When I got started in this business, one of the biggest perks I saw was being able to sit back and relax on the beach with a laptop, because I had the freedom to travel where I wanted and when I wanted.
It’s been a few years since then, and I’ve learned a few things about travel. Yes, it’s possible to go somewhere whenever you want, but even more so than when you have a job you need to plan EVERYTHING out perfectly if you actually want to enjoy your trip.
1. Lost Pay Adds Up
First up, you need to save up money for a trip. When you only go on vacation once every year or two, it’s not a big deal. You have a fund in a jar on top of the fridge and everyone knows you don’t go until it’s full. When you’re a freelancer with itchy feet, you want to get out there as much as possible, but you still need to pay for the trip.
To top things off, you don’t get vacation pay. It seems obvious enough, but too many people neglect his little detail. Sure, you can go away whenever you want, but if you do, you don’t get paid because you’re not working. And if you plan on working while you’re gone, trust me – it’s not going to happen.
2. Juggling Clients During Vacation
![travel[1] travel[1]](http://www.thechatfield.com/wp-content/uploads/2010/06/travel1.jpg)
Getting away isn't always easy...
Another toughie is figuring out how to juggling existing, ongoing, or new clients while away. I’ve learned, over time, to tell my clients about my vacation at least 1 month before I go away…then I remind them weekly in subtle ways so they don’t forget.
The first trip I took, I spent three hours a day in the hotel room replying to emails and editing documents. The second trip, I forgot my laptop at home and came back to a dozen irate emails. By the third trip, I had a system in place where I worked my butt off for 10 days before I left to get EVERYTHING done early.
However you do it, make sure your clients A) know you’ll be gone and B) have a lot of time to unload whatever they need on you beforehand. If they don’t, it becomes their problem, which 99% of them will recognize.
3. Having Work to Come Back To
Here’s why I don’t try to get everything done before I leave, and actually build the trip into my schedules. It’s because, when you get back you don’t have anything to do. I’ve been in this trap twice before – once after a 2 week trip to New York City in 2008 and last year after I got married.
Both times, I took extended leaves of absence (two weeks and three weeks), having planned ahead to cover the lost time and get everything done early. Unfortunately, when I got back, I had nothing to do – no edits, no projects, no responses from those clients.
They hadn’t moved on – they’d just taken a break themselves and I lost another whole week finding work on Elance. The lesson here is to always bid out in advance of leaving and try to convince your regular clients to have stuff waiting for you when you get back.
Ideally, you’ll eventually have regular monthly projects that you can use to fill these gaps, but for now, a good bit of pre-bidding or even a day or two mid-vacation spent bidding, can help stave off the lost week.
4. Enjoying Your Trip Properly
Enjoying your trip is important. What good is all that travel if you’re miserably thinking of your email the whole time. If you’re traveling with family, it can be even worse as you drag down your spouse and kids with you.
So, instead of worrying constantly, be realistic and set aside at least 1 hour a day to check email, hash out work details and make sure everything is okay. The rest of the day, leave your phone at the hotel. A blinking BlackBerry can be the death of a good vacation and your clients should already know you’re away.

Don't miss what you left home for....
If it’s important, they’ll leave a message and you’ll have your hour at the end of the day to deal with whatever comes up.
5. The Best Time to Get Away
So, with no boundaries on when you travel (unless you have kids), when is the best time to get away? I don’t have any preferred times, but I have been very lucky in offseason traveling. For sure, consider taking a trip in December. It’s the slowest month of the year for most freelancers and offers tons of opportunities for cheap travel if you go in the first two weeks.
September-October and April-May are also great times because of the pre and post seasons discounts at resorts in areas that are still quite nice. Avoid mid-summer travel like the plague if you can get away with it, and keep a close eye on nice weekends in the later winter and early spring.
My wife and I had a fantastic weekend in the Redwoods two years ago in April. No one was there but the weather hit a balmy 75 degrees. Last year we did the same thing in Vancouver, Canada in February. If you can time it right, you can get the entire destination to yourself.
The key to successful travel as a freelancer is to cut out as much of your work life as possible. I made the mistake on this one more than once and it can be extremely frustrating. Do it right, though, and trust me – you’ll have a blast and your friends will be super jealous (which is always fun).
chatfielda Freelance Lifestyle freelance writing, home business, make money online, traveling, working on the road
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