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Issy Long

Learning, connecting, and building a routine

Issy stresses the importance of staying patient with themself and taking breaks.

Issy Long // @issyl0

Hey there, I’m Issy Long 👋 I’m a maintainer of the widely-used Homebrew 🍺, a package manager that installs everything a developer might need that doesn’t automatically come with Linux or MacOS 💻. The project is used by millions of users, and is one of the most active community projects on GitHub. I live in London, am a French speaker and consider myself a lifelong learner. [they/them, 🏳️‍🌈]

London, UK

@issyl0

Organizations

Sponsoring

The ReadME Project amplifies the voices of the open source community: the maintainers, developers, and teams whose contributions move the world forward every day.

In school, I studied computing and spent most of my time wondering, How do I do this? Why do I do that? I don’t understand. It wasn’t so much programming to me as it was a bunch of theory. I didn’t really care for the theory. I wanted to write code.

I started with Python, which I didn’t really like because I can’t stand significant white space. When I found Ruby, it finally clicked. In terms of my actual coding skills, beyond the course I studied, I’m entirely self-taught, and have increased my knowledge and grown as a developer over the last seven years. I went through a bunch of confidence crises because so many of my friends seemed way better than me, and I wasn’t sure how to get there.

It didn’t happen overnight and impostor syndrome still kicks in even now. Trying to balance being a maintainer with a full-time job is difficult. But open source is also, and equally, my hobby. Even though I don’t necessarily heed my own advice, I know it’s important to take breaks and be mindful of the fact that burnout happens, and easily. It’s important to look after yourself and look after your mental health. As a maintainer, the work is never going to stop. It will always be there. There will always be things to do. Take things slow, take time to learn, and take time to stop.

Photo of a smiling Issy Long in a red shirt.

Finding something fun and unexpected in Homebrew

One night a few years ago, I was bored and started making pull requests on Homebrew, which I used quite a bit. I didn’t really know what I was doing, but it was fun. The documentation is really good, which is one of the most important things for both contributors and maintainers. It gives you that frame of reference to understand the mission, how naming works, stuff like that.

When I asked for help, everyone at Homebrew was friendly, but it was still scary. I remember writing: “Please close this if it’s not acceptable” on one of my first pull requests. I’ve actually looked back at some of those first pull requests I submitted, and they’re almost funny. Let’s just say I’ve come a long way.

I was initially contributing in my spare time, during my commutes mostly (from my work computer, which was running on MacOS). I took a break from fixing style issues to get a feel for the broader Homebrew ecosystem. I was running Linux at home and realized Homebrew on Linux was a thing. At the time, it was quite new and a bunch of things were broken. My first pull request (PR) was in May, 2017: It was a minor bug fix to match formula names in descriptions on word boundaries. I went on to fix a lot of other issues, and Homebrew liked my changes enough to invite me to be a maintainer. I think the PR that really got me recognition was two years later when I updated an issue that was prompting users to install brew casks on Linux, even though casks were only supported on MacOS. I never expected to be invited to be a maintainer, but it was one of my proudest moments. Now I get to review a bunch of work that our community proposes every single day, and it’s just amazing.

In my full-time job, I work for the UK government, and it’s a very interesting time right now. Most of the work is based on open-source software and occurs in public repositories on GitHub. So I use GitHub for work and then come home and hop back on for Homebrew. My partner worked out that I spend more time on GitHub than I do asleep, which is kind of scary.

Photo of Issy Long seated in front of their laptop.

Every little bit of reach and recognition counts

MacOS doesn’t come with a package manager by default, so Homebrew fills the gaps. Obviously, there are other package managers and people always invent new and competing tools. No software is perfect, but Homebrew makes everything a lot easier. The MacOS software development ecosystem just wouldn’t be the same otherwise.

Without GitHub, we wouldn’t have the funding, exposure, or reach that we do now. I think we were one of the first teams to use GitHub Sponsors for organizations, and it’s been super helpful. We have a Slack channel that automatically populates with emails, and whenever I see “You have a new GitHub Sponsor!” I get a warm, fuzzy feeling. I’m reminded that people appreciate the work we do for free. Which is so rewarding. I’m grateful to everyone who sponsors us.

The pool of funds goes to the entire team (although some individual maintainers have their own Sponsors pages, too), and enables us to do many things, most notably buying hardware to continue running continuous integration, which is important for package testing and to gauge how Homebrew runs on newer macOS versions. We’re trying to make Homebrew faster and increase the amount of stuff we automate via GitHub Actions, so we can reduce the amount of time maintainers and contributors spend waiting and doing things manually. Security is big as well, so we’ve had conversations about investing more heavily in security auditing and tooling like requiring GPG-signed commits. We already use GitHub features like mandatory two-factor authentication for organization members, and Dependabot security updates to ensure our Ruby dependencies are up to date.

In many ways, open source is a thankless task. But GitHub Sponsors is a helpful way to recognize the work and make maintainers feel energized. And, of course, now more than ever, with everything being uncertain in the world, it’s so reassuring to get anything, even just a dollar. It might not be much, but it’s something, and that keeps us going.

Photo of Issy Long against a brick wall, looking into the distance.

Staying motivated and making contributions easy

Homebrew gets millions of users, millions of package downloads, and many package contributions each year. We currently have 25 maintainers, which may sound like a lot but in comparison to the number of daily contributions and the amount of work, there aren’t many of us. Delegation and documentation are huge. A bunch of our contributors are new to open source. To contribute to a package, you don’t actually have to know Git, or how GitHub works. All you have to do is type one command and have a GitHub account.

Homebrew itself is fairly complex and wide-ranging, and then we have the packages themselves, which are in a separate repository called Homebrew Core. The Linux side is a bit different because there are tons of package managers. Homebrew on Linux doesn’t require root access, which enables users to more easily install packages on their home directory. Millions of users across many companies and organizations rely on Homebrew to get up-to-date packages.

We hope that if we treat contributors right, they’ll return. And so far, we seem to be quite successful. Project leader Mike McQuaid makes time for a lot of people, and that’s really hard when you’re dealing with the number of pull requests Homebrew receives. He’s the person I’ve always looked up to in the Homebrew community. He’s considerate and listens. He reassures me that I shouldn’t worry about certain things and that we’re going to figure everything out together.

I measure my success by the amount of enjoyment I get out of open source, and the number of people I help. A bunch of people helped me get to where I am today, so being able to give back to the community is rewarding. When you merge someone’s pull request, it’s always really nice when they say thank you. That keeps me going and makes me happy. Right now, the world is a bit unpredictable. But sticking to these kinds of routines is so important. It feels good to help people, and to deliver and release software that allows others to be productive and helpful, too.

GitHub Sponsors allows you to financially support the people who build and maintain the open source projects you depend on. One-hundred percent of your sponsorship goes toward helping Issy maintain Homebrew.
Support Issy on GitHub Sponsors

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