The Monthly Gut Check: Deciding When to Leave a Job

A former engineer at Microsoft, Meta, and Atlassian, Kun Chen, has shared a simple but powerful method he used to determine when it was time to move on from a role.

In a monthly self-assessment, Chen asked himself one key question:

"What did I do this month that I couldn't last month?"

Speaking to Business Insider, Chen explained how this practice revealed his professional trajectory. After six years at Microsoft, he found himself unable to answer the question for several months in a row.

This silence, he said, was a clear sign of stagnation.

He noted that waiting for a missed promotion is a lagging indicator.

According to Chen, running this monthly test is especially relevant in modern software engineering, where the landscape is shifting rapidly—particularly with the rise of AI-generated code. However, he cautioned that not growing doesn't automatically mean you should quit. Instead, it serves as a prompt to evaluate what changes might be needed.

Chen ultimately chose to leave Microsoft for Facebook, citing different growth opportunities and Facebook's rising stock. Later, he returned to Microsoft to bootstrap a new games platform, applying the skills he had acquired during his time at Facebook.