We all know the biggies (Airbnb, VSCO, etc.) but there are some cool alternatives to those, including:

• Listings project: A curated list of homes and other things (including jobs)

• Blueground: Modern, mid-term rentals (1mo+) in more and more world cities

• Sonder: Hotel-like apartments with kitchens or mini kitchens

• Landing: Fully furnished, flexible-lease apartments for the new generation of renters

• Kindred: members’ only home swapping

• For people in the world of higher education, there is also Sabbatical Homes.

• For traveling professionals, consider FurnishedFinder.

• Outsite - digital nomad coliving

• And lastly, don’t underestimate the power of an email to friends and family asking if they know anyone wishing to sublet or looking for someone for vacation cover.

• Preparing for travel

  • In anticipation of extended exploration, go through every type of mail you get (list of standard ones below) and make them paperless delivery where you can.

  • Create a folder in your email inbox called “Physical Mailbox” or something like that, to keep the emails that now come in separate from your work and other mail. Much easier to track. Then you can go back on a regular basis and “open” your mail.

  • Nevertheless, you’ll need a physical address for some things (often gov’t related). If you won’t be anywhere consistently for a while, consider identifying a relative or friend who is comfortable letting you use their address (and reliable enough to forward it when relevant!).

  • Depending on the mail you’ll be receiving and that relationship, it might also make sense to add in a PO box. You can call periodically and have mail forwarded from it. In the US, both the Post Office and UPS offer this service.

  • Another option could be to sign up with a co-working space. Almost all of them have a mailing address option. Some will open and scan or forward mail for you for an extra fee.

  • In the hub-and-spoke model, you can easily leave or transition everything to your hub location.

• While traveling

  • To save on hassles down the road, proactively check in with your various sources to see if there’s mail waiting for you.

I think the hardest thing about distributed work will be time zones and… taxes!! This is a bugbear.

This is not my realm of expertise and I don’t want to steer anyone wrong, so reach out to WhyBlu (specialists in nomad taxes) or your accountant / CPA. Do this BEFORE you travel/explore. You don’t have to change your plans as a result of their answers, but you’ll be informed of the implications.

Tell them your rough plans, then ask them:

• What is my domicile (tax home)? (For more on domicile, see topic “car/voter registration” below)

• How will the states / places I’m looking to visit impact this year’s tax returns?

• Based on the plans I’ve outlined, would you recommend any changes to optimize my tax situation?

• What will my choices entail come tax time: how many governments will I be responsible for informing?

If you have a car and / or want to stay registered to vote, and you’re going to be doing a lot of exploring, you’ve hit on a murky area. Check with the state of your last permanent address. Some, like CA, will say you can use your previous address if your move is not permanent. But they don’t define what is temporary. To answer these kinds of questions for yourself, it’s helpful to understand the concept of domicile, which is different than residence. Basically, domicile is about intent — do you intend to return to a state? I’m not an expert here, but I gather states have their own definitions of domicile. This is a great, detailed article about this (including some options) from the ultimate nomads: van-lifers.

The rule of thumb here, as I understand it, is that your insurance should match your car registration. Even if you’re on the road away from that location for much of the year, those two things need to match from an insurance company perspective.

• If you’re currently full-time employed somewhere, check on their coverage in the states or countries you’re planning to explore in. If your existing cover is weak for your destinations, consider supplemental travel insurance, e.g., from True Traveller.

• If you’re not full-time employed with insurance, and you’re in the US / a US citizen, consider an ACA plan in the state where your doctors have been (see more on why under healthcare). There are people whose job it is to help you find insurance, so look for those folks in the state you want insurance from.

• If you’re not full-time employed with insurance, and you are not a US citizen, consider an international plan, e.g., from GeoBlue or Cigna Global.

• If you’re operating on a hub-and-spoke model, you can build up a set of practitioners in your hub city. If this city is new to you, don’t wait for needs: proactively get appointments with an internist (GP) and specialists you use regularly. Waits for new patients can be 6+ months. (I’ve even identified and reached out to doctors before even landing in a city, in anticipation of this lag.)

• If you’re in a store-and-explore model, consider retaining your original doctors and flying / driving back to that city when you need non-urgent healthcare. While this may seem extreme, given how hard it is to get in with new doctors and the benefits of having consistency in healthcare, it can actually take stress off. If you feel you want to access care in one of your exploration spaces, plan for the fact that it’s on you to get and transfer all records, and this still primarily happens via CD (in the US).