The January Spreadsheet: Why I Built an AI to Plan My Vacation Days

Every January, I sit down with a cup of coffee, a blank Excel sheet, and a sense of dread. It's time to plan my vacation days for the year.

If you're a European professional, you know this ritual. You've been given 28 or 30 precious vacation days, and now you need to extract maximum value from them. The goal? Turn those days into as many actual days off as humanly possible.

In Germany, we have a word for this: Brückentage. Bridge days. Those strategic vacation days you take between a public holiday and a weekend to create long stretches of time off. A well-placed Thursday Feiertag can become a four-day weekend with just one vacation day. A Monday holiday followed by a Tuesday off? Same thing.

On paper, it sounds simple. But every January, I rediscover how maddening the optimization actually is.

The overwhelm is real

Here's what I'm juggling: public holidays vary by federal state. I live in NRW, which has its own set of Feiertage. Friends in Bavaria get 13 public holidays. Berlin gets 10. If I want to plan a trip with someone from another state, suddenly the bridge day calculus changes entirely.

Then there are the constraints. School holidays block certain weeks if you have kids. Colleagues have already claimed the prime summer slots. Some holidays fall on weekends this year, which feels like a cosmic injustice. And flight prices fluctuate wildly depending on whether you leave on a Friday or a Wednesday.

The mental load is exhausting. I want to plan a trip to Greece in May, but is that the optimal window? Should I save those days for October when the bridge day ratio is better? What if I take four days in June and five days in September instead of nine days in one go?

The analysis paralysis is real. So I do what any engineer does: I open a spreadsheet.

The spreadsheet phase

I download a calendar of Feiertage for my federal state. I cross-reference weekends. I manually highlight potential bridge days. I open Skyscanner in twelve tabs to compare flight prices for each window. I calculate the efficiency ratio: vacation days spent versus total days off gained.

In 2026, Germans with 28 vacation days can theoretically get 60+ days off using just 11 well-placed Brückentage. Theoretically. In practice, I spend three hours in Excel and end up with a headache and a half-baked plan that I'll probably revise in March anyway.

There's a deeper frustration here. This isn't a creative problem. It's not interesting. It's pure optimization — the kind of thing computers are supposed to be good at. And yet here I am, manually counting cells in a spreadsheet like it's 2005.

The “aha” moment

Somewhere around hour two of my January 2025 spreadsheet session, I had a realization: this is a solvable problem.

What if the calendar already knew my public holidays? What if it could automatically identify every bridge day opportunity? What if an AI could suggest destinations that fit each window, filtered by my preferences and budget?

What if planning your year of travel wasn't a draining optimization exercise, but something you actually looked forward to?

I closed Excel. I opened my code editor.

Building takedays

The core insight was simple: start with the calendar. Not with destinations or budgets or wishlists, but with the cold, hard mathematics of your vacation days and public holidays.

So I built a bridge day engine. You tell it your federal state, your number of vacation days, and any constraints — school holidays, blackout dates, colleague conflicts. It calculates every possible Brückentag in the year and ranks them by efficiency. You can see exactly how many vacation days you need to unlock each long weekend or week-long trip.

Then comes the AI layer. Once you've identified your optimal windows, the AI travel advisor suggests destinations that fit. Warm weather in April? Hiking in October? City breaks that work for long weekends? It learns your preferences and proposes trips you'll actually want to take.

The result: what used to take three hours in Excel now takes three minutes. And instead of feeling drained, you feel excited. Because now you're looking at real trips, not spreadsheet cells.

Join the journey

I built takedays because I was tired of the January spreadsheet. But as I've shared it with friends and colleagues, I've realized I'm not alone. Every European professional goes through this same ritual, and most of us are doing it badly.

We're launching soon. If you're as tired of manual Brückentage math as I am, join the waitlist. Let's turn vacation planning from a chore into something you actually enjoy.