On changing jobs and making mistakes
Changing jobs is always at least a little bit nerve-wracking. Not only do you have to go through the interview processes themselves, but even after you’ve proven your whiteboarding worth, gotten an offer, and made a decision to accept the offer, there’s still one big question you have to answer for yourself: Was this the right choice?
Obligatory disclaimer: This series of blog posts was sparked by a not-so-recent conversation on twitter (that has languished in my drafts for a while). It is not an indication that I’m doubting my current role!
One of the hard parts about changing jobs is all the unknowns. Even the most thorough interview process can’t uncover every aspect of what your new day-to-day work environment will be like. If you’re a couple months into a new role, you might find yourself wondering if you made the right decision. How can you tell whether or not you made a mistake?
The bad news is that I can’t answer that question for you. (Unless you’ve just joined some crypto startup that mints NFTs out of puppies, in which case, yeah, that was a bad move, please think of the puppies.) The less-bad news is that there are some questions you can ask and steps you can take to try and find those answers for yourself.
A good first question to ask yourself is, “what was I hoping to accomplish with this move?” Depending on what your goals were, it may be straightforward to figure out if you’ve accomplished them. If you changed jobs for a specific job title after years of fighting for a promotion that never seemed to materialize, the question of “do I now have the new job title” should be an easy one to answer. The same goes for if you changed jobs in order to get a raise. Those are perfectly legitimate reasons to change jobs. I’m not someone who believes that your job needs to fill you with “passion” — if you do really like your work, great, but if your priority is a steady paycheck and you accomplished that, feel free to give yourself a high five and focus your enthusiasm outside of work.
Sometimes, your goals may be a bit harder to measure. Maybe you took a job because it was supposed to give you the opportunity to work with some specific tool or technology. Maybe you were looking for a certain scope of work — as you progress up the IC path, you might find yourself wanting to do things like lead cross-team projects or impact how engineering work gets done in an IC leadership role, and you might have taken a new role based on promises around that type of work. If you’re a few months into a new job and you haven’t gotten to do the types of work you were promised yet, you might reasonably find yourself wondering if you ever will. How can you figure out if it’s worth sticking around to find out?
Talk to your manager. The idea of having a big serious conversation with your manager so soon can be daunting, but in most cases, I’d argue that it’s worth the risk. If you start a conversation around something like, “I took this role hoping to do work like X and Y, can we talk about what it might take to get me there”, the results can be informative. A good manager would want to know if one of their reports wasn’t happy, and would want to work together to try and fix that if they could. If your manager reacts poorly, that gives you valuable information about what working for them long-term is going to be like. Finding out that your manager is unwilling to help probably isn’t the answer you want, but if you know that to be the case, that can go a long way towards answering the question of if you should try to stick it out (hint: probably not). On the other hand, a manager who is willing to work with you or at least be open and honest about the prospects of the role is a good person to have in your corner. I’ve been in that situation and had a manager help find an internal transfer to a team that was a better fit — which wouldn’t have happened if I hadn’t raised the issue in the first place.
Talk to your peers. If you don’t feel like you’re able to have an open conversation with your manager, you can try reaching out to peers instead. Try to find some people at or around your level or who are doing the type of work you’re interested in, either on your team or elsewhere in the organization, and ask them if they’d be willing to talk with you. It can help if you have some questions prepared in advance, to make sure you’re being respectful of their time — most people are more likely to accept a 1:1 meeting invite if there’s a clear agenda of what you want to cover (so don’t just ask if you can “pick their brain”). Questions like “how long did it take here before you got to do projects like X” or “can you tell me about your experiences with the feedback/promotion processes” or other specific questions around the areas that concern you can be a good place to start. Or, if there’s a person on your team who is doing the specific work you want to be doing, you could try asking if you could pair with them on their next project. Maybe they were supposed to work with you on X but forgot, or maybe your manager forgot to even tell them that. Keep in mind, they probably interviewed a lot of candidates, and your manager probably has quite a few direct reports, so while it may be top of your priority list for you to start working with X, that fact could have fallen off someone else’s radar at first, and reminding them of your interest might be all it takes to kickstart the process. Or maybe you find out that some of the people on your team don’t really like sharing their toys and it feels like it will be an uphill battle to get that to change. As with talking to your manager, you might not get answers that are what you want to hear, but remember that unpleasant information is still information that can help you make a decision.
