There's an event
Click to reveal..
where someone offers to get one of your peeps up another level in their career. I've had that several times where the peep is already a master, so it would be a waste of money. Also your peep might be almost on the cusp of reaching the next level anyway, so it's not really worth buying an upgrade.

It would be nice to be able to check the Details screen before deciding whether or not to accept.
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To err is human; to arr is pirate.