Ok finally figured this out (documentation isn’t very clear on this one)
If you have zero rows to start with you need to do this:
$field_key = “field_5657dffe586cc”;
$value = get_field($field_key, ‘user_24’);
$value[] = array(“career_enjoyment_id” => “Foo”, “career_enjoyment_file” => “Bar”);
update_field( $field_key, $value, ‘user_24’ );
The $field_key is located in the wordpress posts table assigned to the main repeater. Use the ID from post_name.