I probably sound like I gripe all the time, but that’s really not what I’m like. I’m an optimist and happy by nature. It’s just that I have high expectations for how things could be and I’m disappointed when I see people fall short of their potential. I don’t complain about companies that are trying their best but fall short. I call out the ones that could be so much better but don’t seem to have the desire to see it through.

Update: 2016-09-17

In July 2016, DEVONtechnologies released DEVONthink 2.9 with an entirely new sync engine. It’s like a brand new program and synchronization has been flawless. Although I’ve only been using the new version for a couple of months now, it feels better, faster, and deterministic in a way the older ones never did.

At this point, I’m cautiously optimistic that all of the problems I wrote about below are fixed and obsolete. My fingers are crossed!

I’m keeping this post up for historical reasons but I don’t think that it’s relevant anymore.

Q: I have DEVONthink Pro Office and I want to sync my home and work computers so that I can access documents in both locations. How can I do that?

A: You can’t. Give up. It won’t work reliably.

Q: No, really. How do I do that?

Longer A: Seriously, give up. It doesn’t work and you’ll just get angry and frustrated. Trust me.

I use and love DEVONthink Pro Office as a document manager. Pretty much every piece of information I come across goes into it, whether scans of utilities bills, PDFs of software manuals, Twitter messages I starred, or the complete collection of RFCs. If there’s any chance I might ever want to find something again, DTPO stores it. Its most important feature is the uncanny ability to return exactly the search results I want when I need to find something. Second only to that is its AI-powered “see also” feature: “you seem to be reading up on an obscure technical subject. You might also be interested in the author’s blog posts about it, some guy’s master’s thesis on the main algorithm, and the popular alternative version written by a teen living in a favela in São Paulo.”

It’s that good. And I’m still desperate to find anything else to replace it.

The main problem is that DTPO refuses - just flat-out digs its heels in and resists - syncing reliably for more than a few days at a time. The pattern always goes like this:

  • I start off optimistic, determined that this time will be different.
  • At home, I add a sync connection to Dropbox, or to my own WebDAV server which has been syncing OmniFocus and other apps successfully for years.
  • I sync one of my medium-sized (2GB or so) databases to that connection.
  • I select the Synchronize menu option and wait several hours as my data gets pushed up to the server.
  • At work, I set up the same connection and import the database. Then I select Synchronize and wait a few hours as all my data comes back from the cloud.
  • I use it for a couple of weeks until I start getting random sync errors that cause it to stop halfway through without copying across all my new documents.
  • After going through all the troubleshooting tips on their forum (of which there are many because this seems to happen to a lot of people), I give up and resign myself to the dreaded “Clean Location…” button which deletes all documents off the remote server.
  • I walk away from it for a few weeks so that I don’t throw my laptop out the window.

So I exaggerated a little. It is possible to reliably sync two machines running DTPO:

  • Pick one to be the primary machine.
  • Pick the other to be the secondary.
  • Do all your editing work on the primary. When you’re happy with it, use rsync or some other file copier to nuke what’s on the secondary and make it identical to the primary, losing any changes you might’ve made there.
  • If you’re at work and want to add a document, just email to yourself at home and import it into DTPO there later when you’d rather be playing with your kids, washing the dog, or doing anything else in the entire world.

That’s how you reliably sync DTPO. Anything else is just a ticking time bomb.

I had a wonderful experience buying new Rockport shoes from Brown Brothers Shoes in Alameda a couple of months ago, to the point that I wrote a gushing Yelp review and told all my friends to go there.


My two-month-old Rockport shoes (which I wear only to work at my desk job) already need to be re-soled. The hard rubber heels have worn through so that now I’m walking on the soft foam cushion, and that can’t possibly last too long. I took them back to the same store and found that they’re a lot better at selling shoes than at helping customers.

First, the salesman said that it was probably because I wear arch supports in them. That would seem ridiculous even if they weren’t the insoles that I bought from their own store at their own suggestion. Next, he recommended a local shoe shop and sent me packing. I asked if they sold other, more durable walking shoes, like some I could wear from my bus stop to the office and still have them last more than two months. The salesman said that no, these are the best.

My shoes are in the shop now and I should have an estimate for fixing them by Monday. Hopefully it’ll be cheap enough that I can have them to wear for a few weeks while I shop for replacements. I don’t know what they will be, but they won’t be Rockports and I won’t be getting them at Brown Brothers.

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