I get asked this question a lot. A lot.

Usually people mean something like “Is this release as cool as the marketing says it is? Will I like it or will it make me sad?”

Since most of the people we deal with use their Macs for business, I answer within a business context, so this may not be true for you.

Here’s my stock answer:

“You probably use your computer to make money. If it’s not working, you can’t make any money. Heck, you probably can’t even issue an invoice.

If that’s true for you, then you should upgrade the OS only under special circumstances:

1.  You can make more money (directly or indirectly) by upgrading.
2. You can offer a service that you couldn’t offer before (which makes you more money or broadens your reach).
3. You are upgrading some essential, non-OS software (Creative Suite perhaps) for reasons 1 or 2 and so, are required to update the OS.

Upgrading because you’re bored or want to try something new keeps people like me in business.

If you do decide to upgrade:

1. You should be able to articulate the business rationale clearly.
2. It should be planned.
3. It should be staged (one, few, many).”

This is a blunt instrument. There are always exceptions. You may decide that communication between staff will be helped (but I’d suggest this makes you more efficient and so, better able to make money, so see reason #1).

But the Law of Unintended Consequences can leave teeth marks on your productivity.