Many things difficult to design prove easy to performance.

Working out how to do a thing is often harder than doing it. In your head the task has every possible complication attached, because imagination is free and adds detail without limit; in reality most of those branches never come up. The dread accumulated during planning is frequently larger than the whole effort turns out to be.

When something has been sitting in the planning stage too long, do the smallest real version of it instead. Send the draft, make the call, dig the first hole. What you learn in ten minutes of doing will reshape the plan more usefully than another week of thinking.