Put your chauffeur on the upgrade treadmill
I don't know if anyone here remembers the "Billion Dollar Brain" by Len Deighton. One scene that stuck with me is General Midwinter making his minion (a chauffeur or bodyguard, I can't remember which) do his time on the exercise bike for him and asking "how many miles did we bike today?"
Wouldn't it be great if we were all rich enough to hire someone to do the horrible chores that have to be done every day (or weekly) like exercising in order to keep our bodies fit?
This is one of the more appealing aspects of Software-as-a-service (SaaS). In fact this blog is a perfect example of upgrade and maintenance avoidance. Rather than hosting the blog in-house and having to maintain and upgrade WordPress every few weeks we decided to simply outsource it to WordPress.com. Now there are some downsides; we can't run all the plugins we'd like to (basically you get what WordPress gives you and you learn to like), but on the upside I will never have to upgrade a WordPress plugin or WordPress itself ever again (which is a security disaster waiting to happen as many have found out).
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