how do you get vacation time?

How Do You Get Vacation Time or Sick Days? 10 Freelancers Weigh In.

In full-time employee roles, you usually have a designated amount of vacation time to take off each year. And, if you’re lucky, you have a good manager telling you to take that time off to rest and enjoy life.

As a freelancer, chances are you don’t have someone telling you to take time off or any backup if you get sick. So how do you manage holidays, vacation time, or when the inevitable happens and you get sick?

It’s not easy and there isn’t one definitive way. Some freelancers simply don’t take time off. Some work it into their schedule. Some decide randomly at the last minute. Here are 10 freelancers offering their strategies for taking time off and accounting for sick days.

How Do You Get Vacation or Sick Days?

1. Elena Vivaldo: Scuba Diving SEO Copywriter and Content Writer

elena vivaldo copywriter

About: Elena Vivaldo is a UK-based SEO copywriter specializing in the scuba diving industry. Before freelancing, she was a diving instructor around the world. She’s been freelancing since 2017.

Her Answer:

I’m very organized, so I always aim to finish my work well before the deadline to leave room for any sick days or lazy days. 

I like to go away a lot, so I usually pack in a lot of work when I can. Even if it means working non-stop for a few days, it’s worth the extra effort because I can then go away for days or weeks on end without worrying about work. I like to disconnect, and freelancing gives me that freedom.  

Obviously, I let all my clients know in advance when I’ll be “out of office” so we can work together to finish what needs to be done.

Read Elena’s full interview.

Visit her website.

2. Julie Brown: Journalist and Editor

julie brown

About: Julie Brown has over a decade of experience in reporting and journalism and has been freelancing since 2018. Based in Reno, Nevada, Julie lives with her husband and has written for numerous outdoor publications.

Her Answer:

I don’t have a system for that. Some people do but honestly, I mirror the schedule of my husband who works a full-time salaried position. So I take a similar amount of vacation as he does. 

I don’t really take sick days because as a freelancer our schedules are so much more fluid that if I’m not feeling well, I might take a nap or work less that day, but then work more on a day I’m feeling better.

Read Julie’s full interview.

Visit her website.

3. Brigid Mander: Writer and Skier


About: Brigid Mander writes for a wide range of publications about travel, outdoor adventure, and the environment. With over a decade of experience freelancing, she’s figured her way around making it work for her needs.

Her Answer:

Ehh. I just do it. If I don’t feel well, I don’t work. I’ve never had that happen where I was really pressed for a deadline and it would ruin everything. 

And vacation, I mean, my life is kind of like a vacation. I guess real vacation is when I disappear into the woods or something and I’m off the grid, or I go on a trip with no assignments. Again, I just do it when I don’t have any other obligations. I could work harder and be less flexible and make more money, but right now, I don’t need to. 

Read Brigid’s full interview.

Visit her website.

4. Shandi Kano: Freelance Creative Producer

shandi kano producer

About: An award-winning producer with over 16 years of experience in the outdoor and sports production realm, Shandi Kano has been freelancing since 2014. She’s worked on award winning films and worked with a wide range of small to large brands.

Her Answer:

This year (2021) I haven’t because I’ve been insanely busy. Usually, you just say, “I’m taking today off.” 

But based on your project load, you can forecast. Sometimes it’s challenging. As a freelancer, it’s hard to say no to stuff because you always want to keep building your network portfolio. But at some point, you have to also build your personal life.

Read Shandi’s full interview.

Visit her website.

5. Ryan Tuttle: Freelance Commercial and Editorial Photographer

ryan tuttle in joshua tree

About: Ryan Tuttle has been freelancing for outdoor brands and publications since 2015. She’s done photo shoots for many different outdoor brands including REI Co-Op, Eddie Bauer, The North Face, and Stio, but she also sometimes shoots for music, architecture, and interior design.

Her Answer:

I don’t. [laughs.]

It’s a good question. I mean I’ve been pretty busy the past couple years and most of my bigger vacations are planned way in advance. I kind of just plan them.

