Creator Profile - James McLeod

Journalist/writer/content and comms guy James McLeod is our latest subject

James McLeod has years of experience as a journalist in Canada and recently moved to a content and communications role. I first discovered James via his prolific Twitter presence, enjoyed his humour and also the longer form pieces he publishes on different topics. I’m pleased that he agreed to participate in this E-mail interview.

Here’s James!

From James McLeod’s Twitter bio - original credit Bill Watterson

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When you were a teen, what did you want to be when you grew up?

In high school I took one of those silly personality test things and it gave me a list of careers that I was suited for. Journalist was right at the top of the the list, and as soon as I saw it, that just made sense. After that I started working toward going to journalism school, and I liked it, and then wound up working for newspapers.

You spent a number of year in NL (St. John's area) and your early work was from writing for the Telegram.  How did you land that gig?  Was it valuable prep for where you ended up?

I’m actually originally from Toronto.  It wasn’t until my fourth year at Toronto Metropolitan University (formerly Ryerson) when I had to do a six-week internship at the St. John’s Telegram. At the time I knew basically zero about Newfoundland and Labrador. I probably couldn't even find St John's on a map. But it seemed like it'd be a fun adventure before graduation. That internship turned into a contract gig that eventually turned into a permanent job. I stayed for nearly a decade. 

Is there any particular food or drink from NL that you miss the most?

I miss the seafood. Fresh caught lobster, and mussels in particular. You’d be insane to eat lobster in Ontario, but fresh caught and boiled up at home? Amazing. Also, fries, dressing and gravy is great.

From there you went to the National Post... was that a huge transition from the Telegram?

So, I'd say I went to the Financial Post. Today it's the business section of the National Post, but FP actually has a long and proud history before the National Post was founded.

The move was a big learning phase for me. I'd been covering politics in NL and thought I knew how stuff worked. Now I was covering tech and innovation in the business section of a national paper. Learning about the tech sector, how business people think, and how write for a national audience was a lot of learning. It was fun, but very busy and exhausting. 

And now you're with the Council of Canadian Innovators... another big transition?

In 2020 I found the first wave of Covid to be quite hard. It was insane covering business and the economy at that time, and I was convinced that I would be laid off at any moment due to the economic turmoil. Frankly, by the summer I was burnt out and needed to get away from the daily grind of journalism, and I needed to feel more economically secure. CCI was a business council I was familiar with and I generally thought their point of view was good, so when the opportunity to join the comms team came up, it made a lot of sense. 

That transition was different. Some of it was learning a new thing, for sure. But most of it was redefining my identity. Journalism becomes this core part of how you see yourself, and I wasn't a journalist anymore. Two years later I'm still figuring out that adjustment. 

How did you get involved with The Line?  Was it an extension from your previous journalistic work?  Is it a regular side gig for you or just an occasional thing?

So, I’ve always dabbled in analysis writing. When I was covering politics in Newfoundland and Labrador I channeled that into my book. A lot of my thoughts and observations tend to show up on Twitter. After I left the Financial Post I occasionally had essays or column-ish ideas to work out. Some of those wound up on my personal blog. Matt Gurney, a friend for a number of years, originally asked to republish an essay that I wrote about my relationship with alcoholism and addiction. After that I started writing intermittently, mostly just as a hobby and an outlet for my ideas.

From a rendition of Futurama characters, James used the Bender image (top left) as his Twitter bio for awhile (EPIK/Lynx Art Collection)

When it comes to writing are you 100% digital or do pen and paper have a place in your writing life?

Fun tangent: in my 20s I once spent $150 on ebay when I was blackout drunk and I bought a typewriter. When the thing showed up I had these visions of writing quaint inky notes to friends and mailing them. In reality I very quickly learned that my writing habits are very reliant on digital technology. I move chunks of text around and have multiple windows open with notes, drafts and everything. I obsessively recorded audio as a journalist and transcribed it to re-digest the information. So no, there's very little pen and paper involved. My writing flow state is very much fingers on a keyboard, not pen on paper. 

The one exception is a big cork board I have over my desk where I write little notes to myself. Just random jokes, or words I like, or reminders about things to think about. They're scrawled in sharpie on little pieces of paper and they remind me to think about things. One note just said “Pirate crew tension” to remind me to think about how to develop a specific plotline in my Dungeons & Dragons game. Another note just says "raconteur" because I like that word and want to use it more. Does that make me a raconteur? 

Delighted to read about your D&D hobby - I played many years ago and it's a part of my own cultural makeup.  Have you been playing long?  Do you play regularly?  Do you normally throw a 20 sided die to help you make decisions?  How's your AC and your saving throw vs. trolls?

I’ve been playing D&D since high school off and on. Just before the pandemic started, I started playing a game as dungeon master for the first time. Just me and three friends. We play on Zoom most weeks, and have been running the same campaign for the past 2 ½ years. There’s a lot of prep work involved crafting elaborate adventures, but it’s a wonderful outlet.

