A few years ago, I was looking to solve a problem that, in hindsight, didn’t need solving. Specifically, I wanted to have a system in place for legal clients to have easy access to their digital documents. After some research and trials (why are nearly all legal-focused software/services terrible?), I ended up choosing Basecamp.

I have read several books by Basecamp’s founders, and I believed (and continue to believe) in the company. So I spent time and money making the transition of many legal files into a Basecamp install and spent client attention getting them into the system. This was no small investment for me. Basecamp costs $1,000 per year. Moreover, it is a web service and not particularly automation friendly. I figured out work-arounds, but my traditional bag of tricks did not work, and everything I did in relation to my legal files took … just … a … little … longer.

OmniFocus recently reminded me that I am a few months away from my annual Basecamp renewal, so I spent some time looking into my usage. In doing so, I realized that only 3% of my clients were using it as I envisioned. I spoke with a few clients about this, and one explained to me, “Dave, I’m paying you for a service. Don’t make me learn software to do so.”

In short, my Basecamp experiment crashed and burned. So over the last few months, I have been pulling my legal data out of Basecamp, and I am now sorting out a more traditional, local file system for that data. There were other benefits available on Basecamp that I will miss, specifically the ability to easily combine documents, notes, email, and other data on a per-transaction basis. So now I am neck-deep in JavaScript and creating tools in Drafts, Hazel, Keyboard Maestro, Shortcuts, and all the other bits to replicate those features locally. It’s all working out, and it probably would not surprise you to learn that I am enjoying building out the new automation.

There is, however, a plot twist. The purpose of the Basecamp experiment was to solve a perceived problem with the law practice, but since I had the account, I also started using it for administration of the MacSparky bits. My virtual assistant liked Basecamp and, from the beginning, it was a very convenient place for us to work together. I spent some time looking at other collaboration tools and none of them are particularly appealing. So while I am going shut down my paid account, I will remain in Basecamp with a free personal account, limited to three projects. That is plenty for us to keep things rolling at MacSparky.

Plan on future posts here about automation and file management since now I am neck-deep in it.