I've been thinking for a while now about starting a newsletter, which is admittedly a somewhat questionable decision for someone who already has more things going on than is probably advisable. This is not an uncommon occurrence for me, which is how we got here and why you're reading this.
The name Boring on Purpose popped into my head while I was thinking about a bunch of seemingly unrelated things I've been working on lately, and it stuck almost immediately. I like boring things more than most people, so I registered the domain, because that's what I do, and then spent some time trying to figure out exactly what I wanted to talk about here.
I think I've figured it out.
A lot of what I believe about building a business, running technology, and just generally getting things done comes down to doing a fairly large amount of decidedly unexciting work so that the eventual outcome is as boring as humanly possible.
Planning is boring, documentation is boring, and checklists can be mind-numbingly boring, both in the creation process as well as the execution of the task itself. Testing something before you need it is rarely anyone's idea of a good time, and neither is going back afterward and figuring out why something didn't work quite the way you expected.
I've also come to believe pretty strongly in all of those things.
This isn't exactly how I've operated for my entire career, mind you. I've spent a good portion of the last few decades being very good at solving problems as they appeared, which is a useful skill right up until you realize you've become the guy everyone expects to solve the problems as they appear and while I am living proof that there is certainly some job security in that, I'm increasingly convinced it's a terrible operating model for pretty much anything.
These days I'm much more interested in figuring out why the problem happened in the first place, what could have prevented it, and whether I can put something in place so nobody has to be particularly clever the next time around.
That last part is important, because I think we tend to place entirely too much value on cleverness in technology, and probably in business too. We celebrate the person who pulls an all-nighter and saves the project at the last second, while spending considerably less time talking about the person who built a project plan six weeks earlier that meant nobody needed to pull an all-nighter.
I've been both people, and in the end I'd rather be the second one.
The same idea applies to most of the things I'm building now. I don't have much interest in adding complexity just because I can, chasing every new idea that shows up in my feed, or adopting a piece of technology so I can tell people we're using it.
I like new technology quite a bit, for the record. I am exactly the type of person who will install something at 10 PM (or register a domain name on a whim) because I read about it twenty minutes earlier and became curious. While that’s fun for me, it’s in no way anything related to strategy.
The strategy part is deciding whether that new thing actually makes something better, whether it's worth the overhead that comes with it, and whether I still want to be dealing with it on some random Tuesday two years from now.
I'd like to take a moment here to talk about Tuesdays. I'm sure for most people they're just, well, Tuesday, but since 1997 I've had a phrase running around in my head that I first heard in the Baz Luhrmann song Everybody's Free (To Wear Sunscreen), which is essentially a spoken word reading of a column written by Mary Schmich that was published in the Chicago Tribune on June 1, 1997 and while the whole column is definitely worth a read, the line that has resonated in my head since I first heard it is "The real troubles in your life are apt to be things that never crossed your worried mind, the kind that blindside you at 4PM on some idle Tuesday."
I've heard it in my head repeatedly over the years, I've mentioned it to a large number of people along the way, and for the longest time I knew it was important but couldn't figure out why. In a strange coincidence and apropos of nothing, the column was published on my 18th birthday, and it took me a few decades to figure out exactly why I couldn't stop thinking about it.
Here's the thing: anything exciting you build eventually has to survive you.
The New Company eventually just becomes The Company. The big technology project eventually becomes the thing everyone uses to get their work done. The shiny new platform becomes another login, another renewal, another thing that needs to be maintained, and another thing somebody will eventually have to troubleshoot.
(I have thoughts on how most of life centers around the desire to prevent entropy while in reality the only thing we can actually accomplish is creating systems to manage entropy, but that will be a different issue.)
Which brings us to: Everything is a Tuesday in the end.
And if you've done the work correctly, Tuesdays should be pretty boring. There should not be anything that blindsides you at 4PM. I recognize that this isn't a reasonable or rational goal, but you can get to the point where you're much less likely to be blindsided.
People show up. Things work. Customers get what they're paying for. Problems still happen, because of course they do, but you aren't rebuilding the airplane every time one does.
That's more or less the idea behind this newsletter.
I spend most of my working life somewhere in the overlap between business and technology, and at this point I find that intersection to be the part I enjoy thinking about the most. Not how to configure a particular setting in Microsoft 365 or which button you need to click in some security product. There are plenty of places to learn that stuff, and I'm not particularly interested in adding knowledge of Yet Another Technology Product to my repertoire.
I'm more interested in questions like how much security a small business actually needs, why standardization is so damn useful, when automation makes things simpler and when it just gives you something new to babysit, what technology choices look like when you're the one paying the bill, and why businesses so frequently spend money trying to solve problems that probably shouldn't exist in the first place.
There will be business topics too, largely because I'm building businesses and therefore spend a fairly unhealthy amount of time thinking about them, but also because business has interested me since my early teens.
I'm sure I'll write about pricing, customers, vendors, processes, growth, mistakes I've made, ideas that worked better than expected, and ideas that turned out to be dumb once they encountered reality. (There are enough of the latter that I could write for years just talking about them.)
I also wrote a book about small business IT, so I'm reasonably certain some of those ideas will find their way in here as I revisit them and inevitably discover that I've changed my mind about a few things.
I don't have any desire to turn this into a running advertisement for what I'm building, though. If you're reading for a while you'll undoubtedly figure out what I do for a living. That's fine. It gives me plenty of real-world material to write about, which is useful because I have very little interest in manufacturing opinions about things I've never actually done. That's probably the best filter I have for what belongs here, and most especially what doesn’t.
There is a phrase I've used to describe my general approach lately: relentless execution combined with a dash of delusional optimism. OK, more than a dash; I'm optimistic enough to believe you can build things that are substantially better than they are today. I'm also old enough, and have screwed up enough things, to know that the interesting idea at the beginning contributes a surprisingly small percentage of the eventual result.
Then you have to do the work.
A lot of that work is boring.
On purpose, as it turns out.