This achievement is story related and can't be missed.
*** Spoiler - click to reveal ***In the present, let Bernard pick up the flyer in the starting room on the lower left of the screen from the flyer stand.
Flush that flyer to Hoagie. Have Hoagie put the flyer in the suggestion box where the Founding Fathers are. That will make a vacuum cleaner appear in the basement in Laverne's future.
After you got give the Club Tentacle dinner prize to the guard in the kennel. Turn off the force field and after you got put the cat in the prison cell.
Now you're free to go throught the grandfather clock.
After you got , and use the sweater with the hamster. Put the hamster in the generator and watch the cut-scene.
Then use the vacuum cleaner with the hamster in the mouse hole to unlock the achievement.