Flashback to 1982 - Ted talks about his dream of building skyscrapers, but there always being problems.
2006 – Ted is an architect, and he discusses his plans for his new building designed with columns, but his boss, Mr. Druthers, destroys his prototype. Mr. Druthers wonders when he will come up with an original idea. The older Ted tells the story about how Hammond Druthers was a legend in the architecture community, but a bad boss. Then, Ted came up with a great idea for a building and was suddenly Mr. Druthers's boss. Mr. Druthers is not happy with this new situation and Ted doesn't really like it. Ted likes being a regular employee so that he can play with the other employees, but now that he is the boss, his life has totally changed. He was constantly thinking about work and making enemies in the office. At the bar, Robin suggests that Mr. Druthers is good looking since only good-looking people can get away with that kind of attitude. Ted tells his friends that he talked to a managing partner and he offered that everyone should go, even Ted. When they get back to the apartment, Robin reminds Ted about when she had to fire her make-up artist. Ted tells Robin that he will fire Mr. Druthers tomorrow, but Barney interrupts them when he finds a naked picture of Marshall. Robin suggests that Marshall is embarrassed by it and then they decide to make fun of him.
When Mr. Druthers shows up late form lunch, he offers Ted some advice on the building, but Ted tells him that they should meet in his office, but the office shows up singing "Happy Birthday" to Mr. Druthers. When Marshall shows up at the apartment, Barney offers him a stool, Robin offers him a rose, and then Barney shows Marshall his new dart, which he runs together to sound like nude art. Marshall knows what they are talking about and then there is a flashback to Marshall and Lily in college. Lily has a nude session in art class, but Marshall doesn't want her seeing another guy naked. Lily suggests that Marshall pose nude, but they jump back to 2006 when Marshall tells them that he is destroying it. The painting is missing and they run out of the apartment and see the painting at the bar hanging behind the bar. Marshall tries to buy the painting back, but Carl, the bartender, refuses to sell it. Robin asks where they should put it next, but Barney tells them that he has plans for the next 5 years for the painting. Marshall runs and grabs the painting form behind the bar and runs outside with it. When Ted and Robin leave, Barney tells Lily that he thinks that the painting is great. When Lily mentions that the misses painting nudes, Barney suggests that she paint him. When Ted shows up at the office, he finds Mr. Druthers in his pajamas. Ted asks him what he is doing and Mr. Druthers tells Ted that he and his wife had an argument and kicked him out and then starts crying. Ted consoles him while he cries on his outfit. Ted wimps out and doesn't fire him, but tells him "Happy Birthday."
Mr. Druthers points out that he is an architect without a home, but Ted suggests that he go to a hotel. Mr. Druthers tells Ted that his wife is man-ish and is very self-sufficient. Robin guesses that he didn't fire Mr. Druthers when she find Mr. Druthers on the couch. Lily wakes Marshall up and tries to explain how they can get a better honeymoon. Lily suggests that they go to Scotland and Marshall lights up when he thinks of the Lochness Monster. Flashback to the bar when Barney asks for Lily to paint him, Lily is not sure about painting him, but Barney has faith in her abilities. Lily tells Marshall this story as she is flashing back to the conversation. When Lily tells him that Barney offered $5,000, Marshall loves the idea. Ted and Mr. Druthers show up at work friendly, but when the talk turns to work and the columns, Mr. Druthers makes fun of his idea. Ted brings Mr. Druthers to the side and asks him why he is not backing his column idea, but Mr. Druthers tells him that business and pleasure are separate. Barney shows up and tells Lily how he wants to be painting. When Marshall thinks about how Lily is earning the $5,000, he regrets the decision and runs to the apartment. When Lily gets to the nude part, Marshall walks in and tells Lily that he has found a better place for them to stay and wants more money. Barney offers $5,000 more and Marshall accepts. Ted finally tries to fire Mr. Druthers, but a few guys show up to serve Mr. Druthers with divorce papers. The rest of the office shows up to sing "Happy Birthday," but ted tells them to stop. Ted gets upset and Mr. Druthers has a heart attack. While he is on the floor, Ted fires him, thinking that he was faking. The EMTs bring Mr. Druthers out of the office on a stretcher and then Ted apologizes to the office. Ted then comes up with Margarita Fridays to not have everyone hate him.
Lily finishes her painting of Barney and Marshall and Lily leave the apartment quickly, but Barney walks out upset that Lily did not put his male anatomy ion the painting.