Laptop Life (in Charleston, SC)

“I hope you don’t mind me asking, but what kind of work do you do??”

I get asked this a lot**, maybe especially when people see me heading down the dock, drybag full of laptop chargers, headphones, work phone, snacks and other electronic paraphernelia (the boater’s briefcase?), while Jon stays onboard with Zephyr.

I always say that I’m incredibly lucky — I have a page from my 2009 dream book that says “cruise the world with a reliable enough source of income that we don’t have a ‘come-home’ date” and somehow by the grace of God and all that is good in the world, that’s the reality we’re living right now.

Most mornings we get up, have coffee and breakfast together, and then I pack up my drybag full of electronics and head out to this week’s ‘office’. Some weeks it’s a coffee shop. Others it’s a marina lounge. I’ve worked in friend’s houses, hotel lobbies, restaurants, picnic tables with good cell signal, laundry rooms, cars, buses, airplanes, the cockpit, and when there are no other options — from the boat, either while Zephyr naps or by kicking them out of the boat.

Jon and Zephyr will usually visit for lunch and nursing breaks, and I’ll head back to the boat in the late afternoon. Some days require working again after dinner, but others I can kick off early and we can go on adventures together. It’s a give and take setup.

Becoming a virtual worker is not that unique anymore — Maine especially seems to attract them, given the remoteness of some areas — but it’s interesting to see what the realities of “remote work” look like for different people.

The first time I met someone who worked 100% remotely, and had a husband who also worked 100% remotely, I imagined that meant Costa Rica in the winters, French countrysides in spring, beaches on the Maine Coast in the summer… but when I asked, the reality was that she had an office on the first floor of their house and he had one on the second and most days they didn’t even have lunch together. I was floored.

Why would you work remotely and not work REMOTEly? I didn’t get it. But for some people, just the ability to pop a load of laundry in while you wait for your next meeting to start or to not have to commute or own a car is enough of a draw. For others, the idea of the complete isolation and lack of structure is not appealing. It varies.

It’s not always ideal — this week I had a cleaning lady trying to vacuum around my feet while I was in the middle of a video conference, unable to move or ask her to please wait without disrupting the whole meeting — but as long as I have internet and my laptop, I can make it work.

I’m an employee working for (an actually wonderful) little slice of Corporate America. When I last worked from the boat (as a self-employed consultant) it was a little harder — I didn’t make enough money to justify staying in marinas or paying for reliable internet, so I’d patch together whatever source of wifi I could find and work like crazy when it was convenient.

Now I have an annual salary with benefits (more critical in the USA), so we can afford to cruise with Jon at home taking care of Zephyr and we can stay in marinas and justify whatever extra expenses it takes to make working work.

Add to that that I actually *love* the work I do, including my incredibly flexible and supportive manager and co-workers, and it’s a pretty sweet position to be in.

I remind myself of this daily, especially any time I feel like complaining that Jon and Zephyr get to play in the sun while I’m tucked away preparing for my video conference call, or feel frustrated that I have to shower from a plastic bottle with water warmed by a kettle while sitting on the head (toilet) or hike across town to the one coffee shop quiet enough for my meetings one more time. I won’t say it’s easy, but it’s been 100% worth it so far.

Jon definitely has the harder job some days — as all stay at home parents can attest to, I’m sure — and I could not do this without his incredible support. I’ve never made a major career decision without him, and playing stay-at-home-dad is not always a dream — so I am super thankful that we can work as a team. We’ve taken turns being primary income-earner over the years and while I enjoy both sides of that coin, I also appreciate that nothing is forever — jobs, lives, homes, babies — so you might as well make the most of the setup you have today.

It’s an amazing world and time to live in, and to be honest, this is a big part of why we continue to choose to live on a little boat — so we can keep our life overhead low, save the money we need to have the freedom we want, and be able to experience cruising with a baby at the pace that we dreamed of.

We came very close to buying (and financing) a bigger boat last year, but when we really looked at the sacrifices that would mean — years of no cruising, full-time daycare for Zephyr, and full-time work for both of us — we decided we could live with 33’ of space after all.

Leah of 2009 had the dream, Leah of winter-2015 definitely didn’t appreciate the grind to get to this setup, but Leah-of-today — enjoying poolside wifi and hot chocolate bars in the afternoon — is super grateful.


**For those that ask, I’m an instructional designer working on global leadership development. Sometimes I tell people that I help design online training to teach managers how to be managers. It’s super fun & always challenging, I work really hard to be a productive employee, I’m always aware of what a privilege this setup is, and I love it!


Laptop Life (in Charleston, SC) — 6 Comments

  1. I am so happy for you that you’re able to pull this off right now, especially during this precious time with Zephyr! Good for you. 2009 Leah must be very proud that you two have fashioned this life for your little family. Xoxo, Jessie

    • Thanks Jessie!! Sometimes we wonder why we still live on a 33′ sailboat hahaha so it’s good to stop and reflect on the freedom that this life has provided us with 🙂 When is your little bundle arriving?? Any cruising plans?? Can’t wait to hear more!! 🙂

  2. Like my appreciation for mountains on the horizon even if I’m not hiking them in this moment, I appreciate and applaud what you are doing, and your openness to share your inspiring experience with others. You show what is possible, and you tell a great story whole doing it.

    Sail on and keep living the dream!

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