Stories Beyond the 9-to-5: How These Women Travel More While Maintaining Their Jobs (Episode 7)
We often focus on the excitement leading up to a vacation. You know the feeling, right?
You mentally tick off the days on your calendar one by one, silently willing time to go by quicker (but not too quick!) so you can get turn on your Out-Of-Office message and get on a plane. You know, back when traveling was a real thing (I’m looking at you, RONA).
But, if you travel frequently – or if you’re hoping to – the days leading up to a vacation can be some of the most daunting. Prepping your workload in advance so you can actually relax, making sure your coworkers have what they need to cover for you without becoming an enormous burden, being vocal with your boss about all the things you ARE doing so that your PTO days won’t later be used against you. In short, the prep prior to your time off can be a dizzying, hyperbolic mess.
So what do you do? Honestly, there’s only so much you can realistically, reasonably do leading up to your time away from your desk. You can make all the to-do lists in the world, send your coworkers dozens of emails so they’re looped in on every last possible project, and dot every single ‘i’ you foresee needing to be dotted while you’re away. And even then, it could still very well not be enough.
But don’t let this daunt you. There is no way to predict every last thing that could happen while you’re gone. And the possibility shouldn’t deter you from taking the chance to take time for yourself. No matter what society might make you feel, taking time off is a good thing. And, it’s been proven to help you return to work with a perkier pep in your step.
I share this because I know it can feel intimidating to want to take time away from work. It can feel like you’re letting people down. It can make you believe you need to work while you’re away instead of taking a true vacation (and hey, every once in a while this isn’t a bad thing). It can make you feel like you’re less deserving of success than the colleague that didn’t take a single vacation day in the last 12 months. Don’t. Your hard-earned PTO time is yours. Use it!
This months’s episode of SB95 features 3 women who each work (or have previously worked) at intense, demanding 9-to-5 jobs. In addition to that, each of these women also maintain side hustles on top of their jobs and travels. These are some of the hardest working women I know, and if they can navigate taking time off with grace (and manage to do it often!) so can you.
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 a 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 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, 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.
But don’t just take it from me. Take it from everyone else – keep reading!
How These Women Travel More While Maintaining Their Careers
1. Where are you based, OR if you’re nomadic, where are you currently?
Jen: I am based in Puerto Rico. They have strong tax incentives for digital entrepreneurs for anyone looking to make a move!
Martina: I live in Northern New Jersey, about 15 minutes from NYC.
Stephanie: I’m based in the magical Midwestern land of beer and cheese - Milwaukee, Wisconsin!
2. 9-to-5 hustle, self-made business grind, or somewhere in between?
Jen: I am 100% on the self-made business grind but I’m also no stranger to the 9-5 life. I used to practice law before transitioning to travel blogging and writing full-time. As an entrepreneur, I work harder than I ever did as an employee but the freedom is invaluable.
Martina: I work in business to business sales and consulting for a Fortune 10 company.
Stephanie: 9-to-5 hustler! I work full time at an experiential marketing agency where I help our clients market to and connect with their target audiences through the power of experiences - think person to person interactions, hosting private events, or authentically participating in large festivals and social gatherings around passion points like music, sports, or culture. It’s such a fun job and I love it so much!
I also work on my travel blog in my free time too. For now, it’s more of a passion project but I would love to grow it into a business one day!
3. What compelled you to make travel a priority?
Jen: I set out to take 12 trips in 12 months before my 30th birthday while still practicing law. Before I knew it, my twenties had passed and while I’d accomplished many professional goals, it felt like my personal life had been on hold. I wanted to do something crazy, carefree and just for me. I ended up taking 20 trips in my self-proclaimed “year of adventure.” This led me to write my first book about finding affordable flights and make an unconventional career change.
Martina: When I was a young girl I knew that I wanted to see the world. Gratefully, before my 23rd birthday, I had lived and worked on three different continents. I am happiest when I am traveling and being exposed to new cultures and ways of life. So it is something that I will prioritize for the foreseeable future.
