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How to Take Vacation as a Freelancer

By Geoff Williams April 14th, 2016

There were many reasons I wanted to be a freelance writer, but being able to take a vacation whenever I wanted definitely seemed like one of the best perks. When I started freelancing full time 20 years ago, I predicted that I’d go somewhere amazing for two weeks every summer and maybe take one or two smaller excursions throughout the year.

I couldn’t have been more wrong.

When you’re working for someone else, you get a paycheck when you take a vacation. You don’t even have to go anywhere. You could just sit around the house playing video games for a week and still get paid for it.

When you’re freelancing full time and actually go somewhere on vacation, however, you get financially clubbed over the head. First, you spend considerable money on your travel costs. Then, your pay stops completely since you aren’t writing articles and submitting invoices or chasing assignments.

That doesn’t mean you shouldn’t take a vacation—we all need them, after all. But to pull off a successful one, meaning you have fun and don’t destroy your finances, planning the itinerary is the easy part. It’s the logistics of taking time off that require real thought.

Think about your cash flow

My vacations have been far more frequent and successful in recent years, but in the first several years of my freelance career, I funded trips on credit cards, coupons, and prayers that I wouldn’t run out of money before getting home. I had a couple early trips where I was packing the car, my now ex-wife and I stuffing our daughters in their car seats, and I’d be eyeing the mailbox knowing that the success of our entire vacation depended on the mailman arriving with my checks before we left the driveway.

Saving for your vacation well in advance is obvious, but it isn’t the only part of taking a successful vacation. You need to think about what happens afterward, said Robert Ellis Smith, a freelancer based out of Providence, and who has self-published the Privacy Journal for the last 40 years.

Ellis pointed out that the month after your vacation is probably when you’ll feel the financial pinch the most. Suddenly all the income you weren’t generating while you were on vacation will likely catch up with you.

So you want to think not just about how you’re going to pay for your vacation, but how you can keep the revenue flowing in afterward. And that’s where front-loading work comes in.

Speed up your work ahead of the vacation

You don’t have to lose a lot of money during your vacation, or afterward, if you’re putting in extra work before you leave. It may seem unfair to work more only to take time off, but there’s unfortunately no way around it unless you’re willing to take the financial hit.

Becky Blanton, a freelance writer in Palmyra, Virginia, blogs for a lot of clients, and if she knows way ahead of time that she has a vacation scheduled, she’ll write blog posts ahead of time. Then, she’ll send the blog posts on the due dates while she’s on vacation; that way she’ll still get paid on her regular cycle.

“Plan, plan, plan and things will go smoothly,” Blanton said.

And, sure, you can back-load some of your work, but be careful. The afterglow of your vacation won’t last long if you return to 19 deadlines that need to be completed in the next week. Plus, if you’re the type that has a hard time escaping work while you’re on vacation, having deadlines looming over your head probably won’t make for a relaxing trip.

Think about ways to stretch your vacation dollar

If money is an issue, you might want to think about taking your vacation when few people go anywhere. Smith said that he likes to vacation during the off-season, since airfare and hotels are cheaper. Of course, that won’t be practical for everyone, particularly if you have kids in school.

To save money, Smith said he often makes a vacation out of a business trip. In other words, he’ll travel for business but then extend the trip for a few days. So if you have a client paying for your airfare, you can pony up for a few extra days at a hotel and have some much needed rest and relaxation.

And while most of me believes that the last thing you should do is work on your vacation, Smith wisely points out that you might end up collecting some material for an article or project, which may help you write off the trip on your taxes, or at least help defray the cost of your trip.

“Often I find something on a trip to write about, and generate some income, as I did when I went to Tokyo in 2014 and ending up writing about the differences between American and Japanese baseball,” Smith said.

Warn clients ahead of time

I used to fret about telling editors I was going on vacation. Don’t do that.

I wanted them to think of me as the person they could turn to whenever they wanted, but the problem with that strategy is that they may well just follow through. Suddenly, they’ll be reaching out to you and expecting you to work not only on vacation, but on weekends and holidays as well. There’s nothing wrong with letting clients know that you’re a human like them and take downtime, too.

“I let all my clients know a few weeks ahead of time that I’ll be traveling during a certain time period,” said Natalie Bidnick Andreas, a digital strategist and marketing consultant based out of Austin. “Depending on the client, I either let them know I’ll have limited accessibility, or that I’ll be completely offline for a set time. The key is to set expectations in advance and in writing.”

Invariably, some client will contact you while you’re on vacation and tell you they need a rewrite in the next 24 hours or the world as we know it will cease to exist. Hopefully you’ll be strong enough to tell them that you’re unavailable to work—and then remind them that you alerted them that you wouldn’t be around.

If they don’t understand that you need a vacation like anyone else, it may be time to dump them as a client, suggested James Mawson, a freelance copywriter who lives in Melbourne. Mawson is a proponent of checking your email on vacation and staying in touch with the rest of the world, however, as long it’s very minimal.

“There’s a huge difference between being left to wait with no reply or an automated reply and being left to wait by someone who has responded to you personally and told you how long it will be,” Mawson said.

Plus, it’s possible some of those emails may come from clients offering you work, which you can tackle when you return refreshed. And that’s when checking your work-related email while on vacation can be a lot of fun, particularly if you’re doing that checking from a beach, a cabin getaway, or some other far-flung place. Then you can look around and remember that this is one of the reasons why you work so hard: so you can stop working, and go somewhere amazing.

Image by Getty Images
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