Redesigning Healthy 365: A UX Designer's Perspective on the Psychology of Self-Tracking

When I joined the team redesigning Singapore's Healthy 365 app, I thought I understood fitness tracking. After all, I'd been obsessing over my daily steps and heart rate data for years. But as we dove into the goal-setting and challenge features, I discovered something fascinating: everyone's relationship with these devices is completely different. What started as a straightforward UX project became an eye-opening journey into human psychology and generational differences. Here's what I learned about the people behind the data.

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The Generational Divide

Millennials and Above: The Rewards Generation My millennial colleagues are all about those Healthy 365 points. "Of course I sync my data!" one exclaimed. "Those NTUC vouchers can go a long way!" This pragmatic approach reflects a desire to maximize benefits beyond physical well-being. We incorporated gamification elements like progress bars, badges, and leaderboards that resonated strongly with this group.

Gen Z and Below: The Self-Aware Generation In contrast, Gen Z focuses on personal health tracking and self-improvement. They view fitness trackers as tools for self-awareness, using data to gain insights into sleep patterns, activity levels, and overall well-being.

When I asked my Gen Z colleagues why they don't sync their data to Healthy 365, their response was unanimous: "Why would I want to give the government access to my health data?" They're more cautious about sharing personal information, even for potential rewards. We incorporated features allowing users to control data-sharing preferences and customize goals, catering to their desire for individualized and private fitness tracking.

Real User Stories

During usability testing, I heard fascinating stories: elderly couples motivating each other to reach daily step goals, grandmothers enlisting grandsons to boost step counts, and aunties confessing to shaking their legs while watching TV to outsmart their devices. These anecdotes provided valuable insights into user behavior and highlighted the importance of designing an adaptable app.

The Dark Side: When Tracking Becomes Obsession

A surprising number of participants admitted feeling hesitant about starting to track their activity. "I'm scared I'm not good enough," one confessed—a sentiment we heard repeatedly.

This fear resonated with my own experience of obsessive heart rate tracking. I would constantly check my fitness tracker, worrying about every fluctuation. Rather than providing reassurance, this obsessive tracking fueled my anxiety and created a vicious cycle of self-doubt.

Observations That Keep Validating

These insights didn't end with the project. Throughout our subsequent HCD research across different demographics, I started asking everyone I met: "Are you a H365 user?" Their answers continue to validate these patterns years later. The generational divide, the privacy concerns, the reward motivations—they're consistent threads in Singapore's relationship with health technology.

The most telling responses often come from the pauses before people answer, revealing the complex relationship between personal health data and digital engagement.

Key Takeaways for UX Design

What This Means for Health Technology Design These insights didn't end with the project. Throughout our subsequent HCD research across different demographics, I started asking everyone I met: "Are you a H365 user?" Their answers continue to validate these patterns years later. The generational divide, the privacy concerns, the reward motivations—they're consistent threads in Singapore's relationship with health technology. The most telling responses often come from the pauses before people answer, revealing the complex relationship between personal health data and digital engagement. The Real Challenge: Designing Love at Scale What I learned is that it's incredibly difficult to find the balance when designing for every walk of life. HPB's objective is beautifully simple: reach out to the masses, insert healthy messages, and nudge lovingly. As designers, our job is to transfer this love to the mass. That's the real challenge—how do you design love that resonates with millennials chasing NTUC vouchers, Gen Z protecting their data privacy, elderly couples gamifying their walks, and anxious users afraid they're "not good enough"? How do you create digital experiences that feel like a caring friend rather than a judgmental authority? The answer isn't in the features we build or the interfaces we design. It's in understanding that behind every data point is a human being with their own relationship to health, technology, and self-worth. Our role is to honor that complexity while gently encouraging better choices. The true joy of movement lies in the experience itself, not just the numbers on a screen. And sometimes, the most loving thing we can design is the space for people to find their own path to wellness.