Stephanie: It sounds cheesy, but I feel the happiest and most alive when I’m traveling and having new and exciting experiences. It’s always been an easy decision for me to make travel a priority. Working in a very demanding, always-on industry, it took a little while for me to figure out a good balance between working and making time to travel. I only had FIVE vacation days for my first year of work which completely SUCKED. However, that experience taught me how to become more strategic about taking time off and fully optimizing the time I do have.
I’m extremely fortunate that I get to travel for work about 6-8 times per year to activate and oversee the events that my team plans. The biggest way I’ve been able to make travel fit with my career has been by taking some time off for personal travel around those work trips. I’ll either fly to a destination early or stay late to have at least a day for myself. If I’m lucky, it will work out for me to take a long weekend or more for exploring!
4. On a monthly or yearly basis, how often do you travel? How do you navigate taking time off from work to travel?
Jen: I normally travel 2-3 times a month. Now that travel is my job I have no limitations. When I was working as an attorney I would carefully plan around bank holidays or long weekends, that way I’d only use 1-2 days off for a 4-5 day vacation. I would also take short trips, often leaving on a Friday night and returning on Monday morning.
There are so many proven benefits to taking time off — you return reinvigorated, more focused and end up performing better at work. As Americans, we need to get over our vacation guilt and realize that we’re not only entitled to take time off but our health and our companies are actually better off when we do so.
Martina: The past few years, I’ve taken about 10 trips (domestic and international) annually. I try to combine my vacations with holidays when possible. I have about 30 PTO days and holidays.
Stephanie: I travel whenever I can! I usually take about 8-10 trips per year both through extended work travel and traditional weeklong vacations during my slow season at work. Even if I can’t go far, I still prioritize taking weekend road trips around the Midwest to go camping and visit friends and family.
In terms of navigating time off, I usually schedule my biggest trips well in advance to avoid any timing conflicts and then work really hard to ensure that my team is set up for success while I’m out.
However, if an opportunity to travel comes up fairly last minute I can usually make an arrangement with my boss to work remotely for a day or two while traveling if the timing isn’t great from a work perspective. I worked really hard to build up a great reputation with my team so they know and trust that I’m leaving my work in a good place even when I’m taking time off to travel!
5. How do you finance and save for your travels?
Jen: For me, the most important part of being able to afford to travel is finding a cheap flight. Once you get to your destination you can find food, lodging and activities for cheap, especially outside the US. I went from paying $1,000+ for a flight to paying $38 for a trip to New Zealand. That makes a huge difference where your travel savings are concerned.
To get cheap flights, I recommend signing up for flight alerts (Scott’s Cheap Flights is my go-to), flying with budget airlines and learning how to redeem points or miles for award travel.
Martina: For years, I lived below my means so that travel was accessible for me. I kept my car from college for ten years and one of my first apartments was named the DollHouse because it was so tiny. These days I live a whole lot better but still try to keep my overhead below my means. Additionally, I partner with travel brands via my blog, That Couple Who Travels and utilize flight deals and credit card points.
Stephanie: My main travel financing/saving strategy includes living cheaply in my day-to-day life and finding ways to make the trips I do take even cheaper so that I’m able to travel more overall.
In general, I live well below my means in order to save most of my money for traveling. I live in an older apartment building with below-market rent, I drive a cheap, used car, I cook at home more often than not, and overall I think twice about purchasing things unnecessarily. My main goal of living cheaply is to save money on my hard day-to-day costs so I can spend my money on the things that matter most to me.
When I am traveling, I also try to find ways of making the overall trip cheaper so that I’m able to travel more per year with the same budget. This typically includes camping or staying in a hostel instead of a hotel, packing lunches on road trips, and splitting trip costs with others when I can. Even renting travel guides from my local library saves me a ton of money each year!
