The Doubleton

Don’t pull an Eeyore

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Meet Dylan, a smart guy in his mid-20s who graduated from an Ivy League school. He comes from a pretty well-off family. Appearance-wise, he is definitely above average, and he is well-mannered. He speaks multiple languages fluently and tends to solve complicated tasks at work that others can’t handle. Dylan sounds like a pretty awesome guy, right? It’s not hard to imagine he’ll go places.


But, he actually struggled to advance his career. He has been with his company for a few years. Everyone sees his effort and potential. He was promoted to a senior officer in his second year with the company, but he wasn’t able to climb the corporate ladder any further. He wanted to be a people manager, but the management would not promote him.


Now, he has been with the company for three years and is still stuck in the same role. He thought to himself, “Perhaps I should equip myself with more professional knowledge.” He then studied hard for GMAT and got into his target business school for a part-time MBA. He thought that would show his employer that he is invested in his role and determined to move up. However, after he graduated, he did not get a promotion. On the other hand, his colleagues who joined the company either before him or around the same time were getting promoted or joining other great companies.


(You would probably think Dylan looks like this guy)


Well, what the hell happened there? Dylan has everything he needs to be successful. What actually went wrong?


There is one small thing I forgot to mention. Dylan isn’t the most positive guy out there. He looks gloomy most of the time, as if someone constantly pisses him off or as if he’s gone through multiple breakups simultaneously. He looks tired and his voice is so soft that it makes his messages sound uncertain.


Dylan looks unconfident most of the time, and that became a problem – people didn’t think his ideas were good (even though they were). Neither the junior members on the team nor the management saw him as a future leader. He would bring in negative energy when he walked into a room. No one wanted to share jokes with him. All the conversations he had with people were work-related.


The management joked about him being like Eeyore from Winnie the Pooh – the gloomy donkey who has the complete opposite personality of Tigger – the bouncing tiger with ADHD.


(Apparently all of the Winnie the Pooh characters represent different mental disorders, which I found pretty fucked up)


The problem with Dylan is that he wasn’t likeable, and that has a huge impact, not just at work, but also in his interactions with others. I’m sure we’ve all come across an Eeyore somewhere. I’m not saying being an Eeyore is an absolutely bad thing. It might be okay in certain roles in some industries, but it wouldn’t work for most, especially when you are in a commercial organisation.


Negativity is contagious. It spreads. In Dylan’s case, his management was most likely worried that if he were promoted, his team could become an “Eeyoreland” where everyone is negative.


So, what can we learn from Dylan’s tale of woe? 


  • A smile can go a long way. Even if you feel like your world is crumbling, plaster on a grin. It’s amazing how a simple smile can change the way people perceive you.
  • No one’s asking you to literally bounce around the office, but try to bring some energy and enthusiasm to your interactions. Positivity is just as contagious as negativity.
  • Work on your tone. A strong, confident voice can make even mediocre ideas sound brilliant. Practice speaking up
  • Share a joke, laugh at yourself, and don’t be afraid to show your human side. People are more likely to follow someone they can relate to and have a good laugh with.
  • Mind Your Body Language. We spoke about the importance of body language in one of our previous posts. Stand tall, make eye contact, and don’t cross your arms defensively. Your body speaks volumes before you even open your mouth.

Remember, most people don’t want to work in an Eeyoreland.