36 questions to fall (back) in love with tech

Remember the allure of a dial-up tone, the anticipation of an MSN nudge, or the thrill of your first tweet? Most of us can summon a magic moment when technology felt limitless. (For me, it’s unboxing a third generation iPod in the backseat of my parents’ car.) Yet, as the years roll on, our relationship grows increasingly more serious, more essential, intertwined with the intricacies and mundane responsibilities of our shared digital life. Our once carefree interactions evolve into a complex web of notifications and commitments, ‘Slack-lash,’ and distrust. The tools that once fed our imagination now seem to sap it. Is it possible to reignite that initial spark?

Drawing inspiration from the New York Times’ “The 36 Questions That Lead to Love,” which tests psychologist Arthur Aron’s hypothesis that mutual vulnerability fosters closeness, we’ve crafted a set of questions and interviewed over 20 professionals about how their relationship to technology has changed. Sharing everything from their first usernames to what they hope for the future, each person delves, with increasing intimacy, into the romance and heartache of living with tech.

Once upon a byte

Cristina Cordova, Chief Operating Officer at Linear, first became infatuated with tech during the college admissions process, when she discovered the website and community, College Confidential. “No one in my family had gone to college,” she says. “I remember Googling, ‘what does it take to get into Harvard’ and finding this forum.” There, she read posts from other students and was able piece together what her own path might look like. “It was the first time that I really saw people with the same interests as me, who wanted to go to the same places that I did—and got an understanding of what it actually took to get there,” she says.

Kristy Tillman, who leads design for Netflix Studios, credits her early experiences playing around with design software with her current professional success. “That time period in technology really represented an open frontier of just pure creativity. I have not felt that in such a profound way since.” Mig Reyes, Head of Product Design at Duolingo, recalls the delight of customizing his AOL Instant Messenger profile. “A lot of it was really just goofy self-expression,” he says. “If I delete this line, hit save, what happens?”

When the digital honeymoon ends

As with any budding romance, the honeymoon phase eventually wanes. Between ad pop-ups and FOMO, the web isn’t everything we hoped it would be (how could it be?). Lauren McCann, Head of Figma for Education, describes the feeling of logging onto Facebook and realizing you’ve been left out: “Oh, all those people were together doing this cool thing, and I wasn’t invited.” “You’re looking at all these beautiful pictures, people vacationing somewhere or looking at all their LinkedIn accomplishments, but a lot of times people are showing their best self,” says Shyvee Shi, Product Lead at LinkedIn. Peter Yang, newsletter author and Product Lead at Roblox, describes the need to pull himself back from spending too much time on social media: “I think time is better spent creating new stuff than consuming stuff.”

Tech tribes and digital bonds

Yet, amidst the challenges, technology still has an extraordinary power to connect. From web forums to dating apps, people shared stories of finding everything from friendships and mentors to true love. Lenny Rachitsky, newsletter author and podcast host, met his wife on the now-defunct site, howaboutwe.com. “Now we’re married ten years later,” says Lenny.

Sho Kuwamoto, Figma’s Vice President of Product, spent some formative years on an online forum called “Midwest Raves” where he met many friends—many who he is still in touch with today. These experiences remind us that at its best, technology builds bridges and nurtures communities, creating a sense of belonging and connection in the vast digital landscape.

What comes next?

It wouldn’t be 2023 if we didn’t talk about AI. Which came up. A lot. “I think that the most magical things happen when you give people the tools to be creative,” says Mihika Kapoor, a Product Manager at Figma. “The innovation we’d see would be absolutely tremendous—if people just had [AI tools] to bring the thoughts in their head to life.” As we ponder an AI-powered future, optimism is met with caution. Marcel Weekes, Figma’s Vice President of Software Engineering, emphasizes the need for thoughtful innovation: “One of my sincere hopes and expectations for software developers, like myself, and others going forward is that we take the time to think about if and how we should do something, not just can we do it.”

“The kind of work that I hope people will do in the future is work that is centered around craft and being able to do the best work possible,” says Cristina. “If there are types of work that can be automated, which means instead, you get to focus on the things that are actually interesting—that’s really exciting.” And, of course, in a sea of apps that help you work faster, better, and optimize everything, there’s always room for joy. Jenny Wen, a design manager at Figma, hopes to see a return to apps that optimize for more of just that.

What’s your relationship to tech?

Now it’s your turn. Ask yourself (or someone you love) the questions. Who knows, you might just find yourself falling headlong into a digital love affair or perhaps fanning the flames of an old spark.

36 questions to fall back in love with tech

Set I

1. What was your first username? Why?
2. Do you aspire to be a well-known tech titan or quiet anonymous lurker? Explain.
3. Share the story of how you first got into technology.
4. Describe a moment when a piece of technology felt like it opened up a world of possibilities for you.
5. Tell me about the first thing you built on the Internet. What did it do?
6. Who in the tech world would you most like to collaborate with? What would you build?
7. Do you ever think through a coding or design problem in your head before solving it? Why?
8. Take me through a perfect web surf. You open the browser, where do you go from there?
9. When did you last feel truly inspired by technology—be that a device, or piece of software?
10. Would you rather have the enthusiasm of a tech newbie or the experience of a 30-year veteran for the rest of your career?
11. Do you have any predictions about your future in the tech industry?
12. If you could gain one skill to improve your work with technology, what would it be?

Set II

1. If you could change something about tech (the industry, or our devices), what would it be?
2. What’s a tech project you’ve dreamed of completing?
3. What do you consider your greatest achievement in your tech career?
4. How has tech helped you find your community?
5. Tell me about a time you met someone via the internet who impacted your life.
6. If you were to meet someone via a chat room today, what would you tell them about yourself?
7. When was the last time you felt happy interacting with technology?
8. When was the last time technology made you sad?
9. How has technology influenced your relationships and connections with others?
10. List five positive outcomes (on yourself or the world) that you directly attribute to technology.
11. Describe your tech ‘family’ or community. Is it supportive?
12. Describe your relationship with mentors or influential figures in your tech journey.

Set III

1. What’s something you wish you could share about your tech experience with others?
2. What do you think the future of tech holds?
3. Share what you admire about one of your peers.
4. Describe an awkward or embarrassing moment in your tech career.
5. When was the last time you felt emotional about something related to tech?
6. Share something you appreciate about this current moment with technology.
7. What tech innovation makes you most excited about the future?
8. Is there a topic you think needs to be addressed with utmost seriousness?
9. In what ways do you hope technology will evolve to better serve humanity?
10. If your entire digital life was about to be erased, what’s the one thing you’d save?
11. Whose passing in the tech world would affect you the most? Why?
12. Share a problem you have with tech and seek advice on how to handle it.

Explore Figma’s 2023 Handoff