Meet Anna: Young Entrepreneur and Avid Punster Taking A Gap Year

By: Anna Nickerson | May 18, 2017
Topics: Gap Year Planning, Student Voices
Obviously I’m going to go back to school and be career-oriented. I’m not trying to just take a gap year and have no idea what I’m doing with my life.

As she gears up for her 9-month gap year with Winterline, traveling to 10 different countries and learning 100 new skills, Anna shares her thoughts on why she decided to take a gap year in the first place, and why traveling is so important to her.


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The concept of a gap year program is still new for many students. When were you first introduced to the idea of taking a gap year before college?

So, I have always been a year young for my grade. Ever since Freshman year I’ve aspired to do a gap year. But never really knew exactly what I wanted to do. This year when I was applying to all my colleges, I started thinking about it more seriously. And that’s when I started seeing online advertisements from Winterline and other gap year programs, getting serious about the idea, and talking to my parents about it.

But it’s kind of been something I’ve wanted to do all throughout high school.

At what point did your parents get on board?

Honestly, there wasn’t a whole lot of convincing I had to do. Both my parents are avid travelers, especially my dad. So they both understood the concept of it and were encouraging about it. Any time I told an adult that I’m taking a gap year or considering it, they’d say, “I wish I had done that when I was a kid.”

So, most of the time my parents were very encouraging about it. The main thing was figuring out how to pay for it. But other than that, they were very encouraging. There wasn’t much convincing to do, which was nice.

anna with family taking a gap year

Why did you choose to take a gap year?

I’ve always been the youngest kid in my class, which has never really been an issue, but something that I wanted to take advantage of it, having that extra year and not being put behind. And I just really love traveling.

I went on a service trip to the Dominican Republic for just 10 days. That was when I was applying to colleges, and when I started considering a gap year more seriously. It really solidified the reasons why I wanted to do it: you know, meet some amazing people, make great connection, travel to parts of the world independently, beyond just being on vacation with my parents.

What really attracted me about Winterline is the skills-based program.

Whenever I mention that I’m going on a gap year, people sometimes automatically assume it’s either a service trip or a vacation. And obviously I am taking a year off, that can be perceived as a vacation. But the way Winterline does it by teaching real life skills, that’s something important to me that I’m really interested in doing before going off to school next year.

anna taking a gap year winterline

What country on our itinerary are you most excited to visit?

Honestly, I’m excited for all of them! I think I’m most excited for Costa Rica. I’ve been speaking Spanish since 7th grade and it’s been one of my favorite classes every year. Going to the Dominican Republic, I got to practice my Spanish and see a different Latin culture. That’s probably what I’m most excited for.

What activity or learning experience captivates you the most about Winterline?

Just looking at the list of all the skills, and everything really, there hasn’t been just one thing that I’m super excited for.

One thing I’m excited for is all the people I’m going to be meeting. In the Dominican Republic, that was the main thing. It really didn’t matter what we were doing, but having those connections — these are friends that I still talk to. That’s one of the things I’m most excited for.

Another thing I’m looking forward to is the independent study week in Europe. I watched some Youtube videos of people that went on the Winterline gap year last year, like Jonathon’s and Molly’s videos. I really liked watching those.

It was cool to see how they viewed their time and what they did. There’s so much I could do, and especially independently. That would be such a great way to end the trip. So I’m definitely excited for that.

Anna taking a gap year winterline

Do you have an idea of what you would like to do in the future?

Yeah! I’ve actually deferred my admission to Babson College. I’m definitely on more on a business track. In my high school, we had this program called High School of Business. Since then I’ve been taking 1-3 business classes each year, and I’ve been involved in business clubs, and both my parents are in business.

I was the CEO of a social enterprise this year for our school. It was a really great experience to see how I could apply all my business knowledge the past four years to an applicable, real-life business. I’m definitely more on the entrepreneurship track. But I don’t know what I’d do with it. I am really interested in social enterprise and marketing, not so much finance.

But I do really like combining my passion for business with a social cause. I think that’s really cool.

You’ve traveled before. Which trip was your favorite and why?

The Dominican Republic was the first trip where I was out of the country by myself — definitely one of my favorite trips. I went with one of my best friends. I’d even say that was my favorite trip ever. I’ve been with family to England and Wales, six years ago, with my dad and brother. We have family there. It was really beautiful.

We also went to Costa Rica a few years ago. One of my favorite parts was seeing Mt Arenal and going to the hotsprings there.

What do you expect to gain from your gap year program and while traveling abroad?

One of the things I hope to gain with my gap year — I’ve been on such an academically focused track. I’m top of my class. And focusing entirely on school is one of the main things that causes stress in my life. That’s been very difficult to balance. And I’m definitely not burned out. But I think taking this gap year will be a great refresher for me, to realize some of the things I’m passionate about that I’ve almost forgotten about.

I think it would be really awesome to step away from school for a bit. Obviously I’m going to go back to school and be career-oriented. I’m not trying to just take a gap year and have no idea what I’m doing with my life. But it will provide me with clarity on things that I’m interested in, and help me step away from being so academically focused for a bit. That’s one of the main things I’m looking forward to.

What is one thing you want your future Winterline peers to know about you?

I’d say, in terms of my personality, at first I come across as very introverted — just because I’m going to be put into new and uncomfortable situations and I’m going to be shy at first. But with my friends and when I open up to people, I’m a genuinely outgoing and extroverted person. A lot of people think I’m really shy at first, but I’m just trying to get to know you and be observational.

I want to make lifelong connections on this trip. I’m definitely open to hearing from other people, hearing their stories. And I’d encourage my Winterline peers to be very open with telling me about themselves. I’m a trustworthy person.

Tell us something fun about you!

I am surprisingly quite a jokester. I don’t think a lot of people know that. But I have a weird obsession with puns, and I’m constantly making up my own jokes and puns. That’s something my friends give me a lot of crap for, but I know that they actually like it.

So that’s something interesting with my personality, I guess.

And finally, Coke or Pepsi?

Coke. But I’m actually not a big soda person. So, I’d honestly say neither.


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2 Comments

Lura 5 months ago

I’m with you – coke all the way! Hope you have an amazing gap year!


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