How I Take an Extended Holiday Trip Every Year Without Ruining My Career

This woman has her travels and career all figured out.

I love the holidays. Decorating a Christmas tree and entertaining at home have topped my list of December highlights since childhood. However, since my life took a new direction a few years ago, every December, I find myself packing a suitcase and heading to the airport rather than unpacking decorations and planning holiday party menus.

Over the past five years, I’ve spent the holidays in fabulous places like St. Kitts, Mexico and Australia. This year, it’s back to Australia for six weeks.

Read More: How to Save Big on Last-Minute Holiday Season Traveling

A little in the way of my background. I’m single and I have friends scattered around the globe. I’m an author and writer, plus a frequent public speaker. My writing commitments can be done from anywhere in the world, so long as there is reliable internet service. I’m tremendously fortunate that speaking commitments have taken me to diverse locations such as Dublin, Aruba, Paris, London and Beirut, both expanding my network of friends and making valuable deposits in my airline rewards account.

After rushing around furiously in the year my book initially came out, I now intentionally take time when I travel, adding a day here and a day there to experience the particular city or location. Perhaps it sounds obvious, but it’s not exactly easy or that simple when you’re an A-type personality and an entrepreneur. If I’m not working, I’m not making money. And, while extending my work travel by a few days has improved the quality of my life, discovering I could afford to take a big escape every year took my lifestyle to a new level of satisfaction.

So, how did I discover that I could escape for an extended winter break? And what are the lessons for those of you who have professions other than writer and speaker?

Analyze Your Work Schedule

I’ve discovered that the period following Thanksgiving and extending through mid-January is not prime time for organizations needing speakers for off-sites, conferences or events. If all I’m going to do during this time is sit around and anxiously wait for the phone to ring, booking my next gig, I can take that anxiety to the beach.

My suggestion for you is to observe the work cycles or natural rhythm of client needs in your industry. What holidays do your customers observe? What time of year are prime for closing deals? When I was still working as an attorney, Thanksgiving was my favorite holiday because my clients used to disappear for most of the week and I could pretty much guarantee that my travel plans wouldn’t be derailed.

More on Travel: 10 High-Paying Jobs That Let You See the World

Be Flexible

If you can swing it, ditch the notion of having to be somewhere on a set date. I’ve taken flights the evening of December 31, and once sucked it up and paid the hefty change fees to avoid flying back to New York City in a blizzard. When booking travel this year, I played around with different departure and return dates until I found reasonable fares (or times I could use airline points) during peak holiday travel season.

Learn: How Long-Term Travel Saved Me More Money Than Staying Home

Communicate Regularly

Being away from home or the office for extended periods only becomes a client problem if you’re unresponsive. I’ve already let my publisher and speakers bureau, as well as key clients, know the dates I’m going to be away. They know how to reach me, my availability due to time zones, etc. I actively use Gmail’s “vacation responder” feature to set expectations, as well as directing those emailing requests to other sources for answers or information. Establishing the times of day that I’m going to work also means I can truly enjoy the time I’m not working.

Adjust Your Work Routine

The first part of my career required me to carry a briefcase and go to an office. The tools of my trade involved the law library and paper — lots of paper. These days, laptop or mobile phone in hand, I can work from anywhere. I’ve had to adjust what I think I need to do my job effectively. My early career self could not have imagined submitting a piece of written work, written in haste while waiting at the Victoria International Airport for a delayed flight to board. But I can check that off the list.

I also pay careful attention to what time of day is my most productive and for how long. My earlier work ethic (when something needs to get done, get it done) does come in handy. Modifying my work mindset has been the biggest adjustment for me — that is, overcoming the need to be at my “desk” for 18 hours a day in order to feel productive.

Know What Is Important

The real key to my ability to take such long, amazing vacations is having meaningful relationships. I realized moving to New York City over 20 years ago that my closest friends and most important relationships would not necessarily be in the same city as me. I make it a priority to stay connected (social media and technology do make this heck of a lot easier than 20 years ago) and, fortunately for me, those friends who want to spend time with me happen to live in some truly fabulous places.

Click through to read more about the challenges of traveling the world for a living.

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