Headspace

Crafting a check-in feature that drives daily engagement

Services

UX/UI
Feature design
Retention strategy
Concept design
Key outcomes
  • Encouraged daily, meaningful interaction beyond just meditation
  • Reinforced habit formation by integrating check-ins into a regular flow
  • Increased user self-awareness through emotional tracking
  • Strengthened retention by making the app feel more personalized and reflective

About

Headspace, a global leader in meditation and mental wellness, wanted to enhance user engagement by integrating a daily check-in feature into their app. The goal was to encourage reflection, reinforce meditation habits, and deepen user connection to the app. Supergood Apps stepped in to design an experience that was frictionless, engaging, and habit-forming.

The challenge
  • Encourage regular engagement without feeling like a chore
  • Provide value in under a minute, ensuring users could reflect quickly
  • Personalize the experience while maintaining simplicity
  • Integrate smoothly with the existing Headspace ecosystem.

Our approach

We focused on designing a low-friction, rewarding check-in flow that naturally fit into users’ daily routines.

From emotional check-ins to daily planning, we helped Headspace design a more intuitive, emotionally intelligent app experience—one that supports users throughout the day with personalized content, mindful nudges, and delightfully crafted UX moments.

Designing for support through the day

To make Headspace feel present across different moments of the day—not just during morning meditations—we helped design a system that syncs with a user’s calendar and daily rhythm. The app now gently surfaces contextual support, suggesting mindfulness exercises and meditations based on what’s coming up in your schedule.

By aligning with real-world moments, the app became a more responsive, helpful companion, rather than a fixed destination.

The Day Planner feature was designed to help users visualise their time and reclaim it mindfully. It identifies free pockets throughout the day and encourages users to take short restorative breaks, turning downtime into intentional care.Tapping on a task block launches a Focus Timer, guiding users through a short countdown that builds anticipation for a mini-break. These moments celebrate the effort users have already put in—and reward them with space to just be.

Frictionless check-ins

We introduced a mood-tracking interaction that relied on emoji-based responses. Users could quickly choose from a range of expressive icons to indicate how they felt. This was:

  • Visually engaging
  • Low effort
  • Universally accessible—no need for lengthy reflection or text input

This made the interaction feel casual, playful, and emotionally honest.

Contextual personalisation

Immediately after a mood check-in, the app surfaced content recommendations aligned with the user’s emotional state—like meditations for anxiety, exercises for calm, or mindful walks for energy. This turned the check-in into a gateway, not just a dead-end input. It closed the loop and made emotional logging immediately useful.

We also introduced subtle moments of joy throughout the product to celebrate consistency and encourage positive reinforcement.

  • Earn-able badges mark milestones and habits, acting as proof that the user is showing up for themselves—even on hard days
  • Completing activities occasionally triggers tiny visual surprises, like gentle shifts in background or animations.

These moments were designed to be non-intrusive but emotionally resonant, reinforcing momentum with delight rather than pressure.

The results: A habit-forming feature that keeps users engaged

Supergood Apps designed a frictionless, rewarding, and personalised check-in experience that helped Headspace:


  • Boost daily app engagement through effortless tracking
  • Reinforce habit formation, increasing long-term retention
  • Provide deeper value to users with personalised insights
  • Seamlessly integrate check-ins into the existing meditation experience