Photography: Giorgio Montersino
Summer is the season that does the most to separate the employees from the freelancers. As the wage-slaves walk away from their cubicles and head to the beaches, leaving all thoughts of work behind them, the self-employed are just as likely to be packing their laptops along with their suntan lotion. It’s not the best idea; time away is vital for recharging batteries, rebuilding enthusiasm and rethinking strategies, but when clients need satisfying and you’re your own boss, there’s no getting away from The Man even when you’re on vacation… because The Man is you. Here are six rules for the best ways to combine work with pleasure.
1. Forget About Working on the Beach
It’s the ultimate cliché for freelancers, the image presented by Internet marketers across the Web. You get to work while lying on your lounger, sipping a margarita and soaking up the rays.
And it won’t fly.
Good work requires focus, and you’re not going to find that focus when the water is calling you in and you’re worrying about sand getting sucked into your laptop fan. The beach is not an office, and anything you can do while working on your tan can be done a lot faster — and a lot better — in a more professional environment.
Head back to your hotel room, drag your computer into the lobby or better still, make use of the hotel’s executive lounge or business services room and give your work an hour or two of undivided attention. That will free up undivided hours of fun.
2. Do the Minimum
Even in a business lounge, you’re going to feel the pull of the pool and the drag of the daiquiri. You’re not going to be as productive, as focused or as inspired as you usually feel when you’re in your office and know that you’ve got the entire day to do your work.
So only do what you really have to do, and try to make the work as brainless as possible. Emails are fine, necessary organizational work can pass, reading, editing and analysis can even be enjoyable. But try to do something that requires serious creativity and deep concentration, and there’s a good chance that you’ll be coming up short. Your client would rather wait and receive the best.
3. Use Automated Messages
Even if you’re checking your email daily, it’s reasonable to assume that your response times are going to be slower than usual, especially if you have to hand out a long reply with lots of details.
Give yourself an excuse.
Use the automated message system to let people know that you’re away and will get back to them when you return to work. If they hear back from you sooner they’ll only be impressed by your commitment and dedication to their needs. They’re also less likely to demand a quick turnaround.
4. Don’t Make Any Promises
Coming up with deadlines and time estimates is difficult at the best of times but it’s even harder when you’re having the time of your life. You might have set yourself two hours of work every day you’re on vacation, but there’s no guarantee you’ll be able to keep to that commitment, and you’ll have little idea of how much you’ll actually be able to get done in those two hours when everyone else around you is having fun and you keep looking at the surf visible from your window.
Keep any delivery dates vague, mention that you’re away and promise to hand the work over as soon as you can. Clients tend to be understanding about vacations and downtime — they wouldn’t want their own vacations disturbed — so this is an opportunity to make small promises, pull out your excuse… and then win points by overdelivering.
5. Consider Your Partner
Anything you do for your clients while you’re on vacation will make them happy. But working for your clients means that you’re not spending time with your travel partner, and that’s going to make them unhappy.
The person you’re with needs to be considered too so pick work times that interfere as little as possible with their plans. Even pool times can be tricky: people tend to want company while they’re lying by the water, even if it’s only a pair of extra hands to slap on the oil. But vacations do have their own rhythms and schedules so there’s often a time in the late afternoon, when the sun is sinking and the touring is over, that vacationers tend to settle down with a book or a light snooze before dinner. That can be a good moment to fire up the laptop and shoot out those emails. Talk it over with your partner beforehand though so that he or she knows what to expect and can plan time alone. Work might be hard to avoid but skipping disappointment should be easy.
6. Clear the Desk
The most important rule when it comes to working on vacation is to plan ahead. You want to be going away with as little as possible to do: just enough to keep things ticking over. So write blog posts in advance so that you only have to publish them. Do the research early so that you’re not making phone calls from your hotel room. Tell your clients in advance so that they don’t have great expectations.
And assume that when you get back, you’re going to be snowed under for the first few days.
Tell people that you’re taking your laptop on vacation and they’ll tell you you’re mad. That’s a reaction that only tells you that they’re not self-employed. Work-free vacations might be ideal but for freelancers who make their own income, they’re also almost impossible. Assume that you’ll be working on vacation but work to make sure that when you’re away, you’re also working as little as possible.
Because if anyone deserves a real break, it’s the freelancers and entrepreneurs who take their bosses with them on vacation.