Reflections, Career Growth, and Personal Development During a Gap Year | Remote Students
Members of the Remote Students Community had the opportunity to meet Kelvin Yu, Matthew Maiale, and Shannon Yang this week and ask them questions about their experiences taking a gap year. Apply here to join our community and meet our amazing lineup of guest speakers, including people like Kelvin, Matt, and Shannon!
Kelvin is a Princeton ’21 studying computer science — after his sophomore year, he took a gap year to work across three startups and a venture capital firm in San Francisco. He’s currently a software engineer at Puzzl (YC S19) and co-founder of Prospect Ventures, Princeton’s first and only venture capital club.
Matthew currently attends Penn State University where he studies finance & economics — he started his gap year last spring to work in venture capital and is currently Operations at Demand Curve (YC S19). He’s also president of Happy Valley Capital, Penn State’s student-run venture capital fund.
Shannon studies Philosophy, Politics, and Economics at the University of Oxford — during her gap year between ‘17-’18, she participated in Global Citizen Year in Thies, Senegal where she lived with a host family, undertook English teaching, NGO apprenticeships, and studied French/Wolof. During that time, she also co-founded e-JangRadio, a radio show that aimed to help students without access to the internet learn English and discuss social issues, a project which raised over $2500 in crowdfunding and won the T-Mobile/Ashoka Changemaker Challenge.
What were some key reflections and takeaways from your gap semester/year?
Kelvin: What I realized, after the fact, was that I should have left my first startup internship two months earlier. A gap year is such a special time where you have complete freedom to design your own learning schedule and set your own goals. If you’re working somewhere for fifty hours a week, you’ll learn 80% of what you need to learn within the first three months, but after that point, it becomes much more about execution than learning. And so I reached a point where the learning curve started saturating but I stayed on for two more months — I wish I had left that earlier to do something else. Taking a gap year is great as a personal career accelerator, but make sure you chunk it up into two, three, or even four things.
Matthew: One of my biggest takeaways was that while I’d entered my gap year focusing on career development, I think I probably got more personal development out of it than actual career development. I really think taking a gap year is about experimentation and rapid iteration. It’s a great opportunity to see what you love and don’t love. It lets you step back from all the normal mantra you go through to actually think about what you enjoy. I was able to learn about what my personality matches with and the kinds of companies/people I enjoy working with. It’s something I’m a lot more cognizant of now, and probably something that will save me a few years of not going into say, banking, or some other field that I thought I could probably fit into but not really. So I feel it’s more about the iteration and setting yourself up to go in the right direction.
The other thing I would emphasize is that you don’t necessarily need great opportunities to go into a gap year. I honestly think the most important thing is to learn new skills, like technical skills. They’re very important because those skills compound.
Shannon: I think one thing that I wish I had done a bit more of was to keep reflecting on my goals throughout the gap year, whether that’s personal development, friendships, or career goals. I think it’s really important to take time and think about these goals, write it down, have some chats to talk through them and refine them. Ultimately, you want to know why you’re taking this gap year and which skills you want to get out of them. That way, you can tailor your time towards them.
The other thing is that the learnings you have don’t necessarily have to be in structured environments. There’s many ways you can do a gap year, whether through internships, a program, or not at all! It’s really about what you’re learning instead of how it might look, and you can take any opportunity and turn it into a valuable learning opportunity. That said, I also wouldn’t discount rest. It’s not about getting a lot, it’s about doing what you can do to thrive in the future. Recognize there’s a future for you so don’t burn yourself out in the present.
How did you structure your gap year? Was it planned in advance or done on the fly?
Kelvin: I took my gap year not knowing what I was going to do. I submitted my paperwork in April and I spent the summer sending out a few cold emails every week. The internship I ended up committing to was something I was referred through by a friend, so that’s how I started. Initially my friend told me I’d be working on business development and expanding their sales team in China, but then I ended up doing a bunch of other stuff. In terms of the actual stuff I learned during the gap year, a lot of it was unexpected. Didn’t really expect to do growth marketing at all, but we got to work with one of the top growth hackers in Silicon Valley. Then, I got my Puzzl internship through the people I met during my first internship, so I’d say my gap year was relatively unplanned.
Matthew: Mine was pretty unstructured — I knew I wanted to take off the spring semester but didn’t really know what I was going to do. I didn’t even get the opportunity until midway through my finals week which was, yeah, pretty hectic. I found my housing in San Francisco within a week and committed to my first opportunity after Kelvin interviewed me for it. It was stuff that I figured out very last minute, but coming into the fall, I knew I wanted to do something new. I didn’t really know what so, like Kelvin said, I decided to take time off and go search for opportunities. For that, I think building a network is something that’s really impactful and one of the easiest ways to find new things. Developing that network of close people who can throw opportunities your way is a great way to structure your gap year. Surround yourself with the right people, people with the right mindset, and opportunities will come from that.
Shannon: For me, it was a mix of being both spontaneous and planned out. For my government internship in the Bay Area Air Quality Management District, I got that through connections from an environmental advisory board that I was a part of in high-school. They sent out the internship to me that way — it was a little last minute, but turned out to be a great experience. As for my trip to Senegal, I’d committed to that program since fall of my senior year, so I was pretty sure it was happening. I was supposed to go to India, but because of visa issues, I switched to Senegal.
