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How To Travel (A Lot) When You Work Full-Time

how to travel with a job

By Michele Herrmann, Jessie on a Journey Contributor

This post is part of Jessie on a Journey’s Inspiring Travelers series

Don’t believe the notion that working 9-to-5 will put your travel dreams on hold! With the right planning and balance, figuring out how to travel with a job is completely possible.

In fact, traveler and blogger Kathy Kass is living proof. A New York State attorney, Kass often goes halfway around the world to visit someplace new for a weekend – even if she has to fly home on a red-eye to be at work on Monday morning.

Hey, her blog isn’t called Will Run For Miles — which combines her passions of points hacking and fitness — for nothin’!

As a runner, Kass has participated in over 100 marathons spanning 50 states, six countries and three continents.

Below, Kass shares how to travel with a job in a way that lets you excel in your career while also pursuing your travel dreams.

It's possible to #travel with a full-time job! Here's how! Click To Tweet

Kathy Kass takes in the beauty of Brazil’s Iguazu Falls.

1) As a full-time employee, how do you successfully make time to travel, in terms of your employer’s time-off policies?

I am lucky that I get five weeks per year annual leave, but that time can go fast. While I do take two or three weeklong trips per year, sometimes it’s hard to get away for too many days at a time. The solution — or the curse, depending on how you look at it — is to take many crazy short trips.

In between my longer trips, I go on short weekend warrior trips, often taking advantage of work holidays. I’ve gone to Amsterdam over Memorial Day Weekend (for my University of Amsterdam class reunion); Hong Kong over Labor Day Weekend; Ho Chi Minh City over Thanksgiving; and Lisbon over Martin Luther King Weekend.

Additionally, I’ve gone to Dubai for a weekend, India for five days and South Africa for five days. I even did an around the world trip in eight days. I don’t think any of those flights were over $500. Each of these destinations — except the Amsterdam reunion trip — was chosen because a good flight deal came along. In other words, the deal chose me! Those trips look lavish, but they were not expensive at all!

2) Is it difficult to juggle travel and working full-time?

Sometimes the juggling isn’t necessarily between travel and work, but between the issues that life throws in the way. For example, both my boyfriend and I have elderly parents, and, in the past year, have had to cancel or postpone travel and instead devote our “vacation” time to helping family members.

3) With all of the travel bloggers out there promoting the “quit your job and travel the world” lifestyle, what has made you hold on to the 9-to-5, along with the blog?

The simple answer is that I’ve been working in the New York State court system a long time and I am only years away from a full pension. The real answer is that my legal profession is part of me, and I enjoy my work.

Becoming a blogger was never a “how can I replace my job” goal, but more of a “how can I incorporate something I love enormously — travel — into my world even more” goal. That is the balance for the moment.

how to travel with a job

An avid runner, Kathy Kass’ blog, “Will Run for Miles,” focuses on travel and fitness.

4) With your legal career, do you face any limitations, in terms of how far you can go with traveling? How do you work past these obstacles?

It has been a while since I was able to spend extensive time exploring a country or region without the need to rush home. I miss that and I would like to do that again soon. At least for the moment, I fly on a lot of red-eye flights, travel off-season and am usually jet-lagged. It’s not for everyone, but I like it.

Check out how this #lawyer balances a full-time job and frequent #travel! Click To Tweet

5) Along with your salary, how do you fund your trips? What are your money-saving tips?

My motto is affordable luxury — getting the best travel deals for the least amount of money! To this end, I focus not only on travel, but also on both frequent flyer and hotel programs, and collecting points and miles via credit cards and other creative methods. Join frequent flyer programs, and use shopping portals (third-party websites, often used by major airlines, that offer miles, points or cash back incentives for making online shopping purchases from major retailers) to accrue extra miles or points.

