More and more millenials are going the freelance or entrepreneurial route, and in a slight break in convention with the generations before us, we financially value experiences over material possessions. Going out on your own is a risk and you may not have a ton of extra cash, but if you play your cards right, you may not have to skip vacation. Mind you, I’m not one of those freelancers who is always on holiday, but in the past few years, I have gotten to visit some pretty interesting destinations, and see some new places. As a freelancer, I’m always taking my work with me, and this makes traveling with work a little different than traveling with a regular job. I’m going to share with you how I successfully travel and work from anywhere.

BOOKING ON THE CHEAP
I like to travel cheap. I’m not a fan of paying more than $300-400 for a domestic round trip airline ticket, $120/night for a hotel, $50/night for an Airbnb, and $35/day for a rental car. In addition, I have a frequent flier account with American Airlines (shocker, right?). As a millenial with a project-based income, I need cheap accomodations and lots of miles. For me, frequent flyer miles are one of my best bets to see the world. You won’t be booking first class tickets or penthouse suite hotels, but you’ll get to see the world. If you do it right, you will be too busy having new experiences to care about how you get there or how you stay there.

Sign up for a frequent flier program with a legacy airline (American, United or Delta). Through the program, they will typically have a dining program, a shopping program and travel partners, such as other airlines, rental car companies, and hotels that you can also earn miles with. If you are with American, Hertz and Wyndham Hotels are both partnered to earn you miles. When you travel, book the rest of your accommodations through one of your airlines partners. However, if your stay will be more than one night, Airbnb will be cheaper. Check your itinerary dates with the flights and places you want to book, and make sure to book your trip 4-8 weeks in advance for the best rates on airfare, which tends to be the largest expense. I also have a feeling it won’t be long before airlines are partnering with Airbnb, and my guess is that Delta will be the first of the American legacy carriers to pull the trigger.

PACKING LISTS + PACKING
I make two lists while I pack. I have one list for everything I’m bringing in my carry on, which is just a canvas backpack. In there, I pack all of my electronics, books, and snacks. In the main pouch, I store my laptop, my camera and a lens, my iPad, a book, my phone, my water bottle, my wallet, keys, and some snacks. In the front pouch I carry all of my chargers: camera battery, phone (including the plugin), and laptop. In addition, I also squeeze in my card reader so I can upload photos as I go. My bag has two small side pouches. In one, I carry dramamine and my SeaBands for motion sickness. In the other, I pack my headphones. My other list is for everything I’m bringing in my suitcase and checking.

On my suitcase list, I divide it up between toiletries, clothing, and other.

So, I have three stages of packing. The first is collecting all the items I need to pack. As I collect them, I put a check by the item on my list. Then I go through the list again, make sure everything is there, and then cross the item off the list. Then as I pack the item into my suitcase, I put a scribble through the item. When the suitcase is fully packed, I close it and if I’m flying, I put it by the front door. Then I go check it off on a list of all the bags I’m taking, usually a whopping three items deep: purse, work bag, and suitcase. My suitcase is ready to go so I can cross that off. With my work bag (backpack/carry on), I have my list for that bag and as I pack stuff I just cross it off. I make sure that as I pack an electronic, I also make sure the next thing I pack is the charger for that item. It’s surprisingly easy to forget a charger. When that bag is packed, I cross it off my list of bags and put it by the door.

If I’m driving, I pack a purse. The only things that go in there are keys, phone, wallet, sunglasses, and maybe a water bottle. If I’m flying, keys and wallet go in my carry on, and my purse goes in my suitcase (because hauling a backpack everywhere is not convenient). Another thing I do if I’m driving is I load my car as I’m packing so all I have to do the day I leave is get up, grab my purse and leave. If I’m flying, all I have to do is get dressed and catch my ride to the airport.

This system has never failed me. I’ve never gotten up to Design Camp and realized that I forgot something on my list. I’ve never had to buy something that was on the list that got left behind. I can tell you that when I haven’t used this system, my trips end up costing more because I have to buy the forgotten items. It’s ridiculous but it pays to make too many lists and check them all obsessively.

