u/JoaoRochaOnReddit

So I built this thing called TimeOffCalendar (timeoffcalendar.com) and I honestly don't know if it's a real business or just a fancy solution to my own problem.

Here's the story. Every January, my partner and I sit down with a Google Sheet and try to plan our year off together. Sounds simple, right? Except I get 22 PTO days, she gets 25. I have Portuguese public holidays, she works for UK companies sometimes so different holidays. And we're trying to figure out when we're BOTH off at the same time so we can actually take trips together instead of wasting days separately.

After doing this manually for 3 years, I finally got annoyed enough to build something. Started super simple, just a calendar where we could both add our time off and see the overlap. Then I realized I needed to track how many days we each had left. Then I added public holidays for different countries because that was our exact problem.

Then other people started asking to try it and they had different needs. Someone works part-time and doesn't work Tuesdays, so I added custom weekend days. Someone else's company makes them take the week between Christmas and New Year but it counts against their PTO, so I added custom company holidays. It's basically grown from "what do WE need" to "what do couples/families need."

Right now it's live, completely free, 11 people using it (mostly couples, a few families). Built it with Next.js and Supabase. I'm a software engineer with 8 years experience but this is my first real attempt at building something people might actually pay for.

The competition is basically Google Sheets (manual and painful), enterprise PTO tools that are designed for managers not personal use, and some holiday optimizer tools that are single-user focused. Nothing really exists for the "I want to coordinate vacation days with my partner" use case.

I'm bootstrapped, working on this as a side project while I have a full-time job. Not raising money, not making money (it's free right now), and honestly not sure what the business model should be. Freemium? Subscription? Affiliate links to travel sites? I have no idea.

My customer acquisition so far has been posting on Reddit asking if people plan their PTO with their partners (got 35 upvotes and comments, about 75% said yes), then DMing people who complained about competitor tools, and word of mouth. It's slow and manual and probably doesn't scale.

I'm good at building and shipping things. I'm terrible at marketing and design (the UI works but it's ugly). I've never successfully built a business before. And I'm not sure if this is a "must have" or just a "nice to have" that people will use once and forget about.

So roast me. Is this market too niche? Should I pivot to B2B and sell to small companies instead? Is keeping it free forever killing any chance of building a real business? Am I wasting my time on something that'll never scale past a few hundred users?

I want brutal honesty. If this is a dead end, I'd rather know now.

My partner and I sit down every January and plan out our entire year of time off together. We have a whole system.

We look at:

• Both our PTO allowances (we get different amounts)
• Public holidays (we sometimes work in different countries)
• When we're both off at the same time
• How to maximize long weekends by taking strategic days off
• Family visits, trips we want to take, etc.

We used to do this in a Google Sheet. Now I built a simple calendar tool because I got tired of manually cross-referencing everything.

Is this normal? Do other couples do this? Or are we overthinking it?

I feel like most people just... take time off when they feel like it? But we have limited vacation days and want to make the most of them, especially the days we're both free.

Tell me I'm not alone in this.

(And if you do something similar, how do you currently plan it? I'm curious if there's a better way.)