Vacation – it’s a fine dream and one that every freelancer feels like they can make a reality. With all that schedule flexibility, though, come a handful of issues that can make it hard to have a successful vacation without proper planning.

To be fair, I haven’t been on vacation in a couple of years. My son was born the same year my wife went back to school and time has been squeezed to its breaking point ever since. Vacations have been on hold as a result, but before Jack was born (and very soon in the future), vacations worked.

Here are some of the things I did to ensure every vacation was as successful as possible, without an excessive burden being placed on me to maintain income levels.

Managing Work Flow

The weeks leading up to your vacation are vital. For now, let’s assume the money issue is a non-issue. You’ve scrimped and saved, paid for your vacation and now just need to wait for the day of departure to arrive.

You can’t work as you would normally leading into a vacation, however. If you do, you’ll have work to do on the trip. Or worse, you will have neglected to get MORE work. As a freelancer, you are constantly marketing yourself to land new projects. If you stop doing this because of a three week gap in your schedule, even if you can afford it, you will end up with a longer gap than three weeks.

I made this mistake before a two week trip to New York (before we moved here) in 2008. I did a month’s worth of writing in two weeks before the trip to prepare for it, got ahead on income, and then stopped. I didn’t bid out on new projects, didn’t send any query letters, and didn’t communicate to clients. The result was a blackhole when I got back.

Plan for these moments. Start telling your clients as soon as you schedule a trip that you’ll be away for some time so you’d like to get ahead if possible. Overbook yourself for the weeks before a trip and then slow book yourself the last week before you go away – bid on numerous projects the last days before a trip, but make the deadlines as long as possible.

Working While Away

The last thing you want to do is work while away. If you communicate with clients and get a lot done before the trip, you shouldn’t have to. There will still be phone calls and emails, though.

Set aside a certain amount of time each week for communications. If it’s urgent, they can always call you, but if it’s not urgent, check your emails once a day at the end of the day. If emergency work needs to be done, do it in that same time period.
Don’t spend any part of the day that you’re supposed to be relaxing with family doing work.

Work in Place Upon Return

Finally, make sure you’ve planted the seeds for new projects so that when you return there is something there for you to do.

This starts with those early slow bids. Be sure to followup on any inquiries or questions while on vacation, and clearly communicate with existing clients or editors when you will be back from your trip so they can give you work accordingly.

If done right, a good vacation will be 90% relaxing. It’s not perfect, but you’re a business owner now, and until you can afford to hire someone to take those calls and emails for you, you’ll always be at least a little connected on a daily basis.

Trust me though – it’s MUCH better than being attached at the hip every minute of every day, working or checking email even as you step onto rides or into new restaurants. Vacation is a time to relax. Prepare yourself to succeed as much as possible in this regard.