6. What’s your biggest tip for balancing work and travel?
Jen: If you’re taking off from a demanding job your life will be made exponentially easier if you identify a friendly co-worker that can step in if an emergency occurs during your absence. As an attorney, I never knew when a client would come in and say they received a time-sensitive eviction notice, requiring me to act immediately. I had two coworkers who handled all the fires that came up in my absence. I always brought them back the best souvenirs!
I also didn’t hesitate to return the favor when necessary and spent more than one Saturday taking over their volunteer duties at events outside of work. It was well worth it.
Martina: Of course you can’t do anything about pesky escalations that may pop up while you’re away, but you can minimize your need to work by planning ahead while you’re still in the office. Try not to allow your mind to start vacation before your body has!
Stephanie: Plan ahead for your workload and know when to unplug. By managing your workload efficiently and allowing yourself to disconnect you’ll be able to balance the best of both worlds by staying on top of your work and being fully present while traveling. I’m always looking ahead at my calendar to predict my upcoming workload and then analyzing what I can work on/finish early in order to give myself more disconnected time while working and traveling.
7. What’s your biggest tip for working while on the road (if you do)?
Jen: I really recommend people don’t work while on the road (unless you have to because you’re a digital nomad). It defeats the purpose of a trip. Even when I’m on a press trip I make sure to amend the contract so any deliverables are due after I return. If you’re taking time off, take that time off.
If you absolutely have to work, set aside a block of time to devote your full focus to the task at hand and get things done as soon as possible so you can return to your trip.
Martina: The biggest tip for working on the road is to choose accommodations with a strong wifi connection. Also, carefully read recent reviews to make sure there are no issues with construction etc.
Stephanie: Set work goals. Practice self-discipline. Utilize down time effectively.
In order to stay motivated while on the road, I set aside dedicated work time and a list of tasks that I need to accomplish in that time. If I finish that list early, I get to go explore. If I don’t, I have to stay late and keep working. Knowing that I’ll have to cut into my travel time to work if I don’t complete my list really motivates me and keeps me on task. Plus, I always make sure to work from somewhere cool if I can like a local coffee shop or relaxed bar so even “work” is a more fun experience while on the road!
8. Do you ever get any negative reactions to your travels from friends, coworkers, or loved ones? How do you navigate that?
Jen: I have been very lucky in that my friends and family have supported my endeavors. They take pride in my successes and encourage me to dream big. Actually, one of the co-workers I mentioned earlier bought me a book about building a writing career the Christmas before I left with the inscription, “go ahead, be happy.”
Martina: My family was initially uncomfortable with me traveling, especially when I did it solo, but they eventually got used to it. To be honest, I didn’t care much. I’ve always done my best to be responsible and safe. I felt as long as I did that, God would do the rest to take care of me.
Stephanie: I’ve been really fortunate to have support in almost all areas of my life for my passion for travel. My mom inspired my love for travel, my team totally understands it as long as my work is done, and my friends have also been super supportive as well!
I think the biggest criticism I’ve received for traveling has been because of my absence at gatherings or events while I was away on an adventure. I’m still working on being more present for my friends and family and have started prioritizing quality time with people when I’m at home or when I know I’m going to miss something that’s important to them. I’m finding that it’s all about balance!
9. Do you have a go-to travel partner, or do you prefer solo or group travel?
Jen: I prefer to travel alone. I like being able to go where I want, when I want and for how long I want. Ideally, I would be able to meet up with friends abroad so I can sprinkle my day with familiar faces but as far as the company I want to keep from start to finish, that’s mainly me. Especially when it comes to accommodations — I’m a light sleeper so I won’t share hostel or hotel rooms. I need to have a space that’s just my own where I can unwind at the end of the day.
Martina: I used to travel solo but now I travel with my husband. We met on a flight in 2015 and have been exploring the world together since then.
