Happy & Ambitious? How to be Both?

Bill and Robin were young boys who wanted to be successful and happy. 

Bill was anxious about the future. He developed a statistical process to reduce making mistakes to achieve his goals: being successful and happy. He thought he needed money or status to be happy. Bill thought when he had those things, he would achieve his goals. 

Robin also had similar goals. He had a different strategy and he focused on living presently. He knew that success and happiness could not be pursued because they ensued. He was happy with the little he had. Robin didn’t have goals or ambitions, he went with the flow.  

Bill came back to visit his parents and saw Robin buying groceries. Robin was happy to see his friend Bill, Robin asked him where he lived and what his job was. Bill says he became an investment banker at a prestigious bank in New York City. 

Robin now knew why his friend looked like he was 10 years older.

Robin told Bill that after graduation he traveled the world for a year. He met his wife in Thailand. Robin says he works as a local tutor and teaches music. He does that part time during the school year. During vacations, he along with his wife and kids travel the world. 

They talked for a bit and decided to meet next Wednesday for coffee.

Bill and Robin met at the local coffee shop. They wanted to ask each other how they were truly feeling. But neither of them dared to ask that question so they talked about memories, family, work, and the usual boring small talk stuff. 

Then, Jermaine entered the coffee shop. When Bill and Robin saw him walk across the coffee shop, they asked each other whether he was the person they thought he was. He walked with the confidence of Tony Stark and expressed kindness by the feature of his face.

Jermaine also went to the same high school. Jermaine was one of those “weird kids” when he was growing up. He was a person who was smart, but who treated school as a day job, meaning he did well, but was focused on other projects. He was competitive in school and sports. He was also creative, ingenious, and wicked-smart. 

When Jermaine walked in, he didn’t see his old high school friends.On the way out, he saw his peers talking to each other. He thought, “Is that one the kid (Bill) who wanted to get all A’s and was anxious about everything? Is he also talking to the happy-go-lucky kid (Robin) who barely went to his classes?

Jermaine stopped by and started talking to Bill and Robin. He asked how they were doing. Jermaine also asked whether they still lived in town. 

Bill and Robin asked what about Jermaine’s job. Jermaine said that he graduated from college and that during college he started working with science professors. He patented inventions and sold them. Also, during his time there he created companies that were sold and one that he still has, which sells real estate in the virtual world.

Jermaine said he would stay, but he had a meeting with clients. Jermaine told them they should come over to his house to meet his family. 

Jermaine left. 

Bill and Robin were baffled. They couldn’t believe this guy had achieved this level of success. 

Bill and Robin had a weird feeling between them. They knew they weren’t truly happy and had a bittersweet feeling. 

It was regret.

Bill and Robin spent about two hours talking and promised to stay in touch.

They couldn’t stop thinking about Jermaine. 

An Unknown Alternative

Bill is an example of insecure people who use “success,” money, and hard-work to ignore his reality and his true feelings. People like Bill aren’t and will never be happy because they will never have enough of what they want. 

They are insecure because they think having X will give them Y. Bill always wants more and more. Therefore, he doesn’t enjoy what he has and is never happy. 

Robin is the other extreme. You may even think he is one of the good guys of the story. He is supposedly “happy.”

He knows he needs nothing to be happy. He decides to be happy and he is. Because of that, he doesn’t want more in the future. While Robin thinks he is happy, in reality, he is running away from his reality. 

Just as Bill ignores his reality by working hard, Robin ignores his reality by thinking he is happy if he travels and works part time. 

Extremes ended up having the same outcome. Here, never being happy. 

Robin and Bill use the perspective of imagining the other's life as a way to understand their regret. 

That is how most people approach their life. You either work hard and maybe you will be happy. Or you are “happy” and relax. 

This is how we think. This is how humans think. We think in terms of either A or B, either X or Y. 

We think we cannot get both A and B or X and Y. 

If you’re thinking of choosing. Choose both. 

As Bill and Robin were talking and having a conversation. Jermaine shows up and just by looking at him, you get a different vibe.

You can appreciate what you have, but you can also have aspirations. 

Jermaine didn’t wait for something to be happy. He appreciated what he had, but wanted more in the future because he believes he could help people. He didn’t want more out of vanity.

We don’t see this often, we mostly see people like Bill and Robin, but not many Jermaines. 

Jermaines are both happy and ambitious, grateful and motivated, and thankful and determined.

Let’s try being like Jermaine!



Thanks to Dipan, Charlie, JC, and Prianka for reading drafts of this essay.

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Tags: philosophy