I found a $100 bill on the sidewalk the other day. It was drizzling on a damp winter evening, and I had just exited the doors of Walgreens. I turned the corner, and that's when I found it: a hundred dollar bill. I think I was bending down and picking it up before the conscious part of my brain even realized how spectacularly awesome this was, let alone what were the chances of stumbling on a bill that big.

“Oh wow!” A voice rang out above me just as my fingers were grasping the wet paper. I turned to look up at the woman stopped on the sidewalk beside me, holding a small child by the hand. Her enthusiasm was infectious, and for a moment I was happy to share my joy with someone else. But I felt guilty just as quickly. Who was I to take this money, when this woman, no matter how rich or poor she might be, had a child who wasn’t out of diapers; which, by the way run twenty bucks a box.  “Good for you!” she said with an earnest smile.

I held the bill out to her, “Do you want it?” I asked. After all, she had seen it almost as soon as I had.

“No, no, no! You take it.”

“Are you sure?” I stepped hesitantly towards her with the bill in my outstretched hand.

She waved it away and kept on smiling. “No, no, it’s yours! Go ahead, take it, buy yourself a nice dinner. Congratulations!” As I continued on my way,  I couldn’t help but feel an uneasy mix of joy and guilt. Did I even deserve it? Should I have insisted she take it? What if the person who lost it wasn’t even a drug dealer or a pimp and really needed it? I checked the bill for any residual blow. It was too wet to tell.

Since uprooting my life and moving to the West Coast, this has been the only serendipitous stroke of dumb luck that I have ever had. The rest of the good fortune I’ve had has come from the generosity of the people in my life, whose hearts are as kind and big as this anonymous mother on the street.

I’ve been thinking a lot about generosity, giving and gratitude ever since Thanksgiving (go figure). Right around the holiday I was wondering why no one moaned about this holiday the way they do about Columbus Day. Both holidays symbolize the oppression and obliteration of millions of indigenous people. But Thanksgiving has remained largely untainted in its reputation, I'm guessing because it was transformed into a ceremony that people actually enjoy, one that forces them to put down their iPhones, pick up a fork, and share some food, and by proxy, their love and appreciation for each other.

Thanksgiving kicks off the season of gratitude, when we all buy gifts for the people we are grateful to have in our lives to show them how we feel. This year, as I struggled to find my footing out here in a new geographic coordinate, I felt really, truly grateful for the warm-hearted people in my life . I was thrust into a period of great need, living somewhere I didn’t know, with only newly minted friends to help me. I quickly learned how uncomfortable it is to take something you really need, even when it’s offered by a friend.

I recently met someone who knows what it’s like to receive the gift of another’s generosity, and the bewildering mix of gratitude and guilt that comes with it. My friend Sparkle Thornton, who I met at my yoga studio, is transgender and in the process of transitioning from male to female. She is planning on completing her transition with gender reassignment surgery this spring, but the operation is extremely expensive, and not covered by health insurance, which she can’t even afford. So she decided to start her own online fundraiser on the pledge site GiveForward.

Sparkle and I chatted about the success of her fundraising, which has garnered $7000 via word of mouth alone, and she admitted it was overwhelming to her. “I felt like I was inside a miracle,” she told me. “To be so honest and vulnerable with people, and  to get support through that is a treasure. I was in shock at first, but now it’s sinking in a bit and it’s inspiring me to keep following my gut and my heart, and to create my own life with an even more empowered approach.”

There is an expectation that you should pull yourself up by the bootstraps, regardless of whether or not you can afford to buy boots.

After hearing about her experience, I shared with her my own gratitude for the people who have helped me throughout the year as I struggled to find my footing. There were many times when I felt ashamed to accept any kind of financial help from friends, even if it was just in the form of a slice of pizza.  I think the sense of shame I felt came from a trait that is deeply engrained in American culture.  There is an expectation that you should pull yourself up by the bootstraps, regardless of whether or not you can afford to buy boots.

When I told Sparkle this, she acknowledged that it’s natural for someone to want “ to give to a friend in need, because you know it’s going to mean the world to them. And at the same time, we are just not really encouraged to be given the world. Or to be given anything at all. I was confronted with my own conditioned sense of what I was worthy of, and I was shootin’ low. And I didn’t even realize.”

Unfortunately, our communal sense of rugged individualism often prevents us from creating the space and opportunity for charity on a personal, one-to-one level. But when you do have enough, when you are OK, and you see someone else in need, it feels so good just to be able to DO something. We are so conditioned to focus on ourselves and on getting ahead that we create a mentality of scarcity for ourselves, which, as Sparkle points out, circles back to feeling like we’re not worthy of anything we receive, unless we fought tooth and nail to get it.

“This society and my upbringing did not set me up to receive things from other people. It was all about making everything happen on my own and working really hard; never asking for anything and not expecting anything. We are so programmed to be prepared for not having what we need. And that’s what keeps everyone trying to get what they think they need all the time,” Sparkle said.

“But giving on a personal level is creating a small bit of happiness that is actually making the world happier just between the two of you. I feel like once I get surgery, I am so there to help someone else go through the same experience with as much love as I had and have now.”

I, too am grateful for the love I had and have now. So without naming names, I will write a short list of the few of the things I was given this year by people I feel so blessed to have in my life.  I want you to know if you gave me one of these things, I am truly grateful—it meant more than you know:

• the open-ended invitation to live on my friend’s couch in her junior one-bedroom
• the slice of pizza I mentioned earlier (which I was actually gifted more than once) ~ the voice on the other end of the line who listened to my frantic, panic attacks and fretting fits
• the wisdom from other people who had taken a leap of faith
• the invitations to family barbeques and parties that made me feel at home
• the new friends I made who made me feel loved and taught me so much more about myself