...because it's always possible you'll get a worse job some day. On the bright side, as much as you learn from regular old failures, you can learn some amazing things from the spectacularly failed ones.
I used to think the worst job I ever had was when I was 17 and I worked at a toystore that is now (thankfully) out of business. The Assistant Manager had a god complex, and I have spatial awareness problems, so of course, we got on great. The hardest aisle in the place to clean at night was the board game aisle, as everything was stuck in tight, like a Jenga puzzle that's never supposed to fall down. When he figured out I couldn't do that aisle, it became my nightly job, and he kept me and everyone else well past closing until I finished it or he relented around midnight and let someone help me.
I think, as a boss, he had some deluded idea that annoying the rest of the staff and humiliating me might teach me spatial awareness. Or he was just a controlling asshole. What I learned from that job is that you can quit bad jobs. My father specifically asked me to resign because he was driving me home and he was tired of the guy keeping me so late. I never told my father why the guy kept me so late, as I assumed my father would punch him or something (The ImPerfect Manager is daddy's little girl, and will be until I'm 101...that is the only case where using "little girl" and my name or The ImPerfect Manager is appropriate, by the way, unless you want to see the ImPerfect Manager punch someone herself). The learning experience derived, however was that sometimes, the paycheck isn't worth it. You don't quit a job lightly, and despite the desire to do so, you don't burn bridges when you go. But you can go, and you can hold your head high (and sometimes that's easier to do when the Assistant Manager's face shows that he has just realized that being down a person means he has to do some chores now, too).
Several jobs later, the next job that I thought was the worst in the world was doing customer service for a popular metropolitan newspaper in the Bay Area (still in business). I wanted to be a reporter, so I walked in and asked if they had any jobs. I also needed a job, so the fact that they did have jobs, even non-reporting ones had some appeal. The manager treated all of us like we were 10 year olds trying to steal candy--from the girls my age paying their way through college to the retired ladies making a few extra bucks, none of us got any respect, at all. That wasn't the main problem, though.
The main problem was the customers. It's a newspaper, not a spleen. I never actually said that to people (nor liver nor heart nor brain, which some of them could have used). An example phone call was a woman that went off on me for 10 minutes, not cursing, but actively yelling (people who called frequently knew that they could be hung up on for cursing but not for yelling) about the fact her newspaper was stolen and how upset she was as a result. When she finally wound down I finally put the receiver back to my ear and calmly asked for her name and address so that I could rectify the issue for her, to which she calmly replied, "That's okay, I stole my neighbor's paper." I then had to ask for their address and dispatch a paper there and hope that no one else was talking to her neighbor in the meantime. Co-workers nearby began actively laughing, creating an issue as the lady on my phone and folks on with other reps were wondering if they were being laughed at, while our boss stormed in because enjoyment was something she was thoroughly opposed to while you were at work.
What I learned from that job is that you can give less than two weeks' notice. It's not polite. It's not professional, but some notice is better than no notice. Turnover in the department was 3-6 people per month in a department of 12. I lasted a little over a year. I gave my notice and the boss read me the riot act about not giving her two weeks'.
That was when I also learned that, yes, work can be a power struggle, but sometimes you are the one with the power.
I asked her, very politely, if that meant she wanted today to be my last day, or if she was okay with me working one more week, because those were her options. She was floored. She was used to having the power all the time. In a way, she had some: she could choose what my end date was, but I got to choose the options she could choose from; also an important lesson. Sometimes in life you don't get to make the actual choice, but you can shape the only available choices. My boss at the time chose the additional week. She was extremely kind to me for the first time I worked there for that week, somehow expecting that would cause me to stay. I was the highest productivity worker, and I earned awards for the department in preventing users from quitting the paper, so I could understand her reluctance at me going. She was, however, still a shrill, power-hungry person with poor people skills and no management skills, and the customers were still angry and/or lonely people, so I still quit on the prescribed day and never looked back.
Later I thought the worst was this tech support gig I had; I was the tech support supervisor, but this not-so-young upstart had moved in and was kissing up to the boss and going out of her way to make me look bad; okay, that sounds like paranoia, and maybe it was, but it didn't mean she wasn't out to get me. As the supervisor, I got all the escalations, the truly angry people that you could hear through the phone from across the room. After six or eight of those folks I was often shaking and red in the face, which would be when my co-worker felt the need to call the boss in to ask about things that she didn't need to call the boss in for. She was prompt at pointing out errors...to my boss, and not to me, often when they were resolved not as errors, when the boss was safely not present. She was a fun person.
