I realized something a few months ago that simultaneously made me feel very old and also kind of proud: I’m now into my second decade of sportswriting.

That’s not all that much in the grand scheme of things, and you don’t get a trophy or collectible pin for it, but it’s still kind of neat. And it feels like the sort of milestone that goes well with a major career change. Today, I can share that I’ve reached that point, too. Earlier this summer, I agreed to join The Athletic on a full-time basis.

And now, I’m writing a post about it, because they are making me do that.

It’s kind of a thing around here.

I’m guessing you know the drill. Computer scientists estimate that the internet produces roughly 1,200 petabytes of data per month, and at this point, I think roughly half of that is sportswriters explaining why they’ve joined The Athletic. By now, you’re familiar with the basics – the industry is going through a tough time, new business models are needed, and it no longer feels unreasonable to ask readers to pay for a product that has value, just like they do in almost every other type of business. Not having to fight through ads or auto-playing videos to get to the content is a nice bonus.

All of that is true. I’m just not sure how much I can add to it. But I’ve always believed in a “when in Rome” type of philosophy. When you move to a new neighborhood, you learn the local customs. When you’re in a stadium and everyone else starts doing the wave, you roll your eyes and join in. When you’re traded to the Senators, you immediately demand a trade away from the Senators. And when you join The Athletic, you write a post about why you’re joining The Athletic.

So that’s what I’m doing.

But how? What’s the angle? How do you make something like this feel fresh? I briefly considered posting an adorable childhood photo of myself sleeping under The Athletic bed sheets, but apparently, somebody else already beat me to that idea. So instead, I’m going to stick with the story of how I got here. Because it’s not one that many of my peers can tell.

I grew up dreaming of being a sportswriter and eventually went on to earn a degree in journalism. Along the way, I did the requisite stints covering varsity sports for the school paper, the unpaid internships, and the summers spent at the community paper. (Thornhill Liberal, represent.) But even back then, decent careers in the field could be hard to come by and once I graduated I ended up drifting into a marketing job instead.

You could say I sold out, or maybe I just accepted reality, but either way it meant giving up on the idea of doing any writing that didn’t include the phrase “buy now” every sentence or two. Got to have a strong call-to-action, after all. You marketers know what I’m talking about.

It was a decent job, and I was relatively happy doing it for the next decade or so. But then a funny thing happened. Blogs came along, and suddenly people like me could have their own writing platform. I logged into Blogspot one day, figured out how to set up a basic site, and then stared at the “Blog Name” field for way too long. Eventually, an idea popped into my head, I typed “Down Goes Brown” into the field – thank you, Joe Bowen – and I was off.

What I was off to was a site where I could write for an audience of roughly five people. But that was fine, because it was fun. And over the months and years to come, the audience started to grow. Thanks to a flow chart here and a top-secret transcript there and a brief foray into impersonating an NHL GM on Twitter (don’t ask), I built up enough of a readership to open some doors. Eventually, I found myself with a book deal and a newspaper column. And all the while, I was still working a day job, spending my 9-to-5 hours testing which color of “buy now” button worked best.

That last part changed in 2012, when “buy now” turned into “bye now” thanks to a round of layoffs a week before Christmas. (In corporate downsizings, as with comedy, timing is everything.) For the first time in my professional life, I really had no idea what would come next.

As it turns out, what came next was the best job I’ve ever had. I was offered a chance to join the roster of a relatively new sports site called Grantland. This was it. The chance to leave the cubicle world behind, and actually be a sportswriter for a living. This was the dream – specifically, the dream I’d abandoned years ago, only to somehow stumble back into all these years later.

I’ve often described my experience working at Grantland as feeling a lot like being a fourth-line winger on the late-70s Montreal Canadiens dynasty. The roster was jammed with an almost ridiculous amount of talent, both well-established and up-and-coming, and I made it my goal to learn as much as I could while trying really hard not to embarrass myself. Some days were better than others in that regard, but over time I started to find my footing. When my original contract expired and I was offered a multi-year extension, I happily jumped at it. A few weeks later, Grantland ceased to exist. I don’t think that part was directly my fault, but I can’t rule it out.

That brought me back to not knowing what was next, and this time there was catch: When it came to the sportswriting world, nobody seemed to be hiring, and most outlets were actively cutting back. There was still freelance work available, maybe even more than ever before. But finding any sort of sense of permanence seemed next to impossible, especially for a fourth-line winger. And after nearly three years of writing about sports as a job, I knew there was no way I could go back to the cubicle world of “buy now” and “keeping regular hours” and “changing out of your pajamas before work.” I started to worry that I may be kind of screwed.

The freelance offers started trickling in, with one of the first coming from a small startup based out of Chicago that was looking to expand. Something called The Athletic. In hindsight, what I should have said was “Yes, and please pay me in stock options.” Instead, I told them my plate was already full – it wasn’t – and politely wished them good luck on the whole expansion thing. I hear it went well for them.

Eventually, some good luck kicked in, and I found a handful of sites that wanted me to do freelance work – mainly Sportsnet and Vice Sports, with an occasional dip into The Guardian and even The New York Times. Freelancing can have its ups and downs, but I ended up having a blast. I was treated well, and had the chance to work with great people. I learned a ton and got to write a bunch of fun stuff. Some days, in a pinch, I even felt like I could handle third-line minutes.

But even when everything is going well, freelance is still freelance, and that feeling that you’re one budget cut away from losing half your income is a tough one to shake. Last summer, I was scrolling through Twitter when I was met with breaking reports that one of the sites I worked for was shutting down and laying everybody off. That turned out not be true – the site wasn’t dead after all, and remains a going concern today – but it was a reminder of the risks of putting all your eggs in the freelancing basket.

So when The Athletic called back earlier this year, I was ready to make the leap. That brings us to today, with a new decade, a new job, and a new chance to join an all-star roster and try to figure out how I’m going to crack the lineup. And fingers crossed, this time, at least a little bit of permanence.

Also, I’ve been told there’s no word count here. I intend to test this theory, and you can look forward to my upcoming eighteen-part series ranking all the organ music in NHLPA 93.

So that’s why I’m joining The Athletic. And it’s why I hope you’ll join too, if you haven’t already. If you’ve been reading my work since the Grantland days, or even before that, or maybe as one of those original five readers back in the blogspot days, then I hope you’ll stick around. I hope that I’ve done enough over the years to convince you that my work is worth a few bucks a month.

Buy now!

(Sorry, old habits die hard.)

If you haven’t subscribed yet, try The Athletic free for a week and get 30% off with this link: theathletic.com/nhlexpansion