanding universe, but if there’s one thing you take away from today I hope it’s this:
Don’t wait to show up. Don’t shelter in place. Run towards the tornado. Raise your prices. Test an offer. Step into a new identity. Give yourself the chance to click your heels and enter the eye of the storm. To twist and turn and spin and swirl and land somewhere lighter, brighter and more colourful.
Somewhere over the rainbow.
Thoughts on AI and how I’m taking short term risks to mitigate long term risk:
Plus here’s the podcast episode I referenced.
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Thank you! Yes! I was always a cautious player re: my career/work. I had a few fabulous positions with horrendous leaders. I worked hard. All the time. Driven. Put most everything else in my life on hold, including my health. Until I couldn't any longer. After my husband's heart attack and triple bypass surgery and no relief at work, I said to myself, "Enough."
I quit my job--did not have another one waiting (but I did have enough cash stashed away). I began doing some consulting work. I began writing again. Within 9 months, a publication picked up a piece of my short fiction. Within a year, a magical part-time gig fell into my lap. I'm doing what my soul was meant to do. I'm heading to a week-long writers conference this fall and I'm working on a novel.
DO IT. Take that risk!
“There’s risk in taking no risks. In a twisted turn of events, playing it safe is no longer safe.” I love this line, and this makes so much sense.