To free or not to free

I’ve been thinking about the apps I use and which ones I pay for — specifically those made by individuals or independent companies that offer both free and paid options. How do I decide who to support?

(Note: I’m in the Apple ecosystem, using a MacBook and iPhone. Some friends are quick to point out that free or open source apps are more plentiful across Linux, Windows, and Android.)

For me, it comes down not to premium features, removing ads, or anything but a simple question: Do I want to make sure this app continues to exist? This is the digital equivalent or shopping local or voting with my dollar. The problem is that I’m not consistent with how I apply this principle. Let’s look at a few examples.

To-do list apps are a dime a dozen; building one is a development tutorial rite of passage. There will never be a shortage of options in this category. That said, I use Todoist’s mobile and desktop apps to organise everything I do, I enjoy their designers sharing their process on Twitter, and I like what they stand for as a company. So I pay.

Code editor Sublime Text is on the WinRAR/perpetual evaluation/you’re-supposed-to-pay-but-no-one’s-counting model. I’ve tuned out their upgrade prompts to the point that I only notice them when someone else is looking at my screen. But I live in and make a living off this one so I have no excuse to not cough up the one-time $80 fee (or ask my employer).

Rocket is a utility app that adds Slack-like emoji shortcuts globally. This is only $5, but it’s just a nice-to-have. I might pay if a particularly useful new feature or set of emoji updates went behind the paywall.

Spectacle is an invisible app that adds shortcuts for resizing windows to helpful positions like left ⅔, top-right ¼, etc. These shortcuts have become such second nature to me that I find myself trying to use them when I’m on other people’s computers. A similar app, Divvy, charges $14. Spectacle is free, but I’d pay $14 in a heartbeat. (Apple should Sherlock this.)

I can think of a few others like Feedly, an RSS reader that I consider my connection to the indie web, or LastPass which my online security depends on completely. There are other options in these categories, but are those causes and benefits not worth it? It’s clear that I’m not acting in line with the principle I laid out above, so let’s look at what I am basing my choices on.

It seems that I’m more likely to pay for apps that are essential for my life to run smoothly (like Todoist). Or ones that can make me forget what my computer was like before I installed them (Spectacle). And maybe I’m less likely to pay if the company is big enough that it’s impersonal — I feel more inclined to support an individual’s effort over that of a small company. The prospect of having to migrate to another app in a category apparently doesn’t get me to open my wallet, but it probably should.

I also wonder how much of this comes down to product strategy. I know I started paying for Todoist after they gamified me into ‘earning’ like nine months of premium before finally asking for a payment. I’m pretty sure LastPass offers free personal accounts with the hope that individuals will convert on family or team accounts. Some of the menubar apps feel like side projects the developers figured they could try to make some beer money from. Should their intentions affect my decisions?

There aren’t any right or wrong answers — and I don’t have them if there are. It’s more of an ethical dilemma that I have to give more consideration.