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.

Picks

• 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.

• Here’s a video where we talk about running our business, even in the face of weird adversity, including pests, interstate moves, and, well, other weird things.
• And here’s another Facebook Live in which we talk about our favorite productivity tools as business owners.  (Hint: I love Trello!)

And, as always, have yourselves a great weekend!

DaedTech Digest: Here We Are in Austin

In last week’s digest, I chronicled our packing for Austin, and I described how packing for several months is different from packing for one month.  Now, here I am, a week older and wiser, and relocated as planned to Austin, Texas.

Slow travel is always interesting.  There’s a fair bit of prep in selecting the place, packing, and traveling, even when this becomes old hat.  You choose carefully, ask questions of your prospective landlord, spend a lot of time packing and even more time traveling.

And then you arrive.

On arrival, you’re always hoping that the place is, well, good.  Your prep, the description, and the pictures can only show you so much.  Imagine the house buying process, but if you couldn’t ask for a showing and just had to buy based on the pictures.

That’s what it’s like showing up in your new place.  Will it be clean?  Do all of the rooms look like you’d envisioned?  Did the pictures do it justice?  Will it have a certain je ne se quoi?

Luckily for us, the answer to all of that has been positive.  We arrived on Sunday, and made ourselves at home in a spacious home in the woods and on a lake, but still in the city of Austin.

And if the location, the creature comforts, and the warm winter weather weren’t enough, check out this photo we snapped during an evening walk the other day.  This is pretty country.

Picks

• I recently acquired a Xenvo Squidgrip tripod to help us with our recording of Facebook Lives and Youtube videos.  If you’re looking for a tripod to hold your phone, it’s definitely worth a look.
• I’ll follow suit with another consumer good in the form of the Roku.  We’ve been hauling this little companion with us on every one of our vagabonding adventures, and it’s nice to have access to Netflix, Prime Movies, TV channels and more, all with a thing that has a remote and fits in a laptop bag.
• Last up, I’m going to pick work life balance.  Seriously.  I threaten this a lot and often fail.  But I took the holidays off and have been mostly knocking off work in the early evening since then, and I feel much more productive when I am working.

The Digest

Another relatively light week with content, as I haven’t been focused on this of late.

• Here’s a Facebook live in which I interview Amanda and Angela, Hit Subscribe’s director of finance and operations, about Thanksgiving traditions.
• And, here’s another Facebook live, where we talk about running the business in the face of various, sometimes weird, forms of adversity.

DaedTech Digest: Goodbye, Frozen North, and Hello, Texas

Happy New Year, everyone!  I’ve gone quiet since post the last digest, a couple of weeks ago.  We managed to take some real time off, getting much needed R&R.

But that’s all over now, following New Years.  Not only are we back to work full time, but we’re also spending our evenings prepping to leave for the winter.  As I mentioned last time, we’re headed to Austin.  More specifically, we’re going to be staying on Lake Travis, at a nice, secluded property (at least, it looks that way from pictures).

As always, packing is an adventure.  But, unlike the first time I started journaling these trips, we’re not going somewhere for a month, and we’re not going somewhere that has predictable, chilly-ish weather.  Here’s what we’re doing instead:

• Going away for 3-4 months instead of 1.
• Not entirely sure where we’ll be after the first month.
• Packing for weather that, over the course of 4 months, could range from “chilly at night” to “deathly hot desert.”

This means that we’ll probably pack more.  But, counter-intuitively, probably not that much more.

In terms of hauling the cats around or our work setups and electronics 1 vs. 3-4 months really doesn’t matter.  And, clothing-wise, we’re only ever really looking for 1-2 weeks’ worth of stuff before doing laundry.  It’s just that in this case, we need 1-2 weeks worth of pants and long sleeve shirts as well as shorts and t-shirts.  And that doesn’t account for a ton of variability in our approach.

So, wish us luck on our travels.  It’s been fun, after a fashion, here in frozen Michigan, but I’m ready to put scenes like this in the rearview mirror.

Picks

• Here’s a simple pick for you, and one that those of you with New Years resolutions about productivity might appreciate.  This site, tomato-timer.com, is a dead simple way to implement the pomodoro technique.
• Amanda and I have been watching this show called Black Mirror lately, which is a series about the near-ish term future.  It’s sort of Twighlight Zone meets sci-fi, and it’s as compelling as it is dark.  (I also suggest watching beyond the pilot, which isn’t really representative of the rest of the show.)
• And, finally, speaking of Amanda, she got me this activity/fitness tracker for Christmas: the Garmin Vivoactive 3 Music.  I’d found Fitbit to be increasingly annoying (especially the mobile app and the fact that you needed a data connection to see how many steps you had), and this is an awesome replacement.  The app is a nice user experience, and it provides an immense amount of data, which I find very cool.

The Digest

The digest is a little light this week, since I was on vacation and not producing content the last couple of weeks.

• Here’s our last video from Vermont, in which we talked about how we, as small business owners, handle things that employers usually take care of, like sick days and health insurance.
• And, here’s a Q&A mailbag that we filmed upon returning home from Vermont.

As always, have yourselves a great weekend.

DaedTech Digest: The Results of Our Winter Destination Lottery Are In

Last week, I asked for everyone’s help in picking a refuge from winter cold for Amanda and me.  And that went well!  Thanks, everyone, for your comments through the various media.  It was fun to read and discuss.

