We’re Gonna Need You to Work That Week

by Mike Dang and Logan Sachon

Logan: Mike, have you filed your vacation day requests yet for the Christmas holiday?

Mike: Hah, thank god that is something I no longer have to do as a person who is self-employed, but yes, my holiday plans are set (Christmas with my folks in California), and I am remembering now what it was like when I worked for companies and had to get all of that pre-approved. So with my regular freelance stuff, I just say, “I’ll be gone these days!” And with our site, we’ll be around somewhat around the holidays, but much of that will be planned in advance. But Logan, you also work for a restaurant so you have to go through the process of requesting time off. How has that been?

Logan: Well the way it works at the place I work is you just have to get your shifts covered. So there’s been sort of this mad dash and exchange of texts and emails to get things covered. I hate it, it’s stressful. I think I finally figured out today when I’m going to be able to go home, and it’s just going to be for five days, with two of those mostly travel days. Which ha, that is still a lot, but I’m used to having more freedom!

Mike: Yeah, I bet those five days will fly by, but I am glad you’re able to get that time off! I imagine the restaurant is busy this time of year?

So I’ve never had a problem with requesting time off for the holidays before. I usually asked for 10 days, and I’ve always worked Thanksgiving so everyone was okay with that trade-off (plus nobody really paid attention either, because they were thinking about their own plans and days off). Have you had trouble before?

Logan: My trouble has always been that I’m not assertive enough about it, and I always want to be accommodating and helpful. In service and retail jobs, when only a few people can take off or you have to get your shifts covers, you really need to be loud about what you want. And I’ve never been very good at that. So other people end up saying, well this is what I need and I end up working around that. Which is a choice, but I don’t like that about myself. I do wish I were more assertive.

Mike: Do you think part of this, though, is that it’s not that you’re not assertive, but that you don’t really know what you need until, like December, when many people have already made plans? I feel like I am similar to you that I will say yes if people ask if I can give up a day to stay and help or whatever, but what has saved me in the past is that I know what I need to take off way in advance because 1) I have to buy plane tickets, and those are cheaper buying in advance and 2) my folks sort of tell me when they’d like me to be home and remind me that I need to have those days off. So I’m essentially balancing pressure from work and family, and family wins.

Logan: I’m pretty flexible and I guess I have this fantasy that when it comes to scheduling things, we’d all sit down and be like, okay, we all want to go home for Christmas, let’s figure out how to make that happen. But it never works that way! Ha. I don’t know. I got some days off, I’m very lucky, I’m excited to go home. Now I just have to figure out transport! I expect I’ll be on a bus.

Mike: I remember once I bought plane tickets to visit my friends across the country for five days and had requested that time off in advance. This wasn’t during the holidays — it was during the last days of summer. And then my boss said that things were getting busier during that time and that he really wanted me to be around. And instead of saying, “Nope! Tickets bought! Time off already requested!” I said, “Okay, sure, I will change my flight.” So I paid $50 to change my flight and cut my trip short — just a weekend instead of five days. My friends were happy to see me, but they kept saying, “We wish you could have been here longer!” And I said, “I know, I know — WORK.” But really, I should have just told my boss to suck it up for a few days while I was gone. I’d like to think that I’m not that person anymore — that if I were in that position again, I’d stick up for myself and for my plans.

Logan: I wish you’d stood up to your boss, too! And you will, next time. Actually you won’t, because you don’t have a boss, and you won’t have a boss, ever again, amen. Every day is a vacation day. Vacation time all the time.

Mike: Hah, well I don’t know if that’s true, but I’ll know what to do next.

Support The Billfold

The Billfold continues to exist thanks to support from our readers. Help us continue to do our work by making a monthly pledge on Patreon or a one-time-only contribution through PayPal.