Workflow Rules and Process Builder's time-dependent operations do not repeat. For each eligible invocation of the Workflow or Process, the platform enqueues them exactly once. That is, the record is modified, it meets the Workflow's entry criteria, and then a single time-dependent action is enqueued.
You can create chains of declarative automations to update records in such a way that Workflow criteria are reevaluated and actions are rescheduled. This, on the other hand, is complicated, difficult to reason about, and prone to errors. Furthermore, the processing limit for time-dependent activities is only 1,000 per hour, which is quite simple to exceed if you use the feature frequently.
Instead, consider using an open source programme like Doug Ayers' Mass Action Scheduler to automate certain actions.
Hope this helps!
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