WDStories: Kat Hagan, Automattic

Name: Kat Hagan
Position: Code Wrangler and Team Lead.

For me, Automattic is my dream job. Self-employed after years of trying to fit myself into different types of working environments, I had a pretty good idea of what worked for me and what didn’t: mainly that I was happiest and most productive with a lot of autonomy and flexibility; that I had a hard time getting work done in offices; that I enjoyed collaborating asynchronously with colleagues in other timezones; and that I wanted a lifestyle that included travel to new and exotic locations. All of this meant I was quite happy as a freelancer; however, I disliked the stress of finding new clients, the varying income, and the fact that I often found myself working solo on projects that didn’t feel meaningful or challenge me to grow my technical skills. From this perspective, I sensed right away that Automattic was the best of both worlds: the flexibility of self-employment, plus the opportunity to contribute to a platform that empowers millions of people to have a voice on the web.

My colleagues are some of the smartest, kindest, and most interesting people I know -- and with wide-ranging interests that are not just focused on the technical sphere. Unlike many Silicon Valley companies, we have a culture that really supports us in those outside pursuits. We’re encouraged (and encourage each other) to take the time off that we need to recharge and do the things we love. There’s a stunning amount of trust and transparency throughout the company, and very little hierarchy, meaning that everyone has input into discussions and decisions that affect them. It boils down to simply knowing, and treating each other as, real human beings, but the effects are profound and magical.

The way that it’s changed my life the most, aside from the obvious (exercising more, no commute, spending more time with loved ones) has been in the experience of leading a highly-autonomous, distributed team. I think of the leadership skills I’m building as “servant leadership”: in other words, that my main task as a lead is to help my teammates excel at their own jobs. Because my interactions with my teammates are as equals, the interpersonal skills that I practice as part of this task have also given me a lot of insight into my own life and my relationships outside of work. The unique way that we work kind of distills things to their essence: Without meetings, without being in an office at 9am, without all that traditional structure to the work we do, how do we measure success? How can we build strong working relationships and contribute to an atmosphere of trust and transparency? What tasks are really important? These questions, and the habit of asking them, has brought a lot of clarity to my personal life as well as my work.

Because I was interested in getting involved with more open source work, I applied for -- and was lucky enough to get -- an internship working on WordPress via Gnome’s Outreach Program for Women (now Outreachy). It was through that internship that I met and worked with some of my now-colleagues, who encouraged me to apply for a full-time job. Not only did I know by then that I would be delighted to continue working with them, but their obvious passion for their jobs really piqued my interest in Automattic’s unique culture and way of working.

I made the move because I was freelancing at the time, which was stressful in terms of month-to-month income. I knew I didn’t want to go back to working in a structured office environment, but as time went on, I also found that I missed collaborating with other developers and having the ability to work on larger, more long-term projects. I craved more challenging work and the push to learn new skills that would accompany that challenge.

My work experience has run the gamut, from large corporate defense contractors to small and stressful just-getting-off-the-ground startups. It wasn’t until I started freelancing that I realized how much happier and more productive I was when I could choose my own work and do that work wherever and whenever I chose. Even at jobs where I was otherwise happy, I often found myself working late or chafing under the restrictions on vacation time or remote work. Once I discovered that I thrived with a lot of autonomy, there was really no going back.

I’m essentially a creative person, preferring to work in focused bursts when I feel inspired (which, since I love my work, is quite often -- though I’m also a night owl, so it’s sometimes in the wee hours of the morning). As is true of many programmers, I work best when I can dive deeply into something and be free of interruptions, so I really dislike working in an office.

I often felt tired and drained from trying to force myself to keep to a fixed schedule. I always struggled to find time for things like exercise and healthy meals, and being stuck in the office on a sunny day made me feel deprived. Not to mention the misery of having to commute in bad weather! I’d often work long hours because I had to be in the office in the morning, but I wouldn’t really find my groove until the afternoon.

Since changing jobs my work-life balance has really benefited from being able to set my own schedule. I don’t lose time commuting every day, and I can take breaks in the middle of the day to run errands or go to yoga. I also don’t miss the constant sense of guilt and the difficulties with motivation that would plague me when I worked 9-5: it turns out a major key to my own happiness is being able to work when I feel inspired to and not trying to force myself into it when I don’t. I’m able to spend more time with my loved ones and to fit more travel into my life -- I particularly enjoy taking “working vacations”, where I’ll divide my time between sightseeing and doing my normal job.

The fact that everyone I work with trusts me to get my work done is very motivating and is one of the reasons I’m so passionate about that work. In the same way a lack of trust can become a self-fulfilling prophecy, Automattic’s revolutionary idea of extending that trust to each of us really inspires me to do my best work, which in turn has given me more confidence as a developer and a leader. Having complete flexibility has allowed me to experiment with my schedule and working environment and learn a lot about my own productivity and what fuels it.

Check out what Kat has to say about working at Automattic below!