I also follow a lot of travel deal websites — such as @TheFlightDeal — on Twitter. I even set up notifications for every time these sites post information on deals, and these types of Tweets show up in real-time on my iPhone and Apple Watch. It’s a little annoying; but deals go by so quickly. I don’t want to miss them.

how to travel with a job

While maintaining her job as a full-time lawyer, Kathy Kass still makes time to pursue her world travels.

6) What’s the craziest trip you’ve been able to book using miles/points? How did you accomplish this feat?

I don’t really consider my trips “crazy,” though I’m sure others do. Instead, what I tend to do is take advantage of sale airfare prices and/or hotel sales, using airfare miles or hotel points when I can. For example, about three years ago I went to Dubai for a long weekend. The airfare on United Airlines was only $300 round trip (a probable “mistake fare”), and I stayed in Dubai for two nights at a Radisson Blu using Club Carlson points.

For a trip to Cape Town, South Africa, I found a crazy airfare from New York City to Johannesburg that was under $500 on American Airlines and Etihad Airlines [partner airlines]. The flights were pretty convoluted, an overnight flight to Paris, and another overnight flight to Abu Dhabi, such that it took me three days to get to Cape Town. But it was worth it to me, as I treated each leg of the trip as part of the journey. I spent four nights in Capetown, split between two hotels, both booked on points.

7) Do you have a favorite miles/points program(s) that enable you to earn them quickly, even with a full-time job?

My go-to program is Hyatt. They treat their highest-level loyalty customers very well. I’m fortunate to currently have Globalist status (aka Diamond), which has many perks such as room upgrades, free breakfast, lounge access and late checkout. The requirements keep going up and up, and I’m not sure, as a non-business traveler, that I’ll be able to keep this status in years ahead.

The key: whenever possible try to concentrate on one brand (or one airline) because the extra points or miles can earn perks or even free flights or nights; however, when I go to a city, I enjoy mixing up my stays between upscale chain hotels and quaint, local hotels.

I did this in Buenos Aires with my friend, spending a few nights at a 5-star top hotel — where we had a suite and a butler — and a lovely boutique hotel in Palermo Soho. We liked the latter better!

As a full-time lawyer, Kathy Kass takes advantage of holiday weekends by going on quick trips.

8) What is your secret for a successful work/life balance incorporating travel?

I think that everyone needs to find ways to seek and follow passions. Since an early age, travel has always been one of my passions; however, I don’t want to quit my job in favor of traveling all the time, so I need to be sensitive and find balances between my travel and my employment. Sometimes this is easier said than done, but that’s my story, and I’m sticking to it.

9) What would you say to someone wanting to travel more who isn’t ready to quit their job?

I would ask them where they want to go, whether they want to travel alone and what their goals are. Ultimately, I would tell them that anything — even figuring out how to travel with a job — is possible. Don’t sit around and think too much; just go.

Do you have any advice to add on how to travel with a job? Share away in the comments below!

Further Exploration:

Why Telling People To Quit Their Jobs And Travel Is Bad Advice [Blog Inspiration]

Clever Travel Companion Pickpocket-Proof Garments [Travel Safety]

The Best Travel Writing: True Stories from Around the World [Great Reads]

Jessie Festa standing in front of grafitti wall

Hi, I’m Jessie on a journey!

I take you beyond the guidebook to inspire you to live your best life through travel. Come join me!

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2 Comments

  1. ES on August 14, 2017 at 1:06 pm

    Great interview! I will add that living in a hub city makes things easier – New Yorkers like Kathy have access to three international airports – but that doesn’t mean frequent quick trips are not within reach. In fact, I have a friend who travels much like Kathy does, and she does not live in a metropolitan area. Still, she makes it work too.

    I am lucky enough to be able to take longer trips, and that actually has a down side: I am reluctant to go someplace for “just” a few days, so often don’t go at all!

    So as we say where I live, “Just do it!”

  2. Tracy on August 15, 2017 at 5:30 pm

    Great piece for those who still work full time and travel. Thank you for sharing. Will look into some of these tips!

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