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DaedTech Digest: How to Start Vagabonding

We’ve been on the move for the last couple of weeks.  Two digests ago we were packing to head from Michigan to Austin for an indefinite period of time.  And last digest, we’d just arrived in Austin.

When we are on the move, I like to chronicle that.  But once we settle, I like to answer questions that people ask me about slow travel/vagabonding.  So let’s do that today.

How Do I Start Vagabonding?

This is a fun one.  I enjoy our nomadic lifestyle so much that I get excited when people ask me, “hey, how can I do that?”  So I’ll lay out how to start vagabonding, at least in broad strokes.

First of All, Let’s Clear the Biggest Hurdles

Before I get into more logistical concerns, you need to understand two important, sort of immutable, things.

  1. You and your spouse would need to figure out remote work arrangements, and I don’t know what to tell you if you have school age children.
  2. You’ll also need to come up with a way to finance the added cost of “road rent,” assuming you own property and want to keep it.  This can be expensive or not terribly expensive.

Regarding number (2), I will say that this is not as big a barrier as you might think.  If you’re a renter, you might just not have a permanent residence for a while, opting to bounce around to AirBNBs between leases.  If you do more than a month at a time on AirBNB, many places cut the nightly rate more or less in half, giving you a relatively reasonable monthly rate.

Another thing to consider is that most people pop for some kind of annual or semi-annual vacation to Cancun or whatever.  All expenses paid, all inclusive, $2,500 per person, or whatever that costs these days.  Now imagine that, instead of taking this trip, you hold those thousands back and use them to rent a place somewhere warm for the winter.  That week in Cancun would get you at least 2 months in our place in Austin.

Hurdles Aside, How Do You Start?

Alright.  Let’s assume that you’ve convinced your employer to convert your jobs to remote ones, dropped the kids off at Grandma’s (kidding, relax), and decided to spend your vacation money on rent for an entire season.  You’re in.

What do I recommend?  Here goes.

  1. Start with not-fun logistics, like mail. Get a digital mail service, such as the one we use, PostScanMail.  Nomadic lifestyle and the permanence of an “official address” don’t mix.  So have your mail forwarded to a service that scans it and sends you emails containing images of your mail.  This lets you decide what to throw out, what to act on, and what to have forwarded.  (You’ll need to open something like a PO Box in each location)  Once you leave, you can just have the USPS forward your mail to the digital service.
  2. Prep for being away from your house.  Amanda and I actually don’t worry that much about being away, due to practice.  But prep yourself.  Line up a friend or family member to check on things.  Install a camera to let you monitor, or home automation stuff to make it look like someone’s around.  Whatever you decide, think about this up-front.
  3. Go domestic, and drive the first time.  If you’ve read The Four Hour Work Week, you’ll find this advice at odds with what he says.  But I stand by it.  Ease your toe in the water by going somewhere within reasonable driving distance.  This means that (1) you can always bail out and go home if anything goes wrong, which offers a lot of peace of mind, and (2) you don’t have to do a crash course in learning to fit your life into a checked back and a carry on.  Also a great option when you have pets.
  4. Start with a month if you’re nervous.  A month is the minimum amount of time to book for a significantly discounted AirBNB rate.  If you’re nervous about this whole thing, try it for a month and take it from there the next time.  Amanda and I threw ourselves into a 3 month commitment the first time, and we loved it.  In fact, we booked an extra month.  And that’s the point.  You can always book more months when you arrive.

I could probably go into a lot more detail, but that would start to get increasingly specific to our situation.  The most important things are to start thinking well ahead of time about what it would mean to leave your place for longer than you ever have before, to plan and pack well, and then just to dive in.  Because, like diving into a chilly body of water, you’re never really going to be ready.  Psych yourself up, and then just say, “screw it” and go for it.”

I can’t tell you how happy we’ve been over the last several years for having taken the plunge.  And a never-ending set of new experiences, like downtown Austin viewed from across the Colorado river, keep reinforcing the wisdom of plunging.


  • I’m going to throw a pick this week to the aforementioned PostScanMail.  I love their service, because it actually turns your physical mail into an Outlook-like inbox.
  • Last weekend, Amanda and I embarked on an epic walking tour of Austin, which included going to a place called La Barbecue.  They have the best brisket I’ve ever had in my life.
  • I’ve used Hubspot for CRM for a long time.  But only this week did I discover that Hubspot makes a Chrome plugin that integrates your Hubspot CRM with your gmail inbox.  I can, without any effort, log every email exchange into the CRM, leverage email open tracking, add new contacts to CRM, and see information about the person I’m talking to.  As the de facto head of Hit Subscribe sales, this is amazing.

The Digest

Another sparse week on the digest.  I’ve been focused on a lot of business development stuff lately, and the content I’ve been writing for pay has been ghostwritten.  So, I’ve had pitifully little to link up to in the digest.  But don’t worry — more will come soon.  In the meantime, here I am on video.

And, as always, have yourselves a great weekend!

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Rick Lobrecht
5 years ago

If you’re looking for good barbecue, you’ve come to the right place. Franklin BBQ is probably the best in Austin, but expect a really long wait. Texas Monthly (its a magazine) annually publishes a piece on the 50 best BBQ joints across the state. You will find that many of them are within a short drive of Austin. I stuck the URL to the latest version of the list as my website, because I didn’t want your comment engine to mark me as spam.