Eight Travel Tips That I Wish I Would Have Known Before I Started Freelancing Out Of Town

Tia Lentini
10 min readMar 14, 2019

One of my favorite parts about being a freelancer is the fact that I get to travel. I remember when I first started out I really had no idea what I was doing. Other than family and friend vacations, school trips, and out of state church camps, I had never really been to a new city by myself before. With that being said, there are definitely some things I had to learn the hard way. So in this article, I attempt to steer you clear of having to encounter some of the hiccups I did while starting out on the road by giving you eight travel tips that I wish I would have known before I started freelancing out of town.

Make Sure Your Travel Costs Are Getting Footed By Your Company

Traveling out of town for work can be an awesome experience, however, it can slowly lose it’s glamour if you’re not educated on what you need to do before accepting any of these jobs. In my experience, traveling freelancers need to make sure that they are getting their travel costs covered (or at least the agreement signed) before they start traveling across the map for whatever company they’re working for at the time.

What this means, is that you make sure that you are negotiating travel fees into your monthly cost. In that, you need to make sure your:

  • Travel costs there and back are covered (such as gas, plane ticket, train ticket, camel ride, etc.)
  • Your transportation while there is covered (such as rental cars, Ubers, subway tickets, train rides, etc.)
  • Lodging costs(such as hotel, Airbnb, etc. )
  • I would highly that you have a food budget factored in as well with additional spending cash if applicable.

Depending on the company, you might have to go out for expensive meals for meetings, drinks, that sort of thing and that in itself can get very costly after awhile. So to avoid all this, you need to discuss budgets beforehand.

Make sure that you have a budget mapped out and approved by the company that’s hiring you to freelance. If you run your freelance by billing your clients after the services are delivered discuss the matter in negotiations and make sure that you keep a detailed account of each an individual cost that you were acquired in an itemized spreadsheet with pdf linked receipts for afterward.

See The Sights, Meet The Locals, And Build Your Personal Brand

You need to make sure that you’re making a point to see things when you’re on the road if time allows. If this means that you need to negotiate some off time during your day to go out I would definitely do that. I had a business trip to Miami once where I spent the entire weekend at the conference or in the hotel at the computer, but regretted not giving myself some available free time between sessions to go explore the city.

Not only does this help you unwind, but it’s also is a great way to boost your personal brand on social media as you were documenting your trip. IG posts with location tags accompanied with a $1.80 strategy with locals can definitely give your profile a boost in the algorithms. You can also network in different places and meet all kinds of people by just being in a coffee shop or on walking the boardwalk. This designated downtime can always be used to deepen the relationships you have with current team members or network friends you met at the tradeshow as well. So take advantage of it and don’t miss out on these once in a lifetime opportunities.

I have had some awesome experiences in different cities with people I just met. Especially the locals. From DC to Owensboro, they were able to show me some pretty awesome hole in the wall spots that I would have never known about unless I was with them. However, in my early days, I would have never even thought about going out to do anything. Nevertheless, as I went on about my career I saw the value in it and was able to negotiate it ahead of time without ever having to make the mistake I made in Miami years before.


OBVIOUSLY, you need to use caution when picking people to hang out with in random cities even if you do know them through a tradeshow or whatever, but trust your gut and go with it. New cities equal new connections which equal new opportunities for you and your brand if leveraged properly.

For Goodness Sakes! Take Out The 18 Pairs Of Shorts Already

During my first few adventures freelancing out of state, I seemed to overpack... I thought I would need tons and tons of clothes “just in case” but truth was, half the stuff I packed, I didn’t ever end up using at all. It took me a couple of times of having to lug all of that stuff through airports, Ubers, and everything else until I realized I might be overdoing it. So seriously, it seems simple but you really need to just pack what you must have to function and not go overboard because truth is, you will regret it later and so will your back. Think light and avoid that bulky stress.

BONUS TIP: Make sure that when you’re packing your clothes that you were putting your clothes in first and then all of your other items on top of them afterward. This suitcase setup allows you to get the essentials out without having to dig through all those clothes. This saves time and keeps your clothes nice and neat so that you are looking super fabulous for whatever event you’re going to, iron free.

The Extra Battery Pack And Shower Bag Is A Good Idea After All

Things can get super hectic when you’re working away from home, so you need to make sure that you have all your equipment and personal items organized and ready to go beforehand. I would recommend making sure that you have a bag for your toiletries that is stuffed in your suitcase, making it super easy to shower and get ready for the day without having to mess up your luggage. Depending on what you’re doing, you also want to make sure your technology is charged and organized so you don’t end up with batteries at a peak moment in your trip.

Mini-Tips From Experience:

  • If you’re a LIVE STREAMER try getting a phone case that has an extra battery supply built in.
  • If you’re a photographer bring as many memory cards as you can get your hands on.
  • If you’re a writer, try not to overload your suitcase with the books that you “think” you’re going to have time to read while out on the road.

