If it doesn't trigger that first step, once you're satisfied that you've completed it along with all the other steps in that milestone you could use the 'Complete Aspiration Milestone' cheat, which completes all the steps in that milestone and moves your Sim onto the next milestone in that aspiration.
Just type "aspirations.complete_current_milestone" without quotation marks into the cheat bar when you're ready.
AFAIK using the cheat still gives you the lifetime aspiration points you'd have got had you completed the milestone 'naturally'.
I use this cheat a lot because I find a lot of the aspirations seem to glitch and not trigger when they should. I had my teen Sim leave and rejoin their after-school activity three times before I gave up and just cheated it for their Goal-Oriented aspiration.
