[19] A Month Long Challenge You Can Steal From Me to Become the Best Version of Yourself

Sunday Ain't Scary

Mar 6 2022 • 16 mins

I started a challenge in March with 8 friends! Feel free to steal it from me below:

The Structure

The challenge is a $31 USD wager. Each dollar represents ONE day in March (hence $31). One dollar for each day.  You can adapt this wager however you want, obviously. The amount of money is less important than the symbol of commitment it provides.

The goal is to retain your bet. To retain your dollar for the day, you MUST accomplish 2 things on that day:

  1. Do a group “check-in” where you text the rest of the group with your status
  2. Complete all the items on your habit list for the day (honor system - if you say you did them, we believe you)

Losing Your Bet

If either of these doesn’t happen (i.e. you don’t text the group, even if you complete your habits, or you don’t complete your habits and text the group), you lose $1 that day.

If you miss multiple days in a row, your losses start to double.

So on the 2nd day of you missing your habits or texting (or both), you lose $2 instead of $1. And so on (e.g. if you miss 4 days in a row, you lose $8).

If you miss enough days in a row, you’ll end up owing money!

How to Play

Everyone chooses something they either want to ADD or SUBTRACT from their current everyday routines in these areas of life for the entire month. These should be challenging yet attainable in your daily life. Adding something means you don’t currently do it consistently. Subtracting something means you do it all the time and want to live without it:

1. Physical Movement (Exercise)

2. Mental (Emotional/Spiritual)

3. Work (Business/Job)

4. Nutrition (Substance/Food)

5. Wild Card (Anything)

Once you’ve chosen the routines you want to add/subtract, you’re responsible to yourself and the group to report every single day and actually do them. Again, only by completing both of those tasks (reporting + doing) allow you to retain your bet on any given day.


Whoever has the most money in their account when the clock strikes midnight on the first day of the next month gets ALL the money.

Tie Breaks

In the event of a tie, the people who tie split the pot between themselves equally.

Are you going to try this challenge for yourself? See if you can get a few friends to start with you! While you can start at the beginning of the month you can really adapt the structure to fit your needs. Have fun with it.

DM me on Instagram and send me a screenshot of you and your group.


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