Come home to a clean home. You’ll thank yourself.

CLEANING HOUSE
You know when you come home from a trip all refreshed and your house is a mess? Dirty dishes in the sink and trash that might be fermenting into some rancid flavor of wine is not exactly a refreshing welcome home. Transitions are hard, especially when you’re going from vacation bliss back to your normal life. Cleaning the house before you leave is a great way to ease the transition. Coming home to a fresh smelling house, clean sheets on your bed, and all of your laundry done makes it feel like you’re coming home to a fresh start. Everything is ready for you to get back to your routine. For me, it actually motivates me to get to work. I usually start cleaning the house two days before I leave, and then pack and finish cleaning the night before I leave. While I’m away, I usually forget that I cleaned the house, and am delightfully surprised to find clean quarters upon my return.

SCHEDULING WORK
Planning my work time on vacation can be really challenging or really easy depending on if you’re traveling with people. When I travel by myself, I usually plan on work time in the evenings and before any plans for the day start. With a conference this can get tricky as they usually start early in the morning and have activities going on late into the night. I usually just plan some time in the evening to get a few things done. If you’re traveling with others, you may have to set boundaries and let people know that you are working and can’t be available to participate in their plans. If you’re traveling with family or friends and sharing a living space, those boundaries absolutely need to be set because it may not look to them like you’re doing anything of importance. I usually just take advantage of any down time I have for work. I try to spend about an hour a day working while on vacation.

When you choose your task list, pick things to work on that a client isn’t depending on. If its a tight deadline, finish it before you leave, and if it’s not, leave it at home or put it in cloud storage. If you bring a client’s work on any kind of external storage, you risk it being damaged, lost, or stolen. (I have had this happen, and while I thought it was backed up, I found that it actually wasn’t and my team and I had to start from scratch two weeks before a deadline.) To keep organized, I make a schedule for the week, designating from a “master list” what I will work on each day. I don’t do anything different with that on vacation. Usually, I pick things like social media, blog posts, documenting my travel, and passion projects. Traveling is so much apart of my work and its important for me to document those experiences and how they relate to my business.

ACTUALLY WORKING
The environment you try to work in is directly related to how much you get done. As great as it looks in movies and on television, working poolside on a laptop is not the wisest move. Aside from possibly having your laptop soaked (and thus, ruined), sitting in the sun can make it hard to see your screen even on it’s brightest setting. While I was in Florida, I found that a cup of coffee and a cozy spot on the couch did the trick. I got a lot of social media work and writing done while I was there.

If you need to tune out your travel companions’ activities, get some noise canceling headphones, or at least a pair of earbuds. Make a good “working-on-holiday” playlist and get cracking. This isn’t any different than a normal day in my Des Moines office. When I build those playlists, though, I make sure its music that will get me excited to work and fits the destination.

IS A WORKING VACATION ALL THAT DIFFERENT FROM A NORMAL ONE? (AND DOES IT SUCK?)
Taking work with you can determine your destination. This is one of the downfalls. If you’re looking for some solace in the woods or mountains, you may want to pick somewhere that has woods and mountains near a place that has free parking and wifi. If you’re camping, make sure your campsite is accessible by car. And if you want to work, don’t pick a destination that has so much you want to do that you don’t have any energy for work. If you’re thinking, “but doesn’t that defeat the point of going on vacation?” Nope, because that’s one of the differences. It’s a working vacation. If you don’t want to be limited, don’t take work with you. There’s nothing wrong with a work-free vacation. In our culture of hustle and workaholism, you probably need it and you probably deserve it.

Normally, I always bring work with me wherever I go. If I didn’t all I would need is my suitcase, and my purse. Traveling with work means an extra bag. It also means an extra demand on my time, and the pressure to take the time I’ve set aside for it.

