Yak Shaving Unleashed!

Yak shaving is the time honored tradition of needing to complete tasks that relate more to the path we have chosen than to the goal we seek.



My most recent incident involved upgrading my wife’s version of Adobe Lightroom on her iMac. My wife is a professional photographer, and she uses Adobe Lightroom to develop and organize her images. She had decided to prepare a “cheat sheet” for herself for the most common tasks, so she could make sure to be more consistent in the way she does things. She decided, though, since she was a version behind on Lightroom to upgrade to the latest and use that to make the cheat sheet, and that is where the trouble started.

We got the Lightroom over the holidays, but I had not time to start the install process, ‘cuz ya know, holidays? Sooo.

Yak #1: 2 hours – we had to clean up her catalogs and archive everything to DVD before the conversion. Fortunately, my wife is religious about backups and archives and only 2 current jobs were outstanding.

Then we tried to install the software… only to find that it is not compatible with the Mac OS version she is on.

Yak #2: 1 week and counting – we had to update Mac OSX from leopard to snow leopard or later. Yeah I know how old that is, yeah I know its my fault for not staying current. However, we never had a reason to upgrade before… soo. Wait, Can I upgrade directly to Mountain Lion? NOOOOOO. I have to get to a version that will let me upgrade from the app store. That is Snow Leopard. sooo… call the Apple $tore:

Me: “Do you have a copy of snow leopard that I can buy?”
A$: “No we don’t stock disks anymore. You will have to order it from Apple.com or if they don’t carry it anymore, you could order it from Amazon.com…”

Back to the interwebs to buy Snow Leopard. Fortunately Apple.com will sell it for only $20, but free shipping takes about a week. I coulda paid another 20 bux to have it the next day, but I am way to cheap for that.

One week later:

Hey the Snow Leopard disk arrived, cool lets try it. Oh wait – will your ancient version of VMware Fusion work with Snow Leopard? NOoooo! So clearly this was bad planning on my part, and it’s a tremendously good thing I checked first because a) my wife had a bunch of stuff she uses under Windows still in a vm and it would really have hurt her productivity if she had no access, and b) backing out an OS upgrade is never pretty. So after a couple hours of research, I start to shave…

Yak #3: In Progress – Upgrade Vmware Fusion from version 1.0 to version 3.1.4 (which will work on snow leopard and leopard). I download the software from Vmware’s site and when the installer asks me to purchase a license… BAM I am stuck again – the website only lets me buy a license for the current vmware fusion 5 which apparently only runs on Mac OSX Lion and later – and also will not migrate my ancient virtual machine (or at least it’s sketchy). So now I have a support ticket open with Vmware around this to see if I can give them $50 for a 3 year old version of their software that will work with a 3 year old version of OSX…

Notice how these tasks are recursive – I can’t finish one until I do something else? YAK #3 is actually not related to installing Lightroom at all – it is related to YAK #2. It is like our plan has a bunch of tangential tasks that we don’t care about except that they are preventing us from doing the one task that is important. Notice, how all of them could have been planned for up front, right? A little more careful reading of the Lightroom requirements would have revealed that it needed snow leopard or better. A little analysis would have revealed that Snow Leopard and Vmware Fusion 1.0 were not sympatico… Truth is if I had known about the hassle, I might have planned a different solution I could have:

  1. Stayed with LR 3. There is not that much advantage in this upgrade except to stay current on tools.
  2. Bought a new Mac. The I start with Mountain Lion and just install stuff. I may still have an issue with the virtual machine, but at least I can get working fast. Her machine is now 5+ years old, so I have to think about an upgrade in the next year or so anyway.

How often at work to we run up against the same kind of issue. We set a goal, and make a plan to achieve that goal, but either our analysis of what is required to meet the goal is flawed, or something completely unexpected and “tangential” to our original work vector. I would say that this happens way more frequently when we are doing a job that is unfamiliar because our ability to “see” the related work is less. Any job or task that you have never done before has a high probability of requiring extra work that you didn’t plan for. Any job that you do infrequently, especially those that you don’t already have a documented process for have a similar probability of requiring extra work because there is “edge learning” every time you do it.

For other references to Yak Shaving see below:

Don’t Shave That Yak – Seth Godin’s Blog
Yak Shaving Day – Ren & Stimpy – Yak Shaving Day – the original source of the term.


  • Rich Stone

    January 22, 2013 at 4:39 am Reply

    So – as the progress of YAK #3 unfolds, VMware no longer sells version 3 or 4 – they only actually sell version 5. They referred my to HP or Dell their OEM partners. Brilliant – HP and Dell are OEM partners for VMware Fusion (their Mac desktop product)? Seriously. I would think that VMware would be willing to sell any version of VMware fusion that was compatible with any version of MAC OS that apple was still willing to sell. VMware explicitly told me that all versions of VMware Fusion prior to the current were no longer supported.

    As of today, I have ordered VMware Fusion 3 from amazon.com – I figure that I should have it by the weekend and there is a 50/50 chance that it will actually install on Mac OS X Leopard.

  • Anonymous

    January 22, 2013 at 7:33 pm Reply

    There’s a huge herd of yaks waiting for you if you go to Mountain Lion. The App Store totally sucks, and that’s just part of it. All kinds of apps will need to be upgraded. Having been a Mac fanboy for years I’m finally seeing the darkness….

  • Rich Stone

    February 11, 2013 at 5:18 pm Reply

    Sooooo – just wanted to share that I finally got my wife’s iMac upgraded sufficiently to run Adobe Lightroom 4 – and even that was a bit of a beast.

    0) backup the windows XP guest virtual machine.
    1) I upgraded to Vmware fusion 3.1.4 (via download),
    1.1) proved that the windows xp guest worked under the new version.
    1.2) Made sure that Time Machine had a current backup of the OS
    2) upgraded to Snow Leopard, 10.6.3 via DVD
    3) did the combo upload to 10.6.8 v1.1 via download.
    3.1) made sure that time machine had a current backup of the OS
    4) Re-installed vmware tools in the windows xp guest.
    4a) made sure that the guest worked correctly
    5) Installed Lightroom 4 from DVD
    6) Upgraded to Lightroom 4.3 via download.
    7) Upgraded her old lightroom catalog(s)
    8) Tested all of her “goto” software on both Mac OS and Guest OS vm’s
    9) Installed Upgrades to Firefox and 2 or three others which were stuck on Leopard.

    Of this only steps 5 – 7 were the actual work required to upgrade Lightroom. The rest were Yak’s…

    – Total wall clock time – approximately 8 hours

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