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5 Tips for Freelance Travelers: How to balance life on the road

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After tying up some paperwork to officially bring a client project to a close, I walked the client’s hallways to say good bye to the friends and colleagues I had made over the previous five months:  “Rich, it was an absolute pleasure working with you.  Do make sure you keep in touch.  So, what’s next for you now”?  To which I almost always reply:  “That’s a good question.  I have no idea, but I’ll be sure to let you know when I land.”  After a few hearty hand-shakes and a couple of heart-felt good-byes, I turned in my security clearance and exited the building.  Before entering the taxi standing by to whisk me away, I closed my eyes and took a brief moment to contemplate the experience.  Shortly thereafter, I opened my eyes, let out a deep sigh and thought to myself:

“It’s time to move on to the next challenge.”  “Where to sir?” replied the patient taxi driver.  “Airport, please.  I’m eager to get home”.

To some, the idea of not knowing what’s “next” is an absolutely horrifying prospect.  In all honestly, I don’t blame them.  Not knowing whom you’ll be working with, where, for how long and in some cases what you’ll actually be doing can be extremely unsettling.  I freely admit (as my wife can attest), I’m not very pleasant to be around while I’m in between projects.  Two parts excitement and one part anxiety have a tendency to keep me on my toes during that transition period.

Image by geralt on Pixabay
Image by geralt on Pixabay

Change is Inevitable

“Change” is really ingrained in the fiber of everything freelancers do. One day you’re working for one client, and the next day you could be working for another.  Sometimes, the logistics work out in your favor, and the client could be located in your backyard (or a remote gig).  Not literally, of course, but you get my point:  The harsh reality is that you can’t control where the demand comes from, even though I wish I had magical powers to do so.  This means (drum roll please…), it’s time to make your reservations, pack your bags and get ready to travel.

Enter the Road Warrior:

To be clear, this post will not offer up tips and tricks for professional travelers, though I’m keeping that in mind for a future post.  This piece is all about establishing some semblance of balance between work and life while living on the road.  I emphasize “living” to establish a very simple, and yet sadly often overlooked, point:



There are some pretty obvious perks when traveling for work:  Airline miles, hotel points, expense accounts, etc.  All good and fine.  But how many times have you heard the following cliché from a seasoned road warrior?  “It’s really not all that glamorous and can get old very quickly.”  Well, quite frankly, I believe this to be an incredibly accurate statement.


Personally, I’ve grown accustomed to the routine over the years, but I would be lying if I told you I don’t have days when I just dread hitting the road again.  Not because it’s “work” per se, but because it means I won’t be able to see my wife, son or even sleep for some period of time.  Even worse were my early years of work travel when I was frequently struck by a profound sense of loneliness.  I kept falling into the trap of filling my time by sitting in my dark hotel room and working late into the night until I fell asleep, only to restart the vicious cycle the very next day.  Not exactly glory days.

I’ll spare you the suspense and openly confess that I still experience some version of the emotions I described above.   The major difference today versus my earlier years is that they only flair up on very rare occasions.  How is that possible, you ask?  Well, I’ve picked up some “best practices” (consulting speak 101) over the years that have worked pretty well for me.  I felt I owed it to the community of road warriors out there to share my thoughts in the hopes that they might improve even one individual’s life on the road.

Image by Myriams-Fotos on Pixabay
Image by Myriams-Fotos on Pixabay

5 Tips to Keep You Sane:

1.  Fine Tuning Travel Logistics:

Establishing your weekly flight (or however you get to the client site) routine is extremely important.  Of course, it may very well be dictated by the client’s expectations in terms of how often you should be located physically on site.  If you’re working a long-term travel assignment, attempt to see if you can work remotely as often as you can.  That extra time at home can really do wonders for one’s morale, especially on a long-term project.

Playing the Numbers

It’s also important to do some homework to really understand all of your travel options.  Just because a 6:30 pm flight home on a Thursday night appears on the surface to be the best option, that particular flight might have a history of poor on-time performance, and a better bet might be the next flight at 7:00 pm.  Carriers like US Airways openly publish flight histories where you can get an instant snapshot (percentage breakdowns) of on-time, late and cancelled performance.   Five minutes worth of research can help improve your chances of minimizing rage-inducing flight delays.

The same logic applies to train rides or long drives.  If hard data is not readily available, spend some time googling “best time to leave from A to B” to give you a sense of ideal departure times.  I used to drive from my home in CT to a client site in Washington DC for a while, and it wasn’t always pretty.  I very quickly learned that if I left even an hour later then my planned departure time, it could make the difference between a 5 hour and a very painful 7+ hour ride home.

