Win At Business And Life In An AI World

RESOURCES

  • Jabs Short insights and occassional long opinions.
  • Podcasts Jeff talks to successful entrepreneurs.
  • Guides Dive into topical guides for digital entrepreneurs.
  • Downloads Practical docs we use in our own content workflows.
  • Playbooks AI workflows that actually work.
  • Research Access original research on tools, trends, and tactics.
  • Forums Join the conversation and share insights with your peers.

MEMBERSHIP

HomePlaybooksHow to Automatically Schedule Tasks in Your Calendar

How to Automatically Schedule Tasks in Your Calendar

Goal: Automatically schedule your tasks into your calendar and prevent people from booking over them.

Tools: Reclaim.ai (Best for Free/Standard users)

Outcome: You regain 4–6 hours of focus time per week by automating your schedule defense.

Most people use a “To-Do List” and a “Calendar” separately. This causes conflict because you have 10 hours of work on your list but only 4 hours of free time in your day. This playbook merges them using AI. It forces your calendar to reflect your actual workload by automatically blocking time for your tasks, ensuring you never overcommit again.

Step 1: Sync Your Calendar

Connect the AI to your main work calendar so it knows when you are busy.

  • Sign Up: Go to Reclaim.ai and create an account.
  • Connect: Authorize it to read/write to your Google Calendar.
  • Set “Working Hours”: Define exactly when you work (e.g., 9 AM – 5 PM). The AI is programmed to never schedule tasks outside these hours, protecting your personal time.

Step 2: Set Up “Smart Habits”

Instead of manually dragging “Deep Work” onto your calendar every morning, you tell the AI to do it for you forever.

  • Create a Habit: In the sidebar, select “New Habit.”
  • Define the Rule: Set it to “Deep Work” for 2 hours, to happen daily between 8 AM and 12 PM.
  • The AI Difference:
    • Scenario A (Conflict Resolution): If a VIP client books a meeting over your work block, a standard calendar creates a double-booking. This AI Agent detects the conflict and autonomously moves your work block to 1 PM.
    • Scenario B (Task Splitting): If you need 2 hours of work but your day is fragmented, the Agent is smart enough to split the block into two 1-hour sessions to fit the available gaps.
    • Scenario C (Deadline Defense): As your deadline gets closer, the Agent automatically changes the calendar status from “Free” (flexible) to “Busy” (locked), preventing anyone from booking over it.

Step 3: The “Task-to-Calendar” Workflow

Stop writing tasks on sticky notes. Put them directly on the timeline.

  • Connect Task List: You can use Reclaim’s built-in list, or sync it with Google Tasks/Todoist.
  • Add a Task: Type “Write Newsletter (Duration: 1 hour)” into the app.
  • Watch it Schedule: The AI immediately finds the next available 1-hour hole in your day and blocks it with the label “Write Newsletter.”
  • Result: Your calendar now shows exactly when you will do the work, not just what you have to do.

Step 4: Add “Meeting Buffers” (Anti-Burnout)

Prevent the exhaustion of back-to-back Zoom calls.

  • Go to Settings: Find “General” -> “Buffers.”
  • Set Rule: “Add 15 minutes after every video meeting.”
  • Outcome: As soon as a meeting is added to your calendar, the AI protects the 15 minutes after it. If someone tries to book you immediately after, your calendar will show as “Busy.”

Step 5: Review Your “Real” Capacity

  • Decision: If your calendar is full, you know you cannot say “Yes” to new requests without moving something else. This gives you the data you need to say “No” confidently.
  • The Reality Check: Because every task now takes up physical space on your calendar, you will see instantly if you are overcommitted.

💡 Alternative Tool

If you need advanced project management features and have a budget, you can use Motion. It follows the same “Auto-Scheduling” logic but is designed for larger teams and power users ($19/mo).

Share this post: