How did you get connected with Winterline?
After a year of teaching in a classroom, I realized I should teach in the way that I learn best - not in a classroom. I started calling up everyone I could find who worked in experiential education to ask them how they got there, what their jobs are like, and what advice they had for me. This landed me at a company in Boston that matches students with different types of enrichment programs. My job was to talk with everyone in the field, which connected me to running programs internationally and selling programs directly to families. I first heard about Winterline from our Vice President of Marketing and Sales; we worked together in Boston a few years earlier.
Moral of the story: talk to everyone, and stay in touch!

Ben Sandboarding in Morocco
Why do you think it’s important to promote the education of "global citizens"?
It’s 2017! Countries, cultures, religions, economies, people, lions, tigers, and bears are all bumping into each other more than ever. We have a unique opportunity to use thousands of years of values and experiences to create solutions to the world’s challenges. It’s also getting harder to ignore these challenges.
Whether you like it or not, you are a global citizen. It is essential that we all do our best to become educated global citizens so that we not only keep from harming each other, but actually improve life for everyone.
When used correctly, a gap year should at the very least give you perspective on the challenges facing the world, if not the solutions to these problems. Gap year programs approach this lesson differently. Some provide service-learning abroad, but Winterline teaches real-world skills so that you have the tools to approach these challenges in your own way.
What does a typical day of work look like for you?
One of the best things about my job is that there is no typical day. My goal is to find the best people for our programs, and there are so many places to look! About one third of our students come from outside the U.S., so some days I work with academic advisors, educational consultants, and schools in multiple countries. Other days, I’m presenting at schools about my own travel as a student or exhibiting at conferences. I even meet with families at their houses to figure out which program will be for them! This job is the coolest.
You took a gap year yourself. How do you use this experience in your current role?
My gap year was the best decision of my academic and professional life, so of course I want other people to take a gap year! Storytelling is a huge part of my job, whether I’m talking about how teaching in Peru sparked my interest in education, or how stumbling into the unknown has helped me enter new life phases with confidence. I made my fair share of mistakes on my gap year, so I’m a pro when speaking with families about what not to do, and what resources are available to help build a safe, productive gap year. I wasn’t very excited about my education in high school, so I love working with students who feel similarly, since I can give them hope that they will find their love for learning.

Ben in the Azores
What makes Winterline different from other gap year program providers?
In my opinion, Winterline is the biggest gap year program in the world. In over nine months, students travel to 10 countries and learn over 100 real-world skills. I know of no other program with as much breadth or with such clear deliverables.
We help create confident, competent people by taking them out of the classroom to learn hands-on skills that will be useful throughout college, career, and life. The program’s breadth also allows students to experience a variety of life paths in a relatively risk-free environment so they can figure out what they want to pursue, and what they don’t want to pursue. It can save them from the wrong major or career path, and in some cases, even uncover a path they wouldn’t have considered otherwise.
How can gap year programs affect student's’ future personal and career growth?
Winterline goes way beyond “cultural immersion”, which doesn’t really tell you, your college, or potential employer what you’re capable of doing. Instead, you will have a long list of competencies and experiences that will show you and your future employers the kind of person you are, and what you will bring to your work. The program’s breadth constantly introduces you to the unknown, helping you build confidence for when life throws you curveballs. Winterline also partners with global leaders in many of the skills you’ll learn, so it’s a fantastic place for networking and resume building.

Ben in the Galapagos
What is the best advice you have for parents who are hesitant to let their children take a gap year?
The best advice I received before my gap year was the advice my college counselor mother gave me: do it, but apply for college along with all of your friends, and then defer for a year. Otherwise, I would have spent most of my gap year sitting at her kitchen table, stressing out about college applications. Deferring before a gap year removes the risk, since your children will already know they are into school, and in most cases they’ll know what aid they will receive when they return to campus.
The most common fear I hear from parents is that if their kid takes a gap year, they’ll never go back to school. That couldn’t be farther from the truth. Statistics show that 90 percent of gap year students return to college immediately and graduate at a faster rate than their peers.
My gap year got me so excited to learn that my first semester of college was my highest GPA yet! Just be sure that your child’s gap year plans are responsible and productive. Look for programs that provide academic resources, safety and risk management, and a breadth of experiences that will lead to better focus when he or she returns to school.
I totally understand that there used to be a stigma around gap years, but that stigma is gone. Colleges recognize the benefits, and almost all of them encourage gap years. College is increasingly expensive, and schools are now measuring “success” as graduating within six years. That is four extra semesters that most families don’t budget for! Give your children the opportunity to go to college because they want to go. Their growth over one year will amaze you.
Describe the ideal Winterline participant.
Winterline students are pretty self selecting, which makes my job easy. We travel to 10 very different countries and teach over 100 skills. Nobody is an expert in every skill, and everyone will reach outside of their comfort zone. People are either turned off by this, or totally fired up. We want the people who are fired up to try new things, see new places, and meet new people. Attitude is absolutely the most important factor in our admissions decisions.

Ben Completing all New England 4000-footers
What is the best part of being the Director of Outreach & Recruitment for Winterline?
Only one best thing!? We have the coolest, most competent team of people who all bring something unique to the program; I love the people of Winterline. Our program is also super fun to talk about, since no one is doing what we do. My job brings me to many different places, where I get to meet fascinating people with wonderful stories, who have ambitious goals. I love that I get to show them options that will change their lives.

