Vacation Preparation

After a particularly mind-numbing week at my old job, I came into work on Monday morning and realized that I either needed to take a serious vacation, or needed to resign and find a new job. I knew things were bad when I logged into the little HR portal and even after seeing that I had over two weeks of paid time off available, my first thought was "That's totally not enough time." I came home later that night and started complaining to Meredith about how I didn't think that two weeks vacation was gonna make me want to stay at my job and Meredith was like "Uh, fuck it. Why not take a month off then?" I was like "But I can't do that? What if I loose my job?" Meredith was like "You mean you're job that you almost quit today?" And then we both started laughing and decided that we were going to see if we could go to Thailand for a month.

Since pretty much everyone I know is always asking me things like "How the fuck did you get away with that?" I figured I'd write up a step-by-step guide on everything you need to do in order to take an awesome vacation without getting fired and without destroying your savings.


Step 1: Be Good At What You Do
This probably goes without saying, but just in case, I'm gonna go ahead and say it. If you're not good at your job, or if your employer is just looking for an excuse to get rid of you, pulling any kind of "stunt" like this will most likely result in you coming home from your awesome vacation to find yourself totally unemployed. (But hey, on the bright side, at least you'll have a great tan when you're interviewing for new positions!)


Step 2: Check Out Your Company's Policy Regarding Unpaid Time Off
Assuming you work for a decent company, they'll most definitely have some sort of documentation that outlines the requirements for taking an unpaid leave of absence. Usually, they require that you've worked there for at least a year, and that your boss doesn't think that the company will go to shit with you gone. Assuming your company offers unpaid leave and that you're eligible, the next step is to...


Step 3: Don't Care If You Get Fired
Ok, so you've done some policy homework and you're positive that your company offers unpaid leave and that you're eligible, but before we press on, it's time for another reality check. No matter how much preparation you do, no matter how much you may think you're the most-needed and beloved employee at your work, you should realize that any time you tell your employer "I'm taking a month off," there's always the possibility that they'll just be like "How about you don't bother coming back?" So, if you're not person willing to risk a job over a vacation, this is probably not for you.


Step 3: Talk To HR
Ok, moving on! Assuming you've confirmed that you're eligible for unpaid leave and you've also done some soul-seaarching to confirm that you're NOT willing to let THE MAN dictate how much vacation you can or can't have, it's time to swing by HR and make sure that what you're planning isn't violating any company rules. This shouldn't be some big official meeting - you just want to run things by HR and ensure that you're in the green and not incorrectly interpreting any company policies.


Step 4: Handle Your Biz
Hey, Hey! You're halfway there! Now that you've confirmed that you won't be flagrantly violating some stupid company policy that will get you instantly shit-canned, it's time to put together a detailed plan that you can present to your boss that outlines how all of the stuff that you'd normally take care of will be handled in your absence. This part is the hardest to a "guide" about because it's dependent on what kind of job you have. For my job, I put together an outline of all the software projects that would be under development in my absence, and I made sure that I had detailed documentation for each of them along with a person to temporarily drive their development in my absence.


Step 5: Tell Your Boss You're Taking Time Off
Now, as far as this whole thing goes, this is the only tricky part (and when I say "tricky," I mean "requires huge balls"). Seriously though, this is the part that's really easy to fuck up. You can't ask if you can take time off, you have to just matter-of-factly state that you will be taking time off.

If you go in and ask your boss if you can have a month off, of course they're going to say no. That's just basic human nature. If your boss doesn't get to take a month off, why should they let you? So this is where all your preparation comes into play. Instead of asking for time off, you explain that you're going to be taking a month off and then before they can offer any type of objection, immediately launch into an outline of all the preparation you've done: "I've spoken to HR and confirmed that I'm eligible. So I'd like to spend some time reviewing a plan I've put together to ensure that everything I'm responsible for goes smoothly in my absence."

Your boss probably won't be excited about it, but as long as you are able to demonstrate that you're within your rights to do so and you can convince them that you've put time and thought into a plan to ensure that everything you do will be taken care of while you're gone, they'll probably accept it and not give you too hard of a time. (One last disclaimer - if your boss hates you and is just waiting for a reason to get rid of you - you might as well start planning to take two months of vacation because you've totally just fired yourself!)