Hacking Freelance: Working on the Road

Everybody knows that the best thing about going freelance is that you get to set your own schedule and work from anywhere. That means we can work from a coffee shop, coworking space, or even the park. However, most of the times we end up sitting in our home office, sometimes even scared to walk away, lest we miss an important email.

But the reality is that we can truly attain the freelance dream with just a bit of preparation. Here are some of the top hacks I’ve learned for working while on the road: 

1 – Don’t set up your out-of-office:

A lot of times freelancers are hyper vigilant of their email, if you miss one, you could miss out on a new project. And so, when people can’t check their emails regularly, they will set up an out-of-office reply message.

However, the reality is that, any given day, while you’re working from home, you might have a call, a client meeting that goes over, or you get caught up in a project and you’re not able to get to all your emails instantly. So, instead of setting up an out-of-office auto reply that might send prospective clients looking for other candidates, just rely on your phone to get to your emails.

It’s totally acceptable to reply to an email a few hours after you’ve received it, and if the client is reaching out to you directly, they most likely won’t have a problem waiting a bit to get a response to book you.

Some of those engagements, if they’re looking for a quick turnaround, for example, you can’t tackle while traveling and you might have to pass on. But it will give you the option to reach out and say, “Hey, I’m currently busy and don’t have the availability to take this on, but let me see if I can recommend someone I trust to help you out”. You can make an agreement with another freelancer with a similar skillset that you both give each other work when each of you can’t handle it. Sometimes, the client might even be open to pushing back their timeline just so they can get to work with you. But offering to help them out, even when you won’t get paid for it, will help you take the relationship you have with your client to the next level.

2 – Plan your gas/bathroom/coffee breaks as your office hours: 

If you’re taking a long drive, you’re going to have to take a break to fuel up on gas or coffee - probably both. Planning the drive ahead of time gives you the chance to know when you will be taking a break from all the driving. I try to always make a stop where there’s a starbucks (they all have free wi-fi) and take any calls from there. This way, when scheduling a check-in with a client, I can let them know ahead of time what my availability is for those days.

No lengthy explanations are needed. If you plan everything properly, you won’t even need to tell them you’re traveling. I’ll just send them an email with my availability for those days and have online meetings from the scheduled stops.

This also works great if you want to take a ski day. I’ll schedule my calls/check-ins in the morning, drive up to the mountain, stop for a morning coffee, have my calls. and have the rest of the day to enjoy the slopes. Freelance life really can be the best if you take the time to organize yourself properly!

3 – Prep your workstation:

My workstation is usually what prevents me from working away from my desk. Everything is set up just how I need it, and my desktop computer is a lot more powerful than my laptop. So before leaving on a trip, think through what you need to bring with you. Cables, tablet, mouse, chargers… It’s a given that, if we’re planning to do work while we’re away from home, we need to bring our tools. But why leave your computer at home sitting idly while you could be using it to help you power through your work?

While some freelancers might just need a laptop and some coffee to get their work done, if you’re dealing with video, animation or motion graphics, you might not want to leave it up to your laptop to output big files, and you don’t want to be sitting at a starbucks ordering your third latte while your laptop is slowly rendering. I set up a Watch Folder on my computer at home that’s linked to my Google Drive. If I need to make any changes to a video or animation, I’ll hop into After Effects on the laptop, make my edits and then send that to my Drive. I can then pack up and hit the road again, and by my next stop my new render will be ready to review.

4 – Stay at Airbnbs:

Yes, hotels are nice and rooms usually have a desk you can work from, but staying at an Airbnb will be better for doing work. They’ll usually have a better internet connection than the free internet hotels offer you. A better wi-fi connection means better upload speeds, which is usually a game-changer while traveling.

I can’t tell you how many hours I’ve wasted uploading files from hotel wi-fi just for it to crash or kick me off. Why am I even travelling if I can’t find time to leave my hotel room?

As an added bonus, Airbnbs give great photo opportunities, and as any good freelancer knows, never miss a chance to create content!

5 – Get your work done early in the morning or late at night:

Let’s not kid ourselves, we’re here to learn how to make the most out of traveling while working. Try and give yourself time to enjoy the city you’re visiting by waking up early or staying up late to get your work done. Use Boomerang to program your emails with deliverables to go out to the client at an appropriate time and use the rest of the day to go out and enjoy yourself.

Pro tip: schedule yourself a couple of extra days on your road trips so you can stop at new and interesting places and don’t have to put in endless hours behind the wheel.

6 – Work from coworking spaces, for free:

Tired of working from your cute Airbnb? Don’t enjoy the hustle and bustle of working at a coffee shop? Or simply need a few extra tools than what you can pack with you? (printer, scanner…) Head on over to a coworking space – for free!

Most coworking spots will actually offer a free trial. All you have to do is get in touch with them and express your interest in checking out their space. You’ll usually get a day pass or even a week pass to test out the space. Come in, set up, and get shit done!

If you move around a lot and are interested in working at coworking spots, check out the Croissant app. It’s a cool service for you to get a desk at different coworking places for a monthly fee. And if people-watching and coffee shops with good wi-fi are more your speed, check out Workfrom, which aggregates places with open wi-fis people have found and left a review of the experience.

7 – Visit out of town clients:

I can’t overstate how important this one is. If as a freelancer you work with clients who are not in your city/state, always try to set up a face-to-face meeting when you’re in their neck of the woods. Clients really appreciate putting a face to the work, and it will do so much to strengthen your client relationship that you took the time to pop by just to say hello. Clients who hire you on a fully remote basis are placing a ton of trust in you. It’s natural for us to prefer to work with people we can see in person, it gives us a false sense of security that the work will get done better, or that the freelancer won’t just ghost without delivering any of the files.

Just the small gesture of sending an email to a client (or potential client) you’ve been talking to, saying something like, hey, I’ll be in your city next week and thought it would be a great time to swing by and meet the team in person, can really solidify a client into a long-lasting relationship.

8 – Take a real vacation:

All these hacks are great and will help you maximize your work time while you’re traveling, but it’s so important to plan a trip that’s an actual vacation. We all need to take time off to decompress and reinvigorate ourselves and our creativity. The biggest mistake I made my first couple of years freelancing was not take an actual vacation, just trust me on this one, you need the time off. Taking time to let your brain shut off, to nourish yourself and reset is so important for your physical, emotional and mental health.

Bonus tip – make your trip tax deductible

8 hacks weren’t enough for you? Here’s an extra pro tip! Make your trip tax deductible. It turns out that if you had to travel over the weekend for work, your stay and any other work-related expenses you might have, are actually tax deductible! So if you’re planning to go visit family over the weekend, extend your trip and set up work meetings on Friday and Monday so that most of the trip is a business expense. Needless to say, I’m not a financial advisor, check with your tax professional on how to best (and legally) do this.

Like any of these tips? Have any extra tips of your own? Leave them in the comments! Would love to hear your Freelance Hacks!