Dropping Out For My Dreams

By: Megan Grassell, IATG ContributorJuly 5, 2016 


Hi Girls!

Alright, so this is my third piece for my I Am That Girl column, and am starting look forward to sharing more with all of you!

This month I want to talk about something I am asked about a lot… and that is, “Megan, what are you going to do about college?”

Well, let’s take a look at my high school and what the plan was (although at this point I’m sure you can guess things are not quite going according to the plan!).  I went to a very small high school; there were 17 people in my graduating class. It is called the Jackson Hole Community School, and I absolutely LOVED it. My teachers were inspiring, my classes were difficult but thought-provoking, and the community I was a member of gave me a feeling of belonging that I really loved.

I also grew-up ski racing. So my life was school and skiing, not much else. That also meant I worked very hard to earn great grades in school, and always knew I wanted to go somewhere far from home, cold, small-ish, that had a great ski team I could race for (looking at you, East Coast). In fact, my dream school was Dartmouth College. I met a girl who raced for them when I was in middle school, and thought she was the coolest, most badass person. I wanted to be just like her, which meant I had to be a fast skier and study hard in school.  

It’s important to remember that I had been working on Yellowberry since March of 2013, and college acceptances came in around April of 2014. Earlier that fall of my senior year, I realized I would not be able to race full-time, apply to colleges, do all of my schoolwork, and continue working on Yellowberry (which at that time was just a couple of samples and unfinished drafts of web copy). Something had to give, and I decided to give up ski racing. That was, and to this day still is, the most difficult thing I’ve ever had to do. Ski racing was a part of my identity so to walk away from it felt like I was saying goodbye to a piece of who I was. My coaches and my parents were kind of supportive, but thought I was crazy. I had a feeling about Yellowberry though…

To make a very long story short, and get back on track here, I did not get into Dartmouth. In fact, I did not get into a lot of great schools. As heartbreaking as that was though, I still had options. I ended up accepting a spot Middlebury College, and planned to start in February of 2015. That happened in April of 2014, which coincidentally is when Yellowberry began to really take off.

I ended up deferring once, as Yellowberry continued to grow.  And then a second time… and then this year in February I was given an ultimatum.  Either I was to come to school, or I would lose my spot.  I was not in a million years going to give up Yellowberry, but that meant walking away from one of the best colleges in the country.

I decided to give up my spot at Middlebury, but told myself to ask this question every single day:

“Would I have learned this today in college?” and if the answer was ‘No,’ then I made the right decision.  So far, I have been able to say ‘no’ each day.

This leads to an exciting new piece of information, which helps me feel more confident in my decision. I received a Thiel Fellowship, and could not be more grateful, excited, or proud! It's essentially a $100,000 grant to drop out of college (or for me, just to not go) for two years and work on your company.  

I remember applying, thinking no way I would ever be picked. Then I went into my interview, trying not to let myself get excited because there were so many qualified, smart and incredible people around me. But, when I received a call a few weeks ago at 10pm on a Saturday night working at my desk, I learned once again how important it is to not only have a big dream, but work as hard as you can to make it happen.

Until next month,



Making big, life changing decisions is stressful, challenging and emotional. Have you ever made a decision that went against the norm, was different then what others were expecting? How did it go, are you happy with how it turned out?


About Megan:

Megan_G.jpgIn 2014, Megan was selected as one of TIME Magazine’s 25 Most Influential Teens and included on Huffington Post’s list of 14 Most Fearless Teens. She has been featured in countless media outlets including The TODAY Show, The New York Times, Fast Company, Inc. Magazine, Forbes Magazine, Seventeen, and Teen Vogue among others. Megan has deferred her freshman year at Middlebury College to continue as CEO of Yellowberry.

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  • commented 2016-07-10 19:30:08 -0700
    About a month ago I made the decision to stop playing college basketball after 2 years. To everyone else it seemed like an out of the blue decision, but it was months long and mentally exhausting. Basketball was a big part of who I was and what I had identified with for 13 years! But it had become a job, and wasn’t fun anymore. It was causing so much stress and heartache and negative feelings that it had never caused before. As hard as the decision was I couldn’t be happier now that I made it! It has given me so much more room to pursue my other passions and get so much more involved volunteering and working with IATG! It was the hardest thing I’ve had to decide, but it was the right decision for me.

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