The Truth about being a traveling artist (mistakes + tips!)

“Business or pleasure?” she asked. “Business,” I replied and instantly felt proud. Going on my first business trip made me feel somehow more adult and professional. I was so excited that I was traveling for my own business!

The very first business trip I took was for a wedding in San Jose. Although it was still within the state of California, I felt so excited to fly for a gig. I could now officially call myself a "traveling artist" and I thought nothing sounded cooler than that!

Since then, we've traveled to New York, Hawaii, Texas, Oregon & Iowa - and have more coming up in 2020! I feel so blessed to be able to visit new places and do what I love while traveling. It is seriously a dream BUT, I won’t lie. It’s not always sunshine and butterflies. Traveling events require a lot more effort and work than local events. You need to plan the day(s) leading up to & after the event to make sure everything runs smoothly. Since I did not do a lot of traveling growing up, this is something I had to learn on the job. I've made lots of mistakes along the way, but now feel confident that I have become pretty decent at this whole traveling thing ;) I wanted to share some of the biggest mistakes I’ve made for work trips so that hopefully, you can avoid them. These tips are not just for traveling artists, but can apply to any freelancers like photographers, performers, florists, etc. 

traveling artist in new york

Mistake #1. Airbnb vs Hotel

Once, I booked an Airbnb for a work trip. We had landed at 10pm and by the time we got our rental car and drove to the Airbnb it was 11:30PM. When I checked my app, I realized the host had never sent me the check-in info. I tried calling then host but then, she did the unthinkable - she canceled my reservation. We had already been exhausted from the flight and this was definitely NOT what we wanted to hear close to midnight. We ended up calling all the nearby hotels and after 30 mins, we finally found one with an open room. The room ended up being twice the cost of the Airbnb due to last-minute booking and the whole experience made me realize - Airbnbs are NOT for work trips. Don’t get me wrong, I loved using Airbnb for our trip to Europe. I loved that the homes were decorated with French furniture in Paris and smelled of bread spices in Italy. However, this is not really what you want for business trips. You want things to be as easy as possible so there’s not another thing to think about when you’re traveling for work! Make it easier on yourself and book a hotel for business trips.

Mistake #2. Hotel Location

Recently, I traveled to Dallas, Texas for an event with Pepsi. I flew in on a Monday & the event was the next day, Tuesday. My team members were flying in on Tuesday morning, so I knew I would have to wake up early to pick them up from the airport. I made the mistake of booking a hotel closer to the venue than the airport, which meant  I had to drive two additional hours to pick my team up. Our flights were scheduled for early the next morning, which meant getting up at 4am to drive the hour to the airport and I am NOT a morning person. Since that incident, I’ve always booked hotels closer to the airport rather than the venue, so we wouldn’t have to stress out on making the flight. Pro tip: Look for hotels that offer airport shuttle so you can save money on car rental ;) 

Mistake #3. Not documenting important details

As we began to book more travel events, it started to get more difficult keeping track of all the different details. Once, we had so many trips going on that I forgot  to book a hotel for one of the events! This is why it’s important to document details such as flights, hotels, and rentals. This is especially a MUST if you’re booking for multiple team mates. Fortunately, we have a brilliant manager who came up with a traveling checklist that has helped keep things in order. The checklist included all the details needed for that event: flight times, hotel information, car rental (if there is one), and all of the information regarding the event & other team members plans as well. It is a lot to keep track, but it is super helpful to have all of this information in one place & be able to disperse it to my team easily. Even if you are a solo freelancer, I would highly recommend noting important travel details in one place right after you book!

Mistake #4. Expecting everything to go as planned

You might see a common theme here. The tips I’m sharing are all about making things easier on yourself! Traveling can come with so many details  that are out of your control: Flights can be delayed. Your bag can get lost. There can be traffic on the way to or from the airport. Airbnb might cancel your reservation last minute. You might get hungry (lol) and the list goes on! Be prepared for the unknown by making things easy on yourself. Something I’ve recently started doing is paying the extra $20 on  Southwest to get seated early. I get to board with group A which means I can:

  1. Get an aisle or window seat

  2. Sit with my team member(s)

  3. Ensure my luggage will fit  in the overhead bin

I used to never get upgrades, but the extra $20 allowed me to avoid:

  1. Sitting in the middle seat in between unpleasant people 

  2. Be separated from my team member(s)

  3. My bag being checked which adds  extra time to go pick it up or potentially having it lost 

I also like to carry snacks, a portable charger, chapstick and a jacket with me at all times. My husband makes fun of me, but trust me, he always asks if he can have some of my snacks ;)

Mistake #5. Overbooking

Events that require travel not only take up more time, but they take up more ENERGY. It can be exhausting, so make sure you leave buffer room for when you return. If the event is on a Saturday, try to come back early Sunday so you can rest a bit before jumping into the week. Don’t cram your schedule during travel events  - make sure to leave room to rest and recharge. If you feel fine once you get back, you can definitely fill your schedule, but it’s so nice to have that buffer room in case you want to relax!

I hope these tips are helpful & help simplify your traveling process so that you can put your best foot forward before, during and after your travel event. If nothing else, hopefully you can relate to one of my travel blunders & I’m not alone in learning the beauty & frustration of being a “traveling artist.” 

If you have any travel-related questions, feel free to drop them down in the comments below!