Reasons to mentor high schoolers: Reflections from my first year

Hector Jaime
Pinterest Design
Published in
6 min readJan 5, 2024
Two students busy drawing and working at a large table. The two students are also shown smiling and standing in front of a Pin made out of Legos.
High schoolers during their job shadowing day at Pinterest headquarters in San Francisco

It was the mid ’80s, I was in junior high school and I was stoked to find out that we had a substitute teacher for one class that day. At least one hour of the day would be a breeze. Somehow my friend Ricky and I ended up chatting with the sub during class. We both loved to draw and mentioned we were thinking of graphic design as a career.

“Oh, don’t go into graphic design,” the sub responded. “I studied that and here I am. It’s hard to get work and when you do, you barely get paid. I make more money being a sub.”

That conversation and many others deterred me from pursuing a career in design after high school, and I didn’t take it up again until much later in life. It wasn’t the only reason — I frankly had too many interests to make up my mind. But, as an adult I told myself that I would never be a bummer and discourage kids from pursuing whatever inspires them.

I live up to that promise as a parent every day, and recently I also had the chance to encourage students’ ambitions as a first-year mentor for Woodside High School’s Graphic and Technology Academy. This included being a guest speaker for one of the Multimedia classes. It was a very rewarding experience, and I’ve signed up to do it for a second year. Here’s why.

Two students sitting at a desk with laptops. To the right, there is a picture of trees with colorful fall leaves and a blue sky.
Students at Woodside High school

I got to connect with my local community via a well-designed program

The program at Woodside is very well organized. Mentors are matched with a high school junior who’s interested in the industry the mentor works in. For example, Isaiah, my mentee was into designing logos, creating videos and coming up with ideas for fashion brands. So a designer who worked at Pinterest was a great match.

Once matched, the school year is a good balance of learning about our personal goals, the design industry and crucial career skills like resume writing, elevator pitches, setting and tracking goals and interviewing for jobs. The pace isn’t too burdensome; about 90 minutes a month from October through May.

It was especially nice to take a break from my home office and corporate headquarters to go somewhere that was brimming with youthful energy and felt — I hate to say it — more organic and less “designed.” There’s something nice about an older high school campus where every teacher and student group gets to add personality and creativity to their spaces without worrying too much about a corporate brand.

It’s also really nice to help out a local high school. I am lucky that Pinterest not only encourages volunteer work, but donates to the school for every hour I volunteer there. Finally, meeting and talking to other local professionals and parents helped me feel more connected to my community. We also got to share ideas for improving the next school year’s program.

I introduced students to digital product design as a career option

Part of what stifled me when I was young was that I didn’t know about all the ways to make a fun and decent living as a person who enjoys drawing and being artistic. As a guest speaker and mentor, I was able to show students a side of graphics and technology that they maybe weren’t aware of: creating and maintaining design systems for popular apps like Pinterest. It was especially fun seeing the students’ eyes light up when I told them the average salary for a product designer and how good the lunch is at the Pinterest office.

Both my mentees mentioned that visiting the Pinterest headquarters in San Francisco was the highlight of the program. They got to hear from designers from both the Product and Brand teams who not only shared the work that they do, but perhaps more importantly, their journey to becoming product designers, which isn’t always a linear one. We also did a bit of hands-on experimentation with our Risograph printer. And, of course there was the cool office decor, the free food and snacks‌ and the video games.

I learned how to improve my pitch

Talking to students about technical things like digital product design systems wasn’t always easy. When I first met Isaiah, I started going through Gestalt, our open source design system for Pinterest products, including some of the details around UI components. I could tell I was starting to bore him and once I was done, he asked “So, have you ever worked on any logos or products like clothing or other physical products?”

During my guest speaker session, I tried to connect design systems to science, since my younger daughter had recently learned about ecosystems in science class. That also fell flat maybe because elementary school science is far from multimedia design students’ minds. What students wanted to see was inspiring design work and a compelling personal story. They also liked sharing their work and getting feedback.

So, it was a lesson for me to present what I do in a more compelling way that can meet my audience where they are. It’s easy to forget that when, on a day-to-day basis, you are talking with people who are already familiar with the world of digital product design.

I got to learn from a variety of students

One of the final activities was helping students with mock job interviews. This included not only students from the Graphics and Technology Academy, but students from the STEAM program in Menlo/Atherton. Here I got to listen to students from different backgrounds with a variety of interests. While my mentee was very focused on getting a soccer scholarship while also working on his design and video projects, other students were interested in careers in radiology and already working part time, while others were considering taking a break after high school to work at a bookstore.

That was another learning moment for me. I assumed all of the students in the program were set on pursuing careers in design, so I was giving advice on the more relaxed atmosphere of product design where you can wear a T-shirt and baseball hat to an interview and no one is going to care much as long as your portfolio is good. It turns out that some students, though currently in the Graphics program, were considering other, very different careers. So, again, for this coming year, I’ll broaden my advice to be less focused on design.

Looking forward to the next mentor session

In short, I learned a lot and had a blast during my first year as a mentor. I was able to connect better with my local community and get a sense for how educational programs are designed. I also introduced students to product design, design systems, open source technology and accessibility while helping them plan for their future careers via goal-setting, elevator pitches, resume writing and mock interviews.

I hope that my work makes a difference to the students at Woodside High School and inspires them to continue working towards their goals. Maybe they’ll even land at a place like Pinterest, with a flexible schedule, free lunch, old arcade games and awesome teammates and leaders who are more than willing to share their design knowledge and experience with visiting students.

If you are interested in being a mentor or guest speaker for Woodside High School’s Academy programs, contact whsmentor@seq.org.

To learn more about Pinterest Design, follow us on LinkedIn.

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