A decade ago I worked at a startup, and at the time landed a job with a dream title: I was going to be doing interface work and just interface work.
The whole thing started well. I was working on interesting projects for internal systems. I was doing serious PHP coding and then-advanced front-end code. Given the size of the company I was also doing databases and something I would call product design today. I also did my first ever user observations at that job, and that was pretty great. (Getting paid to watch people use software I was going to improve? Yeah!)
There were a lot of things wrong with this job and I wasn't willing to admit it at the time. I was most interested in getting a job because I had been unemployed for a long time prior to this. (I left my first job out of college in August, 2001, just a few weeks before September 11th. Given I defined myself by my job at that point in my life, I felt really awful.) So I signed the contract for the new job and was, truly, excited about it.
But I failed at this job. In fact, I was fired for the only time in my life. When I was fired, I felt a sense of terror and relief. I was frightened because, well, where was I going to get money now? It was all in my head. Deep down though a part of me was happy. It held on to that feeling that this was not my ideal job. I didn't really want to be working on this software. I didn't like some of the people and, at the time, I didn't know how to handle that. And the work wasn't exactly what I was expecting.
When I look back at it now, the biggest thing I see was a lack of communication.
They didn't tell me what I was expected to do. I'm not talking about basic job duties, because those were well understood. But the culture of this tiny company (less than 10 people!) was significant. I noticed that most people worked long hours, like many startups as it turns out; I'd leave at 5, sometimes 6, when my wife picked me up on her way home. At one point I asked my boss if it was truly fine that I was leaving at that early hour. He said, "As long as you do your job, I don't care." This wasn't true actually. Staying late and being a part of the company in a very different way was a part of my job, just an unspoken one. I also lacked the maturity and knowledge to pick up on this.
I didn't tell them what I wanted to do. Truth be told I was starting to not really be interested in creating object-oriented PHP. But I was in such a position of gratitude - glad that I had a job at all - that I didn't want to rock the boat and say what I really needed or needed help with. It's odd because the work I was doing back then was something we might call Product Design today, with a UI focus; the lack of understanding of my job even then was present. I didn't stand up and say, "This isn't what I want to do. Here is what I want to do."
Even the way it ended was odd. When I was canned, the CEO wasn't there. Two of the higher-ups were there, and they sat me down and told me everything I did wrong (they had a list!) I was given no chance to fix any of the mistakes because they had never talked with me about them beforehand; they simply expected me to uncover them, as if by magic, during my tenure there.
I was clinging on to this "my identity is my job" thing and pleaded to stay in this not-great job. Then an analogy came up. "It's like when your girlfriend cheats on you. It happens once and you never trust her again." (This argument lacked the nuance of an adult relationship and the idea of rebuilding a relationship but, you know, this is just work.) So I was told, no. You're done. Don't worry about the non-compete clause; just don't work for any of our clients, and leave.
I took the El to my wife's office and remember being very sad, but then also jumping right in and looking for another job. I didn't fully know what I wanted, but I tried to stick to the script.
I learned a few things from this job. First, for god's sake, listen to your gut. If something is fishy or feels "not right" (in that kind of queasy and weird place between your heart and your stomach) then listen to it and understand it. I ignored it.
Second, talk with people, a lot. If there is something someone is doing "wrong", you've got to say something just as if she was doing something "right". (This leads into the whole "how do you talk to people?" and "how do you handle shitty feedback?" thing.)
Third, I already know what's important to me in a job. Environments with long hours and a lack of diversity (in age, gender, race, background, lifestyle, size...) are red fucking flags. A place where design is fundamentally misunderstood isn't a blocker but it means my job will include making it understood. Anyone who wants me to work holidays and weekends (been there!) can fuck off. And doing non-interesting, non-dent-in-the-universe work is potentially way more boring.
But there was one more thing. You know what else? During my tenure at this job, I got married. My wedding was amazing, filled with friends and family, and it was the biggest thing to happen to me. Bigger than any job. So really, no matter what was happening at my day job, the most important thing wasn't happening there.