Original post by Morgan Ostrowsky
Why did you decide to do the Year On [formerly UnCollege] Gap Year?
I knew what I wanted to do, and I knew if I went the traditional route, I wouldn’t be able to do what I wanted until my junior year of college. I didn’t want to wait that long. And I wanted to do it in an awesome environment, so when I found out about Year On, it was obvious to me that I should do it.
How did your parents respond?
They were all for it. They were super excited for me. My older brother is into the same stuff as me, so he blazed the path for me and my parents saw that being entrepreneurial and pursuing a startup is something where people can succeed. And even if you don’t, great things come out of it. You can learn a lot, even from failure.
What are you working on during the Launch phase?
I’m working on my own venture that is yet to be named. It’s an online learning site that teaches 21st-century meta-skills through challenge-based learning. It’s a continuation of something I started in high school. I kind of failed at it back then. I’m looking to breathe new life into it with the help of Year On’s network and being in Silicon Valley around smart, like-minded people.
What do you think about coaching meetings? How have they impacted your progress during this phase?
Coaching is my favorite aspect of the program. Gabe is an awesome coach who really knows how to customize the program and set goals that are both challenging and achievable and make you go outside your comfort zone and stretch yourself to reach them. It has proven invaluable to me growing as an entrepreneur and restarting my venture
How do you think coaching will impact you in later phases?
Right now the hardest part of any startup is pushing the boulder up the hill. Once you reach a certain point, then you finally know what you have and what you’re doing. After that, the starting part is over and you can actually run the company. It doesn’t get easier, but it’s different than just starting up. That transition phase has different deliverables and coaching is helping me to set different goals as my business changes. I think the coaching will adapt as my venture evolves.
What do you plan to be working on in later phases?
I want to spend all my time working on my startup. I’m not taking a voyage. I wish I could, but it’s not what’s best for me and my startup.
What’s it like living with all the other fellows in the Gap Year House?
It’s not a big transition for me because I come from a family of 9, so it’s always been chaotic in my household. I’ve learned to live with others no matter how much of a slob they are or how particular they are because I’ve lived with both sides of that spectrum. And it’s awesome living with a bunch of self-directed people who think and do things differently. It’s definitely making it easier to be away from home, being surrounded by a bunch of totally different people.
How has the Gap Year program equipped you for the real world so far?
It’s reinforcing the idea that I need to lean on and sharpen my instincts, not just rely on external knowledge. And it’s showing me that real-world skills are what really matter. For example, the ability to communicate, collaborate, thinking critically - these are the skills that matter most in the global economy. A portfolio of your work speaks volumes about who you are as a person and what you can do. For me, personally, there’s more merit to a good portfolio than a degree from a university. I’m seeing it every day that I’m here. It’s great to know I’m putting myself in a better position with the skills I’m learning in the program. I’m confident that I’ll find them useful no matter what I’m working on.
In what ways do you think you will continue to be prepared by your experiences during your gap year?
The connections I’ve made here with current fellows and past fellows will be something I lean on well after the program is over. There are so many resources that will continue to be available to me. Whenever you need help or advice, someone from the past cohorts or the coaches or someone they connect you with has experienced the same thing as you, and they can help you along. Year On has an incredibly large network of professional contacts. And I’ll take with me the spirit of self-directed learning - that never leaves you. That will always be an integral part of me as I move forward.
Where are you going for your voyage phase? What do you plan on doing there?
The venture I started is about to take off. We have a product, customers, and orders to fill. And we’re making money. There are two things that govern every startup: growth and momentum. If you have that, you don’t stop. And right now, I have both. Even though I would love to do a voyage, at the moment it’s farther down on my list of priorities. The startup comes first and now that it’s in motion, no matter how much I want to go abroad, I have to stay here. But hopefully, I can travel later on.
Would you recommend taking a year off to other people?
Oh yeah. It’s a year to really discover what you love and what you’re passionate about and what you want to do with your life. Going to college straight out of high school blindly is a waste of money and time, two of the most valuable things we have. It seems more logical to take a year off and figure out what you want to do with your life.
Where do you hope this year will lead you?
Definitely running a successful startup.That’s been my goal since day one and that’s what I’m working towards and will continue to work towards. By the end of the year, I want to say I’m running a successful startup or company.
What are your plans for after your gap year?
I’m still figuring that out. I’m not ruling out college just because I think it’s a great social experience, a place to make friends, make connections, have fun and learn. But I also see myself continuing my startup, renting a place with friends and enjoying life. But I’m still in that phase of trying to figure it out.
What is your favorite memory so far?
The first night we got here. Seeing the house and meeting the people I’d be living with for 10 weeks, getting to know each other. Seeing how different we are, but how we’re all alike in that we’re all motivated, self-directed people who wanted an alternative to the traditional route. It’s cool. Definitely a melting pot, but we all are united in that quality which we all have in common.
What one word would you use to describe your gap year experience?
Uncomfortable. In a good way.
What is your favorite quality/attribute about the program?
Coaching and being in San Francisco. The beautiful weather. *laughs* You can’t beat it. I love this city so much. It’s great that the program is based here.
Who is the most interesting person you’ve met in SF so far?
I met a guy at the party we were invited to at the LinkedIn offices. He went to Harvard, dropped out after two years, started a company, grew it and sold it to another company. He got the golden handcuffs, so he had to work for the company that bought his company, and then that company got bought by LinkedIn and he went to work for them. It was really cool to hear that story of his journey from student to founder to working inside a huge corporation.
What is your favorite part of your weekly curriculum?
Coaching sessions. Every Monday, I look forward to my coaching sessions. They are what I love most. Gabe is the man! He’s the perfect coach for me since I can throw out a bunch of information and he responds with such clarity and insight. He listens and gives feedback and helps me set stretch goals. It’s been so helpful working with him to develop expectations, then I have to work my ass off during the week to meet those expectations because he keeps me accountable. Being pushed and challenged like that is something I didn’t get in high school, and I craved it. Now I’m getting full doses of that at Year On, and it’s great. Gabe’s the perfect coach for that.
What was the best event you’ve gone to during your launch phase?
We met two UC Berkeley students at an event about a coding language called meteor. We chatted them with about what we’re doing at Year On, then we listened to their stories and talked about coding languages. They were cool dudes. We all talked about what we are passionate about, and it was a nice mix of talking as friends and connecting. I wouldn’t even call it networking. That was the best event I went to.