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Palms and crystal clear water. White powder and blue skies. Camels and rippling sand dunes. Whatever your idea of a perfect vacation, if you’re not on a permanent salary, your dream getaway can all too easily stay that way: a dream. If you don’t get paid leave, taking a holiday involves a number of issues. But if you can get over these hurdles, you’ll be on track to check out and kick back…

image by <a href=Palms and crystal clear water. White powder and blue skies. Camels and rippling sand dunes. Whatever your idea of a perfect vacation, if you’re not on a permanent salary, your dream getaway can all too easily stay that way: a dream.

Just last week I was speaking to a new neighbor who runs an interstate consulting business from his barn. But when I asked if he had any vacations planned, he shook his head. “No,” he said, “when you have your own business, you don’t really get vacations.”

I know plenty of people like this guy. They have the cash for a break, but they just can’t seem to make the time to get away. It’s not surprising: If you don’t get paid leave, taking a vacation involves a number of issues. But if you can get over these hurdles, you’ll be on track to check out and kick back…

1. Deadlines
We all have deadlines to meet, whether we’re working on short-term jobs or months-long contracts. Your clients engaged you to do the job in a certain timeframe, and your timeframes will inevitably depend — at least in part — on their timeframes. If your clients are like mine, they probably expect you to be around to support them throughout the process.

When I’m trying to schedule a vacation, I usually plan it well in advance, when I can see the end of a contract and can give fair warning to any ongoing clients. I don’t usually wrap up a job and get on the bus the next day, though — you, too, might want to allow a few days or a week after you deliver before you leave, just so you can provide any post-contract support (alterations, bug-fixes, etc.) to your client.

2. New work
OK, so you’ve scheduled your break to commence a week after your current contract ends. Great! But wait…When this contract’s over, shouldn’t you already be well and truly looking for the next one?

Most of us start looking for the next job sometime before the current one’s finished. And once you have a fish on the line, it can be hard to try to delay a project’s start date by an extra two weeks so you can take time off. It can cost you the project if a competing contractor is ready to start immediately. And few of us want to pass up on a paying job so we can spend money — even if it is an exciting foreign currency.

To stave off these feelings of income-related panic, I usually save more than I need for my holiday so that I have something to live on when I get back and I’m drumming up the next job. If I get a few irons in the fire before I go, I make sure from the outset that my potential clients know that I’m taking a break and when I’ll get back. That way, we can schedule the job with my break in mind, and avoid disappointment.

What about the client who wants you to work on a job and simply cannot wait until you get back? If this is a past client, I might consider asking a friend who’s in the same line of work if they’ll consider this one project, then speak to the client about using my associate for the job. This gives me some certainty that my client will come back to me for the project after this one.

If it’s a brand-new client, obviously I’d have to weigh the job, projected income and market situation (i.e., how much work is on offer) against how much I want to go on holiday, and how much it would cost to change my plans. If I’ve saved enough to see me through a few weeks when I get back from my trip, I’ll usually pass up on the job and take the break — holidays are too rare to postpone without very good reason!

3. Client service and administration
The burden of ongoing client service, maintenance, or administration tasks like chasing up invoices or managing subcontractors can shackle you to your work if you let it. If there are tasks that need to be done while you’re away, the solution is delegation.

If you have a friend you can trust who’s in the same industry, as I do, they may well be able to help you out by addressing client issues in your absence. If you don’t know anyone personally who could help you out like this, you might consider contracting the work out to an organization that provides the appropriate services in your field.

Finding a reliable stand-in might be challenging — and add some serious time to your trip preparation — but once you’ve found a good service provider, you’ll know you can use them again for future holidays, if you get sick, and so on. It’s worth the effort!

If you have a close team, you might be able to ask your most trusted subcontractor to do the day-to-day team management. If you need someone to chase invoices on your behalf, ask your accountant. (If you don’t have one, now’s the time to get one.) If there are tasks that must continue while you’re away, you need to find someone to do them.

4. Dedication
Don’t underestimate the importance of being dedicated to your vacation. Yes, there are many, many cases in which I’d reschedule my holiday for a particular client or project, depending on my circumstances. But the fact is that, overall, if you don’t prioritize time off alongside your work, you’ll never get away.

Holidays can be a great opportunity to spend time with family, expand your horizons and your perspective on life, and learn about the world. If you ask me, these things are as — if not more — important than the daily grind.

Once I’ve solved these issues, I’m usually all set to head off into the wild blue yonder. What’s your strategy for making sure you get a vacation every so often?

By Georgina Laidlaw

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  1. Usually i keep on the scheduler :) If i mad plans for a vacation than let it be.

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  2. Once I schedule it, I start putting it into the signature line of my email. Something like: I will be out of the office June 5-15.

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  3. That’s a really good tip, Emily.

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  5. Like Tim Ferris tells us in his book, “outsource your life and do whatever you want for a year”. He used companies like Brickwork, a company based in Bangalore, India which offers remote executive assistants. And while others do your work, you can start packing your bags.

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