I could talk about D&D for hours. It’s shaped my thinking on a lot of things. Once you really understand the system, it’s beautiful and complex and special. It informs how I think about computers, probability, storytelling, identity and more.

And I don’t roll D20s to make decisions, but I do often flip a coin. It’s a great trick. If you’re ever stuck with some decision, flip a coin. The moment when you catch the coin but before you see the result, if you feel a strong urge like you ~want~ it to be heads or tails … well … there’s your answer. And if you’re truly ambivalent, the coin will tell you what to do.

Would it surprise you to know that Gary Gygax and team originally thought D&D was a $300 idea ($2,000 in today's terms)?  And the core idea has grossed over $1.0 billion, probably on it's way to $2.0 billion.  Obviously there are many factors to consider but to me this is an example of people never really knowing what will be a hit.  Any thoughts on that?

It doesn’t totally shock me that Gygax thought the original idea was only worth a few hundred dollars. If you follow tech and startups, there are a lot of ideas that are vastly under or over-valued in their early stages.

So much of what matters is the actual business development. A great invention is not necessarily worth a lot on its own. Negotiating contracts, developing a product, distribution etc. matters a lot.

Let's talk about humor in social media for a sec.  One of the first things I noticed about your Twitter presence was a healthy helping of humour in your posts with a decent seasoning of sarcasm.  I also remember you having an image of Futurama's Bender as your Twitter profile pic at one point.  Would you say that these influences and approaches give the reader a good appreciation of you as a person?  And do they help you to stand out from the crowd a bit?

So, I have been pretty lucky with Twitter in a few ways. I made a lot of mistakes back when the platform was smaller and less nasty, and while I was living in Newfoundland and Labrador, where the Twitter community tends to be pretty small.
I feel that you can’t really disentangle your professional identity from your personality. Anybody who tries to just have a professional online persona and a private life will spend a ton of energy and ultimately fail, I think. Or maybe their professional identity will just be boring as hell.

I tend to use Twitter as a place to hone ideas, to hear from interesting people talking about news in real time, and honestly it’s a place to hang out with friends. I could write a few thousand words on all my thoughts and feelings about Twitter, but the bottom line is that it's an interesting place I enjoy hanging out, even if it’s also dysfunctional with a ton of toxic elements.

The Bender profile pic was specifically an artist who had drawn various Futurama characters as classical paintings. I like the idea of a robot in a business suit as a sort of joke about bots on twitter and our cartoonish professional personas mixed with the crass fighting of twitter. Personally I think I’m more of a Fry than a Bender.

Right now my profile pic is Hobbes from Calvin and Hobbes cheerfully saying “We’re here to devour each other alive.” It’s one of my favourite comic strips, and I love Calvin’s punchline in the final panel equally.

I think it’s good to remind people not to take things entirely seriously. There should be jokes. All good writing has jokes in it. We’re hanging out to talk about the news, but we shouldn’t just be dour and serious about it. Without some levity and cynicism life would just be boring and exhausting.

Back to gaming for a moment: what kind of D&D character would Pierre Pollievre be?  And how about PM Trudeau and NDP Leader Jagmeet Singh?  And are we playing into stereotypes if we make the Pope a cleric  (I don't think he's a paladin)?

Ok so the real answer is that all politicians in a democracy are bards. The Pope is definitely a cleric.

On this subject I will just rehash something I’ve said on Twitter before. The D&D alignment chart is interesting: Good/Neutral/Evil and Lawful/Neutral/Chaotic.

Dungeons and Dragons alignment chart (via Wikipedia.org)

A lot of people think of themselves as Chaotic Good. In fact, I think most people are Lawful Neutral.

Are you in a good place these days with regards to previous history with alcoholism and addictions?

I wrote about my history in this essay I published last year. I’m in a good place now. I have no desire to drink and I am certain that my life is better without weed in it. I would encourage anybody struggling with these issues, or feeling like intoxicants are a negative element in their life, to talk to people about it. There are lots of us who have been through it and come out the other side. Most of us are eager to be supportive and help show you the way.

What are you reading these days?

At the moment I’m reading The Digital Republic: On Freedom and Democracy in the 21st Century. I’m reading a lot of stuff about tech policy and economics. Capitalism Without Capital and How The Internet Happened: From Netscape to the iPhone were both good.

But I also recently took a detour into The Shards of Earth which was just a fun sci fi adventure by Adrian Tchaikovsky. I’ve also got The Overstory on my Kindle which everyone raves about, but I haven’t had time to really sit with it and enjoy it properly.

Pretend you wake up one morning and you learn that the Internet has been destroyed.   What's the first thing that you do?

I think a lot of people underestimate how much of the world functions on the internet. The phone system and the electricity grid would probably be down, food supply chains would be messed up, and the water system in Toronto would probably be in trouble before too long.

Honestly if the internet had been permanently taken out of action I’d probably try to steal a bike and make it up to my parents’ farm where they grow a lot of their own vegetables. With luck things would be fixed before the weather got cold, but I wouldn’t want to be in Toronto without internet.

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Thanks to James McLeod for providing great answers to these questions!