THE BLOG
12/17/2014 05:24 pm ET Updated Feb 16, 2015

Take the $100 Tip Challenge to Make Someone's Christmas and Your Own

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It's a typical Saturday. The whole fam is off to Waffle House for a breakfast extravaganza in the form of an All-Star special. We don't always have the same waitress, but they all know us, and for certain our bacon will be extra crispy and a smiley face of whip cream will accompany our waffle -- all without asking. But in actuality, today is not our routine Saturday. Today is the day our kids hand over a $100 tip as a way of saying Merry Christmas. And really meaning it.

It's such a fun and amazing ritual, and the kids jump around in their seat in preparation for the gifting moment. After we sop up the last bit of syrup with our waffles, we leave the crisp Hundie in an envelope on the table with our waitress's name on it. We begin to walk out like normal, but instead of revving up the car -- this year -- we crouched behind the hostess table so we could get a look and a video of her reaction.

First she stares at it. Then she picks it up with her mouth agape, looks around, and finally, a big smile spreads across her face. We sneak away at this point -- partly because we looked a little creepy crouching behind a hostess stand, but mostly, because we're not doing it for acclaim. We're giving to a person who is working hard and trying to support her family on minimum wage and $2 tips. But this moment of giving is not just for her -- it's also for us.

The act of simply reaching out in kindness to another person is one of the most fulfilling gifts we can give ourselves. We feel it and our kids feel it too. So that is why we are challenging everyone we know, and hopefully even ones we don't, to take the $100 Tip Challenge to make someone's day, and probably, whole year.

Now, before you get bored and move on to the next article, the $100 Tip Challenge can be the $10 tip Challenge or the $5 gift card to Starbuck's Challenge. The amount is actually irrelevant so long as it is out of the ordinary and is given out of joy, not duty. It doesn't need to be a tip at all if you feel the urge to give at a totally different time. For instance, if you see a veteran or just an elderly person fumbling to pull out cash to buy a few items at the store, try asking, "Can I get that for you"? It may seem small, but to see the expression on their faces --those expressions of true gratitude -- it makes it more than worth it. I think that's what being here on this Earth is really all about. And although this sounds totally cliché, isn't that what Christmas is all about?

Ok, you may still be like, "Not buying it "Weird-Girl-That-Stalks-Old-People-At-The-Grocery-Store." I work hard and am just trying to keep all the balls in the air myself." Fair on all accounts, so I'm gonna throw something out there even if some people will say, "Oh no -- she did not just say that! She be burnin' in hell." Maybe -- but I don't think it will be for this. If you are still on the fence -- and not because you're a jerk -- but because parting with hard earned cash is just that -- hard, then see what you think about this.

I truly believe, and have seen it in action more times than I can count, that when you are generous, the Universe is generous right back at 'ya. And sometimes, in ways much bigger than you could have imagined. So, I would ask you to do the $_______ Tip Challenge as an experiment.

If tipping doesn't move you, then is there a charity or organization that you are really passionate about, or just think they do really good work? Then give to it. You know the one that you always say, "I would love to donate right now, but, well, I spent it all last night on beer and White Castle"? Send it anyway. And an even bigger challenge? Send double what you think you can afford. Do it just once -- and then see if somehow, some extra money doesn't just show up.

You get a reimbursement check from your insurance company that you long since forgot about; you find a check your grandma wrote to you in 2003; or you get a bonus that you never saw coming. If it's given truly from the heart -- the Universe opens its arms and thanks you. Now, don't try to get all crafty. This experiment isn't about finding a new retirement strategy -- if you give only because you want money back, it won't work, because this really has nothing to do with money.

It's about hopefully showing everyone that giving is a two-way street, and we get back way more than we give. It's about taking away the trepidation of "I can't afford to give" that we all feel. Yes, this intensely personal form of giving does produce a tangible return, but it creates something in you that is even greater. Joy. Maybe you will even keep on giving, long after Christmas is over.

So, this holiday, dig deep into your pocket, and see what you can scrape up, even if it's your last few dollars and payday isn't until Friday. Trust me that it will all work out. If you don't have a charity you adore or a waiter who always goes that extra mile, give it to the homeless guy sitting desolate on the street -- who cares if he spends it on Mad Dog 20/20, all that matters is that you gave and gave with your heart. So, take the $100 Tip/Charitable Donation/Thirsty-Guy-On-The-Street Challenge and make someone's Christmas. And I promise -- it will also make yours.