It started with a pair of socks. I needed a pair of socks to ride in, and I found some cute ones at a tack store where I was having a repair done. As with any specialized item, since the socks were “for riding” they cost more than an equivalent pair of plain socks. I weighed my options: buy the slightly-more-expensive-but-cute socks that are exactly the right length and thickness for riding or save money, wait for a sale, buy another pair of socks that will do but are not quite right. You’d think that would be an easy decision, wouldn’t you? It was when I was standing there holding the socks and debating with myself about buying them that I realized just how stingy I can be with myself.

I’ve been thinking about this concept for quite some time. Where is the line between common sense frugality and stinginess? Part of the way I think comes from how I grew up and most of my young adulthood. For a long time, I did not have money for anything except true necessities. I remember carrying a calculator to the grocery store when I was first married; once I hit a certain amount, items were returned to the shelf. There simply was no extra money in the budget.

But it’s not just money but time that I’m stingy with. I’ve begun to feel that if I’m not working—either for pay or for the good of the family—I’m wasting time. Add these beliefs to my naturally cautious and shy nature and you have a recipe for a narrow, joyless life and a lot of guilt. I seem to take a perverse pleasure in denying myself things I want, whether it’s a pair of socks or a half hour to read *gasp* right in the middle of the day.

I don’t want to live like that. I want to be more generous, loving and kind to myself. I believe that will make me happier as well as help me be more generous and loving to others. So I came up with the concept of “a week of yes”—a week where I followed my impulses, indulged my desires and generally loosened up on myself. Three times I’ve set out to have a “week of yes”—and three times I’ve started and stopped.  I can’t seem to sustain the concept of saying yes for more than a day or two. It’s hard! It’s scary. It requires some serious attention and listening to myself.

Why don’t I say yes? Like too many things, it comes down to fear: What if I say yes and something bad happens? What would other people think? What options will I close off if I say yes? I’m a little afraid of what I’ll get myself into by saying yes. I definitely don’t want a life that is overloaded with too many activities and I don’t want yes to be indulgence for indulgence’s sake.

To make things more confusing, sometimes saying no is really saying yes! Saying no to lots of yummy-but-bad-for-me foods is really saying yes to my bigger goals of being leaner and healthier. (However, saying no to all delicious foods can lead to binge eating. Let’s not get too carried away here.) Saying no to an $80 purse I don’t need and am not in love with means saying yes to keeping that $80 for something else. (Here, a friend’s motto, “If it’s not an absolute yes, it’s a no” comes in handy.)

Instead of a week of yes, I’m slowly and gradually bringing yes into my life in small ways. To start, I’ve come up with these basic guidelines. I will say yes if:

• It costs less than $10.
• It’s something I’ve been wanting/wanting to do for a long time.
• It furthers my larger and most important goals: good health, loving relationships, fulfilling work.
• It’s an unexpected chance that might not come again.

And yes, I bought the socks.

The socks that started it all.

Do you think you’re generous with yourself? What do you want to say yes to?

It started with a young man’s wish, left behind in his will: he wanted his family to leave an “awesome” tip for a server—not 25%, but something like $500 for a pizza. Aaron Collins died in July, just after his 30^th birthday, and his family honored his last wish by collecting the funds for that “awesome tip,” eventually giving a $500 tip to a waitress who served them lunch. You can see the video here: