10 Tips for a Successful Working Vacation

We did things a bit differently this year, summer vacation-wise and consequently work-wise.

Most years we head out to the West Coast, exploring one of California's many vacation-worthy destinations before ultimately landing in Orange County for a few days with my extended family who live in Southern California.

This year, we skipped the touristy part, kept the family time and added a twist. It would be a working vacation experience, with recreation and family time reserved for evenings and weekends. And rather than stay a few days, we’d do three weeks at the same location. (The “real” vacation involving hiking and wildlife would happen the following month with Dad.)

Our “work” varied.

A 2-week ballet intensive was my 12-year-old's working vacation.

A 2-week ballet intensive was my 12-year-old's working vacation.

My 12-year-old dance enthusiast opted for a ballet intensive program at the newly opened ABT school at theSegerstrom Center, 20 minutes from our Costa Mesa base.

My 16-year-old happily signed on for a couple weeks of hands-on learning construction with his uncle, thecontractor.

My contractor brother agreed to take my 16-year-old under his wing for a couple of weeks of on-the-job learning construction.

My contractor brother agreed to take my 16-year-old under his wing for a couple of weeks of on-the-job learning construction.

I would work remotely primarily when the kids were out, supplementing with evenings or early mornings as needed, not unlike my normal routine. My husband, literally the last man standing after multiple rounds of layoffs at his firm, stayed home to manage his newly expanded responsibilities and workload.

Shortly after arrival, a discussion on remote working while on vacation emerged on my Facebook group of fellow free-lancers. Turns out that even though we all work untethered for the most part (we are primarily writers, the original digital nomad), many of us struggle with the same issues when it comes to balancing work and play on holiday.

In the course of exchanging war stories, a collection of advice emerged that was so salient, novel and/or impressive; I had to share it here.

1.   Establish boundaries, expectations and a plan for what you want to accomplish and when, if at all, you plan to work. For many people, working on holiday defeats the purpose of vacation, which is to rest and recharge. But as boundaries blur between work and home, and technology bridges communication across time zones, it is a viable option if you so choose.

Define boundaries. “You do have to set some parameters so that you get a break,” advised Kit Brown-Hoekstra, award-winning writer and consultant and principal at Comgenesis

Set expectations. “It's totally doable, according to veteran freelance writer Ed Gandia who is also our awesome coach. “It mainly depends what your expectations are. For instance, if I'm going to the beach for a week, I want to be able to relax. I'd rather not add work to the mix. Same thing if I were going to Italy for 2 weeks. I would want to completely unplug from work.

Make a plan. Successful free-lancers go into a working vacation with a defined routine and schedule for work and play, personal and family time.

“If I go into a trip with the expectation that this is a working vacation, I'm okay working, say, 2-3 hours first thing in the morning and then having the rest of the day off,” advises Gandia. “Or, say I were traveling to Italy for the summer and renting a place there, then yes, I'd have to do some work. But here again, I'd have to draw some boundaries and have a concrete plan.

“I've written from coffee shops, hotels, airports,” writes Michigan-based writer Jeanne Noorman, “but, like Ed, I like to unplug when on vacation. I find the best way to do this is to plan ahead; know what projects need to be done and plan where and when you will do them. I generally plan to only accomplish 25%-ish of what I would get done at home.” she explains.

“It's never been easier to work remotely,” Ed adds. “The real issue is setting the right expectation (and having the right plan) from the start. That way I can be fully present during leisure time and during work time.” That is the key!

2. Manage expectations of your travel companions. Turns out it’s just as critical to outline schedules, plans, boundaries and expectations with your travel companions as it is to yourself.

Carefully planned work schedules leave time for family gatherings like s'mores around the firepit.

Carefully planned work schedules leave time for family gatherings like s'mores around the firepit.

“One thing I've learned: It's important for me to be clear with my spouse about my planned work hours,” explainsPortland-based energy writer Michael Tevlin.  “I've gotten to the point now where I define my trips to account for writing. There are trips where I say that the venue has changed, but the work hasn't, and I work full-time from 8-5. There are trips where I dedicate the mornings to work and the afternoons to fun. And there are trips that are 100 percent vacation.

“You can make traveling and writing work. It takes cooperation from your spouse and self-discipline to pull it off,” he adds.

Or housemates. I know when I’m in Martha’s Vineyard with my girlfriends, there’s usually a good amount of down time. On the rare instances when I have to take care of work-related issues, I find out when those windows are and work within them. Since several of us are in the same industry, I’ve even done some ad hoc research during beach or shopping time.

And if my friend JoMarie had continued to ignore the messages that kept coming in while she was in the Vineyard this winter, she would have missed a completely unsolicited dream job offer. She accepted, by the way.

3. Take advantage of being away from the day-to-day. Working during vacation does not have to mean sitting in front of your laptop for hours at a time. A break from the daily routine and surroundings brings opportunities for personal, professional and business development that can pay big dividends.

I found strong WiFi, power and few distractions in one of my remote work environments.

I found strong WiFi, power and few distractions in one of my remote work environments.

Fewer distractions lead to greater focus and productivity.One of the biggest challenges is focusing on your work while on vacation, Steve Roller of CopywriterCafe.com told Ed Gandia in a podcast. "You want to spend all your time exploring. But in a way, it’s easier because you don’t have the distractions of home so you’re more productive.”

Wonder why so many corporations run off-site meetings? That’s right. Fewer distractions. More inspiration. Makes it easier to focus on those “not urgent, but important” issues like long-term strategy and planning.

“I really like to camp where there is no Internet and use that time for planning, outlining, and writing from the heart” writes Jeanne Noorman.

There’s a reason why ideas tend to come in your head once you’re unplugged, and taking a shower, a run or even a drive.The oversimplified explanation is that when the left side of the brain (center of cognitive activity) is relaxed, the right side of the brain (source of creativity) can be activated.

"When you step away is when you come up with ideas,” said Leigh Stringer, workplace specialist at EYP Architecture & Engineering in Washington, DC. and author of the book, The Healthy Workplace: How to Improve the Well-Being of Your Employees--and Boost Your Company's Bottom Line.

High levels of dopamine in the brain – triggered by things like exercising and showering that make us feel good and relaxed – can also help the flow of good ideas.

“'Total focus' is the opposite of the state your brain needs to create,” Stringer continued. “The more things we can do physically and operationally to encourage that movement and relaxation, the more innovative we’ll be,” she added.

Perfect. Which is why I felt my time bodysurfing and playing tennis was well-spent. Which brings me to another point.

New opportunities arise to make new connections (okay. You can call it networking. But then it really sounds like work.) People tend to be more relaxed and open to meeting new people when on vacation. We also have more time to participate in sports and recreational activities. (I’ve lost count of the personal and professional connections I’ve made through tennis at home and on vacation.)

Sometimes meetings during vacation bring unexpected outcomes. I always try to meet up with a few old friends when I visit somewhere. Though I often set out to reconnect on a personal level, more often than not, some business-related opportunity emerges.

Even if the connection is remote – say via a mutual friend – I have found people willing to meet with me when I tell them I will be coming in from out of town, which is exactly what happened on this trip.

4. If you need high speed WiFi, ensure it’s available. I have found that resorts and hotels have varying definitions of high speed Internet. Even though we paid for WiFi access at a family resort in Vermont, it was not fast enough for me to send an image-filled PowerPoint presentation. I suppose if it was truly urgent, I could have found a coffee shop or other source with enough capacity and speed to handle my document. But we mutually decided it could wait a few days until I got home. Perhaps it was the destination’s subtle way of telling guests to leave the work at home!

Free WiFi can be found in some nontraditional places, according to my writer friends. “Not only have I worked from the house,” wrote Steve Maurer, an industrial and b2b writer who serves an international client roster from his home base in Arkansas, "but also from McDonald's, the local library, just about every restaurant/diner/coffee house in town that has WiFi. Did you know that even Walmart and home improvement stores like Lowe's have WiFi? No restaurant or cafe' inside? No problem. I've sat in my car in the parking lot and checked email!" 

Resourcefulness is a virtue, particularly for the free-lancer.

Turn your phone into a WiFi hotspotBoth Steve Maurer and my friend and neighbor Adam, who travels frequently in his work as a lighting designer, utilize this option when corded or WiFi access is not availableAdam found the added monthly expense well worthwhile, but it seems to be free in many cases now. Thanks to its partnership with other providers, Time Warner, offers cable subscribers access to more than 500,000 hotspots. (I wonder how many fewer cappuccinos I would have consumed at Le Pain Quotidien had I set up a hotspot in the dead zone-lobby of a certain ballet school.)

5. Establish email check-in standards. Since I am rarely completely “off the grid” I tend not to use the vacation reply setting in email. But if you are, you owe it to your clients to set expectations for your accessibility and when and how you can be reached. Ideally in advance.

Communication is key. “Sometimes I’ve let clients know I would have limited access to email,” offers New Jersey-based creative business and marketing copywriter Mary Ellen Landolfi, who schedules just three email checks a day: very early in the morning, mid-afternoon and once in the evening.

Some offer fewer. “I let clients know if I will be traveling and only check email once a day, usually early morning,” reported Jeanne Noorman.

I was extremely grateful for my vendor’s advance notice when I found myself trying to schedule delivery of a large appliance around both of our travel schedules. Fortunately my sales rep had very clearly noted his vacation dates on his email several weeks in advance. It simplified our planning immensely.

6.  The library is your friend. Coffee shops are not for everyone. And despite what Yelp says, that local java joint may have closed up three months before you arrived in town. So assuming you are not on a cruise ship or at a far-flung resort, you may need to seek out some workspace alternatives in the local community you’re visiting.

Michael Tevlin, a veteran of house swaps across the country, has found local libraries to be a quiet work environment in his travels. “I have gotten to know the libraries in Santa Cruz, San Luis Obispo, Seattle, San Diego, Aspen, and South Lake Tahoe well over the past several years," he shared.

With high speed Internet, large desktop monitors and business databases, not to mention highly educated reference experts, libraries of today are a far cry from the book stacks of past. More often called Information Commons; they support the research-based work many of us do on a regular basis.

