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

Original Article ↗ Hacker News Discussion ↗

An online tool that algorithmically schedules paid time off around public holidays to maximize consecutive days off is drawing both enthusiasm and criticism. Users appreciate the visual planning aid but point out practical gaps: company- and country-specific holidays, school calendars, shutdown periods, custom work weeks, and personal constraints all complicate real-world use, and the “stretch your time off from X to Y days” claim is seen by some as mathematically and psychologically misleading. Many call for richer customization (toggling or adding holidays, weighting seasons, avoiding peak travel times, handling year boundaries) and alternative optimization goals such as evenly spaced long weekends rather than one or two large blocks.

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.