I Thought I Needed a Break. Turns Out, I Needed Better Questions

A few weeks ago, I quietly stopped talking about my app. There were no dramatic announcements, no well-deserved vacation, and no burnout post. I just went silent. But the silence wasn’t restful—it was filled with doubt. After months of work, I wasn’t seeing the traction I hoped for. New users weren’t joining, and engagement felt like it was slowly fading. I wasn’t sure what was broken—or if anything was broken at all. For the first time, I genuinely started to question whether the app was working, whether the mission still mattered, or whether I had simply reached the end of the road.

The temptation to give up was real. I considered whether I should pivot, or even walk away entirely. But something inside me hesitated. It wasn’t that I wanted to quit. It was that I didn’t know what I was building anymore—or who I was building it for. That confusion felt like burnout on the surface, but deep down, I realized it wasn’t exhaustion. It was disconnection.

The Wake-Up Call: Discovering “The Mom Test”

In the middle of this fog, I came across a book that shifted everything: The Mom Test by Rob Fitzpatrick. The premise is simple: if you ask vague questions like “Do you think this is a good idea?” people will lie to you—especially your mom. But if you ask about their real experiences, their struggles, their routines, you’ll get answers that are actually useful.

Reading the book made me realize how little I had actually spoken to users. I’d built a product based on a strong emotional insight, but somewhere along the way, I stopped checking whether that insight still held true. I was adding features, tweaking flows, iterating quietly—but I wasn’t having real conversations. I wasn’t asking about people’s lives, and I definitely wasn’t asking the kinds of questions that even my mom wouldn’t sugarcoat.

So, I made a decision. I reached out to nine users and set up conversations. No scripts, no product demos, no hidden agenda. Just a genuine desire to understand what was really going on in their world.

What People Actually Said Changed Everything

What I heard on those calls surprised me. No one talked about traditional pain points or requested more features. They didn’t say, “I’m lonely,” or “I want more from your app.” Instead, they spoke in softer, more human terms.

One user shared, “I feel guilty prioritizing myself.” Another admitted, “I’m always surrounded by people, but no one really sees me.” Someone else said, “Writing to myself feels grounding—like being held.” These weren’t requests for better UX or more notifications. They were emotional truths, quietly spoken. They reminded me that people don’t just want to be productive—they want to be seen, to feel safe, and to reconnect with themselves.

One user even mentioned that she takes screenshots of kind comments people leave about her and keeps them in a folder. Another said he encourages his mom to keep a notebook of compliments from clients for the hard days. These moments weren’t just sweet anecdotes. They were signals. And I realized I’d been missing them all along.

The Problem Wasn’t the Product—It Was the Framing

It became clear that the app wasn’t fundamentally broken. It was just incomplete. I had focused so much on offering people solitude and reflection that I’d forgotten something essential: we also crave connection. Not the loud, performative kind, but a quiet sense of being seen—of knowing that someone, somewhere, understands.

Up until that point, the app had been centered around self-love, encouraging users to reconnect with themselves through writing and mindful rituals. But these interviews helped me see a subtle but powerful distinction. People didn’t just want to love themselves alone. They wanted to feel less alone while learning to love themselves.

This insight shifted everything. The app wasn’t just a journal anymore—it was becoming a space for shared solitude. For reflection, yes—but also for the feeling of being reflected back. And with that clarity, I stopped feeling stuck.

Building for Belonging, Not Just Self-Improvement

We're now evolving the app to reflect this deeper need for connection. In the coming months, we’re rolling out features that prioritize gentle, non-intrusive social design—things like collective rituals users can participate in silently, anonymous shared reflections, and soft signals that let you know others are writing too.

These aren’t designed to drive engagement metrics or create sticky loops. They’re designed to recreate that subtle sense of companionship we all crave—the feeling that you’re not alone, even in silence. It’s a move away from noisy community-building toward something more tender, more honest. Because sometimes, making someone’s day doesn’t mean sending a push notification. Sometimes it means giving them a space to remember who they are.

What I Learned (and What I’d Tell Other Founders)

Looking back, I realize that the silence wasn’t my enemy—but it wasn’t my solution either. I thought I needed rest. I thought I needed space. But what I really needed was to reconnect—with my users, and with the reason I started building in the first place.

The Mom Test didn’t just teach me how to ask better questions. It taught me to listen differently. To stop looking for validation and start seeking understanding. To trade assumptions for empathy. And to let go of the idea that building in isolation would somehow protect me from failure. It doesn’t. It just makes the failure harder to see until it’s too late.

So, if you’re reading this and you’re feeling stuck—if your product feels flat and your purpose even flatter—don’t quit just yet. Don’t rush into building something new. Try asking better questions. Listen for what people really need, not what they think they’re supposed to say. The answers might not come immediately, but they will come. And when they do, they’ll point you toward a version of your work that feels more alive, more useful, and more true.

Final Thoughts

In the end, I didn’t need a break—I needed better questions. And more importantly, I needed to remember that I’m not building for metrics or investor decks. I’m building for people. Real people, with real needs and quiet desires they don’t always know how to articulate. That’s the work. That’s the mission.

And maybe, just maybe, that’s enough to keep going.