It’s hard to look back at the last four years and feel good about much of it, other than managing to remain employed through some serious close calls to being fired (not to mention two pregnancies.) My ego gets the best of me time and again so it’s hard to fight through these last months to get the remaining shares of my main vesting period. But outside of the good compensation, there’s a whole lot of maybe not-so-ok experiences that happened to me in the last 4 years and I just want to hash it out because I’m hurting a lot and I want to make sense of it.

2017 I join the company with an offer from a senior exec who knew me from working together years ago. The role wasn’t defined clearly but he was also very excited to have me join the team. It was a much smaller company at the time. I didn’t negotiate my compensation, but felt it was fair. I was also coming off a pretty bad situation at another startup where I was running a department and didn’t know what I was doing so I lost my job and was having trouble finding another one. I was grateful for the opportunity.

I joined the team and there wasn’t clear direction. I was given a headcount but not enough budget to hire someone with experience. I didn’t want to hire anyone so I was waiting until the right person applied and I lost the headcount because it took too long to hire. I was able to hire a freelancer to help out but still because of the comp level that person was junior. She was good for being junior but still I was figuring out the role and then trying to manage a person who was junior and that wasn’t going well. Soon after joining I was leveled and reported to a new boss. I actually got along with her at first. She didn’t want to give me any guidance on what to do, so I continued to try to figure it out on my own. But I really didn’t know what to prioritize because there were no clear goals on the team. When I asked for goals to help determine what to do I was told that I should figure out what they are with people who then would not want to collaborate with me on this, they were very territorial over setting the goals and all the things that went with achieving them. Hard to explain without revealing too much about who I am but the main point was no one was willing to be collaborative and it made me look like the bad guy who wasn’t collaborative but I couldn’t get the information needed to do the work. Maybe I wasn’t leading enough or influencing enough but because my role wasn’t clearly defined it was really fucking hard to convince anyone to work with me properly.

Meanwhile, I was pregnant with my first child all through the first year of the job. I was given a whole bunch of random projects that didn’t make sense for one role and yet I delivered on them. Then when I came back after having my first child (and my father passing away and a long bout of depression) I really struggled. What was possible to fake it through before became like walking up a hill covered in sludge. While they gave me an acceptable performance review the year I was on maternity leave, the next year I fell on my face time and again. It was a mix of not sleeping, anxiety, depression, and imposter syndrome, and still not understanding my role. Meanwhile as the company grew others were hired around me and they seemed to just fit the corporate culture better. They weren’t necessarily more talented or able, but they knew how to play the game. It was that year that I was put on a performance plan. I was devastated because I felt horrible about letting my boss down. But I was given six months to shape up or get out.

In those six months I managed to pull it together. Those six months were actually the early days of covid. And when I got pregnant with my second child. I didn’t tell my boss I was pregnant for a long time. I wanted to show her I could be a good employee without her feeling like she had to judge me lightly since I was pregnant. And I actually succeeded. Despite being exhausted in my first trimester, I managed to earn recognition for my work done in those first six months. Things were starting to look up.

But then I took on a project that seemed like a good idea. I created the plan, pitched it, and everyone seemed on board. It was going to require collaboration from the larger team. Well, once we set the plan and we were moving forward an important person was put on another project and said never mind we aren’t doing the full project, just a piece of it. I felt strongly about why we had decided to do the full project to add value to the business so I pushed on and took on more than I should have on my own. I wasn’t able to do it as good as it would have been with the support of others, but I still got something similar to the original concept done. The problem was I got it done a month late. Well, it wasn’t even month late, the date that I had given to finish my part of the project was a bit arbitrary. The whole project still launched at the deadline that was committed to the leadership team. Nonetheless, I was in major trouble over missing the deadline. I was told I’m not a leader, not a team player, etc, etc. My boss was so frustrated with me and I felt horrible.

But then we launched the project and everyone saw it as a success. Even now they refer to this project as an example of something we should do more of.

That wasn’t enough, clearly. At that point my boss had already decided to demote me and move me to a role that has a smaller scope.  While that sucked, it didn’t come with a pay decrease, and I thought the scope was more clear (that I own a certain function) so I was happy about that. My new boss, despite being a white man who thinks he knows everything, at least cared a bit about the actual tasks I would be doing and wanted to be more involved than my former boss who had given up on me. This was all during the end of this pregnancy as well, which ended up being high risk. I was a mess and I didn’t want to make a big deal out of it but it really sucked.

When I came back to work this year my new role was clearly not as well defined as I thought it was. Others were doing what I thought was supposed to be my job and no one cared. I wasn’t actually owning the function at all. I was just going to work on one-off projects, pretty much only the one-off projects that no one else wanted and that would make no sense on a resume in applying for future roles. The actual good projects (in the area I supposedly owned) were being managed by other people on the team. And that hurt a lot. But I didn’t say anything because it wasn’t worth complaining at that point. Clearly they wanted me to leave.

