How to Go on Vacation Without Taking a Massive Hit

So for the last few months I’ve been a bit of a digital nomad, if you will. I am a little reluctant to say that because my perception of being a globetrotting digital nomad is someone who of the upper crust in freelancer society, and has money and high-paying clients out the wazoo. I, on the other hand, have been doing it on the cheap. So far I’ve been to San Jose for a conference, sleeping on a friend’s couch, on vacation with the family in Hawaii, which wasn’t quite as cheap, and I’ll be in Chicago for about a month, staying with some friends and dog sitting. It took me a little bit of time to get situated and gather myself mentally, but to my surprise I’ve been loving it!

After freelancing full-time for about eight months, I felt like taking a real vacation and trying to get work done while on the go seemed a little preemptive, but I did it anyway. I’ve talked a little bit about going on vacation as a freelancer, and here are some ideas on how to get away without it taking a massive hit on your finances:

Rent Out Your Place
If it’s feasible and you’re up for it, try putting someone up while you’re away. My friend Megan goes out of town for a few months every year, and she says that subletting is easy peasy. One thing you’ll want to do is create an agreement for the subletter to sign. It should include details such as dates of the sublet, which utilities (if any) the subletter will be responsible for paying. Megan also pointed out including nitty-gritty things such as including a cleaning fee to hire something to scrub the tub and toilet after the sublet is over. Brilliant! I’m not expert on such matters, but it can’t hurt to have something in writing.

Employ the 11-Month Income 
99u has a great article on how creatives can make the most of unpaid time off, and one of my favorite things listed is to create a budget based on an 11-month income. That will account for a month of pay to go on vacation and for “sick days.” To determine how much you need to make to take vacation, work backward. For instance, if you want to make $50k a year, you’ll need about $4,500 a month, $1,100 a week, or about $220 a day. Want to make $60k? That’s $5,400 a month, $1,300 a week, or $340 a day. If you’re shooting for $70k, that’s $6,363 a month, $1,590 a week, or $400 a day. It’s obviously not hard to figure out, you just need to do some basic math and keep these numbers in mind. And it’s not a perfect science, of course, as some months you’re killing it while others, not so much.

There are a bunch of formulas out there to figure out your hourly rate, but I find that as a writer, an hourly rate can be hard to figure out. While ideally your rates should be standard, sometimes it’s hard to gauge this because writers are normally paid per article or by word count. I find it easier to figure out how much I need to make per month, and when I reach that number, I feel a little more at ease.

Set Up a Vacation Fun
Duh. But how? You can sock away money to get away when you’re just trying to eke by and foot the bill for all the taxes and business expenses that are part of freelancing. I’ve been putting away a percentage of my income after “paying myself” a monthly income toward a “fun fund.” This was something I set up when I was working a day job. Any side hustles I did such as test proctoring and petsitting. You can also use any money socked away from your Digit account (which I absolutely love, by the way), or a savings goal in your bank account.


Ramp Up the Workflow Before You Leave
Contently’s The Freelancer talks about how you can stockpile a bunch of work before you leave. I did this before going to Chicago because I wanted to take a train from L.A. to the Midwest, and knew there would be spotty wifi access. It wasn’t easy. I had just four days in between my travels to pack, see some friends, and get all my work done. I got most of what I needed done and wrote a blog post on the WordPress app on my phone. Not ideal, but that is life.

You can let your clients know well ahead of time you’ll be on vacation from so and so date, and then give them the option of having you submit work early. The clients I reached out to preferred the work early and it would benefit you as well. Less work to do when you get back, plus you might run into the risk of missing a deadline if there’s a hitch in your travel plans.

Do the 2/6 rule 
I think I’m butchering the actual name of this rule, but it has something to do with working for a few hours each day during your vacation. You know, just dealing with emails, financial upkeep and admin tasks, and actual work. I ended up having to work while I was in Hawaii, and after talking to my mentor Alan figured out a schedule that would work while I was there. The plan was to head over to the Starbucks down the road from my hotel,  work from 6-9 every morning, then grab breakfast with my family. I didn’t adhere to it every day, but it helped big-time to have a game plan in place.

Taking a vacation is not always perfect but definitely not impossible.

Illustration by Viet Vu

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2 thoughts on “How to Go on Vacation Without Taking a Massive Hit

  1. Renting out your place is seriously the most brilliant idea ever! We went to Africa one summer and rented out our place for the whole summer– it paid for our whole trip! Great share.

  2. Jackie Lam says:

    Such a good idea! Did you find it to be a lot of trouble to find a subletter? I will probably sublet next summer if I end up being gone for a few months.

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