People and Blogs: David Cain

Let's start from the basics: can you introduce yourself?

I’m a Canadian blogger and entrepreneur. I started doing this back when I was in a totally different line of work. I was a surveyor for an engineering company, and where I live the industry slows down in the winter because of the harsh cold, so I began poking around on the internet a little more than usual. That led to discovering blogs, and the possibility of doing that for a living.

I had always been into writing, so having a way to publish my thoughts and for interested parties to read them and care was a revelation. That was 2008 or so, when the internet was a very different place. Social media was a niche and nerdy thing, big companies had no idea how to use the internet, and we were not all algorithmized. I miss that time.

Aside from what I write about (see below), I’m into indoor climbing, reading, religion, history, and lifting weights. I’m also into the idea of the “Oldschool Internet.” As you know if you’re over 30, the internet used to feel different than it does now. It was freer, more creative and weird, and less dominated by big platforms and algorithms. I have a deep, deep nostalgia for it and I wish I could recreate that feeling.

What's the story behind your blog?

When I was goofing around on the internet at work I found a blog about blogging for a living, and one day decided I would do that. I had always been interested in the inner world of the human being. I was always thinking about this conundrum of having mind and a body. You have no instruction manual, and you have to go and live a life and try to be happy. I sat down and listed like a hundred obscure ideas I’d been wanting to tell the world.

What I didn’t realize is that my obsession with the inner human world and managing the human condition was due to having undiagnosed ADHD, which made ordinary life stuff very complicated and difficult. My challenges led me to reading piles of self-help and spiritual-flavored stuff. A lot of it was crap but I did learn quite a bit about making the most of the mess that is human life, and shared what I found.

The blog I started was called Raptitude. It was just a made-up word, combining “rapt” and “aptitude.” The idea is that you can get better at appreciating life, at being rapt by the day-to-day experience of being alive. Many of my posts were little tricks I’d figured out for getting yourself to do things, not realizing it was coming from a rather crippling psychiatric condition. I finally got diagnosed at age 40, after twelve years of blogging.

I always tried to stay away from writing in the kind of mushy, therapeutic tone that dominates the self-help and spiritual space. I wrote about weird and hypothetical things instead, and I found an audience pretty quickly.

This year I launched a second site to help other “productivity-challenged” people. It’s called How to Do Things, and it’s more practical and less philosophical than Raptitude, and is aimed at adults with ADHD.

Today my writing is more focused, less wild. But Raptitude is the same blog it was 17 years ago when I first launched it.

What does your creative process look like when it comes to blogging?

I have ideas all the time and take voice notes when I’m out and about. If I’m home I just mind-dump into a text document.

Later I go through my ideas and find one I think I could actually write about. I play around with it, find an angle, and start typing. I do a lot of moving things around, cutting and pasting. Sometimes I’ll write 3 or 4 thousand words and end up with a 1200-word post. Sometimes I even delete the original idea and just riff on a tangential idea.

It is not an efficient or structured process, it’s just habit. I take forever to write posts, even now. I don’t do drafts exactly, I just barf out the idea, try to find a bottom-line point, then revise what I’ve written to point to that bottom-line idea. I do a couple of passes to try to shorten it, which just as often ends up lengthening it. Then I add pictures with funny captions so people don’t get bored and publish it.

I don’t involve anyone else in the writing and there are typos sometimes.

Do you have an ideal creative environment? Also do you believe the physical space influences your creativity?

I have a home office and that’s pretty much exclusively where I work. Everything I need is there, my desk has a lot of space, I have multiple monitors. I play instrumental music. Classical or ambient electronic.

I’ve worked in coffee shops, and I do get inspired by being out in the world. But I always feel guilty about taking up their seats for too long, and the travel time seems like a waste so I don’t do that much.

A question for the techie readers: can you run us through your tech stack?

I have always used WordPress, and self-host on BigScoots. I love the host and am so glad I switched from a large, well-known terrible company I will not name. WordPress is good and a lot less clunky than it used to be.

Given your experience, if you were to start a blog today, would you do anything differently?

Today I would just do a Substack. I still might switch to Substack one day. It seems like a well-contained environment that takes eliminates a lot of technical and design considerations that can suck up writing time. You’re also built into a network of other writers and readers.

What I would do differently is learn to make a kind of content that doesn’t take long to make. I take forever to do one piece and it is still hard.

Another thing I’d do differently is define my topic more narrowly. I write about anything pertaining to human life, which makes it difficult to know what to write about, and difficult to do any marketing or intentional growth, because there is no identifiable crowd or demographic that I know would be into my “topic.”

Financial question since the Web is obsessed with money: how much does it cost to run your blog? Is it just a cost, or does it generate some revenue? And what's your position on people monetising personal blogs?

It costs a fortune, all told, because it’s a business and not just a blog. Hosting isn’t bad – a few hundred dollars a year. I pay someone on a monthly basis to update and maintain the site and deal with downtime and crashes and other stuff that used to blow up my life once a year or so. I’m not a super savvy technical person so this is necessary.

The highest cost is the email management system, which is essential for the layers and layers of emails I send. With 40,000 people in the system it costs over $400 a month. There may be cheaper options but switching would be too big a pain. I also have tons of little subscription costs that have become necessary for product delivery (Dropbox for example). Altogether my monthly business expenses are more than my rent.

I make a full-time living from my blog by offering products to my readers. I also have a Patreon.

The whole operation would be way cheaper to run if I didn’t sell anything. I am all for monetizing personal blogs. Good content is hard to make and takes time, and if you want to offer something bigger than blog posts, you have to charge for it or it doesn’t get made.

Time for some recommendations: any blog you think is worth checking out? And also, who do you think I should be interviewing next?

I am a fan of David Pinsof’s Everything is Bullshit and Scott Alexander’s Astral Codex Ten, both of which are Substacks now. Mostly I read books these days.

Final question: is there anything you want to share with us?

I just want to say this was a lot of fun. Not to be the old man in the room but the internet has changed immensely since I started in 2008. Part of what has dropped away (at least for me) has been being in the “world” of blogs. Answering these questions and reading other people’s answers on your site has reminded me that some semblance of that community spirit still exists. Thanks for keeping it alive.