You've answered the question!

A player could make the effort to develop a long checklist of sensible things their character does before going drinking/delving/dancing etc. Now, ideally they'd do this because such a strategy is something their character would do - such behaviour might suggest their character was lawfully minded, in terms of planning and organisation, sensible and disciplined. Or it could be taken to extremes, with compulsive list making and checking, fretting and panicking.
Of course, if a player adopted such a strategy for a character when it was clear that is was not appropriate, we'd call them on it and ask them to either not do so or recognize the difference between the character they to be roleplay and the character they're actually roleplaying.
(To my mind, they'd be attempting to, 'win' rather than, 'roleplay.) An example might be a player claiming their character is a thuggish, loud mouthed barbarian pirate with an average to low Wisdom score. Such meticulous planning and list-making seems unlikely for such a character and as such, a player claiming that said character 'always' adopted such a strategy would be challenged.
Of course, if they wished to change their character to a thuggish, loud mouthed barbarian with an average to low Wisdom score who delights in make meticulous lists and developing/adopting various safety protocols in response to danger, then hey, we're all good!
Saying this, I believe it is important to note the difference between attempting something and actually doing it. Continuing with our example of the loud mouthed barbarian pirate - a player could readily claim such a character has adopted a strategy of meticulous list-making and checking.
(Perhaps the character was influenced by a particularly wise and charismatic cleric when they were you, or are operating on the wise words of a loved one?) However, with their character's background, attitude and Wisdom score there is no guarantee they'd have the discipline to reliably employ their strategy*. In this case, we could ask for straight-up Wisdom checks to
'remember to make and check their list' or what have you, as needed. Ideally though, our player should take the responsibility of faithfully portraying their character on to themselves and represent their character appropriately.
(And the battle between a strategy of care, discipline and foresight versus a character whose nature is chaotic, reckless and short-sighted could be rather awesome!)
*..another example would be a player roleplaying a 'devestatling charming' character who has Charisma 8 and no Persuasion skill. The player is welcome to communicate all manner of carefully planned and considered social strategies in order to net some tasty Advantage. However, with such a stat line and skill set, they should not expect such strategies to succeed, at least not reliably!