In the early 2000s, an acquaintance mentioned that he’s been working in an IT department of a large organization for 10 years, starting right after college. My only reaction was a horrified “Fuck this!” The idea of a long career in the same place was something from a generation of my grandfather, who was building the USSR’s biggest warships for 35 years. I was skeptical of traditional employment and instead freelanced for American and European companies that outsourced design and development to Ukraine.
Soon after that conversation, I was introduced to Chris Nagele from Wildbit. We started working on a project, then on another one, and another one…
Today marks my 15th anniversary at the company. I’ve been a remote freelancer for a few years, then took a leap of faith and joined the company as a full-time remote employee, then moved countries and worked from our headquarters, and now became local-but-mostly-remote again. I’ve been involved with projects ranging from a few months to 12 years long. Some of them are long gone and others are still thriving. Honestly, sometimes it feels like many careers in one.
It takes a combination of personal qualities and unique company traits to enable a long career. On a day of a big anniversary, it’s only natural to look back and try to understand what made it possible.
15 years in the same company is rare, but tech companies that old are unicorns by themselves. Unlike traditional businesses, most of them come and go with a new wave of hype. Wildbit is product agnostic, privately owned, and built to be sustainable in the long term — that’s key to being in the business for 20 years.
Currently, there are 6 people in our team of 28 who’ve been with the company for over 10 years. Basecamp — another company with a similar culture and values — has 10 people out of 56 who have been with them over a decade. These numbers are unheard of! Long career can be possible only in the business built for the long run, not in a short-lived startup.
For me personally, being in a company with multiple products is really important. Building the same thing for 15 years would be daunting. I started working on Newsberry in 2004, switched to Beanstalk in 2008, then worked on Postmark for a couple of years until setting off to launch DeployBot in 2013, and finally started building Conveyor in 2016. For the first 5 years or so we were also building client projects and I worked on a number of them. This range of projects kept me on my toes, forced to learn new things, try new approaches, and sometimes allowed to start from a blank slate.
After working on a project for a few years you start making decisions differently. You realize that shortcuts taken today will backfire tomorrow, and you’ll be the one putting out the fires. When building something I assume that I’ll be looking at and supporting it in 10 years, so it makes me think twice to deliver a fragile result, add a new dependency, make a sloppy commit, skip documentation, or ship something I am unhappy with.
Applying the same skills to different projects over and over won’t make them any more interesting. Growing professionally, learning new things, and trying new hats is important for overall happiness. Every time I got bored or burned out was when I got stuck doing the same thing for too long.
On my very first project at Wildbit, I was doing visual design and HTML/CSS markup based on interface prototypes designed by someone else. It didn’t take long to understand that I enjoy working on interfaces the most, so my focus and priorities changed. For a while, I’ve been reluctant to learn programming and JS, until the designer who handled it left the company and I had to step up and do the work. Years later I’ve been missing out on React revolution and looking for a place to apply it until we started building Conveyor and there were perfect use cases for it. Soon I got to learn TypeScript and Electron as well while building our desktop client.
Some projects are more interesting than others, but there are no boring projects. Trying something new or introducing constraints can turn even an ordinary task into a curious experiment. Sometimes it’s important to deliver a quick or pragmatic solution, but otherwise I try to tweak the task to make it exciting to work on. It’s my responsibility to make work interesting for myself — no one else will take care of this.
Getting to know the team well and building personal relationships is the best part of these 15 years. It takes time to build trust, respect, and good rapport. After working with someone for a few years the flow changes and you know what exactly they are looking for and how you can help them.
Some of my teammates became close friends and with a few of them we stayed connected long after they left the company. We went on multiple trips and vacations with my coworkers, who were close friends at that point. (Can’t think of a better friendship stress test than vacationing together!)
This part of “Happiness Traps” in Harvard Business Review rings very true to me:
In fact, good relationships are the backbone of successful organizations. People who care for one another give generously of time, talent, and resources. Gallup found that close work relationships boost employee satisfaction by 50% and that people with a best friend at work are seven times as likely as others to engage fully in their work. Mutual respect motivates us to resolve conflicts so that everyone wins. And when we believe that we will be accepted for who we are, that we have important roles to play, and that we’re part of a team, we are more committed to collective goals.
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I decided to write about my experience mostly to counter a popular assumption that you have to jump ship every couple of years to have a fulfilling career. I don’t have a specific sense of accomplishment from working at the same place for 15 years, but I am proud to be a part of the company where it is possible. Wildbit co-founders Natalie and Chris Nagele built an environment where meaningful work, professional growth, and personal relationships can thrive. I’m grateful and honored to be a part of that story for so long.
Looking forward to what the next 15 years will bring!