Multiple ways to take a vacation

True confessions: I love vacation 

I really enjoy my job, but I love traveling so much that I even love the things most people hate about travel:

• The people-watching 
• The tiny snacks
• The animals people bring along on their trips 

Case in point: day one of my recent Europe trip was a “positioning” trip from Denver (my home airport) to New York that involved landing at LaGuardia and getting to a JFK airport hotel for the next morning’s flight.

I was by myself with minimal luggage, so I thought, let’s spin the adventure wheel and take public transportation instead of an Uber. This involved the airport bus to the subway, a subway ride, a 20-minute walk, a wait for a bus that never came, and a wait for a bus that did come. Basically most people’s idea of hell, and to be honest, I loved it. 

It’s hard to describe the array of humans that ride public transportation in New York, what they wear, what they talk about, what you see from the bus window. Such as: a restaurant advertising “Trinidad-style Chinese food.” So many questions: how did these two cuisines fuse, what do they serve, who eats there (people from Trinidad, people from China, people who just like this kind of food?).  An Uber would have been $65 plus tip, this cost me $6.50, and honestly it was better than a movie! And the trip just got better from there. Every day was literally perfect. 

But how do we take a vacation, without paid vacation? 

When we pair the words “freelancer” and “vacation,” there’s good news and there’s bad news.

• No boss to ask for permission (yay!)
• No paid vacation (whoops!) 

The real consequence: in the U.S. at least, most freelancers just don’t take vacation. Pre-COVID, the accounting platform HoneyBook did a survey showing that 92% of freelancers felt that they could never take vacation, or worked during what they called a vacation.

As someone who really believes in the benefits of vacation, I find this sad. To me, vacation isn’t just fun; it’s a mental and physical break that gives me renewed energy for my business, and new ideas. I find that when I’m not working, my mind can think about the bigger picture of freelancing: what do I want more of and less of in my work life? Where do I see myself in three years? What’s working and what’s not working? 

Three options to try

If you want a vacation but you’re struggling with how to do it, here are three possible models I’ve tried all of them, so I’ll give you my perspective on each one. I’ve also got an option if your vacation budget is close to zero. 

Option 1: Just unplug 
As I often remind people, you’re a freelancer. You can honestly do whatever you want with your business. “Can’t take vacation” is something you’re telling yourself, not something someone else is telling you. If you can afford it (in terms of money and client retention), just put on your auto-responder and go. 

Pluses: You get a complete break from work, and I think a lot of freelancers never really get that.
Minuses: It’s expensive and risky. To do this, you really need a paid vacation fund (so that your bank account isn’t at zero when you get back), and you need to either have a workflow that lends itself to this kind of thing (i.e. your work slows down a lot at a certain time of year and you take vacation then), or you need to accept that you may lose work because you’re neither available for work nor responding to e-mail. 

Option 2: Don’t work, but keep up with e-mail
This is what I did on my recent two-week Europe trip. Sadly, it’s fairly uncommon in U.S. business culture to take two consecutive weeks off, but I really needed a break, and because I was moving around a lot during this trip, I wanted to take only a carryon backpack and not haul my work computer with me. I did not put on my auto-responder, and I relentlessly answered e-mail (came home to 12 messages in my Inbox, less than an average weekday morning). 

Pluses: Clients may not even know you’re gone, and you have less FOMO about what might be happening in your Inbox, yet you’re not really working. I did no paid work during my two-week trip, and I took only my phone, no computer. It was liberating!
Minuses: You’re not truly on or truly off. You’re not earning money, but you’re not totally unplugged from work. However I will say that of the three options I’m suggesting here, I liked this one. I despise coming home to 975 unread e-mails, and I really didn’t mind spending around 30 minutes a day on e-mail. 

Option 3: Workcation
Although I think we all need true breaks from work, I’ve become a big fan of the workcation (I wrote about it in this blog post in 2024). Workcation is what it sounds like: you go to a new location, but you work from there. I’ve done this for as long as a month, and it went well, but I think you need to be strategic about time zones and other logistical factors. My husband and I have now done three workcations in British Columbia in the summer, and it’s honestly a huge advantage that it’s light until almost 10 PM: we usually work until around 4 PM, then go mountain biking or hiking for a few hours, and it’s still broad daylight! Likewise, you could go from the U.S. to Europe, have most of your day free, and start working in the afternoon when your U.S. clients get into the office. 

Pluses: You’re getting at least sort of a vacation without losing income. When I’ve done workcations, I felt that they were totally worthwhile even though I was still working.
Minuses: You’re, well, still working on vacation! Zero unplugging! Time zone can be a big factor, as can reliable interpret if you’re an interpreter or if you do online meetings. For example, I will not interpret over wi-fi, only in a location where I can bring my own ethernet cable and plug it into the router (I ask the lodging host about this before I book). 

An option that’s close to free

Maybe you’re thinking, “Nice idea, but I can’t afford any of this. I can’t take time off, I can’t spend any extra money, I can’t even go on a workcation because I’d still have to pay for a place to stay.” If you’re not a traveler and you’re fine staying home, do that. I’m not here to shame you into taking a vacation if you’re a homebody.

But if I wanted to travel and couldn’t really afford to spend much/any extra money, I think I’d take a workcation while housesitting in a situation where I either got paid, or at least didn’t pay anything. A couple of ways to do that:

• Join a platform like Trusted Housesitters (mostly involves pet care; you don’t get paid) or HomeExchange (house exchange, but it doesn’t have to be 1:1; you accrue points that you can use anywhere)
• Find a group of like-minded people; oddly enough I’m in a Facebook group for cat-lover translators, and people commonly exchange live-in cat sitting 
• Travel somewhere that people pay a lot for house/pet sitting. Where we live (fairly high-cost and dog-obsessed area of Colorado), people on our neighborhood e-mail list will offer up to $1,000 a week for live-in dog sitters if you’re willing to spend most of your time with the animals 

Some people take this to the extreme: here’s an interesting article by an American remote worker who went more than eight months with no permanent place to live while housesitting full-time through Trusted Housesitters. I was honestly tempted! 

I hope these tips are helpful if you’re planning a vacation! I like to have something on the calendar before I come back from a trip so that there’s always something to look forward to. And if you went on an adventure this summer, I hope it was great!