Before I found my co-working space, a couple branches of the Brooklyn Public Library were my go-to spaces for research and writing. I still visit them frequently for classes in Adobe Creative Suite, social media marketing or research tips.

And did I mention it was free?

7.  Have laptop (or desktop!). Will travel.  Just like the frequent traveler who keeps a packed bag of toiletries and travel necessities on hand for quick exits, free-lancers who work on the road know what they need to maintain seamless workflow wherever their travels take them.

“I travel all the time and work from wherever I am,” said Kit Brown-Hoekstra, who blogs at PangaeaPapers.com. “I do prefer my home office setup when I have something that requires a lot of back and forth because I have dual monitors, but it doesn't really slow me down to work while traveling. I have a travel backpack set up with everything I typically need: power cables, stapler, pens, notebook, etc. and take with me whatever is specific the current project.”

Since I walk to my co-working space on a daily basis, I use a roller bag to tote my computer and supplies. When it comes time to travel, I swap out unneeded project files for clothing and carry it on board.

Go big (and don’t go home). Michael Tevlin brings the comforts of his Oregon home with him on extended visits to see his grandchildren. “I love my giant iMac so much that I recently brought it with me on a two-week trip to California. I decided I'd work during the day and socialize at night. But I wanted to re-create my home setup as much as possible. So I boxed up the iMac and headed south. Not exactly a portable, but I loved it.”

8.  Keep the drama to yourself.  I have been on both sides of the remote worker situation and I can assure you: the most important thing is to deliver the WHAT, not explain the WHY or WHY NOT. Deadlines and contracts are there for a reason.

“The deliverables are due as promised, no matter where you are,” emphasized former college instructor Pamela Hilliard Owens,founder, Writing It Right For You

Which is why I have had client calls while in the emergency room with a sick child, signed off on graphics while at Field Day and put my kids in front of one too many Dora the Explorer episodes. The client doesn’t care if there’s a snow day or flight delay. They just want the project done.

Of course, occasional medical and family emergencies arise that require coming clean, at least to some extent. Hopefully the client will be as understanding as Mary’s, a free-lancer who travels throughout Montana writing about local food. “I have never missed a deadline except when I twisted my ankle falling down the stairs in the London Underground -- and the editor happily gave me an extension. (I didn't tell her where I hurt my ankle; I didn't want to make her jealous.).”

9.  Use technology to your financial advantage. Online banking has lifted one of the last hurdles for digital nomads, particularly those who travel for long periods of time: electronic billing and payment.

While I have had clients who ONLY pay via bank transfer, my colleagues' experience is otherwise. However, once payment is arranged, absorbing a small fee from PayPal or credit card carrier is often considered a worthwhile expense that is offset by getting paid earlier and not having to wait for funds to clear.

10.  Make the most of your time on planes, trains and automobiles.  Sure, this is not always the most comfortable way to work as I discovered on my recent transcontinental flight. I normally use plane time to catch up on business and personal reading, but in this case, I had to do some writing. I was doing well enough until my neighbor decided to recline. Ouch. I managed for several hours until my battery ran out. Only on my return flight did I discover that American Airlines now provides power under the seat cushion. Unfortunately, I learned this when it was announced that said power source was NOT working properly on our particular flight.

Planes and trains can also be ideal times to catch up on work that requires long uninterrupted concentration time, as is the preference of my former boss and current client David. We would time the project due dates to sync with his travel schedule so he would have a sizable chunk of quiet, distraction-free travel time to review drafts. He even managed to get changes to me mid-flight on one particularly time-intensive project and has called in other updates from a cab.

But I have to give a shout out to a couple of colleagues for truly maximizing their car travel time in impressive fashion.

At least two of my colleagues admitted to writing in the passenger seat while traveling at 70+ MPH.

At least two of my colleagues admitted to writing in the passenger seat while traveling at 70+ MPH.

Oregon writer Michael Tevlin recalls “in addition to writing in libraries, I have written in the passenger seat of our car doing 80 down the 101.”

Steve Maurer shares a similar memory. “I even wrote an article in the car while my wife was driving us back home ... at 70 miles an hour.”

Maurer continues. “I finished, we stopped for gas and food at a diner/gas station, and I emailed off my work, along with the invoice. When we got home a few hours later, I got a thank you email from the client ... and got paid via PayPal.”


Now that’s a road warrior, who aptly summed up the remote working challenge and opportunity quite eloquently:

“So yes, it's not just possible to work ‘on the road.’ It's feasible and not too hard to do. All it takes is a little planning and making sure you have the right tools and software to do it. Freelancers are the mobile business nomads of the world. And THAT rocks!”

To learn more about the remote working lifestyle, tune into Ed Gandia’s podcast with Steve Roller of copywritercafe.com.

Would love to hear what challenges you faced when working on vacation and how you handled them.

Our working vacation was planned around a 2-week ballet intensive at the ABT Gillespie School at the Segerstrom Center in Costa Mesa.  Photo: Segerstrom Center

Our working vacation was planned around a 2-week ballet intensive at the ABT Gillespie School at the Segerstrom Center in Costa Mesa.

Photo: Segerstrom Center