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

stretchmytimeoff.com

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

#1

Post by zachd »

Hey HN! I built StretchMyTimeOff as a quick experiment using Cursor (Anysphere's AI code editor) and GPT-4o to see how far AI could go in building a simple, functional site.

What it does: The site helps you get the most out of your vacation by suggesting optimal days to take off around national holidays, maximizing long breaks with minimal vacation days, anywhere in the world and for any calendar year.

It's an idea I've had for a while, and building the algorithm with GPT was a fun challenge. Any feedback or ideas I'm all ears :)

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

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

#2

Post by shmoogy »

This is a great idea for something I typically do manually to plan around maximizing vacation time around when my kids have off.

Would recommend being able to adjust the public holidays - for example: Juneteenth and Veterans day off were not days off of school+work.

Other future improvements would be some kind of tie in for airfare - these are typically some of the most expensive times to fly.

Love the idea

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

#3

Post by helios_invictus »

shmoogy wrote: post #2

This is a great idea for something I typically do manually to plan around maximizing vacation time around when my kids have off. Would recommend being able to adjust the public holidays - for example: Juneteenth and Veterans day off were not days off of school+work. Other future improvements would be some kind of tie in for airfare - these are typically some of the most expensive times to fly. Love the idea

Also it would be great to be able to add "corporate" holidays, where the whole company is off because of X reason.

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

#4

Post by xutopia »

If you add the ability to toggle days in various states this could be a really useful tool for me. Unfortunately I have family obligations that occur at various times in the year. Clickable cells that would change them from day/off or not could really help here.

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

#5

Post by geostupid »

Most companies don't take all public holidays; this ends up being primarily for Federal workers who do get each of those holidays.

If you make a table of holidays and then check on/off those applicable, then have the algorithm fill back in as needed, that would be helpful.

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

#6

Post by sksksk »

Awesome idea, some suggestions (to fit my use case)

My annual leave resets on April 1st, so being able to change the year would be handy.

I worked compressed hours (I have every Friday off)

I can carry over 5 unused days to the next year, and buy 5 more days. This might impact what days I take off.

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

#8

Post by jimjonah »

helios_invictus wrote: post #3
shmoogy wrote: post #2

This is a great idea for something I typically do manually to plan around maximizing vacation time around when my kids have off. Would recommend being able to adjust the public holidays - for example: Juneteenth and Veterans day off were not days off of school+work. Other future improvements would be some kind of tie in for airfare - these are typically some of the most expensive times to fly. Love the idea

Also it would be great to be able to add "corporate" holidays, where the whole company is off because of X reason.

I second that request!

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

#9

Post by abeppu »

This seems like the start of something handy, but isn't yet useful. As others have mentioned, which holidays a company offers will vary. But more than that, given a number of days off and a calendar year, this currently seems to output only 1 result, though of course there are a large number of ties (in terms of consecutive days not worked). The current tool doesn't allow the user to 'edit' or swap between 'equally good' allocations. In my attempt, it produced a very skewed result, using the vast majority of days between November and February, and using zero days in July through October. If it suggests using 4 days to extend a holiday into 9 consecutive days, there's no way to express that you'd rather do that for Labor Day than for Veterans day. If it's extending a 3-day weekend into a 4-day one, you can't indicate that you'd rather do that with Columbus Day than with Presidents Day.

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

#10

Post by quickthrowman »

Like others have mentioned, being able to toggle which days are holidays would make this useful.

I get (8) holidays each year: New Year’s Day, Memorial Day, July 4th, Labor Day, Thanksgiving, Black Friday, Christmas Eve, and Christmas Day.

Two of my company holidays aren’t federal holidays, so being able to toggle arbitrary weekdays as holidays would also be useful.

Also, sometimes holidays fall on the weekend and the observed holiday date is arbitrarily chosen.

Your algorithm did pick the same vacation days as I did this year for December, so it does seem to be working properly in that sense :)

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