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I feel that what you’re attempting is probably better with a different setup of ACF fields.
Flexible content fields are typically used when you have completely separate areas of content that are just as likely to be used (i.e. some text could be one column, two columns or three)
In this instance it seems that you’re looking for something like:
Headshot - text or icon Headshot - text or icon - text or icon - text or icon Headshot .... etc.
In this case it would be best to use a second flexible content field within your first one, so that your Headshot is always ready and available, and then you can have a second loop for your text or icon layouts.
This also makes it very easy for you to wrap anything in any divs you need.
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