I'm currently working with a client that is moving from their legacy AMS to a new system. Their legacy system is a completely custom build that has been used for nearly 30 years. As a result, the system contains a very large amount of data and data fields that the association no longer uses.

My client has repeatedly said that she's "embarrassed by how much junk there is" in their system. But the reality is, any system that's been in place for 30 years is going to have all kinds of data and fields that are no longer needed. (See here for how data accretes over time.)

It's very easy, in hindsight, to ask "Why did we ever track that data?" Remember fax numbers? And before that there were telex numbers! And we used to actually track social security numbers! Why would we ever do that?

The reality is, we make decisions with the best information we have at the time.

Yes, you should periodically take time to clean up your system and data. But don't beat yourself up for decisions you made a decade ago measured against today's standards. Hindsight is always 20/20.