tips to balance travel & work

I was fresh out of college when I took my first business trip. It was a 2-day, 1-night trip to the beautiful city of Chicago in late April to visit a brand new client and new colleague.

I met my boss (at the time) at the airport and we boarded our plane to sit in our separate seats. It was a mid-afternoon flight to O’Hare, and I remember for the first time in my life I had an entire row of seats to myself. I plugged in my headphones and was ready to take a nap, watch movies, or read for the duration of my flight.

I remember looking up and down the aisles of the men in business suits typing away at laptops on the plane- my boss was one of them. I felt instant guilt for taking my “travel day” as day where I got paid to be on a plane and watch movies. Should I have been trying to get some work done? I was technically being paid to travel, did matter if I was in responding to emails or trying to get work done? After all, I had worked all morning up until I left for the airport.

In traditional jobs, a partial day off is a full-day off and business travel days are “business travel days”.  If you aren’t in the office – you were docked time off. If you were required to travel on behalf of work, you were compensated for travel whether you responded to emails or not. While I was a full-time employee taking “time off” meant I took time to unplug and not worry about deadlines. Paid time off was a luxury – I didn’t have to worry about missing out on part of my paycheck to take time off to travel. But paid time off was one of those luxuries that I left behind when I left to pursue my own business of part-time and freelanced based gigs.

While I may have left behind paid-time off, leaving allowed me to gain a new set of advantages.

I set my own schedule. I needed to make deadlines and promises. It didn’t matter when or how the work got done, as long as it did get done. And I could work early morning, late afternoon, on China’s time – it didn’t matter.

I could work from anywhere (with Wi-Fi). At my desk at home or half-way across the country. It didn’t matter where I worked anymore.

When I set off on my own, I wasn’t confident that I would sustain or grow as a freelancer and I didn’t look at it as a permanent situation. So in 2015 & 2016 I decided to use my position to do as much traveling as I could afford before I lost my ability to work & travel without having to use paid time off. Between 2015 & 2016 I went on a total of 9 trips, spending over a month on the West Coast in 2016. I wasn’t making nearly enough money to take time off for all of those trips – so I learned how to best work my schedule and plan my trips to balance work with travel in a way where that I minimized “true time off”.


  • I got as much done beforehand as possible to shorten the to-do list. Two to three weeks leading up to a trip were stressful. But it was well worth it. I always looked ahead to see what deadlines I had in the upcoming weeks and what I could get a head start on. I extended my 8 hour days to 10-12 hour days to get as much done before I left for a trip. I was then left with a shortened list, which I committed to.
  • Yes, Stephanie, you work on the plane. Especially on long flights. But only because having the discipline to work on the plane can save you time and money. Flights are cheaper mid-week and mid-day. So travel time and in-air time can be used as typical work time. At this point, you aren’t missing out on your trip yet. The plane is boring and you aren’t going anywhere. Check beforehand to see if there is WiFi on the plane. If there isn’t, be sure to cull through your to-do list, download things beforehand and see if there are things you can accomplish without an internet connection (I have plenty) and make sure to schedule those items into that timeslot.
  • Lengthen your trip a bit. It doesn’t necessarily ALWAYS have to cost more. I started using AirBnB to cut my costs of hotel rooms when I planned to stay in places for 1-2 weeks. Hotels and condos often have discounts for extended stays. The longer you have on your trip, the less you will feel that you are “missing out” on the place you traveled to. I also used condos because it saved money on meals. I could cook and prepare meals for myself to keep the costs low and keep me around while it allowed me to afford a lengthier trip.
  • Create a plan and itinerary. And make sure it includes work time. Plan in advance and let coworkers know when you will be in and out of the office.


  • Look for unexpected time you could be working – there is a lot of it. You can sneak these into places you don’t expect. When I was in LA a few years back there was a day I had dedicated strictly to museum touring and art galleries. But I still needed to each breakfast and lunch and dinner. I dedicated 30mins to an hour to eat, while also popping open my laptop to get some work done or answer emails. You can make a “day off” into a day in which you put 3 hours of work in and didn’t miss out on anything. Plus, if you are traveling alone like I was, sometimes the laptop gives you company.
  • Use jet lag to your advantage. The best way to combat East à West jet lag is force yourself to stay up later. In the first couple of days of a West Coast trip, I was up around 5-6am PST. So I maximized my first few days. I used the early wakeup to get work done in the early AM and packed my afternoon and evenings with things that would force me to stay awake. The first couple days were prime for me to get things done.
  • Wednesday – Wednesday trips were a godsend. A) They were cheaper. B) they worked well for a business schedule. Wednesday was a traveling day, and also with WiFi, a working day. If you could push through Thursday as a “chill” day, you could take off Friday and have Saturday and Sunday (3 full days) of vacation, relaxation and exploring if you played it right. Monday could be a work day where you dedicate some time to work in the AM, and play in the evening. Or a split day. And Tuesday you could have another full day off before leaving on Wednesday (another travel day and work opportunity). For a 7-day trip, you may miss out on only 2-3 days of work – a lot more manageable in terms of being out. When coupled with the long weeks before your trip, for me sometimes I missed out on only 8-10 hours of work overall. A miss I could afford to make.
  • Be disciplined. I think the hardest vacation I went on was this year’s family vacation. Though it was easy for me to travel and work when I was alone – traveling with family was 10x harder. I always felt like I was missing out on something. But the opportunity I was catering to was too important to miss.
  • Don’t take it for granted. There are not many people who have the opportunity to have the freedom to travel and work at the same time – use it as a catalyst to remain disciplined. You have to give to get – think of the time you MUST put in the work and the GIVING you have to do in order to have the kind of lifestyle you do.

Last, you are allowed to unplug! Everyone takes time off – even freelancers. Even when you love what you do. Gary Vee is one of the hardest working entrepreneurs and businessmen I follow – and even HE is refreshingly honest about taking time off to unplug and spend with family.  I’m a huge advocate that “unplugged time” can lead to increased productivity and a clear head. These tips were simply meant to help balance travel and work. Make sure to take proper time off a few times a year. If you work your butt off for your clients, GOOD clients will not be mad at a few re-arranged deadlines (as long as they are known up front).