Traveling And Working As A Creative Entrepreneur


When I worked as an art director at my nine-to-five job at an ad agency I would leave for a week of vacation with no concerns about work. (I was never what you would describe as a workaholic.) Tara, as a very important creative director, had the same policy – upper management and her team of designers and art directors, myself included, were given strict instructions to not call her while she was out of the office. Work was work, and vacation was vacation. The two shall remain separate and never meet. 

Tara and I have found many creatives work for themselves because travel is a priority – they insist on the flexibility to be able to set their own schedule and take time off without permission from upper management. But now I'm exploring the question of whether us creative entrepreneurs, myself included, have the flexibility (and balance) to travel and work – at the same time.

During my first year of self-employment, back in the Fall of 2010, I took advantage of unlimited time off to trek through the Nepal Himalayas of Nepal. I used that adventure as an opportunity to completely unplug and find my breath in a new uncertain world of entrepreneurship. But it was cool, because 4 months into freelancing, doing mostly project work, I was able to completely clear my plate before departing for the other side of the world for a month. I also still maintained the philosophy that work and travel were like oil and water – never to mix.

I was chasing the same kind of unplugged adventure last summer when I went on a trek through the High Tatras mountains of Slovakia and Poland with my husband, Jeremy. I gave myself strict rules in hope to recreate my Nepal experience: no blogging, no emailing, no texting, no planning or even thinking about work. But the difference was Braid was just 6 months old and Tara and I were just starting to settle into our business vision of working solely with other creative entrepreneurs. We weren't only doing project work and branding identities for other creatives but also honing our own method, developing ecourses, and truly embracing our expertise. I was attached to my work because for the first time ever my work had a higher purpose. Forcing myself to unplug from it all for three whole weeks while backpacking in Eastern Europe felt a bit forced and unnatural. 

Work / Travel Quote

Last summer Tara went on a couple beach vacations and surprised herself when she felt the desire to check her emails and maybe even do a little bit of copywriting or brainstorming. She had a routine that involved going for a coffee run with her laptop first thing in the morning and after an hour or two of work she'd dedicate the rest of her day to vacation. She shared with me that it made her feel surprisingly productive. It also helped alleviate some of that dreaded "I gotta go back to work" feeling you get after vacation. (Yup, even when you're your own boss you still get inklings of that work-dread feeling. We love what we do for a living but I'd be lying if I said we didn't love lying on the beach – or trekking through the Himalayas – even more.) 

So this last week I went on my first of many summer vacations to Tulum Mexico. You can read about my picture-perfect adventures of swimming in a murky cenote and exploring the Mayan jungle here. Every morning I woke with the sun, wrote my morning pages, and downed 2 liters of water. In the afternoons I would lay on the beach and listen as Claire, a Braid client and friend, would read aloud from a book on Indian mythology. I would wear my favorite scarf as a shirt and would eat whole roasted fish for dinner every night. We sipped on cold white wine and made friends with locals and other travelers alike. But at the same time, and for the first time ever, I was attempting to kinda sorta work during my tropical time off. 

Every morning after yoga by the beach and a dip in the ocean I would eat a green smoothie, check my email, and work on a blog post in the hotel lobby – which subsequently was the only place I could plug my laptop in for electricity and get a somewhat unreliable wi-fi connection. I was committed to writing a blog post (it is a dream that blogging is a part of my job description) and would check my email to schedule life coaching for creatives and respond to client's needs. Some days I spent up to 3 hours working. Other days, maybe only 30 minutes. With an ecourse launch and our first real-life workshop coming up there were a few wrinkles to be ironed and fires to put out. But somehow, the distance from home made me feel a little less stressed, a bit more objective, and somewhat detached (in a zen way) about things that would usually have me all in a tizzy. I'm sure the ocean breeze and tropical sun didn't hurt either. And of course I'm lucky to have Tara, Kristin, Liz, and our Braid ECourse developer Emily holding down the fort in my absence. Even so, the little bit of work I could put in every day kept me feeling productive and connected to the job I love. 

I'm constantly emphasizing the importance for creative entrepreneurs to blend (and balance) who they are with what they do in order to create a dream job for themselves. I also love a routine to stay balanced. I fantasize about a day when I'm completely location independent, traveling the world, and able to work from anywhere. But I know that even as glamorous as that seems it probably comes with its own set of challenges to be navigated. So merging work and travel is a bit of an experiment in practicing what I preach, and leaning into my dream life, as I move into my summer vacations.

Work / Travel Balance

Here are some tips for work / travel balance based on my most recent kinda working vacation: 
• Set the expectation with your coworkers and clients that you will have limited availability while you're out on vacation. I told my team that my phone would be off, but that I would try to check my email when I could. If they heard from me it was a pleasant surprise and I never felt guilty when I chose not to work. 

• Let people know where you're going. I shared my travel plans with my dream customers in our wrap-up meetings and set my email auto-responder to let potential clients know that I would be kicking it in Tulum for a week. It makes my being "out of the office" response relatable and warm – and it was often received with enthusiasm with just a hint of jealousy. 

• Don't plan to do too much. Prior to this trip, I ambitiously had the idea to redesign our Braid website while on vacation. I'm really not sure what I was thinking. Knocking out a blog post and trying to maintain a zero inbox was plenty. 

• Find a time to work. While on vacation I would work at the hottest point of the day – between noon and 3PM when I wouldn't want to be out and about anyway. For Tara it was early in the morning before her kids would demand her attention. It might not be your typical work schedule, but setting a few rules for your temporary mini-routine, will keep you from dividing your attention from the fun you're supposed to be having. 

• Establish some boundaries. I couldn't help but check my email on my phone any time I could take advantage of the limited wi-fi. But when you're having a candle-lit dinner of a whole roasted fish under a full moon it's time to put the work away. I tried to keep the bulk of my work contained to a couple hours at the lobby juice bar.

• Do what you want. Sometimes that might mean working over kite surfing. Other times it may mean ditching the laptop for a Jeep and the jungle. 

We want to hear from you. Do you like to keep work and travel separate? What are some of your tips for maintaining a good work / travel balance? Let us know on Facebook. 

Braid Method Branding for Creatives ECourse

The Braid Method Branding ECourse is for creative entrepreneurs who are ready to support themselves financially with their business, create a blog or consistent online presence, and finally turn the work they’re already doing into a digital product, package, or offering for dream customers. This branding ecourse comes with 7 learning modules in a 300+ page digital download, a workbook with 20+ branding exercises and scripts, a quarterly masterclass, and an exclusive Facebook group so you can connect with us and other students.



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