100+ Digital coffees later
A pulse check on the creative community
In 2021, feeling isolated at home, I started having virtual coffees with people from the internet. What began as a way to help my students make connections during the pandemic quickly became my own lifeline. Now, over 100 conversations in, I’ve gathered insights from across the creative community. Here’s what I’ve learned.
Find common ground
These conversations are intentionally open-ended. You may say, “Okay… so like a regular conversation?” To which, touché, but it’s easy to fall into a routine or start treating them like yet another meeting on the calendar. Part of the exercise is being present and finding a mutually interesting topic. As part of the sign-up, I ask attendees to share something that interests them, which can serve as a natural entry point, or a fresh input for me later. (Like the wonderful Ruxandra introducing me to the work of Piet Oudolf!)
I try not to start by asking the other person what they do for work, and aim to avoid route talk, but given the nature of it all—people finding me from my work, online, et cetera, all roads eventually lead there. Sometimes people come with questions ready. Those can be fun, especially when tailored to me. (Who doesn’t love being asked about themselves?) My least favorite are when someone starts presenting their work under the guise of a portfolio review, when they’re actually interested in a job where I work. That’s fine, but it’s not why I do these. (I also frequently find that those who say they want portfolio feedback, rarely actually do. But that’s for another newsletter!)
Forge community ties
There is a self-selecting nature to those who sign up (your author included). At the very least, they are open to a new connection. At the most, they’re actively seeking it. Amidst the isolation of remote work, the yearning for authentic connection—both online and off—has emerged as a recurring theme. “I miss the serendipity of studio life,” one freelance illustrator told me. “You can’t replicate that water cooler magic on Slack.”
Folks are exploring new ways to cultivate community, from therapeutic video calls to intimate dinner parties. A product designer shared how being part of a monthly Zoom with four others had become their “professional lifeline.” For many, community serves as an emotional and creative safety net during turbulent times—a vital component of overall well being, not just career development.
Embrace the career roller coaster
Many I’ve spoken to are grappling with the twists and turns of professional reinvention. One brand designer charted their path from the stability but creative constraints of advertising, to the autonomy but unpredictability of freelance graphic design.
The idea of a linear career path feels increasingly outdated. People are embracing zigzag journeys, taking sabbaticals, or pivoting to entirely new fields. There’s a growing acceptance that our professional lives can (and should) evolve. “I used to think changing industries meant starting over,” said a brand strategist turned UX researcher. “Now I see how my past experiences inform my current work in unexpected ways.”
Balancing person and paycheck
The challenge of separating self-worth from creative output came up often. This blurring intensified during the pandemic and continues in our hybrid work world. The juggling act extends to personal creative fulfillment and professional obligations. A design lead opened up about how hard it is to keep up an individual creative practice while juggling the demands of being a boss. Personal projects often infused and enriched professional work, but also made it tricky to unplug.
There’s also a growing appetite to align commercial work with personal values. “I’d much rather my laptop be closed than work on something I don’t believe in,” a designer told me, echoing a sentiment I heard repeatedly. This quest for meaning often leads to tough choices. A UX researcher shared, “I turned down a high-paying gig because the product felt ethically dubious. It was scary, but I slept better.”
Keeping pace with change
The relentless tempo of advertising, tech, and media industries and pressure to constantly upskill featured heavily. A product manager noted, “There’s this constant pressure to stay on the cutting edge—to keep learning new tools and technologies. It can be overwhelming at times.”
Coping strategies included carving out time for learning and finding knowledge-sharing communities. For some, enjoying the process of ‘always learning’ helped deal with the demands. For others, the emotional toll of delivering top-notch work under aggressive timelines led to some tough realizations about sustainable work practices.
Getting hands-on
A designer taking pottery? Woodworking? Textile weaving? It’s more common than you think! It won’t surprise anyone who spends time around digital product builders to know that many of them are rekindling their love for analog creative practices. As one shared: “It reminds me why I got into this field in the first place.” These tactile rituals offer a welcome screen break and a way to reconnect with the fundamentals of creativity amidst the digital noise.
Are you my mentor?
Mentorship came up often, with many wondering where they’re supposed to find mentors. For those who do participate, they mention being both mentor and mentee. This back-and-forth of knowledge and experience often had to be sought out, rather than forming organically. I encourage those seeking it to keep getting coffees with the same person repeatedly until those bonds coalesce.
AI on the rise
Unsurprisingly, AI came up in nearly every conversation. (That one may be on me. Sorry, folks.) Opinions ranged from excitement to existential dread, often within the same chat. “AI is simultaneously the most exciting and terrifying thing happening in design right now,” a UX writer shared. While the long-term effects remain to be seen, the consensus seems to be that while AI will undoubtedly reshape our industry, human creativity and critical thinking will always have a central role to play.
Cautious optimism ahead
Despite the complexities and ambiguities, a spirit of cautious hopefulness prevailed. A creative director summed it up like so: “Yes, our industry is changing at a dizzying pace. But that’s also what makes it exciting. We get to shape what comes next.” As someone who tends towards cynicism, I’ve found the optimism of these chats to be unexpectedly uplifting.
Personal takeaways
These digital tête-à-têtes have become a huge part of my own growth. Each chat is a chance to soak up new ideas, think about my own work, and connect with incredible people. It’s not just networking—it’s about holding space for candid dialogue.
What has struck me most is the resilience and agility of folks navigating career pivots, and the vulnerability with which they share their challenges. Time and again, I’m reminded of the power of community and loose ties; Frequently one of us will know of a connection or an opportunity that could help the other, which makes all the difference. And my extroverted self gets energized as I head into my day.
Curious about starting your own coffee chats? My calendar is open. Let’s talk design, tech, writing, or whatever’s on your mind. (Though heads up—I’m getting married in two weeks, so October might be better for that pumpkin spice latte.)
In the meantime, have any questions? Or your own stories of sliding into someone’s DMs for an impromptu chat? Did it lead to any surprising revelations or opportunities? Tell me in the comments.
—Carly
Another banger! And I shared this with all of my recent grads as encouragement to keep reaching out and connecting!
This is such a good idea. Love that you're trying to make connections for your students.
Also congrats!