When Works?
An evolving experiment in self-initiated design, AI curiosity, and scheduling across time zones
Context
When Works? is an ongoing personal project exploring the intersection of AI, design, and the everyday chaos of independent consulting. Unlike polished, outcome-driven projects, this one is deliberately evolving. It is a living, breathing exploration driven by curiosity, constraint, and creativity.
As an independent consultant working across multiple time zones, I frequently encounter a seemingly small but consistently frustrating problem: scheduling meetings with collaborators who don’t share a calendar system.
There are existing tools (e.g.WorldTimeBuddy, Calendly, Google Scheduler), but none quite solves my problem. They often assume a fixed team structure or limited participants. My reality is more fragmented: freelancers, teams across continents, ad-hoc collaborations, and no shared infrastructure.
Rather than compromise or search endlessly for the perfect tool, I decided to use the opportunity to experiment with Lovable and design one for myself.
When Works? is still evolving. It may never be “done.” Some days I take two steps forward, others five steps back. But it has already served its purpose: it’s made my life easier, sharpened my AI skills, deepened my understanding of time-based interaction, and reignited the joy of making something just because it’s interesting.
In an industry obsessed with polished portfolios, this is my dedication to the unpolished, the personal, and the in-progress.
This work is important to me because…
It’s a creative outlet, a space to experiment without pressure or predefined outcomes.
It allows me to explore and play with emerging technologies in a way that feels personal, joyful, and open-ended.
It’s an opportunity to build technical fluency in generative AI and sharpen my skills through daily iteration.
It reflects how I learn best: by doing, making, testing, and refining in real time.
It helps me grow not only as a designer but also as a thinker, planner, and problem-solver.
This work is important to you because…
It showcases my initiative, the ability to self-identify friction points and pursue solutions outside of a formal brief.
It highlights my curiosity and fluency in emerging tech, especially generative AI and large language models.
It displays my interdisciplinary thinking – blending design, behavioural insight, and technical experimentation.
It demonstrates iterative problem-solving under constraints (like prompt limits).
Constraints
Using the free tier of Lovable (limited to five prompts a day), I created intentional boundaries that shaped my process. The daily prompt cap serves as a creative constraint that forces me to be deliberate, economical, and inventive with how I interact with the model.
Over time, I’ve seen the quality of my prompts evolve dramatically, a reflection of my deepening understanding of AI systems and how to design with them, not just for them.
The interface, features, and functionality shift and grow with my needs. I add elements not based on user testing or stakeholder approval, but based on lived frustration and small sparks of inspiration.
