Hey Olivia: Two Jobs, Two Titles, Just One of Me

Welcome to Hey Olivia, a Cushy advice column. In this series, we’ll be tackling any questions you may have, whether it’s about work, relationships, home, that elusive work-life balance, setting boundaries, or just about that thing we call living life.

Without further ado, here we go!

Hey Olivia, 

I need advice on how to deal with the “obliger” side of my personality. I recently got offered an opportunity to take on a new position at my work, while still maintaining the position I currently have.

In short: two jobs, two titles, one salary. It’s a great opportunity for me to learn and flex my skills in areas that I’m keen to learn more about, and currently use for freelance work I do on the side, but I’m concerned about balancing both positions.

Both employers have agreed to a split in how my time gets divvied up, but, I fear that the part of me that wants to please people and be obliging is going to get me stuck in a place where I’m doing ALL the things and I’m giving 110% of my time. What should I do? 


Balancing Act

Hey Balancing Act,

I am very impressed with your ability to take on this challenge with a positive attitude. While I don’t know enough about the circumstances that brought about the splitting you between two bosses (whether it was necessity, budgetary issues, or both), the fact that they approached you about this decision means they believe you are suited for both positions.

But let’s not kid ourselves here: when you are a salaried employee, many employers can take advantage of this fact and load you with tasks until you say, “Um, I am not a robot, you guys.” I’m concerned that instead of giving up 110% of your time, you’ll be giving away 200% of your time.

Before we talk about setting boundaries, though, I want to tell you that managing these two positions is not all on you. “But my people-pleasing side!” you exclaim. Sure, you may have a people pleasing side, but I have a sneaking suspicion that your bosses already know all about that people pleasing side and are counting on making the best use of it. Sure, you cannot control your two bosses, but you can make sure that they are talking to each other and coordinating how they will use your time wisely.

If you haven’t done so already, I suggest you sit down with them (together, preferably), and ask how the split is going to be managed, logistically. Is Boss A going to be kept abreast of what tasks Boss B has assigned you (with clear deadlines and priorities) and vice-versa? Will Boss B talk to Boss A if they have something very important for you to do that would require you to drop tasks from Boss A? Get a feel for the communication system they will have in place, and make sure it is transparent. The bad news here is that if they do not have a good communication system going, you’re going to end up with more work and having to play messenger for them, as well.

Now that we have bosses communicating to each other, setting boundaries is going to be extremely important in these new roles. Learning new skills is very useful for your future, but learning skills at the detriment of your mental health? Not so much. Depending on how your job duties/titles are split, I recommend you start tracking the amount of time and effort each job takes you.

For instance, let’s say that Job A is 70% of your salary, while Job B is 30%. During the first three weeks, you work 40-45 hours and it’s starting to become clear that Job B is taking more like 50%+ of your time while there are tasks of Job A that keep falling through the wayside (because, again, you are not a robot). In this case, where a pattern has emerged, have a frank conversation with both bosses. In this conversation, you can factually state how one job is taking over the other one (if you have been tracking hours and effort, you can easily wow them with your statistics), firmly remind them the hours and days you will be available for work (barring a true work emergency), ask them which tasks are priorities, and offer any solutions/insight you may have. This may take some fine-tuning, but I suspect that if they take care of the communication part within themselves, the setting boundaries part will be much easier.

Setting boundaries is twofold: you’re setting boundaries for them, but you’re also setting them for yourself. For example: Make a point of not checking email, slack, or any mode of communication after a certain point in time during the day (say, 6 PM). Communicate this boundary to your bosses, but also make sure that you abide by it. The most important relationship here is the one you have with yourself. Work is important, but your worth as an individual is far more than your professional prowess. Be kind to others, but more importantly: be kind to yourself.

TL;DR: Make sure your bosses are talking to each other about your workload. Track your time and see if patterns emerge (and you’re working way more hours than you should). Speak up before you’re rocking back and forth at your desk (been there). Your worth is not measured in your productivity/output. Be kind to yourself.


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