How you get AI to access your data to answer this question really depends on the scale of the project.
As a simple prompt, yes, you’d have to include the full data source every time. Not delightful.
@jeffinbournemouth is correct, if you just want to explore personal data and analysis over the last year, use a CustomGPT. Here’s a case study.
Download your data as spreadsheets, name them, and reference them in the cGPT’s Instructions and Knowledge Base with Code Interpreter enabled. The GPT will understand the full breadth of your information without having to prompt it.
If you have something more robust in mind than just a personal running coach, you’ll look into connecting the GPT / Assistant to your data via API. Then solutions scale up from there depending on just how much information you need the model to make decisions with.