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Summary:

Are you the kind of person who has to have the latest versions of hardware and software? If so, don’t bother to read on; for the rest of us, it’s worth considering if and when to move to a new version.

Are you the kind of person who has to have the latest versions of hardware and software? Do you stand in line to buy a new gadget as soon as it’s released? If so, don’t bother to read on; for the rest of us, it’s worth considering if and when to move to a new version.

I generally wait to see how a new product is received before upgrading. I’ve been holding off on moving to Mac OS X 10.6.4, for example, because it’s reported to break some software that I depend on. But for some reason, I decided to upgrade to iOS 4, the latest version of the operating system for my iPod touch, the first day it was available. Unfortunately for those of us who use Exchange to sync our mail, calendars, and contacts with Google Apps, the upgrade required the re-syncing of this data, which in turn slowed Google’s servers to a crawl. It took almost 24 hours before I again had a usable device.

During that time, I got to thinking about the questions I should have asked myself before starting the update. Here’s what I came up with; please add your thoughts in the comments.

  • Do you need the new features of the update? If it fixes security issues, then probably yes. If not, then you should consider whether the update will actually improve your workflow. For example, one of iOS4’s new features is the ability to create “folders,” or groups of applications, on the home screen. Is this important to you, even given its limitations? Another feature is multitasking, which has gotten mixed reviews, at best.
  • What will the update cost? Of course, some new hardware and software isn’t free, but even if the manufacturer isn’t charging, what is the value of the time and effort it will take you to move to the new version? I suspect that evaluations of this question are why many companies are still using Windows XP and IE 6.
  • Are there technical issues in the new version that may cause problems? This is where blogs and discussion forums can be lifesavers. If I had waited only a couple of hours before starting my iOS 4 upgrade, I would have found several posts and threads describing the exact issues I encountered, and would have known to wait until they were resolved.
  • What are the consequences if something goes wrong? How easily can I revert to a previous version? Can I afford down time? Luckily, I wasn’t going anywhere the other day, but if I had been, it would have been very inconvenient not to have access to my email, calendars, and (especially) to my contacts.

How do you decide when to upgrade?

Image by Flickr user .schill, licensed under CC

Related GigaOM Pro content (sub. req.): Report: The Real-Time Enterprise

  1. From 6th grade to 12th grade and 2 years of college (10 years total), I had TWO Sony Walkmen. The second one was waterproof, had an excellent FM radio, and had direction selection i.e. you don’t have to flip a tape to change sides. Total cost was about $120.

    In the past 4 years I have already owned 2 iPods at $299 each, and I’m already fearing buying another. Consumers have been duped into buying disposable electronics that used to be considered “durable” goods. If you are a person who is let down by upgrades and wait online for a piece of electronics, I think you need to take a long look in the mirror and see that your reflection is a person and not “the latest tech”.

    That said, can’t wait for my phone contract to expire ha ha.

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  2. [...] stopped taking the latest and greatest of software some time ago. Web Worker Daily has an article, “When the Latest Isn’t the Greatest” about when you should, and shouldn’t, [...]

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