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How-to guide · Playbook

The Calendar “Choose A Date” fundraiser

The friendliest fundraiser there is: each player gets a calendar, supporters pick days and give that date’s value — the 12th is $12 — and every dollar goes to your program. No luck, no payouts, free to run.

Start free →About the Calendar fundraiser
Free on Kickoff · you keep 100% · Teams, classrooms, PTAs & clubs with a goal · 6 min read

Some fundraisers ask people to gamble; this one just asks them to give — and makes it easy. A Calendar fundraiser (you’ll also hear it called “Choose A Date” or “fill the calendar”) puts a single month in front of your supporters and invites them to claim days. Each date is worth its number: the 3rd is $3, the 18th is $18, the 30th is $30. Pick the days that mean something — a birthday, an anniversary, a jersey number — and pay the total.

Fill an entire 30-day calendar and you’ve raised about $465 — and because there’s no prize to pay back, all of it funds your program. Give every player a calendar of their own and those calendars add up quickly. Here’s how to run one, what the platform handles, and a calculator to set your goal.

Why it works

The easiest ask in fundraising

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No luck — everyone gives

There’s no drawing and no winners, so nobody walks away empty-handed. Supporters give because they want to support the program, which makes it an easy ask for any crowd.

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The price explains itself

Each date is worth its number — the 5th is $5, the 20th is $20. It’s instantly understandable, and supporters can give as little or as much as they like by picking the days that fit their budget.

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100% goes to your program

Because nothing is paid back out as a prize, every dollar collected funds your cause. A full month calendar adds up fast — and you keep all of it.

How it works

One calendar per player

You set the month and a goal, then give each player their own calendar to fill. They share a personal link; supporters tap the days they want and pay that date’s value straight to your program. A progress meter climbs as dates get claimed, so the whole group can see how close you are. When a player fills their calendar, that’s roughly $465 raised — and if you want more, you can let multiple supporters claim the same day or add a second month.

Set your goal

How much can your drive raise?

Slide in your sellers, months, and how full each calendar gets. Everything updates live.

Calendar calculator

See what your drive can raise

Each one gets their own calendar to fill.
months
One month per calendar — run more months to raise more.
A full calendar = $465 (the 1st is $1 … the 30th is $30).
%
Most drives fill 80–100% with a little hustle.
Total raised
$9,300
20 calendars · $465 each
🎯 Each player just fills one $465 calendar.
Per player
$465
1 calendar
Full calendar value
$465
sum of 1–30
Calendars in the drive
20
20 × 1
Avg raised / calendar
$465
100% full

Estimate. Supporters pay the sum of the dates they pick — there’s no drawing and no payout, so 100% of what’s collected goes to your program. You set the month, the goal, and whether more than one supporter can claim the same day.

The ask, made small

Every player fills just one calendar

The magic of this fundraiser is how small each person’s job is: fill one calendar. That’s a few relatives, a couple of coworkers, and a neighbor or two — most of whom are happy to grab a meaningful date for a few dollars. Put a per-seller goal and a leaderboard up, and a roster of twenty players quietly turns into thousands of dollars without anyone feeling stretched.

The automation

What the platform runs for you

No paper calendars taped to the fridge — just one link per seller and a live goal.

A calendar and link for every seller
Each player or volunteer gets their own calendar and a personal link to share. Every date they sell is credited to them.
Live goal & progress meters
Set an org goal and watch a progress bar climb as dates fill in. Great to post in the team chat or show at a meeting.
Per-seller goals & dashboards
On Varsity and up, each seller sees their own full-calendar goal and progress, with a leaderboard to keep it friendly.
Reward your top sellers
Set prizes for the players who sell the most — cash or items — and the leaderboard tracks the race automatically. A little incentive moves a lot of calendars.
A countdown to the deadline
Add a live countdown with your own message to create urgency in the final push.
Assign, release & mark paid
Add a cash supporter to a date by hand, free a date for resale, and track which pledges have been paid.
You keep every dollar
Supporters pay your program directly by Venmo, PayPal, check, or cash. ChooseASquare never holds the money and takes no cut.
Run it this week

Four steps to a filled calendar

1

Pick a month & goal

Create a Calendar fundraiser, choose the month, and set a total goal. Add more months later to keep the drive going.

2

Add your sellers

Add players or volunteers — each gets their own calendar and link to share with family and friends.

3

Share the links

Sellers post their links; supporters pick the days they want and pay that date’s value. The goal meter climbs in real time.

4

Track & thank

Mark pledges paid as money comes in, watch the progress bar fill, and export a clean record when you’re done.

FAQ

Calendar fundraiser, answered

What is a Calendar “Choose A Date” fundraiser?
It’s a no-luck giving drive built on a calendar. Each seller has a calendar for a month, and supporters pick days and donate that date’s value — the 10th is $10, the 25th is $25. Fill the whole calendar and you’ve raised the sum of every date in the month.
How much does one calendar raise?
A full month equals the sum of its dates: about $465 for a 30-day month, $496 for 31 days, $406 for February. The calculator above lets you set the month length and how full each calendar gets, then multiply by your number of sellers.
How is this different from squares or a raffle?
There’s no game, no numbers, and no drawing — and nothing is paid back out as a prize. It’s pure giving toward a goal, which makes it the friendliest fundraiser to run and the easiest to explain.
How do players sell their calendars?
Each seller shares a personal link. Supporters open it on their phone, tap the days they want, and pay that date’s value directly to your program. A handful of relatives and coworkers fills a calendar quickly.
Can more than one person claim the same day?
Your choice. By default one supporter claims each date, but you can raise the capacity per date so multiple people can sponsor the same day — which lets a calendar raise well beyond its face value.
How do supporters pay, and do you take a cut?
They pay your program directly through your own Venmo, PayPal, check, or cash. ChooseASquare is software only — it never holds your funds and takes no percentage. You keep 100%.
Is it free to run?
Yes. The Calendar fundraiser is available on the free Kickoff plan, and you keep everything you collect. Varsity adds per-seller goals, a leaderboard, and a countdown bar. Supporters never pay a platform fee — they only give the date values they pick.
Can we run more than one month?
Yes — add more months as separate calendars to extend the drive, each with its own goal and progress. It’s a great way to turn a one-month push into a season-long campaign.

Start your calendar fundraiser free

Pick a month, add your players, and share one link each — you keep every dollar your community gives.

Start free →
Free on the Kickoff plan. Per-seller goals, leaderboards & a countdown bar come with Varsity. See pricing
Calendar Fundraiser Playbook — “Choose A Date” (Free to Run) · ChooseASquare