Initiativeness means: A nonstandard noun meaning initiative, drive, or the quality of taking action independently - essentially 'initiative' expressed with an additional abstract suffix. More verbose than necessary and. There is no real cause for parental concern; it is descriptive vocabulary rather than risky behaviour. If your teen uses it, context will usually make the intent clear. A short, curious question about where they heard it is usually all that is needed to know whether to follow up.