My wife and I have a game going where we are racing to give away $100. The trick is we need to give $1 at a time to 100 different people. We’ve found it far tougher than we expected.

We’ve learned a lot about our attitudes towards generosity. Here’s what we’ve noticed with our internal chatter:

It’s not enough – we hold ourselves back because we are worried that we can’t give enough. This fear permeates all aspects of my life – particularly within family relationships.

What if they get mad at me – because “it’s not enough” there is a fear that there could be recriminations. My antidote is to remind myself that I’m giving what I can and something is much better than nothing. That said, my irrational mind is still afraid and it easier to avoid involvement than risk by helping a little.

To counteract the above, I use my (wildly outgoing) four-year-old daughter to insulate me! She doesn’t have my fears, or chatter, and loves interacting with people. She’s been a positive influence and looks for situations where “we” can give money.

My wife’s been experiencing the same dialogue in her head. Her antidotes have included explaining the exercise and apologizing for not giving enough.

When I reflect on my reasons for closing off – not enough to give, person doesn’t deserve help, fear of rebuke… they don’t hold up to scrutiny.

Without a doubt, my community would be better from lots of consistent little gifts. Going further, I’d certainly feel better.

Based on the gifting rate of our Dollar Game, which is embarrassingly slow, it would take us close to two decades to get through our annual gifting target…

…either we need to increase the bill denomination or change our attitude.

Once I relax and give to everyone, I find myself more open. I don’t need to choose, judge and rationalize.

To give an extra dollar in every interaction I have in a year would cost me less 1% of my net income.

If you see me then hit-me-up!

I have a stack of ones that I need to share.