Most issues with Waypoint come down to how the app stores data locally. This page covers what's happening, why, and what to do about it.
Everything you write in Waypoint is stored in your browser's localStorage — a private storage area on your device that nothing outside the app can access. Your reflections are never sent to a server or synced. (For paid access we store only your email and subscription status on a secure server — never your reflections.) The reflection data physically exists on the device and in the browser you're using.
This means your reflections on Chrome on your laptop are a completely separate data set from Safari on your phone. They don't share storage.
The one thing to know
Clearing your browser data deletes your reflections permanently. This includes "Clear browsing data," "Clear site data," or resetting your browser. There is no recovery path — the data is gone. Before clearing, export your reflections first (see below).
Use the export function inside the app — it downloads your reflection history as a file you can save anywhere. Do this before clearing your browser, switching devices, or switching browsers.
If the app doesn't show an export option yet, copy your reflection text manually. It's not elegant, but it works. A dedicated export feature is on the roadmap.
You can open Waypoint on any device, but your data won't carry over. Each device maintains its own local storage. Pick one device as your primary and stay consistent — the practice works best when you're writing in the same place each week anyway.
Cross-device sync is not currently available. That's a deliberate tradeoff for privacy: sync requires a server, and a server means your reflections leave your device.
Private/incognito mode doesn't persist localStorage between sessions. If you close a private window, everything written in it is gone. Don't use Waypoint in private mode unless you're just testing it.
No. The synthesis reads your reflection set locally and generates a summary on-device. Your reflections are never transmitted to an external server during this process.
Check your spam folder first. The first email often lands there before your mail client learns to trust the sender. Mark it as "not spam" and future emails will arrive normally.
If it's not in spam, the subscription may not have completed. Return to the notification section on the Waypoint page and re-enter your email. The system will add or update your subscription.
The first email arrives on the day you subscribe, then repeats weekly on that same day. If you subscribed late in the day, the next one may not arrive until the following week.
Unsubscribe from the old address using the link at the bottom of any Waypoint email, then re-subscribe with your new address on the Waypoint page. The new sequence starts from the week you re-subscribe.
Download the .ics file from the notification section, then follow the steps for your calendar app:
Google Calendar — Open Google Calendar on desktop. Click the + next to "Other calendars" in the left sidebar → Import → select the downloaded .ics file → Import. Events appear immediately across all your devices.
Apple Calendar (Mac) — Double-click the .ics file. Calendar opens and asks which calendar to import into. Select one and click Import.
Apple Calendar (iPhone/iPad) — AirDrop the .ics file to your device, or open it from Files. Tap Add All when prompted.
Outlook (desktop) — Open the .ics file directly — Outlook detects it and offers to import. Click Open to add all 52 events. In Outlook on the web: Calendar → Add calendar → Upload from file.
Delete the events you imported, then return to the Waypoint page and generate a new .ics file with the correct start date. To delete in bulk: filter your calendar by the "Waypoint" event name and delete all matching events, then re-import.
Access is tied to the email you paid with. On the device you purchased from, it unlocks automatically after checkout. If it still shows weeks 1–4, give it a moment (payment confirmation can take a few seconds), then reopen the app.
On a different device or browser, open any locked week, tap Restore access, and enter the email you used at checkout — your weeks unlock immediately. Still stuck? Email learnwithmaydwell@gmail.com with your payment confirmation and I'll sort it out.
Weeks 1–4 (Q0): Free. No payment, no account required.
Weeks 5–13 (Q1): $19 one-time. Unlocks the rest of the first quarter and your first Quarterly Synthesis.
Weeks 14–26 (Q2) onward: Monthly ($12/mo), Quarterly ($29/quarter), or Annual ($89/year). All plans give full trail access from wherever you left off.
Open the app on the new device, go to any locked week, and tap Restore access. Enter the email you used at checkout and your access unlocks right away — no link needed. (Your reflections live on each device separately, so past entries won't carry over, but your paid access will.)
If it says no active access is found, double-check the email spelling, or email learnwithmaydwell@gmail.com with the address you used at checkout.
Use the customer portal link in your Stripe billing email, or email learnwithmaydwell@gmail.com and I'll cancel it within 24 hours. Your access continues through the end of the period you've already paid for.
Yes. Your reflections are stored locally and nothing is locked. You can return to any week and update what you wrote. That said — the more useful practice is writing a new note in the current week's reflection about what you'd change, rather than rewriting the original. The gap between what you wrote then and what you think now is data.
Nothing. There's no streak tracking, no penalty, no notification that escalates. The trail picks up where you left off. A missed week is just a missed week — the only consequence is one fewer reflection in your Quarterly Synthesis set.
You can, but the practice is designed for one per week. The gap between scenarios is part of the design — you're supposed to carry the question into real decisions before the next one arrives. Moving faster skips that. If you're catching up after a few missed weeks, completing them sequentially is fine.
After every 12 scenarios, you can trigger the synthesis from inside the app. It reads your reflection set for that quarter and generates a short structured summary — recurring tensions it noticed, decision patterns across weeks, anything that appeared more than once.
The synthesis runs on-device. It doesn't send your reflections anywhere. The output is text you can read, copy, or delete. There's no grade, no score, no comparative benchmark. It's a mirror of your own writing over 12 weeks.
Some scenarios will feel closer to home than others — that's by design. The practice asks you to engage with the decision as presented, not to filter for direct job relevance. The judgment being practiced is the same across contexts: what do you prioritize, what do you avoid, how do you respond under uncertainty. The scenario is just the occasion for that.
If a scenario feels genuinely irrelevant, write about why. That response is often more revealing than a direct answer would have been.
Try these in order:
1. Hard refresh: Cmd+Shift+R (Mac) or Ctrl+Shift+R (Windows). This forces the browser to reload without cache.
2. Try a different browser. If it loads in Safari but not Chrome, the issue is browser-specific — usually a privacy extension or content blocker.
3. Disable browser extensions temporarily, particularly ad blockers or script blockers. Some block localStorage access.
4. If none of these work, email learnwithmaydwell@gmail.com with your browser, OS, and what you see on the screen.
The most common causes: browser data was cleared, you're using a different browser than usual, or you're on a different device. Check those first.
If you're on the same device and browser and the data is gone, it's likely your browser automatically cleared site data — some browsers do this under storage pressure or after a set period. There's no recovery path from here. Going forward, use the export function periodically to keep a backup.
The synthesis requires at least 8 reflections in the quarter to run — fewer than that and there isn't enough material to surface patterns. Check how many weeks you've completed and filled in a reflection for (not just opened).
If you have 8+ reflections and it's still not running, try a hard refresh and attempt again. If it continues to fail, email learnwithmaydwell@gmail.com.
The app tracks your progress in localStorage. If it's showing the wrong week, the stored progress may be out of sync. Hard refresh first. If the issue persists, check that you're marking scenarios as complete before moving on — the trail advances on completion, not on opening.
Email learnwithmaydwell@gmail.com. Include your browser, operating system, what you were doing when the issue appeared, and a screenshot if you can. I respond within 24 hours on weekdays.
Email is the fastest way to reach me. Include your browser, OS, and what you were doing when the issue appeared. I respond within 24 hours on weekdays.