Working Vacation 101

In the past few months, I've gotten really lucky: I've gotten the opportunity to go on three really random, really spontaneous trips. Friends and family have called me last-minute with an opportunity to chill on the beach or in a swanky hotel for free or very cheap, and each time, i've gone. I didn't need to get permission from my boss, negotiate use of sick days, or trade off vacation time. I just went.

That's the beauty of what we do, right? We can pick up and leave whenever we want. However, real life is often not that simple. if I've got an ongoing project that's on a delivery schedule, a lot of the time I can't afford to just drop off the face of the earth for a week--I have to keep working and keep in touch with my clients throughout most of the vacation. If this was planned in advance, the way most regular employees plan their travels, I could schedule this out-of-touch time and make sure future projects won't interfere with it--but last minute, I have to be more flexible. Here are a few tips i've found effective for taking your work on vacation.

Know your party's schedule. In the recent few months I've been out of town for a week or so with my sister, my brother and a group of friends. All times, I've told the party beforehand that I need to work during this vacation. Luckily, all the groups so far have had the same schedule: they've gotten up around ten, hung around for a leisurely breakfast, and not been ready to head out and do active things until noon--sometimes later. This has worked to my advantage, because I've been able to get up at eight in the morning and finish a good portion of my work while most of my fellow travelers have been asleep.

When you're on a working vacation, you'll have to be able to negotiate work time. You probably won't be able to spend all day out and about. If your friends want to hang out on the beach, negotiate a chill by the pool instead--bring your laptop and sit as far away from the pool as possible to prevent splash issues. If you're traveling with a bunch of early risers, you may need to do your work at night. But have an idea before you go how much time you can expect to spend at work every day--I usually count on a half day to a few hours--so you can have a realistic idea of how much you can get accomplished.

Make sure your regulars know. In the past, I haven't told my regulars when I've been out because it hasn't affected my delivery schedule. But now I'm starting to think I should--just so they know I may be a little slower in responding to emails than usual. Generally I'd tell them that I'll be on a working vacation, will respond to emails but possibly a bit slower than usual, and to expect an away message when they email me.

Set up email away messages. I set up an email away message as well--just to give myself less to do. It's more for new prospects than regulars. When a new prospect gets in touch, they often want a price quote or detailed response to a question about a project--and I can get a bit stressed out responding to those requests and trying to jam a full-day's work into a few hours. I leave those requests for when I return, and send automatic messages so they know why I'm not responding right away.

Get as much done beforehand as possible. This is so important. My blog posting drops off when I go away, mainly because I think I can handle blogging and working in the limited time I have to do both--and it turns out I can't. Pull a few long days, work on a few weekends to prepare for your trip--and sometimes this is possible and sometimes it's not--and you'll do much better on your vacation. I definitely recommend having a few emergency posts lined up and turning off comment moderation.

Have a backup plan. Or three. I can't count how many times someone's assured me there will be wireless Internet at so-and-so's vacation cottage--and there isn't. Or there is, but for some reason it doesn't work on your computer and nobody can figure out why. Know where all the wireless Internet cafes are within walking distance of where you're staying. have the phone number of a local tech support company. Invite your friend's brother who has a networking degree. Plan to bring a thumb drive or external hard drive to back up your work and transfer to the house computer, which IS connected to the Internet. Plan for things to go wrong.

It takes some forethought and experience to do the working vacation right. In the best situations, everything goes smoothly and your work doesn't need to slow down. Remember: impromptu vacations are part of the reason our job rocks--so enjoy it!