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Issue #22

How to Choose A Productivity Tool

John Loeppky

September 13, 2023

A Mac computer is open on a desk that is filled with art supplies, a phone, a coffee, and various other extras. The desk is vibrant with many colours, most of them primary.
In the Midst of Chaos /Adobe Stock

A Lesson In Failed Experiments

Choosing productivity tools can feel like  the ultimate example of analysis paralysis. Especially if you’re neurodivergent, the absolutely cyclical chaos of trying to figure out which tool is best for them can be entirely overwhelming.

For example, early on in my writing career I swore by the writing tool Scrivener. Then, paradoxically, I shifted to Microsoft Word. Now, I use Google Docs for almost everything and use Word when required by clients to send and receive documents. My document storage has undergone a  similar transition, with different back up solutions being used until I settled on a secure solution that saves my work in three separate places. Name a problem—password storage, video editing software, which email newsletter provider to use—and choosing a solution can be torturous.

So, from a cripping productivity perspective, here are the three things I take into account when I’m choosing a tool. This is, by no means, a fantastically new set of ideas, I’m just hoping they might help you in easing your choices.

Q1: Is this a nice to have change or a required change?
New and shiny things are certainly hard to ignore. If a product requires a membership fee that is too expensive, or if it no longer works, or if it has become suddenly inaccessible, then this choice is made for me and it’s time to move on. However, if a tool (waves at stack of never opened journals in the corner of my office) is calling to me for no other reason then the fact than it is new then I need to do my best to stop myself. Making changes just for the sake of making changes is a fast track to a productivity hellscape. If I were to put an arbitrary percentage on it, a tool has to make me at least 15% more productive in some way before I can consider a change.

My best example here is my invoicing software. In my first months of freelance I stuck to making excel documents. This worked fine when I had one or two clients and one or two pieces a month. It worked horribly when that expanded. What finally convinced me to make the change was doing the math on how much time it was costing me not to use Freshbooks.

Q2: How easy will it be to transition my mindset with this new tool?
This might seem counterintuitive, but I worry less about whether I can move over my notes, or documents, or whatever to a new tool and more about whether I can transition my mindset. If I can’t fit the new tool into my routine as well as my previous choice then it is a point against making a switch. For example, shifting from Word to Google Docs was fairly simple because they are essentially the same and I could still use Word when needed. Clients were clearly preferring Google Docs so it wasn’t a difficult change.

On the other hand, I’ve regularly looked at switching away from Otter.Ai, my transcription tool, but none of them have the simplicity of an interface. Again, change for change’s sake would just lead to more confusion for my brain. 

Q3: Do I know people who use this tool? 

This is so, so, so important. If you have people in your circles who you can ask about the tool then you’ll be much better off when you switch. I’ll give you two examples for this one. I felt comfortable switching from PC to Mac in the middle of university because most (if not all) of my theatre classmates were already using one. I trusted myself to be tech savvy, but I also knew I had people to go to that I wouldn’t have to pay.

However, this circle can also be expanded out. I chose ConvertKit because I am a fan of a staff member (Charli Prangley) and her YouTube channel. Knowing that the company was willing to be so public with their processes, that they were willing to admit when they screwed up, and that they had a healthy seeming relationship with freelancers as a fully remote company before it was cool allowed me to feel like their promises of help wouldn’t be empty.

Why does all of this matter from a cripping productivity perspective? Because we’re not only spoiled for choice in the digital world, but we’re also constantly being told (whether that’s by society, our doctors, or our teachers. to pick just three) how to be better. Just like any other aspect of productivity, being able to understand why (or why not) to make a particular choice can help you build consistency. It’s all about stretching those muscles and putting them into action. Even if you do choose a tool and realize that it isn’t for you, it can be helpful to revisit these questions later down the line to recognize the mistake and revert (or try another new thing). It’s okay to get it wrong, we all do, just try not to compound the problem by sticking to a tool when it’s no longer serving you.

Until tomorrow!


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