Stories Beyond the 9-to-5: How These Women Travel More While Maintaining Their Jobs (Episode 4)

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Rachel Off Duty: Stories Beyond the 9 to 5 - Episode 4

In honor of Women’s History Month and International Women’s Day, I want to recognize just how much women do, and juggle, and navigate in order to squeeze lemonade out of lemons. Regardless of whether you work a full-time job, are a solo entrepreneur, or wear a zillion hats, there is something absolutely remarkable about how we show up each and every day, even when society tries to tell us to sit down (& be humble?).

Take, for instance, the simple act of taking a vacation day.

Rather than just deciding whether or not to take time off, it seems like these days, there’s another equally nagging consideration pulling at your sleeve: whether you’re actually going on vacation (you know, 100% unplugging), or whether you plan to still be available for calls, texts, or emergency meetings throughout. Rather than time off VS. no time off, these days, it’s about whether you’re truly unplugging or just pseudo-vacationing.

Frankly, it’s exhausting even just writing about.

But the reason I bring it up is because sometimes, working while traveling is simply inevitable. This is especially so if you own your own business or are higher up in your company. The reality is, it’s not always piña coladas and lounging at the beach.

What side are you on? Complete unplug, or keeping one eye on your inbox at all times?

On this month’s episode of Stories Beyond the 9-to-5, I’ve interviewed 3 incredible women with stories, and opinions, that are pretty distinct from one another.

One woman, Laura, built her own advertising business after realizing working for a bad boss just wasn’t for her. Another, Mikkel, owns her own photography business on top of running a travel blog with her husband. And finally, there’s Katie, who manages a full-time hospitality job while saving up to see the world on both solo and group adventures. Their perspectives on work-life balance, and travel, and pulling back the curtain to reveal what social media isn’t showing you, are fascinating, diverse, and honest.

Feel free to skip down to the good stuff (the interviews!) or read on for the backstory on how SB95 came to be.

RELATED: If you’re new to Stories Beyond the 9-to-5, catch up by checking out Episode One.

Why Stories Beyond the 9-to-5? Don’t Most People Quit Their Jobs to Travel the World?

I get asked these questions all the time – how do you manage to travel? Don’t you have a job? How do you balance it all? If there’s one thing I became painfully aware of as I joined the working world after college, it’s the tenuous line between “work and play.” Most of us call this work-life-balance. And for many of us, the idea of work-life balance feels like an impossible one to achieve. There are several reasons for this that I’ve encountered personally: 

1. Limited vacation days (the standard base vacation package in the US starts at just a mere 10 days per calendar year) 

2. Money and/or financial obligations 

3. Negative stigma surrounding taking time off 

4. Lack of time in general

5. Stress of maintaining, and growing, a career and achieving success

If you’re reading this blog post, I’d like to guess it’s because you are the kind of go-getting woman that wants to travel the world but isn’t as convinced about halting your career goals or losing a salary.

Maybe you do already travel a decent amount but you’re hoping to go even further.

Maybe you work at an office that won’t budge when it comes to granting time off, and you’re feeling stuck.

Or maybe, you own your own hustle but have a hard time disconnecting from work and focusing on taking time for yourself.

If you’re any of these women I just described, I am incredibly excited. You’ve come to the right place!

Why? Because no matter who you are or what situation you might be in – whether you are a woman in a new job with no vacation time, or a freelance entrepreneur struggling to find balance, or a full-time traveler looking to start a career without stopping the adventure, I can tell you that you are not alone. And that navigating your career or personal ambitions while prioritizing travel is an achievable, 100% respectable pursuit. 

RELATED: Travel Shaming in the Workplace (and Beyond) – What it Is and Why it Needs to Stop

But don’t just take it from me. Take it from everyone else – keep reading!


How These Women Travel More While Maintaining Their Careers


Rachel Off Duty: Stories Beyond the 9 to 5 - Episode 4 - Laura Holmes
Rachel Off Duty: Stories Beyond the 9 to 5 - Episode 4 - Mikkel Woodruff
Rachel Off Duty: Stories Beyond the 9 to 5 - Episode 4 - Katie Dickinson

1. Where are you based, OR if you’re nomadic, where are you currently?

Laura: Michigan’s west coast, Nunica, MI (my local playground includes Muskegon and Grand Rapids areas).

Mikkel: I’m currently dually based in Raleigh, North Carolina and Fort Lauderdale, Florida when I’m not traveling for work or pleasure, or in the NY/NJ tri-state area (which is also mostly for work and family).

Katie: I’m based in Boston, MA!

2. 9-to-5 hustle, self-made business grind, or somewhere in between?

Laura: I co-own a boutique advertising agency and digital communications firm called FineLine Creative. We specialize in helping small businesses with everything from branding, to traditional advertising, to website development, to online marketing.

Mikkel: Self-made business grind! I own my own photography business. (It’s if you’re curious!)

Katie: Living that 9-5 life. I work full-time in hospitality sales, so at least when I’m not thinking about or writing about travel stuff, I have a job that is in the field.

