Planning a Cashflow Positive Vaction

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Makin' the dollar dollar bills, y'all

Sure, we talk about travel a lot around here because there’s nothing more frustrating than grinding through your job and being stuck in one place. It’s easy to get excited by a cheap fare out of town or out of the country, but it’s just as easy to forget that if you’re not on salary, you’re probably not making any money while you’re gone either. Which means you might be even more broke when you get home.

On the other hand, if you’re a freelancer, contract worker, or someone who works from home anyway you might be able to turn part of your vacation into billable hours to even out those travel expenses. Thanks to modern miracles like wireless internet and long battery life, anything you could be doing from that cafe down the street you could probably be doing just as well from a bar on the beach. You’ll just need to do a minimal amount of planning ahead of time.

First, be honest with yourself about how many hours you will actually want to devote to working. This is, after all, a vacation so don’t kill yourself. Figure out the best times during the day to work. If you’re going to the tropics where it rains all afternoon, you’ll probably want to keep your mornings free for exploring. Oh and take into account time differences. You might be able to sleep in and hit an early deadline if you’re a couple hours ahead of the home office.

Second, make sure you can communicate with the outside world: If you work from home you’ve probably already got a good sense about how much or how little you need to communicate with your boss or clients. If all you need deliver is an excel sheet at the end of the week, then you can probably get away with vacationing in a town that has only has one Internet cafe. On the other hand, if your boss needs constant contact or you do a lot of work online you might want to make sure you’ll have internet access. Over my last few trips abroad, I’ve noticed I can pick up WiFi in more and more remote places. Recent editions of guidebooks even make a point of highlighting who has it available.

Third, (and this one works for everyone, not just the Working Vacationers) keep your daily spending at about the same level as when you’re at home. It’s tempting to eat out three meals a day when you’re traveling and to just sit in beach bars drinking beers, but supermarkets and local, divey restaurants are your friend. Just from anecdotal experience, I’ve found a beer in a bar tends to be the same as a happy hour beer at my favorite place back home – cheap, but not dirt cheap. More often than not, though, you can hit the supermarket for a 6-pack that costs the same as two beers at the bar. Same goes for food. Stock up on peanut butters and bagels from the free continental breakfast and you just turned that into two meals. Or swipe some toast, add avocado and tuna you got at the grocery store and you’ve got lunch for less than a dollar.

Finally, you might have to set some expectations back home like “I’ll be available on email, and I can call in if necessary”, but be realistic. Don’t try to hit 18 goals on a deadline you’d never hit at home anyway. Not unless they all have to do with getting better at surfing or working on your tan.

Pic via: Certified Dad

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Andrew Dalton - Aggressive Panhandler

Andrew Dalton - Aggressive Panhandler

Andrew is an East Coast transplant from Virginia hamming it up in San Francisco without any intention of leaving. Having worked every typical job from Bike Shop Employee to Bartender to Ad Agency Hotshot, to Dotcom Layoff he now busts his ass covering the "weird things to do" beat for gracious local audiences at and rallies the Western Addy/Lower Haight/Panhandle neighborhoods into action at His work was published in a real, paper magazine one time. One day he might even figure out how to make money from it.