Like last year, I planned a Hawaii vacation over December. Usually December is pretty slow, so I know that I’m not going to usually have major things going on. It’s important to carve out that personal time, but I can’t say that I do it on a structured basis. 

Read Ryan’s full interview.

Visit her website.

6. Marquis Matson: SEO Analyst and Copywriter

marquis matson travel

About: Marquis Matson spends her time traveling the world and helping her clients rank in Google. Freelancing since 2015, she’s worked with a variety of clients in different industries from eCommerce to travel to yoga.

Her Answer:

Usually it’s really easy cause there’s like things I want to do. I’m very into yoga and there’s usually some kind of retreat or center or an ashram or something that I want to visit.

So I’ll just look at what’s going on there, and then I’ll book it and then request that month off. It’s not even a request is just like “Hey, I’m going to go do this, let me prep and make sure everybody’s ready for me to be gone.” Now [in 2021], it’s been a lot harder because of the pandemic, I can’t really go anywhere, so I’ve just been working. And only right now I’m like wow, I just need to take a few weeks off and not be online all the time.

So yeah, that’s my personal experience. But for the most part, nobody’s given me a guilt trip. Nobody’s made it hard for me to take time off. They’re usually pretty okay with it. 

Read Marquis’ full interview.

Visit her website.

7. Johanna Flashman: Freelance Writer and SEO Strategist

johanna flashman freelancing

About: Founder of The Freelance Outdoorswoman, Johanna has been freelancing since 2019. She’s written for various publications and helped multiple clients with their SEO strategy. Her first book Beer Hiking Southern California is out April 2, 2024.

Her Answer:

It’s really hard! A lot of it is just planning and managing your income so you can make sure to have enough to cover a vacation.

I try to book in vacation ahead of time and schedule clients and deadlines in a way where I can finish deadlines before time off and then not take on new assignments that will interfere with that time I’ve scheduled off. If I have a lull, I’ll try to take longer vacation, but recently, it’s mostly just been a day, half-day, or a long weekend here and there.

Read all of Johanna’s answers.

Visit her website.

8. Megan Michelson: Freelance Writer and Editor

Megan Michelson Outside

About: Megan Michelson covers all things outdoors for publications like Outside, Backcountry, San Francisco Chronicle, and many others. With 13 years of experience freelancing, she is a wealth of knowledge.

Her Answer:

Haha. The benefits of being a freelancer is that you can work whenever, wherever you want. The downside? There are no vacation or sick days, no paid time off. You are on call at all times. I bring my laptop with me everywhere. I take plenty of trips, but I wouldn’t say any of them are actually “vacations,” as I’m always checking in and finishing up projects on the road.

Read Megan’s full interview.

Visit her website.

9. Cameron Walker: Freelance Science Writer

science writer cameron walker
Photo credit: Sara Prince

About: A freelancer for almost two decades, Cameron Walker is an award-winning science writer based in Santa Barbara. She is also author of the new book National Monuments of the USA.

Her Answer:

I don’t know. I think part of it now is just being a parent. Like you don’t have those things anyway, so now I don’t even think about it.

Read Cameron’s full interview.

Visit her website

10. Kate Siber: Freelance Journalist and Author

kate siber with book

About: Author of 50 Adventures in the 50 States and 100 Hikes of a Lifetime, Kate Siber started freelancing full-time in 2005 and never looked back. Along with her books, she writes for various publications including National Geographic Traveler, Outside, and New York Times.

Her Answer:

I probably have a different relationship to time off than most people. I feel like the nature of a creative existence is cyclical. There are periods of time when I work extremely hard. I’m obsessed. I work through weekends for weeks at a time. Then the cycle ebbs and I have time off and I am not afraid to take it. 

Cumulatively, I probably take several months off a year. I disappear into the wilderness and also on silent meditation retreats on a regular basis, sometimes for four weeks at a time. (I don’t have kids, obviously, and I have a very understanding husband.) 

Some might see the off-time as a luxury, but I think of it as a crucial piece to being able to show up fully. While there is often a compression of tasks before and after, say, a monthlong meditation retreat, it always seems to work out financially. 

Read Kate’s full interview.

Visit her website.

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