How can I design at a time like this?
A Pinterest product designer and author helps us each find our answer with a choose-your-own adventure approach to challenging our cognitive biases. Try it out!
In a world afire, the DO team turned to our most trusted confidant — the design community — to help answer a question so many of us have been asking: How can I design at a time like this?
In her new book Ask This Book a Question, Vicki Tan, a product designer at Pinterest, Spotify, and Headspace, reimagines the self-help tome as a choose-your-own-adventure, resowing linear paths with question-based navigation, visual mapping, and story-driven learning that better suits our busy brains.
“I’ve spent years exploring how our minds’ greatest quirks — our cognitive biases — shape our decisions,” Tan, who also has a background in behavioral science, tells us. “Rather than treating cognitive biases as flaws, I’ve reframed them as valuable signals that help us understand ourselves better, like a trusted friend helping us navigate uncertainty.”
Since showing is better than telling, we asked Tan to apply her novel approach to book design (which you can read more about here) to the nonfic book’s kid sibling: the article.
We asked this article a question, and here’s what it told us.
— Delaney Rebernik and Rachel Paese
The question: the world feels unpredictable, and everyone is overwhelmed. How can I design, create, and lead at a time like this?
Below, each path answers that question from a different angle, borrowing from the wisdom of cognitive biases. Start with the path that speaks to you:
- If you’re feeling the urgency to take action and wondering how to square what’s happening in the world with what matters in your own life, jump to the Urgency section.
- If you’re questioning your purpose, or how to access the joy and creativity that make you a better leader or designer, or how to channel those strengths to meet the moment, head to the Purpose section.
- If you’re simply feeling a swirl of emotions like confusion, invigoration, worry, hope, powerlessness, and anxiety, or feeling paralyzed or unsure how to move forward, the Emotions section might speak to you.
And if you’re feeling all of the above, just keep reading.
The paths
Urgency
When the world feels urgent and unpredictable, it’s easy to get caught between overwhelm and detachment, as if the real risks are happening to someone else. This is because we have a tendency to believe that bad things are less likely to happen to us (Optimism bias) and that life will continue as usual — even when everything seems to be shifting under our feet (Normalcy bias).
The antidote isn’t to brace for disaster at every turn. Instead, try this: pause and ask yourself what’s actually within your control. Notice when your mind is quick to minimize threats (Optimism bias) or assume everything will eventually be fine (Normalcy bias). Then, give yourself permission to prepare for a few different futures — not just the one you hope for. Small acts of safety (like packing an extra layer for a trip, or setting aside time to check in with family) can anchor you in times of uncertainty. These little gestures of care help you stay resilient, so you can respond to the world’s unpredictability without losing sight of what matters most to you.
Explore more:
Purpose
For a creative like you, like us, finding purpose in a day job can feel disorienting, especially when the world’s challenges loom large. It’s easy to question the value of your daily tasks — ideating, creating, iterating — when they seem insignificant compared to global crises. Hoping for a more visible, instant win can make you dismiss longer, slower projects that might have real impact over time (Hyperbolic discounting), or keep you waiting for a “meaningful” moment to begin, instead of getting started on a big idea that’s been simmering.
Purpose is about showing up, even when the path ahead is uncertain.
Explore more:
Emotions
You might find that you feel stuck, unable to move forward because uncertainty feels overwhelming. It’s common to overestimate how long discomfort or anxiety will last (Affective forecasting). This can keep you from taking risks or making decisions, as if you’re waiting for the fear to pass before you act.
But emotions are temporary, and you’re more resilient than you think. Simple comforts — like bringing your own pillow on a trip or making your favorite comfort food before making a tough decision — can help you feel grounded. The key is to acknowledge what you’re feeling, but not let those feelings dictate your choices. Try asking yourself, “What would I do if I weren’t afraid right now?” With practice, you’ll see that you can adapt and move forward, even when the future is uncertain.
