Show HN: Stretch My Time Off – An Algorithm to Optimize Your Vacation Days

Original Article ↗ Hacker News Discussion ↗

Overall Reception

  • Many find the tool clever, visually appealing, and genuinely useful for planning PTO, especially compared with manual spreadsheet/calendar hacks.
  • Several say they’d likely use it a few times a year; others see it more as a fun experiment or “start of something handy” than production-ready.
  • Some are skeptical of the core premise, preferring to take time off based on burnout, seasons, kids’ school, or travel costs rather than maximizing contiguous blocks.

Holiday Data & Customization Needs

  • Strong recurring request: fully customizable holidays.
    • Toggle on/off public holidays, add company/corporate shutdown days, school breaks, Jewish holidays, and other custom dates.
    • Handle regional differences (US states, German/Bavarian holidays, UK regional bank holidays, Swedish Christmas/Midsummer eves).
    • Some countries’ data is incomplete or off (e.g., Sweden, France “faire le pont,” missing UK holidays, year-crossing issues).
  • Users want:
    • Editable work week (e.g., 4-day weeks, compressed hours, Fridays off).
    • Ability to mark mandatory-on/mandatory-off days and blackout dates (on-call, Monday bans, etc.).
    • School schedules and constraints for families.

Algorithm Behavior & Requested Features

  • Current algorithm:
    • Maximizes long contiguous blocks, often piling days in late-year periods (e.g., around Christmas or Easter), sometimes leaving big gaps with no breaks.
    • Only shows a single “best” solution, despite many ties.
  • Desired improvements:
    • Multiple options / rankings for tied solutions; ability to “shuffle” or reseed results.
    • Per-day manual overrides: force a day on/off, lock existing trips, then optimize remaining days.
    • Preferences/weights: preferred seasons, distance from major holidays, even spread vs. long blocks, maximum days per block/quarter, legal constraints (e.g., Brazilian PTO rules).
    • Better metrics and wording: users find “stretch from X to Y days” misleading; want clearer accounting of true “extra” days, block sizes, and year-spanning clusters.

Usability & UX Feedback

  • Requests for:
    • Monday as first day of week (often per locale).
    • Custom year range or fiscal year start; planning between now and year-end.
    • State search that behaves like typical typeahead.
  • A few note corporate firewalls blocking the domain, or dislike IP-based geolocation.

Broader Reflections on PTO

  • Some optimize the opposite: avoid public-holiday periods due to crowds and prices, or prefer frequent 3-day weekends / 4-day workweeks.
  • Several argue that “unlimited PTO” or simply having many days off makes optimization less necessary.