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Disclaimer: I know that the lifestyles available and/or desirable to me, a 26-year-old, single, childless woman, are inevitably different than the lifestyles available/desirable to others. I’m not trying to put down or even remotely comment on anyone else’s lifestyle—I’m merely elucidating a lifestyle that works for me. As I like to say, you do you 👌
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When I left Silicon Valley in 2018, I felt like I was putting my career on hold in order to embark on a new adventure, and at the time, I was willing to do just that. I quickly learned, however, that without work, I go a bit mad and feel generally unfulfilled 🤷🏻♀️ I loved my years at MIT because I was surrounded by people who were ambitious, industrious, and passionate about making the world a better place. It was exciting and challenging and very, very fulfilling.
Being jobless made me feel like I was turning my back on that side of myself. But, in my usual stubborn way, I decided that I needed to have it all. I needed to work on my career, not for prestige, renown, or conventionality, but because I wanted to feel like I was having a positive impact on some small part of the world. I also needed to feel free to satisfy my curiosity, wanderlust, and adventurous spirit.
It seemed like an impossible thing to do at first, but I’m finding that I can in fact balance the need for a career and the need for adventure—with remote contract work. This means that I work from wherever I am, on a part-time basis, on a tight scope of work (like a short term project or set of specific tasks). I’m not an employee of the companies I contract for so I don’t get any benefits, but in exchange, I get flexibility.
Working in the Airstream.
Now, I’m developing out a one-woman consulting shop that is portable and flexible but still fulfilling. Here are a few tips that helped me get started as a remote contract worker on the move.
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Tip #1: Be creative about finding work.
Job boards are okay, but they usually advertise very specific jobs with inflexible parameters. There are other ways to find remote contract work, and if you go off script, you can unearth interesting projects and negotiate terms that work for you.
One strategy is to look for an opportunity within your network and branch out from there. I landed my first contract with the company that I had quit just three months earlier. There, I was the product experience manager, but I also functioned as a hiring manager and found that I quite liked it. I had no official recruiting experience, but three months after I quit, I got in touch with the Head of People Ops and proposed how I could help the recruiting team. He gave me a shot for a one month trial contract that led to an ongoing contract. This gig opened the door to more work and more connections.
When looking for jobs, don’t be afraid to take on work that you’ve never done before. If you believe you can be successful at it, there’s usually a way to make that happen. Don’t falsely advertise yourself—always be honest about your experience—but elucidate why you think you’d be good at something new, then learn on the job.
If you’ve already exhausted your network and want more work, don’t be afraid to put yourself out there by writing cold emails (emails to people who don’t know you). Be personal, genuine, and concise. Don’t worry if there’s no official job opening. If you can convince them that you’ll add value or, even better, alleviate a problem they’re having, you can still land a contract. The worst that can happen is that the person doesn’t reply or says, “No, thank you”.
Tip #2: Communicate very clearly about your availability.
This is key. Start by thinking about how many hours a week you can commit. Next, consider the nature of those hours, and remember that there’s a big difference between asynchronous and synchronous work. Asynchronous work means you can do it on your own time. Synchronous means you have to work with others or make yourself available at specific times. Perhaps you can swing 15 asynchronous hours/week by working odd hours and only have 5 hours/week to dedicate to synchronous work, like taking meetings during work hours or being on call.
After you’ve figured out your availability, communicate it clearly and honestly before signing any contracts. You might be tempted to oversell your availability in order to land that contract, but in the end it’s a lose-lose situation for both you and your client. You can damage your reputation as a consultant as well as screwing over the people who depend on you to do your work.
During the contract, be vigilant about communicating your day-to-day availability. If you can’t attend a meeting, RSVP as early as you can, and ping the meeting organizer with any information you were going to bring to that meeting. Review notes for meetings you’ve missed. If someone is waiting on you for a deliverable, give them a realistic timeline and then hold yourself accountable to it. Communicate delays as soon as you know they’re inevitable. Always be honest, upfront, and, perhaps most importantly, be realistic!
Get used to unusual “offices”.
Tip #3: Use the right tools to stay connected and organized.
Working remotely is one thing—working remotely from an Airstream is another. These are some of the tools I use to make remote contract work happen when I’m on the move:
Use one or more mobile hotspots like Airstream Connected, Verizon’s Jetpack, or the GlocalMe to stay connected.
Scope out cell service with Campendium to make sure you’ll be available to work when you need to be.
Use a power bank like the Jackery Explorer 240 to stay charged up. The Jackery Explorer 240 is portable and powerful—it can recharge a 12” MacBook three times over. You can also purchase a portable solar panel to recharge the power bank!
Use freelancing tools like Bonsai and QuickBooks Self-Employed for organization and book-keeping. I use Bonsai to track hours, organize the work I have to do for various projects, and invoice clients. I use QuickBooks Self-Employed to track income and expenses.
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We’re in a day and age where remote work in general is easier to pull off. Contract work allows you to piece together projects that interest you and start to develop your niche. Put the two together, and it’s a great lifestyle if you want to work on your career but stay mobile, say, in an Airstream 😉