3. What compelled you to make travel a priority?

Laura: Working for a bad boss made me realize climbing someone else’s corporate ladder was not worth it. I quit my agency job in 2003 and embarked on BYOB (being your own boss) and built my own business with a partner who shared my values. She and I still work together and recently celebrated 15 years in business!

Mikkel: Seeing the world truly fulfills me in a way nothing else can. I love the exhilaration I get from exploring unknown (to me) locations, meeting new people and experiencing new cultures. When something fulfills you like that you can’t help but make it a priority in your life. We also have a travel website (Sometimes Home) so it’s become its own travel incentive as well!

Katie: I lived in South Korea for four years and was able to see new places in Asia about once every six months. I had a really eye-opening experience on a bus going between Phnom Penh and Siem Reap in Cambodia and realized that my worldview was uncomfortably narrow even though I had been living in a culture other than my own for about 18 months at that point. I knew it was one of those times where you get a small glimpse into how little you know about the world and how different people move through it, and I knew I needed to keep chasing after answers through traveling.

4. On a monthly or yearly basis, how often do you travel? How do you navigate taking time off from work to travel? 

Laura: I am a true believer in life-work-play balance so I try to keep my day job at 40 hours or less to give me the flexibility to travel. As the owner, I have flexibility to travel often and typically take 6-8 weeks per year, but some of that time is long weekends and shorter trips regionally with usually one international trip per year. We promote flex-time at FineLine, where anyone can work longer days Monday through Thursday (but no working past 40 hours) and leave early on Friday or skip Friday to take a long weekend away.

Mikkel: Internationally I travel about three times a year. Domestically I’m constantly traveling, probably about one to two weeks of four a month.

Katie: I can usually manage one longer trip and a few smaller trips. I try to plot things out so that the longer trip is during a low period at work, but also an off-peak time for the destinations I’m visiting. November tends to be the sweet spot for me. The smaller trips are usually extended weekends, so I can take them more frequently. When I’m feeling weird about taking vacation days so frequently, I remind myself that I earned those days and they’re mine to use as I would like.

5. How do you finance and save for your travels?

Laura: A combo of setting money aside monthly in a specific travel account and using credit card Miles for flights and discounts on other travel-related purchases.

Mikkel: They’re financed from my full time job! I don’t buy a lot of “material” things. Most of my money every month goes to student loans, our apartment rent and groceries or restaurants. Saving isn’t too hard when you have a good business/full time job and you’re cautious about spending day-to-day.

Katie: The company I work for is a non-profit, so my salary is a little sad. I start thinking about trips 9-12 months before I go. I choose locations based on how expensive they are and use apps to help me figure out the best time to buy my flights. I have a budget spreadsheet for my daily life that I use to track and plan out my expenses, so that offers great insight. For example, I’m planning on taking a trip to Georgia (the country) in May 2020 and I know I’ll need about $3600 not including flights, so I’m putting $180 per pay period into a savings account and I’ll have enough by the beginning of April. I’m paying my life bills with my credit card and will have enough points to cover probably ½ my flights.

Rachel Off Duty: Stories Beyond the 9 to 5 - Episode 4 - Laura H.
Rachel Off Duty: Stories Beyond the 9 to 5 - Episode 4 - Mikkel W.

6. What has been the biggest sacrifice you’ve had to make in order to travel?

Laura: Because I balance a career as an ad agency owner, when I am traveling and out of the office, inevitably upon my return there are issues to manage or employee issues that others in my office are not able to handle. 

Mikkel: Traveling a lot means other things in my life are neglected. They’re a bit inconsequential – like, my apartment could be a lot more organized than it is – but they would still bring me joy if they got done. I also spend a good amount of time away from my husband, which we’re used to. When it’s your favorite person in the world to be with, but traveling is also one of your favorite things, you sacrifice and find a balance. Also, this may sound trite, but we don’t have any pets. And we LOVE pets. Traveling just isn’t conducive to us owning any right now! (Like a dachshund, which I will get one day!) 

7. What’s your biggest tip for balancing work and travel?

Laura: I need the carrot of travel or the next trip to look forward to in order to be truly happy, so by upping my travel dosage I am more productive and efficient at work and tend to be more focused and able to complete tasks.

Mikkel: I know it isn’t for everyone but I answer work emails all the time even if it’s 6:00am in Europe before I head out for the day or 11:00pm in Asia after a long day of touring and I just want to go to sleep. To me that’s the business price I pay for travel – answering emails while traveling, which is essentially synonymous with just staying on top of things with my business. So my tip is: if you have to work while traveling, do it.

Katie: Don’t feel guilty about using vacation days (because that’s totally a thing)!

8. What’s your biggest tip for working while on the road (if you do)? 

Laura: I just respond personally to key accounts but I limit my screen time/email time to checking once a day while on vacation.

Mikkel: Upload any PDFs you may need to attach to emails to iCloud or Google Drive (that enables me to answer emails more efficiently on my phone). Also, don’t neglect your inbox!

