Sisters, Travelers & Professionals: Interview with Caileigh & Holly
Posted on November 5, 2015
As someone who is a part-time traveler, and full-time marketing professional, I am living proof that you can maintain and build yourself professionally in your career, while still getting to see the world! I started this interview series, because I wanted to show people that I’m not the only one that makes it happen, in fact, there’s hundreds of people out there just like me—two of those people being, Caileigh & Holly of The Brave Little Cheesehead. I met Holly back at the Women in Travel Summit in Boston this year, and we hit it off right away—to the point that people actually thought we were longtime BFF’s, so it just seemed like a natural fit to interview her and Caileigh for my work and travel interview series. As bloggers, marketing and communication professionals, travelers, and most importantly, sisters, find out how these two balance their careers and their passion for travel.
Tell me a bit about what you do for a living.
[Holly] First of all, we love you and your blog, so thank you so much for letting us share our story with your readers! I’m a content advertising strategist for a popular global, cross-platform news and entertainment company, and Caileigh is a social media content strategist. We like words.
Do you have a certain amount of vacation days a year at your job?
[Holly] Yep! We each have to cram all of our travel for the year into three weeks, which is actually pretty common for most U.S.-based companies. I get a few more holidays than Caileigh, but for the most part, we have to stretch our time off as long as we can.
How often do you try and travel within a year?
[Holly] As much as humanly possible! We wrote a post on our blog about how we try to cram as much travel into our time off as we can. Before the year will be up, I’ll have taken somewhere between 8-10 trips, including two international ones. Caileigh is a master of the weekend getaway, which is an awesome way stretch time off. She’s always posting pictures on our Instagram of someplace new she’s visiting, and half the time I didn’t even know she was going until she’s already there!
Do you ever feel limited to how often you can travel because of your job?
[Caileigh] Truth be told, even if I had unlimited vacation days, I think I would feel limited to how often I can travel—so I can’t say my job is to blame. My list of places to see is never-ending, which limits me all on its own. At this point in my life, I really enjoy the ability to travel and work because they are both very fulfilling to me and help feed my different interests. I can’t promise I’ll always feel this way, but for now I’m just fine with the balance (though, a few more days off wouldn’t hurt).
[Holly] I feel pretty fortunate to have had really supportive managers that understand I’m only able to work at 110% like they know and love if I get the time off I need to recharge and zone out. We both have ambitions to embark on long-term travel at some point, but for the moment, we’re really happy with and proud of the careers we’ve made for ourselves.
Do you find it hard to unplug from work when traveling?
[Holly] No way! Once I’m traveling, I’m so heavily immersed in whatever is going on around me that there isn’t even room in my mind for a work thoughts. But again, I’ve been fortunate enough to have had managers that get that. Caileigh and I pride ourselves on our accountability and good rapport with our teams. We both make it a point to wrap up as many loose ends as possible before taking off, and we leave comprehensive coverage plans for our teams while we’re out. I think if you demonstrate yourself as dependable and are committed to your work while you’re there, your managers and team will be understanding and supportive. It also helps to be a team player and go out of your way to support others while they’re taking time off.
Why is it important for you to have a career but also incorporate travel into your life? (As oppose to just quitting life to travel solely)
[Holly] This is a really great question, and I’m so glad you’re asking it! We’ve heard the argument that desk jobs will always be there, but the opportunity to travel won’t. It’s true that some jobs might be waiting for us if we quit and took off, but not these jobs. We worked very hard to get where we are today, and we are proud of our successes. I’m committed to traveling for my whole life, so I’m looking for a blend that keeps me happy. I want to love my job just as much as I love to travel so that heading home from a trip is almost as exciting as leaving for it. While this may not always be the case in our lives, we’re fortunate to have this so early in our careers.
[Caileigh] I second that. But, for me, it’s also about independence. We’re privileged to have the career paths we’ve had, and we want to take advantage of what our education and careers afford us. Not because it’s what’s expected of us, but because it challenges us, rewards us, and teaches us. I like the security of knowing I can provide for myself, with or without a relationship, and my career supports that, and it’s a damn shame not every [American] woman has that basic necessity in life. Although I’m comfortable with my work/life balance, there’s not a doubt in my mind that I’ll eventually take a break from work, slow down, and travel long-term, but I’m not there just yet, and that’s fine by me.
What inspired you to start a travel blog?
[Caileigh] In 2010, we jetted off to Europe for our first trip abroad without our parents. We started the blog to help calm our Mom’s nerves but, to her dismay, we didn’t write much. When we came home we started to put our pens to paper and slowly realized how big of a community is behind travel bloggers—including readers desiring to know how we did it and bloggers who’ve already been there, done that.
[Holly] We wanted to show other people like us that you certainly can quit your job to travel the world—and if that’s your jam, by all means, we support and salute you—but it’s not a requirement. You can have your cake and devour the shit out of it too!
If you had a piece of advice for someone that is trying to maintain a career, and also see the world, what would it be?
[Holly] If traveling and your career are equally important to you, then evaluate each career opportunity you receive with your passion for travel in mind. And try not to view working as the opposite of travel, and vice versa. Remember that each can be a means to pursuing the other more happily or comfortably.
[Caileigh] It’s okay not to scrimp all the time. A lot of advice I read about balancing work and travel suggests that we should restrict our spending at home so we can indulge while we’re away. If that’s your style, don’t change. But for me, limiting pleasures at home can cause me to resent my lifestyle or even my job—and it doesn’t really let you embrace all the mini adventures you find in your own backyard. We work hard. So, treat yo’self. Take weekend trips, try that new restaurant, or give acro yoga a shot. Just make sure it’s worth your hard-earned pennies, wherever you choose to spend them.Follow this unstoppable pair and their adventures on their blog, The Brave Little Cheesehead, or on Twitter and Facebook.