Side hustle to full-time – part 1: quitting my job to pursue my passion

I laboured over that resignation letter for hours. Hours.  

It ended up only being a couple paragraphs long, but I was paranoid about coming off as too flip or arrogant.  

I kept it quick and gracious in the end: “Thanks, it’s been a good eight-and-a-half years…but I quit.”  

I sent it to my managers and copied HR. That was it—done deal, no take-backsies.  

I wish I could say that I instantly felt joy and satisfaction, but alas—that would be a bald-faced lie. Instead, my brain raged with all kinds of questions. Some practical, some VERY judgmental:  

“Are you insane?”  

“Have you thought this through?”  

“Is this officially your mid-thirties crisis?”  

“Do you ENJOY paying full price for dentistry sans benefits?”  

Once I had my mini freak-out, things felt a little better. There was a good-ish reason behind all of this quitting: I wanted to pursue my passion—my longtime side-hustle—full-time.  

And unless I got clear of my day-job, there would always be another comfy excuse to put off the side-hustle and everything that came with it.  

What was that side hustle, you ask? Freelance copywriting.  

There’s just something that’s always drawn me to being a solo writer, ready to take on anything from ad copy to long-form travel blogs. I love the idea of going where the jobs take you, diving in and coming out with a good story that moves people.  

All romantic notions aside—leaving my job to become a full-time freelancer would either be the awesome-est or most foolhardy thing I’d attempted in a long time. And that’s counting my ultra-brief stint as lead guitarist in Guelph, Ontario’s fifth-best Weezer cover band.  

Why am I telling you about my side-hustle?  

Well, I want to give you a peek behind the curtain at what it’s like to take a side-hustle and turn it into a small business.  

Thousands of your fellow Canucks do it every year. They follow their passions, grind it out and find success. I’m just trying to be one of them.  

So in this series, I’ll take you first through the joy and pain of giving your business a name, then move on to shopping for a .CA domain, building a website—and beyond.  

But here’s the thing: I’m no expert—just a guy offering up his thoughts and learnings while he does his best to wade through.  

The pains of naming my side-hustle

Now that I’d left my day-job, I figured one of my first tasks would be to name my new venture. After all, if I wanted to build a website, I would need to come up with a good .CA domain name, anyway. Now, could I come up with anything not too cringeworthy?  

First, I thought, “What do I do?” That’s easy: professional copywriting.  

Okay, but can I make that into a clever, memorable and short name? 

What about…joeyink.ca. Get it? Writers, ink, quills.  

My wife wrinkled her nose at the suggestion. “It sounds like you run a sketchy tattoo parlour,” she said. Okay—point taken.   

I thought outsidevoice.ca might fit the bill. I’ve often been accused of being unfiltered and using my ‘outside voice’ in many situations…and what I’d be doing is helping my clients find their true ‘outside voices’ with my writing.  

But after a little more thought, outsidevoice.ca kinda sounded like I led corporate nature retreats, or took people into wooded areas to shout at trees.  

My third attempt at a name was joeywordsmith.ca. A bit of a mouthful, I know.  

“Now, you’re trying way too hard,” said my wife.   

Then, I went down a rabbit hole of silly throwaway names, like “mortadellamarketing.ca” (after my favourite Italian luncheon meat), before I realized: my domain name didn’t have to be a wordy masterwork.  

I could torture myself to be creative, or take the more “direct” route. That’s what led to joeywrites.ca.  

Why? Well, it’s active, it speaks to what I do, and it gets across the whole “solo freelance copywriter vibe” I was going for. It’s not, “Harold or sometimes Sonia writes when Joey’s got better things to do,” it’s just Joey. There’s a personal, human element to it.  

Next, I plugged joeywrites.ca into CIRA’s domain search tool below to check whether the domain name was available to register…and it was—huzzah!  

What two things did I learn from this .CA domain naming exercise? 

Try to keep your name short and easy-to-type: as tempting as it is (for me, anyway) to come up with something long-winded, you’re not doing yourself any favours if people can’t remember your domain name, let alone type it into a search bar.  

Handy rule of thumb: keep it under 14 characters!  

It’s never a bad idea to go for function over form: look—I’m a big fan of creativity, but if it comes at the expense of clarity then there’s no shame in opting for something simpler that “just works.” Ideally, your domain name should tell people what your business is all about at a quick glance. Check out CIRA’s blog that shares other tips when choosing a good domain name. 

And—hey—if you can thread the needle and come up with something that melds creativity AND clarity—then, you win!   

Look at genuinetea.ca, for example. They sell ethically sourced, whole-leaf tea…doesn’t get any more “genuine” than that! Another good, creative-yet-straightforward example is sellers of pool floaties, float-eh.ca. That’s just too good.  

What’s next? Hunting for a domain deal and building my website  

Now that I had my domain name, I needed to find a domain registrar (the folks that sell and register domain names) and get joeywrites.ca up and running for real.  

In part two of the Side hustle to full-time blog series I’ll go over how I picked my registrar, what services came with my .CA domain, as well as the sometimes-sweary process behind building my very first website.  

I hope you’ll come along for the ride! Ciao for now.  

 – Joey