The Four-Phase Journey to Eradicating Calendars: Embracing Digital Serendipity

Dario De Santis
4 min readAug 18, 2023

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With AI at the forefront, imagine a world where back-to-back meetings no longer dominate your workday. A time when calendar invites and the mad scramble to schedule are a relic of the past. Welcome to the era of Digital Serendipity.

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A Familiar Story

Picture this: A Sunday evening glass of Chianti, followed by a reluctant Monday morning where alarms force you out of bed for that early meeting. Hours blur, as you’re pinned to your chair, jumping from one meeting to another. You snatch short moments for bio breaks and struggle to manage myriad messages. Does that sound familiar? For those entrenched in matrix organizations, this might be the daily grind.

Current Solutions Fall Short

Even with tools like shorter meeting durations, various messaging apps, schedulers, and AI calendar assistants, the desired work-life balance remains elusive:

  • Meeting overrun is commonplace.
  • Quick chats often seem faster than waiting for message replies.
  • Calendars remain packed, making spontaneous discussions near-impossible.

The modern work structure hardly promotes sustainable work habits. In a hybrid working era, each accidental interaction becomes yet another calendar event, bogging us down further.

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The Evolution of Communication

Two decades ago, an urgent phone call sufficed for immediate information. Then, smartphones deluged us with constant notifications, creating a shielded society that prioritized individual productivity over team-based decisions. But is such a focus-centric approach the best for collective growth?

Introducing Digital Serendipity

Tweelin introduces a groundbreaking paradigm: Digital Serendipity. This concept seamlessly integrates focus and fast communication. You can work undisturbed or instantly engage with others, depending on your current task. This adaptive communication style does away with stringent calendar events.

We predict a major shift from calendar-driven lives to this free-flowing model within the next 3–5 years, revolutionizing productivity.

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The Four Phases of Transformation

The transformation of the way we work will likely follow the following phases.

Phase 1: Internal communications

Starting with product or project teams, Digital Serendipity will prioritize event acceleration over fixed schedules. This boosts delivery speed and economic benefits.

Phase 2: Extension to partners

Recognizing the efficiency of this model, companies will incorporate partners, expanding the benefits beyond organizational confines.

Phase 3: Extension to customers

Soon, the ease and effectiveness of Digital Serendipity will touch customer interactions, making support and communication smoother and more efficient.

Phase 4: Extension to everyone

Once the masses experience the magic of this hassle-free communication, they will adopt serendipitous AI technologies, making the traditional calendar obsolete.

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Evolutionary Trends in Digital Serendipity

While the four phases of transformation roll out, there will be two additional relevant trends that will contribute to diffusing the new paradigm.

From 1:1 to multi-party meetings

Initially, Digital Serendipity will tackle the simpler 1:1 meetings, leveraging AI to transform them into spontaneous yet relevant conversations. As these meetings disappear and calendars open up, Digital Serendipity will then accommodate more complex multi-party interactions, only requiring scheduled slots for particularly large assemblies.

From one-off to recurrent meetings

Modern organizations swear by recurrent meetings as pivotal tools for constant progress and stakeholder updates. With Digital Serendipity, the focus will shift to replacing singular meetings first. Then, as teams witness unparalleled productivity from these impromptu discussions, they’ll begin to question the efficiency of recurrent meetings. Hence, teams will lean toward convening when certain conditions or milestones are achieved, avoiding wasted time on unnecessary scheduled check-ins.

Are you poised to step into this innovative future?

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Dario De Santis

Long-termist visionary technology Entrepreneur and Product Leader, with a strong passion for improving people's productivity through innovative solutions.