Stephanie: My boyfriend, Travis, is my all-time favorite travel partner! He’s my best friend and although we have totally different personality types, we really balance each other out and travel so well together! He’s always encouraging me to try new things and often pushes me out of my comfort zone - which I love and hate at the same time.
I’ve also gotten really comfortable traveling solo through my work trips and now enjoy the experiences I have traveling alone too. However, I’ve found that I really miss having the companionship and bonding experiences that come from sharing travel moments with someone else.
10. 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?
Jen: No matter how well you plan a trip, something always goes wrong. To quote Outkast, you can plan a pretty picnic but you can’t predict the weather! Travel is not about having perfect moments. Travel is about having imperfect moments and learning about yourself along the way.
My favorite memories are not from all-inclusive resorts or picture-perfect locations. When I tell the story of how I trekked to Havasu Falls, I only briefly mention the gorgeous waterfall at the end. The bulk of the story circles around me taking 10 hours to hike what most could do in 5 and seeing vultures circle around me like if they could spot their next meal walking. Terrifying in the moment, hilarious in retrospect.
When I talk about Meteora, Greece, the elaborate monasteries perched on impossibly spaced boulders is an afterthought. The story I tell is about how I ended up in the back of a minivan with a 9-person Italian family to visit them all. That is what travel is all about. The picture you see on Instagram is an advertisement encouraging you to choose your own adventure.
Martina: For every victory that I experience, there was a ton of prayer and God’s grace. I do experience fear, doubt, sadness and sometimes even depression. But through my relationship with God, therapy and intentional mindset development, I am able to conquer my giants. So can you!
Stephanie: I wish people understood how much work goes into managing work and travel at the same time. On social media, it may look like I’m hardly working while I explore a new city or enjoy a wine tasting on my work trip. But, what people don’t see on social media is that I worked until midnight the night before or planned my schedule a week in advance in order to have that afternoon off. It can be absolutely overwhelming and exhausting to juggle it all but it’s so rewarding and 100% worth it!
11. Any can’t-put-down reads (or podcasts) about either travel, career, or personal development that more adventure-loving women should know about?
Jen: I love Marie Forleo’s podcast. It’s basically the audio from her YouTube videos repurposed but it’s great content for entrepreneurs. Same for Melissa Griffin’s podcast, Pursuit with Purpose. I also have friends that host podcasts so shoutout to We Travel There, The Thought Card, She Hit Refresh, Travel Tales, and the newly launched Spanish and Go podcast!
Lastly, I recommend female travelers sign up for the Wanderful community. You will not find a more supportive group and they are filled with valuable resources and opportunities.
Stephanie: Oh yes! I recently found the Overheard podcast by National Geographic where they cover random and interesting stories focusing on science, psychology, and travel all around the world. They’re quick 20 - 30-minute episodes on really unique and interesting topics. I think they’re absolutely fascinating and have definitely been inspired to add different destinations to my bucket list from them!
12. Where will you go first once we can travel again?
Jen: I had a trip booked to Cairo in January 2021 for my birthday. It is uncertain if that will go through but I want to see the last of the ancient world wonders while I still can, so the Pyramids of Giza are calling my name.
Martina: Depending on Ms. Corona, my first trips will be to weddings in Philadelphia and Ohio. My first leisure trip will be to the Getaway House in Catskill, NY. Staying close to home for now but gosh I miss jet setting.
Stephanie: I’m going to continue to watch everything really closely regarding the pandemic, states/countries reopening, and travel safety overall but for the remainder of 2020 I’m planning on only traveling domestically (when it’s safe) and focusing on outdoor, nature-centric trips for the remainder of the year. (Which is normally how I like to travel anyway!)
Travis and I actually finished up our camper van conversion in quarantine so we’re really hoping to take that out on its maiden adventure! We’d love to visit either Yellowstone or Glacier National Park for some backcountry hiking and camping depending on the permit availability and crowds. We’re keeping our fingers crossed and are hopeful we can travel again soon!
13. How can others follow your adventures?