Stories about Software


DaedTech Digest: Deciding How Long We Should Stay

It’s been a few weeks now since the last DaedTech digest.  In that one, I chronicled the last little bit of our trip to Vermont.

We haven’t gone anywhere since then.  Not really, I mean.  We’ve been back and forth to Illinois a few times, visiting family and taking care of logistics.  But that hardly merits a slow travel chronicle.

So let’s go back to answering questions about slow travel until we embark on our next adventure.

How do you decide how long to stay in the places you go?

I’ve seen a lot of family and old friends of late, so I’m plucking a question that one of them recently asked.  They wanted to know how we decide what amount of time to spend somewhere.

Well, on the short side, that’s simple.  We only go somewhere for at least a month.  If you’re under a month, sites like AirBNB and VRBO charge the sorts of rates per night that you see on the site.  But at a month or more, a monthly rate kicks in, which often cuts the nightly rate in half or so.  This means that such a place, while not as economical as a year lease on an apartment, is somewhere in between that and a hotel.

As for the duration of stay, that’s historically depended for us one one of two things:

  1. When does the weather change (i.e. when does winter end)?
  2. Do we have somewhere to be or something to do?

If we’re somewhere to escape the cold, we leave in something like May, to make sure that we really do miss the cold.  But other stays, like our recent one in Vermont, end when we have something to do.  This might range from some kind of plans with a family member or friend to, well, Christmas.

And that’s really all there is to it.  We stay as long as we feel like or until we have reason to go elsewhere.  And we don’t always know how long we’re going to stay when we leave.  Sometimes we book a month or two and then extend.

That was the case when Amanda took this picture of me in Ocean Beach, San Diego.  It was bonus San Diego time.


  • I just recently started using a new ad blocking plugin for Chrome called uBlock origin.  I’d been dealing with some flakiness from the Ad Block plugin, and this one has been great.  Lower memory footprint and it blocks more things.
  • We’d been trying forever to sell our townhouse in Illinois, and we finally managed to with the help of a great realtor named Christine.  We’d had the place on the market for almost 2 years without luck.  When we listed with her, she got us an offer that we accepted within 2 weeks.  If you’re in the Chicago suburbs and want to sell, give her a call.

The Digest

And, as always, have yourselves a great weekend.

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5 years ago

first time poster! I saw your comment about uBlock Origin. This is one of my favorite tools. I use it to block annoying popups and ads, too. It’s a strong part of the tool that isn’t well advertised! I did a write-up on blocking elements here: https://josh.works/take-back-your-attention My wife and I have done the long-term slow-travel thing as well. (we both work remotely) and have a similar philosophy for determining how long to stay in a given place. Two years ago we settled back in the Denver area, for a few reasons, but we are planning on starting traveling again… Read more »

Erik Dietrich
Erik Dietrich
5 years ago
Reply to  josh

Wow, I had no idea — thanks for sharing! I just viewed it as an ad block replacement, but that’s some powerful stuff you’re documenting. I need to carve out some time to explore, because that will change the way I browse (I too would like to turn off Twitter “moments”)

And, cheers on the slow travel. We’ve been enjoying this life a lot the last several years.

Francesc Rosas
5 years ago

Is that “self” in “start freelancing while self employed” meant to be there?