Be Vigilant

The important thing to take away here is to be vigilant with fine tuning your transportation routine in order to, hopefully, minimize travel frustrations.  The ideal travel schedule is one that becomes a non-event or mundane over time.  Of course, that won’t always happen.  Only last week I was stuck on the highway for an additional 40 minutes because of an overturned tractor trailer as I made my way to the airport to catch a 6 am flight.  I eventually made it there only to see my plane pull away from my gate at 5:55 am.  This came on the heels of a valiant wind-sprint across the entire terminal.  Yes, it was every bit as dramatic as that sounds.

At the end of the day, play the statistics to improve your timing odds and accept the fact that you’ll eventually be on the losing side of those numbers.  That reality doesn’t mean you should stop trying.  Remember, you’re living on the road.  Find your happy place and fine-tune wherever you can.


There are instances where freelancers might not really have a choice in terms of where they stay while working on the road.  The client, with good reason, may have preferred hotel or corporate housing options to control costs.  In that case, be sure to explore each option until you find the best one for you.  I tend to stick with the Marriott brand (if available), as they have a great points program and have wonderful coverage all over the world.  Hotels really do make an extra effort to help out travelers with status, so pay attention to those points.  Free upgrades are a wonderful thing.

Negotiate Intelligently

In other cases, the onus will be on the freelancer to adhere to the expense policy set forth in the contract signed to work there.  You’ll have a lot more options in that scenario.  I’m personally big on convenience, so I always aim to find a hotel within a 10 minute cab ride.  Do your research and don’t be afraid to negotiate with the hotels.  You won’t have much leverage if you’re solo, but if you’re with an extended team, that can change the equation entirely.  I’ve seen many instances where nightly rates at high-end hotels were reduced to extraordinarily low levels in order to secure reservations for an entire team.  Everybody wins if you play your cards right.

Where you’re staying can have a direct impact on your mood, so take the selection process seriously.  In my view, you really can’t LIVE if you’re uncomfortable with your living situation, so do whatever you can to improve your arrangements.   My selection criteria (provided price is accounted for) for finding the right hotel goes something like this:


Being relatively close to the client site is important, but equally important is taking advantage of where I am, especially if I’ve never been there before.  I like to be within walking distance of decent places to eat and interesting things to see, or be close to convenient public transportation.


I’m not terribly picky as long as my bed and pillows are to my liking and things feel well maintained and clean.  But, I know some road warriors can be extremely picky if anything feels remotely “off.”  I once saw a colleague of mine check into her hotel only to check out the next morning and go through the hassle of finding another hotel for the very next night.  Bottom line, she didn’t feel comfortable and knew she wouldn’t have a good night’s sleep if she stayed in that environment.


I’ll touch on this a bit later, but a hotel without a nice gym will instantly get nixed from my short list.  Less important to me but also noteworthy are things like a nice lounge where I can gather with fellow travelers.

Image by PhotoMIX-Company on Pixabay
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2.  Stay Connected

Now that your weekly travel logistics are sorted out, it’s important to remain connected with family and friends back home.  There are many obvious reasons to do this, but one that is not so obvious is the perception of your travel to others.  To some, a job on the road just doesn’t compute, so assumptions can be formed rather quickly.

For example, I was working in Detroit for a couple months, and I noticed I was losing touch with a close friend of mine.  I wasn’t getting invited to the normal weekend events I was typically invited to and began to wonder why.  When I confronted him to see what was up, he just assumed I wasn’t around and didn’t connect the dots that I actually came home every weekend.  So he didn’t want to make me feel bad by inviting me to weekend events he thought I couldn’t attend.  Honest mistake, right?

Over Communicate 

Of course, you want to inform friends and family of your travel schedule. That goes without saying. But even more important, they should be educated in order to understand that your life doesn’t stop just because you’re on a travel gig.  I’ve found that to be a difficult concept to convey to some, but over-communicating usually helps with folks who fall into that bucket.  Social media can be a tremendous tool to keep a large number of folks abreast of what’s going on with your travels.  Once a general understanding with your circle has been established, make the time to stay in touch.  Texting, like it is for most people, is my go to move.

In all honesty, the most difficult part of staying connected is actually REMEMBERING to stay connected.  Keeping up with your immediate family is easy enough, but don’t forget about everyone else!  Freelance life moves pretty fast; the last thing you want is to distance yourself unnecessarily from friends and family because you’re traveling a lot.

