proactive-messages

What This Skill Does

The Proactive Messages skill transforms your AI agent from a reactive assistant into a thoughtful, human-like companion. It is designed to track significant life events identified during natural conversation and schedule unprompted, casual check-ins. By monitoring for milestones such as career changes, high-stakes presentations, travel, or personal challenges, the agent creates one-shot cron jobs that trigger at the exact right moment. The core philosophy of this skill is the element of surprise; by never asking for permission and avoiding robotic confirmations, the agent provides genuine emotional support that feels indistinguishable from a close friend checking in.

Installation

To integrate this capability into your OpenClaw environment, execute the following command in your terminal: clawhub install openclaw/skills/skills/vmehmeri/proactive-messages Ensure your agent has the necessary permissions to manage cron tasks and interact with your messaging channels. The skill resides within the openclaw/skills repository.

Use Cases

This skill excels in high-context scenarios where personal rapport is valuable. Use it to keep track of:

• Professional Milestones: The first day of a new job, a major project launch, or a high-pressure board meeting.
• Personal Transitions: Moving to a new city, significant travel, or recovery periods after medical procedures.
• Emotional Check-ins: Providing support when the user has expressed anxiety or stress regarding upcoming life events, ensuring they feel heard without having to prompt for support.

Example Prompts

1. "I'm a bit nervous, I have my final interview for that dream job tomorrow morning."
2. "Finally, the last day at this office! I'm moving to Chicago on Friday to start the new role."
3. "I have to present my quarterly results to the executive team this afternoon—really hope it goes well."

Tips & Limitations

To maintain the effectiveness of this skill, adhere to the frequency cap of 2-3 check-ins per week. Over-usage can degrade the quality of the interaction and turn a helpful assistant into an intrusive one. The skill is intentionally designed to skip trivial daily tasks; if you find the agent checking in on routine matters, it is likely too sensitive. Always prioritize the 'quality over quantity' rule. Avoid the temptation to tell the user you have scheduled a reminder; the magic lies in the silence between the conversation and the timely, thoughtful follow-up text.