I’ve always struggled with planning. Setting a deadline was easy, but figuring out what I should be doing today was always the hard part.

Most tools assume you plan forward from day 1, but in real life you usually start with a fixed date — an exam, a trip, a launch, a wedding. I kept failing to stay consistent because forward planning never told me when each step should realistically happen.

A few years ago I discovered “reverse planning”: start with the deadline → work backward → define the checkpoints → then fill in the tasks leading to today.

It worked extremely well for me, but I couldn’t find a tool that supported it properly. Everything was built for forward scheduling.

So I ended up building one.

Some interesting challenges along the way:

- Figuring out how to anchor tasks to dates backwards (not trivial when dependencies overlap).

- Getting AI to output strictly valid JSON so it wouldn’t break the UI.

- Handling real-time collaboration while preserving formatting and task states.

- Designing timelines that feel achievable rather than overwhelming.

-Letting users tweak the plan while keeping the structure intact.

- Dealing with vague goals like “financial independence” vs concrete ones like “launch v1 by Dec 1”.

What surprised me most: reverse planning reduces anxiety dramatically because you always know the “next critical checkpoint”, not just a long list of tasks.

I launched it recently and I’m still improving it.

If anyone here has experience with productivity tooling, AI timeline generation, or planning methodologies, I’d love feedback or critique.

Link (if you want to see it): https://reversemyplan.com