Explore more:
What comes next
In a world that often feels too big, too fast, or too uncertain, it’s easy to get lost in the noise or to wait for the perfect moment to act. But as we’ve seen, our minds have their own rhythms and shortcuts — biases that shape how we see reality and what we believe is possible. Instead of fighting these tendencies, we can learn to work with them: to notice when we’re minimizing risk, chasing quick wins, or overestimating how much discomfort we can handle.
The real power comes not from eliminating uncertainty, but from learning to move through it, with small acts of care, playful experiments, and the courage to start before we feel ready. Whether you’re balancing urgency with what matters most, searching for purpose, or simply trying to find your footing in a swirl of emotions, remember: you don’t have to have all the answers.
After all, the future isn’t something to predict or control. It’s something to shape, one choice at a time. And the best way to navigate uncertainty is to design for all possible paths — starting with your own.
The story behind the story
That stack of unread books on your nightstand is more than a monument to good intentions. The Japanese call it tsundoku: the practice of acquiring books and letting them pile up, unread. This collection, sometimes called an “antilibrary,” reflects not what you know, but the vast potential of what you could know.
As a product designer at Pinterest, Spotify, and Headspace, I’ve often wondered why we’ve poured so much creative energy into making digital experiences intuitive and engaging, yet left books largely unchanged for centuries. Americans now spend over eight hours a day with digital media — enough time to read a 400-page book daily — yet most of that attention is scattered, leaving us feeling more overwhelmed than enriched.
The real challenge isn’t willpower or attention; it’s how knowledge is packaged and delivered. What if we applied the same user-centered thinking that makes apps usable and adaptive to the way we design books and other sources of meaningful knowledge? Instead of expecting readers to follow a single, linear path, we could create experiences that offer flexibility, choice, and support for navigating uncertainty.
Ask This Book a Question is my experiment in this direction: reimagining the book as something that listens and adapts, meeting readers where they are and helping them find what they need in the moment. In a world that feels uncertain, flexibility isn’t just a luxury; it’s essential. When so much feels out of our control, perhaps the most radical thing we can do is create tools that listen and adapt to us, not the other way around.
And for the lovers of linearity, the “explore mores,” all in one place
Biases
- Optimism bias is our tendency to believe that bad things are less likely to happen to us than to others, so we might underestimate risks or avoid preparing for the worst.
- Normalcy bias is our instinct to assume that things will continue as they always have, even when evidence suggests otherwise.
- Hyperbolic discounting means we often prefer smaller, more immediate rewards over larger, longer-term benefits, which might lead us to procrastinate on creative projects or undervalue future goals.
- Affective forecasting can cause us to overestimate how bad (or good) a future event will make us feel, which can make us avoid risks or get stuck in indecision.
Stories
- “Airport Optimism:” I used to love timing my airport arrival down to the minute, squeezing in every last moment at home and trusting that everything would go smoothly. But after traveling with a partner who was an early arriver, I realized how my optimism sometimes left us scrambling, and how building in a little extra cushion wasn’t just about catching flights, but about caring for both of us.
- “Yancey’s Mustache:” While wrestling with writer’s block, Yancey Strickler, cofounder of Kickstarter, decided to grow a mustache, adopting a creative alter ego to help him push past self-doubt. That playful experiment became a turning point, showing how stepping into a new persona, even in a small way, can unlock courage and possibility when we’re feeling stuck.
- “Memory Foam Pillow:” For years, I avoided travel, wary of sleepless nights and unfamiliar beds. Watching a fearless colleague breeze through a hectic work trip helped me discover a solution. Bringing my own memory foam pillow wasn’t just about comfort; it was a small act of self-assurance, a way to carry a bit of home wherever I land.
- “Mapo Tofu:” In the midst of a big career shift, I found steadiness in the simple ritual of cooking mapo tofu, just like my mom used to make. Each week, preparing and having my favorite dish at the ready offered me a sense of home and clarity, and helped me save money in a comforting way, even as everything else in my life felt uncertain.
Observed
View all
Observed
By Vicki Tan
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