Fighting trellophobia

Doing good work is a lot more than a smart workflow, but being organized never hurts. A little over a year ago, as I started planning to expand in earnest, I built a simple but effective job-tracking system. I was at a point where I was letting too many tasks slip through the cracks, so I wanted to design a workflow that allowed teammates and me to see an overview of where all our jobs were.

There is a boatload of commercial products that purportedly do the same thing. Over the years, I’ve had experience with Trello, Basecamp and Asana (along with a handful proprietary systems) and have found all of them to be largely useless. Rather than make things easier, they create a bucket of busywork; boxes to check off, (clunky) messages in need of reply and general tedium. The endless tiny tasks they create give me a pathologic sense of dread that I call trellophobia. I’m lobbying for it to appear in the next edition of the DSM. I wanted to work smarter, not more. I figured there wasn’t much that creative use of Dropbox and macOS couldn’t accomplish.

My primary goals were to be able to find jobs, files and assets a little more quickly, and to be able to quickly see where in the process my projects were. And my primary goal in writing about it isn’t to show off how smart I am (okay, I lied and I’m definitely writing for that reason) or to evangelize this exact way of setting up a file structure, but rather to show that critically thinking about how to work and using a little creativity can lay the groundwork for a custom system.

In 2017, we worked on more than 200 jobs, so I needed a quick system that’s easy to navigate. The first step for me was developing a naming convention. Having worked in newspapers – who manage huge volumes of photos, copy and graphics – through my 20s, I had a lot of experience with the subject. I borrowed from them (particularly including a dating mechanism) liberally and came up with this:

It breaks down this way:

  • Client code: HPS (a two- or three-letter abbreviation for the client)
  • Month: February in this case
  • Year: 2018
  • Job number: what number job of the month it is for that particular client; fifth in the example above
  • Description: a couple-word description of the job


The next step was to come up with the slots a job could fit into, the steps from start to finish. We’ve got six of them, though it’s the first four we use most regularly. Each has a custom tag in Finder:

  • Open: Actively working on the project
  • Billable: The project is wrapped up and ready to bill, which we try to consolidate and do on the first of the month
  • Billed: An invoice for the job is in the client’s hands
  • Closed: The invoice has been paid
  • Pending: While we’re not working on the project, it’s on our calendar for later
  • Scrapped: The project was cancelled

That’s the groundwork. From there, it’s a matter of using Finder’s saved searches to make navigating the system easy. A search I use constantly is for all my currently open jobs from the year, for example. All I have to do is tell Finder to search for files with “.18.” (for 2018) in the name, a kind of “file” (to filter random JPGs from the job folders I’m looking for) and a tag of “open.” Hit the “save” button in the upper right corner and Finder will plop a shortcut in the sidebar. I repeated those steps for the handful of the most common searches, and I’ve got a system that’s baked into the operating system and syncs across Dropbox. It beats Trello and Basecamp any day.


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