When I joined the team redesigning Singapore’s Healthy 365 app, I thought I understood fitness tracking. I had been obsessing over my daily steps and heart-rate data for years. But as we dove into goal-setting and challenge features, I discovered something fascinating: everyone’s relationship with these devices is completely different.

The Generational Divide

My millennial colleagues were all about Healthy 365 points. “Of course I sync my data,” one exclaimed. “Those NTUC vouchers can go a long way.” This pragmatic approach reflected a desire to maximise benefits beyond physical well-being. Gamification elements like progress bars, badges, and leaderboards resonated strongly with this group.

Gen Z, in contrast, focused on personal health tracking and self-improvement. They saw fitness trackers as tools for self-awareness: sleep patterns, activity levels, and overall well-being.

When I asked my Gen Z colleagues why they did not sync their data to Healthy 365, their response was unanimous: “Why would I want to give the government access to my health data?” They were more cautious about sharing personal information, even for rewards. That pushed us to think harder about data-sharing preferences, privacy, and individual control.

Real User Stories

During usability testing, I heard stories that stayed with me: elderly couples motivating each other to reach daily step goals, grandmothers enlisting crawling grandsons to boost step counts, and aunties confessing to shaking their legs while watching TV to outsmart their devices.

These were not funny edge cases. They were signals that people adapt systems into their real lives, sometimes in ways the design never intended.

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. We heard this sentiment repeatedly.

It 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, tracking fuelled anxiety and created a cycle of self-doubt.

Observations That Keep Validating

These insights did not end with the project. Throughout subsequent HCD research across different demographics, I kept asking people: “Are you a H365 user?” Their answers continued to validate the same patterns: generational divides, privacy concerns, reward motivations, and ambivalence toward health data.

The most telling responses often came from the pauses before people answered.

The Real Challenge: Designing Love at Scale

HPB’s objective is beautifully simple: reach the masses, insert healthy messages, and nudge lovingly. As designers, our job is to transfer that love to the mass.

How do you design love that resonates with millennials chasing vouchers, Gen Z protecting privacy, elderly couples gamifying walks, and anxious users afraid they are not good enough?

The answer is not only in the features we build. It is 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 honour that complexity while gently encouraging better choices.

The true joy of movement lies in the experience itself, not just the numbers on a screen. Sometimes, the most loving thing we can design is the space for people to find their own path to wellness.