Pursuing Your Passion

Pursuing Your Passion

Quick, what makes you so excited that you could be immersed in it all day? On the flip side, what do you hate doing the most? These two seemingly obtuse questions are related to the two most important concepts of your working life-pursuing your passion and excelling at it.

Most people think that when you pursue your passion, you’ll have fun for the rest of your existence and “never work a day in your life”. There is also the common belief that if you get to pursue your passion, you won’t have to worry about working hard to become really good at what you do-it will all just happen naturally. Welp, that’s wrong, wrong, and more wrong.


I’m going to put two pictures on top of each other. Let me know what you think:

Clearly, we recognize these people-Kanye West and Lil’ Wayne. We see these two as the fortunate gentlemen who were able to get obscenely rich off their passion. Most see it as pure luck and a little bit of hard work. What people fail to realize is that despite their prodigious talent, these two guys literally make their time in the studio like a full time corporate job and some. Kanye will only stop working to take a 2 hour power nap and Lil’ Wayne won’t leave the studio until he has sufficiently knocked out a few final version tracks. In other words, “If you truly love something, you will give it your all.”

Of course, this sounds easier said than done. These people are clearly celebrities and their work paid off in the end. It was a simple journey. Ah, so you think that this doesn’t happen to normal people. Let me show you another picture. Then I’ll tell you a story:

Do you recognize this guy? Probably not, but this is my good friend, Sean Castillo. Sean is a community strategist at Chegg and he writes and manages the content on Chegg’s high school blog, More Than a Test Score. Sean is the epitome of passion combined with hard work. You see, Sean went to college so he could be a creative writer. It helped that Sean is an amazing writer already. He even managed to help start a magazine. However, like all college graduates, Sean wanted a steady source of income. He began working at a company called Zinch.


At Zinch, he began to help find and create scholarships, contact winners, write blog posts, and did a lot of accounting assistance in between. Sean will tell you quickly that numbers are not his favorite thing. However, Sean recognized that to continue doing the part of his job that he loved the most, writing and helping kids, he still had to do other things in order to pursue his original passion of writing.

I’ll tell you what, in addition to writing excellent content and helping build the site, Sean would also double up on work by making sure he kept track of the budget, while helping accounting with processing checks, among various other things. At one point, he was writing every single blog post on the site. He was doing the work of 3 people. Because of this, Sean got better at his job and learned new useful skills that have made him the successful, well-rounded person that he is today.

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Because he did not give up on his passion and worked at it constantly, Sean has been able to now focus most of his time on his original passion and skill set and help millions of students and parents navigate high school while preparing for their next phase of life. He is the living embodiment of the fact that you won’t necessarily start out working with your passion, but if you have a good attitude along the way and only focus on getting better, you will achieve a breakthrough. Sean trained me when I first started at Chegg and has been a great source of support for me, using his non-writing skills that he learned to help me become a better professional and helping refine my individual skills. Like Kanye and Wayne, his passion is now extending to me and helping fuel my passion. It sounds familiar:

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