In fact, when I went on maternity leave my former boss said she would join my performance review (with my new boss) since she was my manager the year before. But then she bailed on that meeting where I was given a 2/5 and no stock refresh or raise. While I wasn’t surprised about the low score due to missing the deadline, I also was hurt that she didn’t join this meeting. I finally got up the guts to ask her to meet to discuss the review and consider changing my score to a 3. She met with me and in so many words told me that she wasn’t kicking me out immediately but to look for another job soon. So that was that.

Meanwhile, the (single male) guy who took my former role (who happens to be a friend) is doing a good job but I’m not certain he’s doing a better job than I was doing. He tells me that he misses deadlines too. He was handed a lot of better organization already so he was able to move forward and make progress in a way I never was. Not to sell his talent short, he’s really good at his job. But so much of his success is tied to how well he speaks and how he just has this confidence that I’ll never have. And really I should have managed this guy (we hired him as my fill in when I went on maternity leave the first time) but I was never allowed to manage him so instead he now has my role. And as he’s my friend I’m happy for him but really I wonder did I suck so much at the job and is he that much better?

The reality is that I know how to manage budgets (he is self-admittedly horrible at that.) I took on some of his projects before he was promoted into the role because they should have been mine to lead in the first place and he was ignoring them and I thought they were important for the business. He didn’t care so I took over and I took on too much so that’s on me. But if I was actually set up for success in my role (where I was supposed to be leading the broader function) he would have been my employee and I would have had another employee to manage this area that was important and being ignored. That was a big mistake. But I just wanted to fix the things that mattered. Do meaningful work and add value.

I also hired a bunch of freelancers towards the end that he’s using now… if he didn’t have them I don’t think he would be able to successfully find freelancers to do the work. But I managed to get everything set up well for him to take over. So nice of me. Good thing he’s my friend. I’m rooting for him. But still, man, I feel like a sucker. And that sucks. Sucks to be a sucker.

And the kicker is that even though he was given my former role, he’s actually doing work that should be part of my new role. I’ve never had a clear job or clear objectives so there’s no real way to measure my success outside of if people like me or not (spoiler alert – they don’t.) It’s all sorts of a shit situation and I want to get out. But I also want to get out to somewhere I can start over and really go in and be a new person from the start.

I’m scared I won’t be able to find another job and I’ve started applying but I’m not getting any calls. It’s going to be a long and painful climb to get to my next position. It will probably pay less and who knows if it will be any better. I’d like to believe that a job with an actual job description and clear success criteria will be a little better.

I know I should stay until April. It’s not that far off. I hate the projects I’m working on now and part of me wants to leave before I get too into them and see how the team manages these assignments that no one else wants to do because they suck. I can’t complain really because they pay me a lot so of course I’ll do them. But I’m so over being assigned the work that no one else wants. And I hate it even more when the head of the team tells me I’m doing good work when it doesn’t matter, when I know my boss wants me out. And when I get invited to other meetings that aren’t related to my main role because now it feels like she’s just trying to motivate me enough so I might stay to finish the projects that no one else wants to do.

I know why she doesn’t like me as I’ve been the worst version of myself in this company. In meeting I get frustrated and interrupt people. Because the people who get ahead in this company are the ones who can sound like they know what they’re talking about and be “leaders” but often they are just better at talking and sounding confident. They don’t look at what makes our company different and our unique problems to solve but instead rattle off what other companies do things and seem to be caught up in being just like everyone else and that makes them so smart. Well maybe sometimes it makes sense to copy others but I love to look at problems and figure out how to fix them in a way that makes sense not just how everyone else is solving them in a generic way.

Every time I feel a tinge of frustration now I apply to another company. It doesn’t actually help since no one is calling me, but it feels good to send my resume out to the world. Unfortunately the last four years have done nothing to help me build a resume or make me a desirable candidate. This is why I’m stuck. I mean, maybe someone will hire me eventually. It seems to always happen when it feels like it won’t. When I’ve sent out thousands of resumes. Someone gets confused and thinks I’m a good person to hire. I’ve never gone more than 4 months without a job in the last 15 years. So I guess tenacity gets me hired. But each job seems to be more of a mess than the last one. Yes they may pay more, but I’m more and more suffocated.

I just want to do go good work. To solve problems. To do things in a logical way. To not have to put all of my energy into trying to be anyone but myself.

And at the end of the day I don’t have anyone to talk to about this, other than anonymous people on the internet. Because… my husband doesn’t get it. He knows I’m a hot mess and so it’s clearly my fault. Well, maybe it is. But what do I do about it? It’s my fault but it’s not getting any better. And then I feel depressed, like this deep, horrible depression that’s like a wire ripping through my gut every day because I feel guilty and like a total fuck up at the same time. But what total fuck up has managed to save $1.6M in 15 years? This one. This one right here.

So I can’t breathe again. I sometimes question at what point I call it quits for good. But I have kids now so I can’t make that choice. It just sucks to feel so alone in all of this. I try to tell myself I need to suck it up and just be better. Maybe I can be better. I don’t know. I don’t think I can be. I seem to have proven the hypothesis that I always end up sucking plenty of times over.