06/15/2012 03:30 pm ET Updated Aug 15, 2012

The Giving Triage

We often feel compelled to give, whether it is a material item or an hour of listening time to a friend in need. It could be that someone is in trouble and needs our reassurance, or a toddler is in the midst of a tantrum and could easily be soothed by a toy from the drugstore. However, when it comes to giving, are we secure in our motivations and how we've prioritized? Charity is a great example when it comes to prioritizing: You may be passionate about a certain cause and that is what inspires you to donate, whereas another cause holds little personal significance to you. It is human nature to give more when we feel we're helping another person to whom we can relate.

Sometimes "giving" is about pacifying -- and it's not only about trying to keep another person happy, but placating ourselves. We may feel guilty about our own past actions (i.e. yelling at a child) and decide that a gift (i.e. the toy) nullifies our shameful behavior. Philanthropists have told me that each opportunity to give charity gives them a "fresh start." Some have expressed that they look at charity as a way to "make up for" personal shortcomings and misdeeds.

My friend Alexandra* started a charity several years ago and says that part of the motivation behind its launch was feeling that she was not a "whole person." When I ask her to elaborate she says "I've done so many things the wrong way. I look back at my mistakes and the things I feel bad about. As a result, I force myself to move forward and do good things! Helping those who are less fortunate boosts me up. You may call it selfish or narcissistic because it is a healing process for me, but I choose to call it 'charity.' And in the process of giving, I relinquish my selfish thoughts and focus outward. The cure for self-absorption and, essentially, misery, is to help others!"

I agree with Alexandra, but like my friend Candice, I've found myself in what I've termed the "compensatory, silly over-giver" category at times. Candice was once forced to fire a colleague who had become a close friend. The former colleague (and now, former friend) subsequently gave Candice "a piece of her mind." Candice, who was pained before and during the firing, began having anxiety attacks afterwards. She began obsessing for weeks on end about her former friend's welfare, the loss of the friendship and she heaped blame on herself. Certain without a shadow of a doubt that the friendship was over and that she would never hear from the woman again, Candice sent a very extensive apology note on her best stationary and a $300 gift certificate to a luxury spa (Note: Candice is not a rich woman and $300 is $300 she does not have.).

"I'm heterosexual, but felt like this woman's lover on some level," says Candice bashfully, "But not like a lover trying disgracefully to woo her back so much as successfully bid her adieu."

From a psychological viewpoint, Candice was easing her own conscience through an elaborate act of apparent contrition and an intense effort to be thought of well. However, Candice contends that she wanted her friend to be happy, to enjoy something, fully knowing she would not receive anything in return.

In fact, she never did hear from the friend again, but she greatly hopes the spa day was thoroughly enjoyed.

In my own Candice-like moment, I once sent a basket of edible arrangements to an offended acquaintance. The acquaintance affirmed what I already knew, that the fancy delivery was completely unnecessary, and perhaps greatly over the top (especially with the addition of the chocolate dipped fruit sticks that her children attacked within mere seconds), but I can't say that I regret it. If I feel I've done something offensive, I have the innate desire to right it -- in my own mind. The "mentally healthy" thing to do in most similar cases is to "let it go," but for the somewhat obsessive compulsive among us, that's easier said than done. Although I heard back from the acquaintance in this particular story, other "compensatory, silly, over-giving" overtures of mine have gone unheeded.

On a related note, I've spoken with many professionals who've had to treat incredibly rude clients to lunch in order to keep them happy, all the while enduring insults and inflated restaurant tabs. Sometimes "over-giving" is expected as part of one's job, while at other times, it is an instinctive part of one's quirky and neurotic nature.

The key is to step back and think before giving, to say to yourself: "What is my true intent here? How will my gift be received and how will it benefit the recipient? What is the most appropriate way in which to give?"

Once you have those answers, your gift will give back to you. Giving freely (while having the mental clarity that you are, in fact, giving for the right reasons) is a fulfilling act.

In the inspirational tome What About Now? Reminders for Being in the Moment, author Gina Lake writes "When we give freely, we feel full and complete; when we withhold, we feel small, petty, impotent, and lacking. We are meant to learn this great truth, that giving fulfills us, while withholding and trying to get causes us to feel empty and even more needy. This truth runs counter to our programming, which drives us to try to get something from others to fulfill our neediness, only to end up even more needy, grasping, lacking, and unfulfilled."

I open up the floor to you, readers. I'd like to hear your experiences with giving, both negative and positive, as well as the lessons you've learned along the way...