Lead by example. If you were hired into a role that the company hadn’t hired for before, whether that be the first full-time ops person or the first staff-plus engineer, the company might not know how to best make use of your skills. In these sorts of situations, it might be helpful to lean towards the “ask forgiveness, not permission” side of things and try showing some examples of the sort of work you want to do. Of course, the success of this will depend a lot on the culture of your new team, but for example, if you’re coming into a team that hasn’t historically done much planning and you wish there were more design docs that got written before implementation, try dusting off your favorite design doc template and use it yourself for the next project you work on. A lot of times, change is easier and less scary when people can see it in action, so if you can do work that showcases the positives of changes you want to see, that can help warm people up to the idea. (Or again, if people react extremely poorly and you get the impression that the team is very change-resistant, that can be valuable information as to whether or not this is the place you want to be.)
Sometimes, you might change jobs not because you were working towards something specific, but rather because you were trying to get away from a particular toxic work environment. There’s no air quality monitor you can use to objectively measure workplace toxicity, and especially for underrepresented people in tech, changing jobs often feels like leaving the devil you know for the devil you don’t. Are you just trading that one mansplaining team member you knew how to deal with for another mansplaining team member you don’t? Are there any ways then to tell if your work life has improved?
How frequent are the bad days? There are always going to be good days and bad days at any job, and focusing on the bad ones can make them feel bigger in your mind. This isn’t to say at all that if you just smile and “think positive” that you can tolerate an abusive environment. However, if you’re trying to determine relative levels of bother, trying to figure out how often the bother actually happens can be good — especially if you came into the job a little burned out. I’ve used mood-tracking apps in the past to help me keep an eye on how much or how little work was bothering me — if you find that the bad days are increasing or outnumbering the good, that can be valuable information. On the other hand, if you’ve gone from having an annoying colleague you interact with every day, to an annoying colleague who you only have to deal with in meetings once a week, that sounds like an improvement, even if it isn’t perfect.
What support systems are available? Having other people around who can understand what you’re going through and commiserate can help you feel less isolated. This might be other people on your team who are going through the same re-org, or members of an ERG who understand what it’s like being a member of a particular underrepresented group at your company. At best, these sorts of groups (whether formal or informal) can be an invaluable source of emotional and practical support. However, they can also be a bit of a double-edged sword: spaces focused on venting frustrations can end up focusing your attention on the negatives. Again, this isn’t to suggest that you should bury your head in the sand and ignore problems if they don’t impact you directly, but remember that you have a finite amount of energy to spend, and if you’re in a position where you can’t do anything — either to help colleagues who are struggling or to leave for a new opportunity — then being surrounded by complaints can end up being a net negative for your mental health.
How close is the circus? How much the annoyances bother you can be impacted by how close the problems are to your day-to-day work. This can affect the scope of the problems as well, which can in turn influence how tolerable the situation is in the short versus long term. For example, if your immediate team is dysfunctional, or you have unpleasant teammates, or your manager has made it clear they aren’t willing to help you, that can make your everyday work life pretty unbearable, even if the rest of the company seems good. That might not be a situation you’d want to deal with even in the short term. However, if the day-to-day with your team is solid, you might be willing to stick around for longer, even if there’s disconnect elsewhere such as problems with the executive team or company values that don’t align with your own. In that situation, you might decide to say, “not my circus, not my monkeys,” focus on what you can control, and get as much done on your current team as you can before moving on.
In any situation where what you are dealing with doesn’t align with what you might want, you’ll have to decide for yourself how tolerable what you’re dealing with actually is for you. Some situations are changeable — if everything is good except for a couple specific technologies you’d prefer to be working with, that might be easier to sell with a couple more months’ tenure under your belt, especially if you have a manager who’s willing to work with you. If you’re the first person doing something, whether that be the first IC at a particular level or the first member of an URM working in the company or team, you might have an uphill road ahead of you, but if you have a manager who is willing to learn and if you have the energy to teach them, you could be in a position to make things better for yourself and anyone who comes after you.
You won’t always have the energy to try to fix those sorts of problems. Don’t force yourself to try — it is not your job to single-handledly fix a broken culture. Only you can decide for yourself if the situation you’re in seems like it’s able to be improved, and only you can decide if you want to spend the energy to do that. It’s more than okay to put on your own oxygen mask first and move on if that’s what makes sense for you. In the next post, I’ll go over some signs that an organization isn’t willing to change that you can look out for, which can hopefully help you decide if trying to improve things is worth your time.