Image by NeuPaddy on Pixabay
Image by NeuPaddy on Pixabay

3. Embrace Fitness & Watch What You Eat:

Eating out can be great, especially if you’re a foodie.  I can’t say I fall into that camp, but I enjoy a good meal just as much as the next guy; however, I must tell you that it’s a slippery slope when eating on the road.  You see, the freelancer is usually not personally picking up the tab for the meal, since that generally gets expensed back to the client.  So there might be a subconscious feeling to make the most of the situation, especially for individuals new to the routine.  Early in my career, that was the exact logic as I gorged myself on elaborate pasta or steak dishes every night.  My own vanity and expanding waistline caused me to put the kibosh on that trend rather quickly.

Don’t get me wrong: There’s nothing wrong with having a nice meal.  But watch what you eat!  Poor eating habits on the road (or even at home, for that matter) extrapolated over a long period of time can do some serious damage to your health.  I personally try to limit my unhealthy gastronomical consumption to a couple of days per week, once during the work week and another saved for the weekend.  Now, I’m not insanely committed to that routine, but I usually cover my bases by keeping physically fit.

Fitness is King

I touched on this briefly when I mentioned earlier that I won’t stay at a hotel that doesn’t have a nice gym.  Why?  Well, keeping active is incredibly important to me for multiple reasons:  First, if I’m not working out regularly, I’ll frequently experience a decline in energy throughout the course of the day.  When I do, it has the completely opposite effect, and I tend to be more productive as a direct result of feeling more alert and focused.  Secondly, quite frankly, I just enjoy working out.  It’s a great stress reliever and a great way to keep you healthy.

I’m a strong proponent of eating right and working out as a joint strategy to better living on the road; but if working out is something you absolutely despise and avoid, then it’s especially important that you eat right.  On the flip side, working out does not give you a free pass to eat whatever you want, not unless you’re training for a triathlon or some sort of extreme endurance event, in which case have at it.  Find the right ratio of eating right to working out for you.  For me, the most sustainable approach is striking a balance between eating right and staying in shape.  What’s that, you say?  You don’t have time?  Nonsense!  Make the time; otherwise, there’s a good chance you won’t be able to live on the road for very long time, anyway.

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4. Socialize

Whether it’s taking the client out for drinks, having dinner with fellow ream members or meeting up with old friends, don’t forget to socialize.  Of course, as a freelancer, getting to know the client is part of your job, but there’s nothing preventing you from actually becoming friends, either.  Not to get overly philosophical here, but work will come and go, but relationships can last forever.  Open yourself up to making new friends and experiencing new things.  It will make for a much more enjoyable experience, and – guess what? – it will probably make you feel happier in the process.  Studies have shown that there is a direct correlation between happiness and socializing with groups of people.

Become a Social Butterfly

I know:  It’s much easier to socialize when you’re on a travel gig with a group of colleagues instead of being solo.  But socializing doesn’t have to start and end with your team or client.  If you turn up your social butterfly juice and engage people, you can make friends very easily on the road.  How?  Well, there are many people out there just like you, living their lives while working on the road.  I once struck up a conversation with a fellow work traveler on an international flight, just before taking off.  Five hours later of non-stop chatter, we were like best friends.

Over the years, I’ve made friends while working out, talking to the concierge, hanging out at the hotel bar, attending local special interest groups or events, etc.  The key is being open to your environment and just going with the flow.

Image by rawpixel on Pixabay
Image by rawpixel on Pixabay

5. Fill Your Calendar

OK, so you’re staying connected with friends and family, working out regularly, eating right and getting your social on.  What’s next?  FILL THE REST OF YOUR CALENDAR.  That’s right.  Have something lined up for every day of the week you’ll be away from home.

Whether that means having an evening to yourself to relax in the tub or pursue that professional certification you’ve been putting off, add it to your itinerary for the week.  When you mentally earmark daily activities, it helps keep your mind focused on things you want or need to do.  That helps keep your mind from wandering to thoughts of loneliness or frustration as a result of being away from home.

Make the most of it

I know some colleagues who actually get more done while working on the road than when they’re at home.  Why?  Well, sometimes life on the road offers fewer distractions than when you’re actually at home.  I have a colleague who has a wife, four kids and a couple of dogs.  He lovingly describes the home-front as organized chaos, but he readily admits that when he’s traveling he tries to make the most of it.

I’ve seen some pretty creative ways to fill up that calendar, such as exploring the sites, taking lessons to learn a foreign language, charity work, joining special interest groups, working on a new side hustle, etc.  The list is really only limited by your own imagination.  Is there anything else you can add to your weekly routine?  Give it a think and see what you come up with.

These steps have served me well over the years, but I’m always open to new ideas.  I’m quite certain my road-weary brethren out there will keep me honest, but if you have any additional steps or perspective that might improve my ramblings, please do let me know.

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