Katie: I don’t do any full-time job-related work when I’m on vacation. I’m an hourly employee and on top of that most of my job functions can’t be done remotely. In terms of content production (because I have a blog, as well – Weird Travel Friend), I usually take good notes and take loads of pictures, but I don’t worry about processing anything until after the trip is over. My trips are usually fairly short (7-10 days) so I try to be as present as possible instead of constantly trying to push out fresh posts on social media.

9. Do you ever get any negative reactions to your travels from friends, coworkers, or loved ones? How do you navigate that?

Laura: I do have some family/friends that seem to wonder “how you can afford” to travel but it is really just a matter of personal priorities. We (my husband and I) spend as much on travel per month as our mortgage!

Mikkel: Not negative, but a lot of people say, “Oh I wish I could travel…” and I reply: “I’m not lucky. I built this life for myself. You could do it too if you really wanted to.”

Katie: The comments center more around the places I choose versus the fact that I’m traveling in general. Occasionally people will make snide remarks about how they wish they could travel the way I do, but I try to shut that down real quick. I save for a long time because my job basically pays me just enough to cover life expenses, I almost exclusively stay in hostels, travel by bus, and eat whatever is cheapest at the local convenience store. Maybe they mean that they wish they had the intestinal fortitude to treat budgeting like an extreme sport? Who knows.

10. Do you have a go-to travel partner, or do you prefer solo or group travel? 

Laura: I do a combination of all of those: solo, group travel, or with my husband. Depending on local vs. international, I would choose to hire or not hire an outfitter or guide.

Mikkel: I often think about my favorite people to travel with! The list is short: my husband is my #1 favorite person to be around and travel with, myself as a solo traveler is #2 and maybe traveling with a good girl friend is #3. Maybe. Traveling with friends is really hard sometimes. Not all friends equate to good travel buddies. I try my best to stick to #1 or #2 😉  

Katie: I really like traveling solo but won’t turn down a friends trip or a super cool group trip. I took my first group trip in 2017 and it was really awesome to not have to think about my itinerary, but I really derive a lot of pleasure from a well plotted “things to do” map!

11. Social media creates a world of ‘perfect travel moments’ online. What do you wish more people would know about what goes on in your life and work behind the scenes?

Laura: In my blog and book (details below!), I focus on the unexpected or funny things that happen and that travel is not always perfect. The message is that you can really change the outcome with an attitude shift and your sense of humor even when dealing with missed flights, logistics gone wrong, weather issues and more. 

Mikkel: A big part of me wishes that yes, we could all just be honest that the apartment is messy, the to-do list written in Sharpie on many Post-It notes instead of a cute Instagram-worthy notebook, and that the boob sweat is real as I run to the gate at the airport to catch a flight. Or our tummies didn’t react so well to dinner in a foreign country. I guess the flip side of that is I’m slightly private with what I post on social media so I’d minimally post that anyway. But yes, I do wish social media was more real. 

12. Any can’t-put-down reads (or podcasts) about either travel, career, or personal development that more adventure-loving women should know about? 

Laura: Rick Steve’s book, Travel as a Political Act, is a must-read.

Mikkel: I love How I Built This, the NPR podcast about entrepreneurs. They’re easy, good listens and always inspire me to work hard at my business, which is how I fund traveling.

Katie: My podcast feed is filled with true crime and weird humor for the most part. But if you’re someone who is curious about the world (which most travelers are) then the Stuff You Should Know and the Stuff Your Mother Never Told You podcasts can scratch that itch. Each episode is a deep-dive into a single topic that you never realized you wanted to learn about until you saw the name of the episode.

13. Where in the world are you heading next?

Laura: I will be in Duluth, Minnesota over the 4th of July exploring the shores of Lake Superior with friends on bikes,  in kayaks, and on two feet! A Park City mountain bike press trip this fall (September) is on the docket as well, and I will be leading a group of 8-10 people on an active adventure to Chile and Argentina this November. G Adventures will be our guide for this trip as we navigate the Andes, central valley wineries, and hike an active volcano.

Mikkel: We are in Valencia and Barcelona this month! Then, we have a fun weekend trip to Bald Head Island, in North Carolina, planned for May. I’m also really looking forward to a bunch of trips in and around Florida this year to explore the Sunshine State more! We have a newsletter we love that documents all our adventures, and we’d love if you signed up!

Katie: My next planned trip is to Kansas City in early May 2020, followed by Georgia later in the year.

14. How can others follow your adventures?




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Rachel Off Duty: Stories Beyond the 9 to 5 - Episode 4
Rachel Off Duty: Stories Beyond the 9 to 5 - Episode 4

Hey there! I’m Rachel, a travel writer and a full-time advertising / marketing expert. In 2019, I traveled more than 25 times while working 9 to 5, and since then I’ve committed myself to living a more adventurous life, even if it means bringing my laptop along for the ride.

Are you hungry to travel more, but overwhelmed with how to juggle work and play? You’ve come to the right place!

Recent Adventures:
Let's Go Places!

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