We were still not supporting brain surgery, but people can be very passionate about video games. We had one lady go through each person in tech support over the course of a couple of weeks because she would eventually get fed up with them not helping her and declare they were part of the CIA conspiracy behind her being unable to play her games online. One day I was listening to her spout about the fact that her house was bugged and her internet was being deliberately disrupted through the use of aluminum foil when she interrupted herself to briefly say, "Bye honey, I love you" and kissed someone in the background. That day I learned that even crazy people can find love. This cheered me considerably. I, too, shortly thereafter found the love of my life. I don't think he believes in CIA conspiracies directly related to the Internet, but you never really know a person.
I also learned to document, document, document. When my co-worker attempted to usurp the job I was doing and my boss asked me what job I thought I was doing (as she suddenly couldn't remember), I pulled out the document I had her sign with my job description and duties. I found a nice job in QA at another company shortly thereafter, and in the pretense of good faith, gave her the template for my job description so she could promote my co-worker to that job, knowing in my heart of hearts that the co-worker actually didn't meet the requirements to do the job. Which I knew they would notice very shortly as she went through the "perfunctory" HR interview process. I didn't learn that revenge is a dish best served cold, but I did learn that revenge is a dish best served politely, with the rope that you've given the person in question that is the proper length with which to hang themselves.
Revenge in the work place, by the way, is not about revenge at the end of the day; people don't respect that, and you don't respect yourself (no matter how food it feels to get someone at first, you always know that you should have been professional). But comeuppance is an entirely different thing. Tattle tales do not prosper in business. People who are competent and shine brightly can't help but reveal the shadows around other people.
The next job, the QA job, was great for a long time. It was the Dot Com Boom, and I learned so many things and was so eager to come to work every day. It was only towards the end when my days were all 12 or 13 or 14 hours long that it became my latest "worst job ever." The team would meet and send in a sacrificial lamb to the boss's office which was right next to the door to get out of the building to the parking lot (and he had a large window on the parking lot itself). If no lamb was chosen, the first person that walked past his desk would get pulled in and persuaded to work longer. It took us a while, but eventually we took turns, most of us getting to go home after only 10-12 hours and the unlucky one staying at least another two. In this job I learned that while I love my work and my friends there, I love not working and my friends outside of work more. The boyfriend at the time (now husband) missed me, which was a unique feeling, both awesome and scary.
This job taught me that work-life balance was not just a set of buzzwords for Buzzword Bingo. If I didn't get enough down time my work suffered, and if my work suffered, the people who reported to me and depended on me suffered. I saw that directly, and I couldn't allow it to continue. So I eventually moved on to a more normalish 40-45 hour work week and the ability to have dinner at home every night.
The next worst job also started out well; I was working for a new Dot Com...and then the Dot Com crash happened. Of 130 people, I was one of 13 to actively help close the doors. For the last six weeks we were open, we couldn't touch the code, so the team came in and played Diablo 2 every day. That part was fun. But the looks on people's faces, the not knowing about their livelihoods as the desperately tried to sell the company...that taught me that my youth and work viability was probably not going to last forever. Which sucked, because Diable 2 is pretty fun if you're being paid to play it.
The company did eventually get bought out by another company (still in business today). One of the 13 was a strange little man who only got stranger. And stranger. Then creepy. Then legally harassing. You never want to know that a person at work wants to know what it would be like to stroke your hair. Or that he thinks your co-worker should jump out of a birthday cake in a bathing suit. Or that he wishes another co-worker would lie naked on a bear skin rug so he could observe. That dude creeped out everyone, and our bosses wouldn't do anything about it. They had a soft spot for socially awkward coders...and no respect at all for those of us being harassed.
I learned in this job that men and women can be sexually harassed and that being sexually harassed is very unpleasant. Eventually, my friend and I gathered the group, took statements, and wrote a nine page back and front single spaced document that we gave to the HR maven. This taught me that sometimes, you have to take things over your manager's head. I felt good about it. I felt empowered...only to learn that since our bosses had refused to address this problem with him, this was "technically" his first offense, which, pursuant to the HR handbook, meant they could not automatically fire him.
I had never thought the world was fair, but this job taught me that it could be really, really far from fair. Sometimes doing the right thing still ends up without a happy ending. This sounds so logical, and my thinking very Pollyanna, I'm sure, but when you have 9 front and back pages on disgusting behavior you kind of think you're going to win. We didn't.
This man who knew us and what we'd said about him remained, playing his music so loud the entire room could hear it through his earbuds, not talking to any of us directly, but leaving pictures of his hot Russian mail-order bride in various states of undress around (I wish I were making this up). It was a mercy when Microsoft hired me and moved me out of state.