One reassuring thing I’d say to everyone that’s hoping to do last minute internships is to reach out to your network! I reached out to my LinkedIn network and explained the situation — “I was supposed to go to India. Didn’t work out because of the visa and now I’m considering staying at home, doing a gap year, and taking on some internships.” And tons of my connections gave me opportunities, whether they were startup founders or knew someone that was.
Anyways, I went to Senegal and a lot of the programming there was planned in advance. I was lucky to have a program, but in terms of social entrepreneurship and the other projects I took like, that was all very spontaneous. A lot of it just kinda happened, but I did have to actively seek them out. If you want to do social entrepreneurship, for example, try to find mentors, people to pitch to, venture capitalists, and others along those lines.
When I got back from my trip in April, I wanted to make use of my time before Oxford started in October. A lot of the stuff I did in that time was spontaneous — getting a job as an ice cream scooper, being a camp counselor, and so on. Just be okay with uncertainty, be open to new opportunities, keep your schedule open, and keep your network open too.
I feel that I don’t have the right skills to contribute meaningfully to an internship. What can I do during my time off to develop skills and help advance my career?
Matthew: I came in with much fewer skills than, say Kelvin, so all I really had going for me was a gritty attitude. When I first started finding opportunities like my internship at Puzzl and another company in Switzerland (they were both unpaid opportunities), I just said, “I really want to learn new skills and really like what you guys are doing. Is there any type of role that you guys have available that I can help you guys out with?” And honestly, people are really receptive to that. You’d be surprised at how rarely people put themselves out there. So get comfortable with being uncomfortable and just put out a lot of asks. There’s not much downside to it and people are usually going to be very open and receptive to your help. It was easier for me because I offered to do it unpaid, but if you’ve got skills of higher value, you can ask for paid work. There’s also a lot of little things and skills you can build upon like CRM management, growth marketing, and content SEO. It’s non-technical but really needed for the development of early-stage companies. All in all, I’d say find an opportunity where you can learn on that spot and find stuff where you can learn really quickly.
Shannon: People are willing to give you a chance! As long as you’re passionate and willing to get behind their idea/vision, they’ll be willing to have you onboard. One way to figure out what your skills are is just to ask your friends what you’re good at — those skills could be as simple as emailing people or being very organized. And especially if you don’t have technical skills, they’ll want to see your strengths in non-technical skills. A lot of political offices have intern positions where you don’t need to know a lot about policy; they’re just operational roles and that goes for a lot of startups and other various industries.
Kelvin: Agreed. When you’re reaching out to these companies, make sure they can see the grit in you and that you’re a hard worker. The way I did that was by reading up on the company, their vision, TechCrunch articles on them, and integrate those insights into my outreach email. Whenever you’re selling anything — in this case you’re selling yourself — you really have to emphasize the value you can bring and the synergy you have with them.
How do you balance depth and breadth during your gap year?
Kelvin: With any opportunity in college — whether that’s a club, part-time job, or internship — I like to use the learning versus execution axis. As with switching contexts from internship to internship, I think it’s a good thing because you’re running into friction, which means you’re doing something you don’t know how to do and therefore learning. For me, going from product and engineering to growth hacking and sales was a steep learning curve, but definitely something that was super valuable because it was a brand new domain. Embrace taking on things you normally wouldn’t!
Matthew: There’s a good book called Range which talks about how diversity of experience is really important and I think having different perspectives on new things is really useful. I honestly like being in that kind of friction situation. I also don’t necessarily think that at our age, we need to focus on depth. That’s probably something to do when we’re hitting maturity, but right now, I think it’s best to get a breadth of experiences and then dive deep into one specific thing later on.
Shannon: Agreed. I think it also depends on your goals, stage of life, and what you want to do. If your goal is to discover new things and you find yourself in a position where you doing the same thing, you might as well switch it up to avoid diminishing marginal returns. Even if you know what you want to do, it’s good to explore. It’s always worth being open-minded.
How do you network and meet new people?
Matt: One thing I regret is not spending enough time reaching out to new people — I wish I was more open about trying to meet new people. I think COVID is a unique opportunity where you’re almost forced to talk to others or else there’s literally no social interaction. People are going to be a lot more receptive to meeting people, and that’s definitely something I’m going to try and take advantage of for this second half of my gap year.
Kelvin: In general, whether you’re reaching out to professionals or someone you follow on Twitter, you can usually reach out with a cold email and ask if they’d be open to hopping on a call. But another question to ask yourself is: do you really need to add more nodes to your network? In a lot of cases, it’s more important to engage your current network than to keep adding to it. When I got a referral for my first job, it was because of a friend I’d met at Princeton where all we talked about was startups and venture capital. So try and make it when an opportunity or a resource comes to one of your friends, the first person they think of is you.
Shannon: I definitely agree with that. I was not the best at this during my gap year but make sure you’re meeting the right people and giving them the right first impressions. When you have a meeting with somebody, always put them first. Don’t make it all about you. Ask them what their goals are and genuinely be interested in helping them. Otherwise, they’re not going to want to help you. Take advantage of this now, especially since people are more open to meeting new people due to the pandemic.
Andrew (Remote Students Co-Founder): Remote Students is a great way to meet other people during your gap year too, join our Gap Year community 😊
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