Lily Aldrin went through quite a few job changes in How I Met Your Mother, and some of her career decisions were definitely better than others.
Best: She Was A Great Kindergarten Teacher
Even though Lily was not completely at peace with the choice of her career as a kindergarten teacher, she was clearly very good at it. She cared about the children in her class. One could argue she was actually too kind to them.
When she was supposed to be their basketball coach, she just let them run around and do whatever they wanted. Her approach was a bit too permissive; not because she didn’t care, but because she couldn’t bear to discipline them and make them feel any ‘negative’ feelings.
Best: Selling Her Paintings To Make Money For The Apartment
What seemed to be one of the worst career decisions at first turned out to be a surprisingly decent source of income. In order to make money for the apartment she was buying with Marshall, Lily decided to sell her paintings on the street. Eventually, she found two buyers, but as it later turned out, they were only interested in the frame.
Best: Becoming The Captain’s Art Consultant
The Captain was one of the shows best recurring characters , although Ted didn’t appreciate his existence one bit. After all, he was married to his romantic interest, Zoey. Lily, however, was very lucky to meet him.
The Captain was a wealthy man and an avid fan of fine arts. He made an offer Lily couldn’t refuse and so, she became his art consultant.
Best: An Art Consultant – In Rome!
Lily had dreamed of living abroad from the beginning of the show, so it’s only fair that she took this once-in-a-lifetime opportunity. She tried following her dreams many times before but always failed. It was nice to see her thrive for once, even though Marshall had to put his plans on hold. In the end, he became a judge anyway, so nothing was lost.