Most would agree that The Office has been one of the most endearing television shows to grace our screens for some time. The parody of our day-to-day workplaces manages to be outlandishly humorous and endearingly sincere at the same time. Despite not having aired a new episode since May 16, 2013, The Office maintains a huge fanbase.

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Much of the hilarity found throughout this series revolves around Michael Scott. Michael is the branch manager for the Scranton branch of a paper company known as Dunder Mifflin. Throughout the series, Michael makes several questionable decisions. Here are 10 that left us scratching our heads and taught us a lesson at the same time.

Dating Jan

When we first see Jan Levinson, she is depicted as the distant boss of Michael, who tends to have little patience for his humor and incompetence. Jan expects Michael to act according to his role in the organization, typically ing only professional actions which benefit the company.

Jan and Michael’s relationship develops through the second and third seasons of The Office, beginning with an ill-fated night in a hotel room following the successful persuasion of a potential client. Their relationship builds and eventually crashes. Over the course, Jan loses her job and Michael is repeatedly placed in horrible situations. This teaches us the potential horrors of office romance, as well as the dangers of relationships which begin while intoxicated.

Michael’s Condo

For many, one of the ultimate goals in life is to become a homeowner. This long-term goal solidifies one’s ownership of a piece of the world. Three episodes into the second season, Michael accomplishes this goal, but there is a litany of issues involved in the process.

For starters, Michael seems to be disappointed by the price of the condo. At this point in the series, Michael has clearly shown his distaste for Dwight, yet he offers Dwight residence in exchange for rent before Dwight unintentionally changes his mind. When Michael attempts to walk away from his realtor, he is reeled back in by the potential loss of money. The first lesson to take is that smaller amounts are generally negligible over the course of a 30-year mortgage. The second is to weigh these investments with your income before committing.

The Michael Scott Paper Company

This might have been a great decision, given that Michael was offered as much as $60,000 for this failed venture, but let’s not lose sight of the actual result. Michael, Pam, and Ryan all ended up working for Dunder Mifflin in the end. Ryan even became a temp again. Pam benefited in the sense that she became a salesperson, but this was largely pointless.

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Neither Michael nor Pam was forced to leave Dunder Mifflin. Michael resigned due to issues with Charles Miner. Pam essentially left because she was bored in her current role. Everything worked out for all three, but it came very close to failing. The lesson here is to make sound decisions regarding your future.

Holly

We don’t mean that Michael’s relationship with Holly was a mistake. Clearly that turned out fantastic. What we’re referring to is the hardship that Michael and Holly put themselves through because of their schoolyard PDA exhibits.

We’ve all had new and young love. It’s a beautiful thing. Most of us have even fallen into the trap that Michael and Holly did – displaying our love publicly. The thing to learn here is that you can’t broadcast those affectionate gestures in the modern workplace. As a result of their action, Holly was forced to transfer from the Scranton office, and Michael and Holly broke up to avoid a long-distance relationship.

Threat Level: Midnight

Michael firing two guns in The Office

To be clear, Michael’s screenplay was amazing. It was the perfect comedy skit that we didn’t know we needed. It added the perfect break from the typical tone of the series. But we’re trying to emphasize with Michael the character. We don’t think that Michael appreciated the opinion of his employees.

To be clear, we aren’t referring to the episode in season seven with the same name. We’re referring to an earlier sequence from season two. We’ve already examined Michael’s success with Jan while the two are out with a client. Back at the office, Pam finds Michael’s screenplay and shares with everyone for a read-through. Michael made two mistakes here; leaving the screenplay accessible and casting his loyal employee Dwight in a negative light.

That Joke

Kelly wearing a blazer with gold sequins as she smirks in The Office.

Rule number one around the modern workplace is to be as inoffensive as possible, that’s why a good rule of thumb is to never discuss religion or politics. Among the list of things which should always be avoided are slurs of any kind, especially racial ones. On his climb up the corporate ladder, Michael must have missed that one.

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In the cringeworthy second episode of The Office, we find out that Michael has been repeating a racially charged skit which he saw Chris Rock perform. Included in the skit is a racial slur which could easily offend half of his workforce. As a result of his actions, everyone has to undergo diversity training. Michael still doesn’t learn this lesson at the end.

His Description Of Prison

Prison sucks. We all know it, and so did Michael Scott’s alter ego Prison Mike. Due to the statement that prison is better than the office, Michael introduced the group to Prison Mike, who explained prison life in a misguided detail. While he was right that prison life isn’t enjoyable, we’re not sure about the Dementors.

As Prison Mike, Michael is mocked by those around him. He is questioned about things he doesn’t know in an effort to expose his ruse. Michael should have stuck to the facts and used his own experiences to win over his workforce. It would have been much less embarrassing.

Running Over Meredith

The Office

Kicking off the fourth season, Michael is giving an update on where he is in life as he looks toward the camera and inadvertently hits Meredith with his car. This prompts corporate to worry that Meredith will file a lawsuit and cost the company money. Michael assumes the worst and seeks to avoid catastrophe through animal sacrifice.

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We should always pay attention to the road while we’re driving. Neglecting to do so is dangerous for ourselves and those around us. An incident of hitting another person through negligence could be a serious criminal offense which no one would choose to endure.

Outing Oscar

Since we already discussed Michael’s offensive history with racial slurs, we would be remiss in neglecting his insensitivity to sexual discrimination. A full season before he would run over Meredith, Michael managed to not only reveal Oscar’s sexual orientation to everyone at work, but to also offend him once it was in the open.

While everyone is entitled to live their own life, no one is entitled to force others to reveal their truth to others. In this example, that is exactly what Michael did to Oscar. To make matters worse, Michael very seriously harassed and even assaulted Oscar sexually after. This is an easy example not to follow.

Scott’s Tots

A classroom of students in the "SCotts Tot's" episode of The Office

Scott’s Tots was a group of inner-city children who Michael once promised to send to college once they came of age. Unfortunately for Michael, they never forgot his promise. In fact, they banked their future on it. Unfortunately for these kids, Michael never obtained the wealth to fulfill his obligation.

The lesson we can learn here is to never promise something that we are incapable of providing. Michael thought he would be more advanced in his life that he was when these kids were ready to begin college. His inaccurate assessment potentially destroyed the future of a whole group of young adults. This is easily one of the worst things Michael ever did.

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