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September 29, 2025 20 mins

It seems like every day there’s a new tool designed to help us be more productive. They promise to help us to more, faster, better, with fewer resources. And it’s easy to get shiny object syndrome. So how do you know when it’s time to switch, or when it’s a waste of time and energy?


Luckily, as a chronic tool switcher, I’ve thought a lot about this very problem. And I have a framework to help you decide.


We’ll go through the 4 questions you should ask yourself when evaluating whether or not to switch. Then we’ll apply these tests to case studies so you can see how they work with actual examples.


Wondering if you should switch? Go to https://shouldyouswitch.com to apply this framework!


What do you think? How do you decide when to switch tools? Let me know at https://streamlinedfeedback.com

  • (00:00) - The Rapid Evolution of AI Tools
  • (01:26) - Framework for Tool Switching
  • (06:39) - Case Study: Dropbox to Google Drive
  • (11:22) - Case Study: Cal.com to Calendly
  • (13:30) - Case Study: Switching from Arc
  • (18:30) - Final Thoughts on Tool Switching
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