In everything, organization is key so be sure that you’re paying attention to where you are putting things and the battery life of your gadgets.

Hey Chase Bank, Can You Unlock My Debit Card So I Can Get Home

A locked debit is something that you really do not want to deal with while on the road. With that being said, I would always advise calling your bank and letting them know that you will be going out of town prior to leaving your home. There’s nothing scarier than having a locked debit card out of state so make sure you take care of that beforehand.

I would also recommend making sure that there’s not gonna be any surprise withdrawals from your account while you’re on the road. You don’t want to get three states away and I have a random pre-authorize/you forgot about it withdrawal come out of your account leaving you with not only a negative balance and overdraft fees but no capital to get around eat or enjoy your trip with. So keep a record, and make sure you know what’s expected to come out and when so you don’t end up in a pickle out of town.

Don’t Waste Personal Brand Opportunities While Out On The Road

You need to make sure that you are documenting your entire experience on the road for your personal brand. This may not apply for some, but for most a personal brand is where it’s at. Gary V currently has 16+ people working on his personal brand alone so you have to know by now it’s kind of a big thing.

However, if you don’t have a “D-Rock” or a team of people following you around and taking videos of your every move and then putting it into an aesthetically pleasing display for your social media use, later on, do yourself a favor and start by posting pictures of your trip on Instagram.

For example, when you're in the airport take a photo of you getting ready to board the plane. Hashtag the city you’re leaving and the city you’re going along with some other relevant tags plus a creative caption for it.

You can LIVE Stream on FB or Youtube when you land about how your flight was while building anticipation for the job or event you’re going to then use photos from the entire trip and put them in a carousel method on Instagram afterward. If writing is more your thing, you can always write a blog post on LinkedIn or Facebook note documenting the highlights of your trip like what you learned, what restaurants you liked, and what aspects of the city surprised you. Whatever you do just do something don’t waste the experience as I did in the beginning.

The first couple trips out of town, I barely took any photos for my personal brand nor did I check in or anything with my new network friends. Eventually, I learned to do some significant branding while out in Denver or in DC which really increased my social media presence and following but I definitely missed out on utilizing trips before that to build followings on my social platforms. So learn from me, and have a plan to start out with and don’t waste time. This might be the only time you get to fly to this city for work so be sure to take advantage of it.

Get Enough Rest, Even When You’re In A City That Doesn’t Sleep

Sleep is very important. If you don’t get enough rest, you won’t be that shining superstar that everyone knows you are. However, when you’re on the road and everyone’s enjoying the nightlife and the excitement of a new city, it may be hard to go back to the hotel room and sleep while everyone else is enjoying those late night extracurricular activities. Nevertheless, you want to be on your game no matter what the job and even though it’s appealing to stay out all night with team members and networking friends, from personal experience I would not recommend it.

Each time I stayed up too late, I felt like my performance the next day was super poor when it came to the tradeshow or whatever I was doing. Eventually, I learned that just because I got invited to go out doesn’t mean that I need to go. I remember leaving a VIP after-party early while in Columbus once and walking back to my hotel almost regretting that I left but I knew I needed rest. The next day however when a lot of those attendees came to the conference super hungover and tired, I knew I had made the right choice. So, do what you want, but I would recommend keeping after hours to a minimum so you can put on your Lebron James game face on in the morning.

Please Make Sure You Have All Your Belongings Before Exiting This Work Experience

The last travel tip that I learned the hard way is to make sure that you have everything before exiting the lodging. When I was in Columbus for a conference I managed to leave my iPad at the Doubletree. Blessed, was I had a wonderful boss who picked it up for me and mailed it to me from Cincinnati. However, I did have to go without it for a significant amount of time which really stunk.

So with that being said, I would highly recommend making a checklist and checking it twice trying to find out if you forgot your iPad at a random hotel room.

Here’s the recap:

  1. Make Sure Your Travel Costs Are Getting Footed By Your Company
  2. See The Sights, Meet The Locals, And Build Your Personal Brand
  3. Don’t Overpack… EVER!
  4. The Extra Battery Pack And Shower Bag Is A Good Idea After All
  5. Call Your Bank Telling Them You’re Going Out Of Town Before You Leave
  6. Don’t Waste Personal Brand Opportunities While Out On The Road
  7. Get Enough Rest, Even When You’re In A City That Doesn’t Sleep
  8. Keep Track Of Your Belongings And Keep A Checklist To Go Through Before You Leave

I hope all you traveling newbies will benefit from the mistakes I made early in my career as a freelancer.

Lots of love,


Currently Listening To: https://youtu.be/sCNlt5nvSI8



Tia Lentini

Friendly human with a passion for writing and startups. Blogger for 5+ years and Digital Marketer for 7+. I enjoy poetry and creative writing on the side.