This week, we’ve arrived at a decision.

I carefully took all of the input from last week, aggregated it, and thought “wow, I’m insanely busy this week, so I’ll think about this later.”  And, that went well.  The part where I didn’t think about it, I mean.

In the meantime, Amanda went on AirBNB and fell in love with a place near Austin, Texas, on a lake called Travis.  It’s affordable, it’s spacious, it’s got great scenery, and it kind of looks like a tree house.  What’s not to love?

So, by the time I had a few spare minutes, our path was all but chosen.  And, that’s actually perfectly fine with me.

In fact, I’ve historically been the one more likely to feel the allure for a particular locale and pick it.  It was about 3 months ago that I said, “hey, let’s go to Vermont for when the leaves change.”  So, she’s overdue to have the whim and decide our fate, and I was more than happy to ride shotgun on this decision.

This winter will be a bit different, though.  I think we’re going to think about it month by month, rather than laying everything out until Memorial Day.  So, it’s going to be a month near Austin, and then, wherever we feel like heading next.

In honor of that, here’s a picture of Amanda eating Mazapan in El Paso (the last time we were in Texas, which was about a year ago).

Picks

• I might have mentioned that I’ve been listening to an audiobook called the Pumpkin Plan.  Well, that audiobook has a companion site, and that companion site includes a pretty helpful worksheet for evaluating your book of business in order to 80/20 your client roster.
• For all of you Diablo 2 players out there, I just stumbled across this recently.  I haven’t actually tried it yet, but if you ever get the nostalgic itch to revisit an old favorite, this might spice things up.
• And, finally, I don’t have a specific link for this, but Amanda and I received an air fryer as a gift recently.  We did an inaugural run with breaded chicken strips, and it was quite good.  All of the texture, none of the grease.

The Digest

• I participated in an interview this week, around the general topic of software engineering management.
• For the make me a programmer blog, I soldiered on with introductory topics, this time addressing what programmers do at work, day to day.
• Here’s an episode of the freelancers show, where we talk about dealing with contracts.  Should you have your own?  Should you sign clients’ contracts?  How does all of this work?
• And, finally, here’s a Facebook Live we filmed in Vermont, talking about how our lives had changed since the founding of Hit Subscribe.  (If you view the Thumbnail, you’ll see probably the worst still image of me ever taken.)

One bit of housekeeping here.  Hit Subscribe is officially on company holiday the week between Christmas and New Years, and we’re going to try to do a little R&R.  So there’s a pretty good chance of a quiet DaedTech the next two weeks.

And, with that, as always, have a great weekend.

DaedTech Digest: Where To Go This Winter? Seriously, What Do You Think?

Let’s do something a little different today.

With the digest posts, I’ve been answering questions about slow travel and chronicling our adventures.  But today, I’d like to get a little more interactive.

Where Should We Go for the Winter?

It’s that time of year again, and I don’t mean the Christmas holiday.  I mean, it is that time of year as well, but I don’t really care all that much.  I don’t count myself among the people who mark the passage of time by drifting from one themed holiday to the next.  Holidays, for me, are just a chance to see friends and family and have a good meal.

The time of year I’m referring to is when, for people with a highly mobile lifestyle, the US Midwest becomes unacceptably cold and oppressive.  It’s time to go south.

This year, Amanda and I don’t really have any specific destination in mind, though we’re most likely going to remain in the United States.  But still, even with that restriction, the southern/warm part of the United States is pretty large.

Here are some parts that we’re thinking.

• Coastal Texas.  We could head to South Padre Island or something there along the gulf coast.
• Inland Texas.  We could base around the Austin or Houston areas, somewhere like Lake Conroe.
• South Florida.  Places in the keys can get pricey for the whole winter, but whether inland or on the coasts of the mainland, this is a nice, warm place to be.
• Gulf Coast.  We’ve spent time in and around New Orleans and in Bay Saint Louis in the past, and we find that coast to be really appealing.
• Southwest Desert.  Maybe we stay totally away from water and do winter in the desert, somewhere in New Mexico or Arizona.

What do you think?  What would you do or recommend in our position?  The only real criteria for us is warmth this year.  Weigh in below in the comments.  What would you do if you had this kind of open road in front of you?

Picks

• This last weekend was Amanda’s birthday, and I got her a weekend getaway that featured a wine tour.  The hotel we stayed at was great, if you’re looking for an atmospheric getaway within a 2 hour radius of Chicago.  It’s on the lakefront town of New Buffalo, in Michigan.
• I’ll also pick the wine tour company, which showed us a great day on the southwest Michigan wine trail.
• Finally, something related to tech.  I’m incorporating more and more stuff into our home automation situation at the home base.  And I’m doing it by and large through this, the Wink hub.

The Digest

• Here was a fun-to-write post that I wrote for Raygun, featured on the New Stack.  The prompt was about how to use APM to guide architectural changes, an interesting premise.
• Here’s a Facebook live that we did when we first arrived in Vermont.  Don’t worry about the orientation — we fixed that pretty quickly.
• And, finally, here’s another Facebook live where I interview Amanda (same thing — we fix the orientation).

And, as always, have yourselves a nice weekend.