If you’re wondering if it sucks to bring work with you, it depends. Do you like your job? Do you like what you do? I do. For me, working on vacation makes my vacation more enjoyable. You have to be able to set boundaries with your work. If you have a boss or a client that requires you to work on vacation, they are overstepping their bounds. Your time away is first and foremost YOU time. If you want your work to be apart of your you time, I say go for it, it’s not something you should let someone demand of you. If you have someone forcing you to work on vacation, it might suck. My solution is to always let my clients know that I will be out of the office for vacation, that I will be out of reach, and taking a brief break from client work. All of my clients have specifically requested that I don’t work on vacation because they care about me. At the very least, your client will respect your wishes. If they don’t, you’re not obligated to answer.

7 THINGS TO BE AWARE OF WHEN TRAVELING WITH WORK:

Stickers everywhere! And not one of them is has the potential to piss off anyone handling my bags.

This should tell you the aircraft type, services and amenities for the specific flight.

Don’t try to work in economy, even if it’s premium economy. It doesn’t work. I tried it and I couldn’t open my laptop all the way. You’re probably thinking, I know, dummy. Everyone knows that. But I didn’t and I found out that working on a 15” laptop in premium economy is very much not a thing. If you need a screen bigger than your phone, bring an iPad.
Airport WIFI is generally free. O’Hare, DFW, Sky Harbor, ATL, Palm Beach International, Omaha and Des Moines all have free WiFi. DFWs got sketchy and Palm Beach was good but a little flaky. In some places it may only be good for an hour, and then you have to reconnect, but I’ve never been to an airport and paid for Wifi.
If you decide to work on an airplane using a smaller device than the 15” Macbook Pro, check your flight information before you fly. Newer aircraft tend to have USB jacks in the seatbacks. When go to select the flight you want, see if there’s a place where it offers more information (on American’s app, it says “Details.” Also flights to Phoenix in September are dirt cheap.) This should tell you if the flight offers Wifi, and power outlets.
Other people bought the same bags as you, and a red ribbon won’t make yours stand out in baggage claim. This is important if you have to check your work bag (cringe, I know). Plaster your suitcase in stickers, paint it. Do something big, loud and TSA-approved to your luggage so that you can not only spot it easily at a busy baggage carousel, but so that there is no way someone is getting the wrong bag. If your bag is cloth, stitch a patch or two on to it!
Along those same lines, be cautious with the way you mark your bags. I have stickers all over mine, but not one of them identifies where I live (and my luggage tag only has my phone and email), my religious views or my political views. Some religions are illegal in other countries, others are sharply frowned upon, and for the same reasons you don’t want to start up conversations with strangers about politics, especially abroad, don’t go advertising your views on your bags. The last thing you want when you’re traveling is to get profiled by security or have your bags carelessly tossed around because they don’t like who you voted for or how you worship.
NEVER check a bag with camera gear or your laptop. Take it through TSA and make it easy to dig out. Even if your bags are covered in stickers worshiping baggage handlers, don’t check it. Baggage handlers just want to get the plane loaded so you can have an on-time departure. If they treated every bag like a newborn kitten, it’d take hours to get off the ground, and you’d probably have a grouchy flight crew.
Air travel is stressful for many people. Part of flying is the possibility that plans change or something isn’t satisfactory, and you’ll have to interact with the airline’s staff. They understand that you’re unhappy, and they understand that you probably want to bring their company to rubble, but they deal with jerks all day. There’s no reason you need to be one of them. It’s not their fault your flight was canceled, so don’t take your frustrations out on them. There are a lot of things that go into getting a plane off the ground and to it’s destination. The person serving you, yes, serving you, has control over pretty much none of that. Be kind and thank them for doing their job.

If you found this helpful, I’ve included a freebie packing list template! So many available packing lists (like what you can find abundantly on Pinterest) have stuff already filled in and I get why that’s helpful, but because of the nuances of working away from home and how everyone has different travel needs, I’ve left them blank to give you space to make your own list. Download the packing list for the traveling freelancer.

Happy travels!!