I get asked a lot about self-employment.
I started working when I was 11. I was desperate for a pair of Doc Martens, but when my parents saw the price tag, they told me I was on my own to get the money. My allowance was $2.50 a week. I had to come up with something.
So I found an ad in the back of the paper and got a paper route. I delivered papers twice a week, every Saturday and Wednesday, for 18 months, which was how long it took me to save up the money I needed for those Docs. But I did it, and it felt good.
I’ve been working ever since. Sure, I’ve had some employment gaps along the way, but overall, that was the start of learning how to make my own money. I wasn’t old enough to work many other jobs, so I started a pet-sitting business and also did babysitting for the kids next door.
I was always entrepreneurial, even though I’ve had many jobs – about 30 at last count – working for other people. (I know…it’s a huge number. I’ve lived a lot of life.)
When I was in my 20s, I started working as a freelance writer, which was the first time I learned to truly embrace uncertainty. I would spend hours pitching stories to editors.
No one knows you when you’re starting out, no matter what industry you’re in. So when I was first freelancing, I was truly making cold connections, sending out shots in the dark, hoping that an editor would actually open my email in the first place…
And like anything, it all came together in time. I didn’t start out freelancing full-time, but eventually writing became my main source of income. It took about two years, and there was a lot of disappointment on that road. Hell, even once I was getting more established, the disappointment was still there.
There would be times when I would have absolutely no work on the horizon, and then I would get an email from an editor. “Yay!” I would think, expecting it to be an editor assigning me a story.
But some days, it was an editor telling me they had no more freelance budget for the season. Or that they just weren’t interested.
And that was hard, because the word NO often came up when I most needed a YES.
A couple of times, there were talks of getting my own column, but both opportunities fell through after those publications went through major restructuring. Even though the decision wasn’t about me, it was hard not to take it personally.
But these are the ups and downs that come from self-employment. Eventually, I transitioned out of freelancing writing and into communications, where I worked in the non-profit sector for eight years. By then, I wanted stability…but I also didn’t.
The truth was, I missed the uncertainty I’d had before. When you’re self-employed, anything can happen on any given day.
There’s something about believing that a golden opportunity could be just around the corner. There’s something about waking up every day knowing that you are creating your own reality with your own ideas and strengths and experiences.
Self-employment brings a lot of unknowns. The highs can be incredible, and the lows can be pretty lonely. But you also build a lot of faith in yourself when you’re faced with having to get back up on your feet after a particularly disappointing day, week, month, or even year.
When I was working 9-5, I missed the mystery of things.
So it was no surprise when I found myself returning to self-employment again, only this time, in a totally different incarnation. Because throughout those eight years of office work, I had gotten deeply into tarot and astrology, and had started to do tarot readings here and there as a side gig.
After getting laid off from my last job, I decided to dive into a full-time business giving tarot and astrology readings. Which, admittedly, is kind of a weird, unconventional path.
But it is how I make most of my money. I’ve authored six books, so I have a bit of income from my writing, too, but to be honest, being an author is a total gamble of a career choice that typically provides little to no return on investment. (If you ever want to ask me about money and writing, don’t be shy. I hide nothing and offer no illusions.)
Neither of these paths are easy, though. People don’t randomly buy readings. They put a lot of thought into trusting a reader and it takes a long time to build enough clients to stay busy – if you are looking to sustain yourself wholeheartedly from readings alone.
People also don’t randomly buy books, or at least not the books that I write. They put thought into those purchases, too, just like they do with anything else.
The truth is, self-employment is really hard no matter what you are in business with.
I don’t think it matters if you’ve chosen something conventional or not. Either way, you have to continue to let people know you exist, and you have to be consistent with your presence. You can’t ghost for months at a time because you got tired or scared.
Those early years of freelance writing really prepared me for the grind of my current business. And when I say grind, I don’t mean it derogatorily. But that is what it is. There is a dangerous illusion out there that features sunny, beachy images of well-manicured people sipping drinks while lazily gazing at their laptops.
And that may be a reality for a few entrepreneurs out there. But I know a lot of self-employed people – successful, ambitious, well-respected – who struggle to give themselves a day off most weeks.
This is hard work. You really do earn every single dollar you make, whether you’re selling tarot readings or t-shirts.
You have to be ready to commit to it day in and day out.
I am very all-or-nothing in my approach to life. For me, deciding to put full-time hours into my business is what helps it keep growing.
Sometimes, the uncertainty taking the plunge keeps people in part-time mode, splitting time between a job that offers a steady paycheque and working on their business the rest of the time.
But the reality is, you end up working way more than is realistic this way, or you don’t end up putting enough time into your true priority – your business – because the paid work gets the best of you.
I did work part-time for a handful of months when I was getting this business going, but it held me back from putting the dedication and routine I needed to get to where I want to go. Plus, I felt conflicted about the energy I was putting into someone else’s business – even though I loved it and supported it and had a great experience working there.
But it came to trusting in what I knew was more important to me, and that was my own growth and success. Even if I fail, I told myself, I would rather fail full-time.
In business, there is no endpoint: The hustle is always on. That’s also why it’s important to stay present and give it your all. Because even when things feel like they are gelling, you have no idea what next month will bring.
For me, I have times where I am so slammed that I might not have a day off for weeks. And then…crickets. Everything happens at once or not at all.
At first, it freaked me out. Now, I know it’s just part of the rhythm of my work.
This is part of the trick to self-employment. So many people want to quit their jobs, but they aren’t sure about the uncertainty that will bring.
The reality is, if you want to be self-employed, you have to be okay with not making the same amount of money all the time. You also have to be okay with knowing that there might times you don’t make any money at all, especially when you’re starting out.
You have to embrace uncertainty and be willing to do something precarious, but back it up with healthy, grounded boundaries and realities.
For example: I have learned to say no a lot, because you can go broke saying yes to every friend and acquaintance who wants a discount, or an exception to your rules. It can be really hard to say no when you need the sale – but it’s also important to learn how to respect yourself and your business by asserting yourself.
In the first year of my business, I was often afraid to spend money, even when I didn’t need to worry. Still, I would fret about even buying myself a coffee sometimes.
That’s another reality of self-employment: Your mindset shifts. Eventually, new comfort and security set in, but it might take time before you can really let yourself relax – especially if you are coming from a salaried job or other steady work.
Some days, being self-employed is amazing, and other days it’s sad and frustrating and terrifying because you don’t know where you’ll be in a year, though you’re hoping it will be the place you’re aiming for.
But you know what? I felt exactly the same way when I was working at a steady job. I used to worry that my life would always feel smaller than I’d expected it, that I would never get to experience the things I’d hoped for if I stayed between those office walls.
Having the stability of a day job didn’t give me any promise or guarantee of where I might be one day, or whether things would get worse or better.
Stability really is only an illusion. Yes, it can be harder to create if you are building a business, but it’s not impossible.
Just remember that it all takes time. Self-employment isn’t for everyone. Neither is writing. Both start with a willingness to commit to the unknown.
But when you think about it, we’re all moving towards the unknown, anyway. But you get to decide which turns you want to take along the way.
Until next time,