A couple of jobs later was the death march project from hell. In interviews, when interviewers ask me about the worst project/things that went horribly wrong on projects, I mention this one. It is, to this day, still the worst job, ever.
I was a new project manager. I took what we were calling "The Boston Job." My first inclination this might not be good as that no one else wanted to touch it with a ten foot pole. A 6 hour plane ride to Boston in the middle seat later, I met the nice people, laid out a backlog to use Scrum and set up sprint planning, and then spent another 6 hour uncomfortable plane ride back a few days later.
In the ensuing weeks, the project was transferred from the original team who contracted us to a small and growing fiefdom. The new owner wanted the entire consulting team to move to Boston for the six months of the project. That was danger sign #2. When we declined, he hired everyone with a pulse that could touch a keyboard in his native area. This was danger sign #3.
Things started out okay...we planned sprints and started working. He agreed to everything. He met on the phone for daily stand up meetings to discuss team progress and to agree to the day's work. Then he'd randomly order his team in Boston to do ANYTHING ELSE BUT WHAT WE AGREED. He called repeatedly to change things mid-sprint. Me, my mentor, my dev lead. I had to change the number for my dev lead (switch phones with a different group and take the dev lead's phone) to get him to stop calling the poor guy. This, at this point, was Danger sign #37 or so.
Then the daily calls about how I was a horrible project manager and person for not changing everything daily for him began, in addition to his calls to my boss and the daily stand ups where he pretended he was a normal human being. He began instructing his team to undo work my team had done (and he had actively paid us to do).
This was the first project where I understood the concept of "firing the customer." Sometimes, customers will price themselves right out of your working for them, not by the negotiation of a contract, but by the amount of money you end up spending trying to manage them. This project also taught me how to talk to upper management. I wasn't exactly confident all the time, but frustration can make you braver than you'd normally be.
The CEO, however, wouldn't let us end the contract, despite the customer actively working against us. The customer was not well liked within his organization; if we could complete this work, we'd look amazing to the rest of the org, who'd likely sign on to spite him and because if we could handle him, we could handle anything. He called it a "prestige" project. I did not tell him what I called it, as I maintain that swearing in front of senior management is a quick way to get fired.
So returned to my team with the news...and a bag of goodies. The customer's team would undo their work and write crappy, horrible, non-project related code in the morning well before my guys got in (they were in Boston, we were in Redmond). For every piece of code they had to undo, rollbacks they had to manage, thing they had to explain for the 10th time, whatever, they could reach into the bag and get a Starbuck's card, a Farside book, or a toy. I couldn't make the project less bad, but I could make their immediate circumstances less bad. I paid for a lot of lunches and listened to a lot of venting. Most of all, I kept the yelling at myself; the customer was hung up on when he started going off on the team. This did not make me more popular with the customer.
What I learned, though, is that if you put it all on the line for your team, they'll do the same for you. They worked longer hours. We worked on a continuous integration platform; if the builds were building right and the tests were passing, all the bars would come up green. This didn't happen because crazy people three timezones away were frequently breaking things (like the VPN connection to make this thing work). On the first day they got all green I was out sick; so they took a picture of themselves (all thumbs up and smiles) and the monitor in the background, with all the bars green.
I had always known that people are what make a job great. I just learned, in that moment, how great they could make a job.
Towards the last few months the customer was more and more irate, but I cut scope, re-arranged resources, and set the schedule. I suggested to the CEO and my mentor they tell the customer I'd been fired from the project to make him happy; in fact, it would have made me happy, too. They agreed to do it on the condition that I wasn't actually fired from the project. I'd keep doing my job, managing the project, but they'd let him think I was no longer on it; my mentor became the new face of the team. This thrilled the customer...until he learned my mentor wasn't any more maleable than I was. However, it bought us some time and good will.
We did it. On time. In budget. Within scope. We partied that day at lunch. I brought boardgames that afternoon. That weekend, I got a hoop permanently set into the top of my right ear to remind me of how bad this all was, and to be greatful for what I have now comparitively. I still reach up and touch it sometimes, and smile, because no matter how hectic things have become, no one was planning on calling me daily and telling me I was a bad person over it.
I learned from that project that I'm stronger than I thought I was. That a group of people is stronger than any individual. That in the midst of anger and frustration and chaos there are moments of magic and bonding. Most of all, I learned that being a manager--project or people or both--was what I loved more than anything else I'd ever done, and even the worst job I'd ever had didn't diminish that. Instead, it made it bigger and brighter.