Want To Travel As A Self-Starter? Here’s How ✈️

Sure, it’d be great to take a proper vacation, where you don’t have to even think about work. But, unlike those who work for a big corporation, you don’t have paid time off. Passing up work can affect your bottom line, so putting up that OOO reply isn’t always feasible. (Another thing? Depending on what your trip entails, you might not want to take the time off.)

As the world slowly starts to open up — I’m talking glacial-pace slowly — I’m looking forward to getting back to my regular travel routine. However, a little part of me is nervous to juggle business and pleasure again.

So, how are you supposed to master the work from anywhere lifestyle? I’m by no means an expert. If I’m being totally honest, it’s something I’m still figuring out. But, I hope sharing my tricks and tips will help make your jet-setting lifestyle in the not-so-distant future manageable.

Plan Ahead

One of my favorite things about being a self-starter is that every single day can be packed with new possibilities. (Who knows? You might wake up to a dream opportunity in your inbox.) Depending on what you do, it can be really hard to have everything squared away before you leave for your trip. But, if you can, I encourage you to get as much work done beforehand as possible.

I try my best to leave a few days before my trip free to double down on work. My friends know I’m not available to hang, my boyfriend covers my chores, and my schedule is free of distractions. While I don’t always get everything done, this time in self-starter solitude allows me to focus on work so I can spend more time enjoying my trip.

When I went to New Zealand and Australia in 2018, I worked overtime to ensure all of my work was done before I landed in the land down unda’. Fortunately, I was able to check off everything on my to-do list — and promptly took a nine-hour nap on the way to Auckland. (It was glorious.)

Seek A Strong Connection

Repeat after me: Good WiFi is your BFF. I cannot tell you how many times I’ve wrestled with subpar service — leaving my clients hanging for hours on-end. (When my boyfriend and I went to Costa Rica, we inadvertently went on a four-hour boat ride — only to check into a hotel with the weakest service I’ve ever had. As a self-starter, that’s my worst nightmare.)

Whether you’re embarking on a road-trip or traveling internationally (remember the good ‘ol days?!), you won’t have impeccable WiFi 24/7. So, it’s important to make the most of a strong connection when you can. Book Airbnbs with a stable service, ask your waiter for the password so you can check your email for some peace of mind, or make the most of your flight’s online access. (I’m a huge fan of Go Go Inflight!) And, in a vaccinated world, I’m going to buy a mobile hotspot.

When you make the most of your current connection, you can avoid moments like these:

Communication Is Key

Whether your client asks for a last-minute meeting while you’re chilling on a beach or your hotel’s WiFi fails you, nothing ever goes according to plan. (Alexa, play “Ironic” by Alanis Morissette.) If you want to err on the side of caution, let your clients know that you’ll be working remotely.

On my last trip before the shelter-in-place order, I told one of my editors I could quickly churn out a last-minute story as I was about to board the plane. I didn’t mention anything about my flight because I assumed the WiFi would work like normal. Well, Go Go Inflight was out of commission — and I spent the next few hours feeling terrible about the delay. While my editor was completely understanding, I still wish I had said something before boarding the plane.

Keep your client in the loop with this short and sweet message:

Hi! Just wanted to give you a head’s up I’ll be working out of [INSERT IG-WORTHY DESTINATION] from [INSERT ARRIVAL DATE] to [INSERT DEPARTURE DATE]. I’ll be working as usual, but appreciate your patience should I run into any connectivity issues.

Or, if you want to really work on those boundaries? Send your client your hours of availability when you’re away. (Now that’s a boss move!)

Optimize Your Time Zone

Before we moved to San Francisco in 2019, my boyfriend spent the summer living and working in Berlin. I would visit him every few weeks, and let me tell you: Working from Europe was the best. I loved waking up hours before my America-based clients and doing a full day’s work before they even clocked in.

If you’re traveling to a different time zone, think about how you can make the most of that difference. Can you clock in a few more hours during those chill west coast nights? Maximize your mornings if you’re on the east coast? Have an ultra-productive Monday if you’re in Australia? Once you get over that jet lag, make that time difference work for you — so you can soak up your new location.

Stick To Your Boundaries

When you’re working from your normal set-up, you might strive to hit your deadlines, reach inbox zero, and plan for the weeks ahead. But, when you’re working remotely? It’s virtually impossible to do all of that and enjoy your destination. Instead, create a list of priorities — and stick with them. Whenever I’m working remotely, my priorities are always communicating with my clients and submitting whatever work is currently due. Any superfluous emails or invoicing will wait until I’m home.

Though I think self-starters are the closest things to superheroes, we’re all human. Fulfill your priorities and take the time to enjoy your trip. You deserve it!

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Hustler of the Week: Caroline Gutman

What inspired you to become your own boss?

I’m self-motivated and had done freelancing on the side for a while, but I learned it’s hard to find clients and craft strong pitches without doing it full-time. Previously, I worked as an investment fund analyst and also managed partnerships across Asia for a fintech startup.

What is your favorite part about being your own boss?

Working for myself means I can really focus on stories and subject areas that matter to me. I love the challenge (and the chase) of researching, pitching, writing, and photographing stories.

What’s the biggest lesson you’ve learned since becoming your own boss?

Opportunity comes when you least expect it — a.k.a. rarely when you want it to. During the pandemic, I’ve had some very slow and frustrating months, and months where I’m trying to squeeze in everything.

Give Caroline some love by following her on Instagram, checking out her website, and buying one of her prints!

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