• Written by Rob Kleiman

Checkpoint: A Tap on the Shoulder for the Hyperfocused

Some brains have two time modes: now and not now. Hours vanish, priorities drift, and you look up to find it’s dark outside. Checkpoint is a macOS menu bar app that periodically breaks through that tunnel. It’s a time-perception aid, not a discipline tool.

How it works

  1. Set what you’re working on, with an optional estimate and an “if I drift, I will…” plan.
  2. Work. The menu bar shows time on task. There’s no countdown: check-ins arrive at unpredictable times, so you can’t brace for them.
  3. Check in. A card shows the time, your objective and how long you’ve been on it, and asks whether you’re on track, have drifted (see your plan, park the distraction) or have switched.
  4. Review. A Today view shows time per objective, estimate accuracy and the thoughts you parked.

It’s interruptive on purpose, but polite: check-ins wait until calls end, hide from screen shares and pause while you’re away. It’s also private, with no network connection and no telemetry.

How it’s built

SwiftUI, with unit tests on a fake clock and end-to-end tests that drive the real app, both run automatically on every pull request. Version 1.0 is in daily-use testing.

Code on GitHub