11/18/2013 05:16 pm ET Updated Jan 23, 2014

Read This Before You Give to Those "in Need"

Have you ever received a gift that offended you? Or a gift that as you put on a smile made you think, "Do you even know me?" Or a gift that as you tried to hide your hurt feelings made you wonder, "Why do you think I need this?" Please keep this to yourself, but I tend to be a really bad gift giver. Most of my gifts are unwrapped gift cards, and I may or may not have picked it up the day before Christmas. I give my grandpa socks and a pack of cigars every year. My family has learned that if they at all hope to be happy with the gift I give them, their best bet is to text me EXACTLY what they want and keep it under $25. The truth is that most of us are guilty of lousy gift giving at some point, and as we enter into the giving season it's important to take the time to consider just how difficult giving really is.

The year I lived at the Star Gospel Mission on the receiving--rather than the giving--end of gifts taught me that some of the most difficult giving can be to those "in need." It showed me that kind people with the best of intentions can give gifts that cause more pain than benefit when we aren't thoughtful. I recently heard a story that resonated with the things I felt during that year from Robert Lupton, a man who has spent most of his life working in inner city Atlanta. Robert tells the story of how for years he had been on the giving end of gifts at Christmas time to families "in need," but that the year he and his family decided to move into inner city Atlanta they had the privilege to be in the homes of those on the receiving end. When the givers showed up they had huge smiles on their faces, bearing the gifts the receiving family could never afford. He says that the children of these receiving families were always ecstatic. The mother, though, he noticed was a little embarrassed, but did her best to hide it because of her children's joy. The father though, Robert noticed, always disappeared. The truth was, according to Robert Lupton, that for the first time he realized how the fathers of these families were being demoralized in front of their own wives and children, and that the givers who had the best of intentions had just publicly put his shortcomings on display in front of his entire family and possibly neighborhood. It turned out things were a lot different from the other point of view.

This kind of giving happens a lot. During the year I lived at the Star Gospel, I remember distinctly receiving gift bags full of all kinds of goodies around holiday time. The most vivid gift I remember was a hand knitted scarf that I could only imagine took a really long time to make. It was gorgeous and for the record I wore mine all the time. But more vividly, to me, it sadly reflected just how distant the giver was from the receiver. Charleston doesn't get that cold in the winter and the men all had scarfs. They were poor, sure, but not naked. Putting it on might have meant admitting that you had sunk so low that you couldn't clothe yourself. Since then, I've taken a lot of time to think about the hearts of people when they give and their honest intentions, and I try to focus mostly on my own.

1) The best giving is based around relationship.

One year my father was transitioning between jobs. I wouldn't say that we were struggling, but I'd imagine it was a tighter Christmas than most. I was on my cell phone talking to a friend when a lady came up to me that I'd never seen, asked if the house I stood in front of belonged to the Snook's, and put an envelope in my hand and walked away. I went inside and opened it to find $500. Although I'd never met the lady before, over time we figured out that she and her husband worked for the company my dad would soon join. These were friends of ours, who knew us and knew our situation. They didn't embarrass us or tell their friends or the whole community about it. Instead, they gave because of and out of the relationship we had.

The best kind of giving is based around relationship. Random acts of kindness are great too, but relationship increases the chances that you'll give something to somebody that's truly meaningful when it's truly needed. The best givers when I lived at the Star Gospel Mission weren't the people who handed things off and left. That kind of giving created dependency. Instead, they were the people who stayed, asked us our names, listened to our stories, and then came back over and over. They made it clear that giving wasn't for them a one and done, once a year kind of thing, but instead a by product of a real intention to get to know us. Too many people fail to realize that the relationship they can offer is more valuable than any gift they can give.

2) Understand that everybody has something to give.

I learned more from the year I spent living at the Star Gospel Mission than I did from four years at college that cost over $150,000. Hands down. I received far more than I gave. It was the best year of my life.

Most of the lessons I learned were kicks in the pants. I'll never forget the first weekend I spent there when one of the men told me, "All any of us really need is hope." I'll never forget when my bunkmate challenged me to start the company I'd been dreaming of. I arrogantly couldn't believe that he, a man living at the Star Gospel Mission, would challenge me, a college graduate. But once I thought about it I realized he was right: Success has nothing to do with where we start or end up in life; instead it's our willingness to address and conquer our fears, face rejection, overcome obstacles, persevere, and spend our lives living our best story.

Those lessons were true gifts.

Maybe all that those "in need" have to give is their time and the wisdom they've gained in life. But it's quite possible those who are "in need" have just as much to teach and give as those who aren't. After all, the greatest things in life are often times born out of great difficulty and challenge. When you give it's important to have the humility to receive.

3) Remember our best gifts fall short.

Giving is truly complex. Most of the time we truly give out of the best places of our hearts. The truth is that we should give, give of our lives, give of our hearts, give of our time. The greatest joy is to completely give our lives long before they are over. But understand that giving is messy, and a lot of times our hearts just aren't that great. Giving isn't perfect and often times the receiver understands a different message than you meant to send. But it doesn't mean that we shouldn't give. It is an innate, hard wired, essential part of life. It's just that when we give at this time of year it's important to recognize we ultimately imperfectly imitate a kind of giving that is perfect, that's year round, and for those that accept it, completely free.

Anyway. I've got a lot to learn, but this year, if you really want to try something different, try this: Don't give to those "in need;" give with a heart that understands "we're all in desperate need."