Generosity + Joy: A Reflection on Matthew 6

Young group of smiling adults walk at sunset under a bridge

Take heed that you do not do your charitable deeds before men, to be seen by them. Otherwise you have no reward from your Father in heaven. Therefore, when you do a charitable deed, do not sound a trumpet before you as the hypocrites do in the synagogues and in the streets, that they may have glory from men. Assuredly, I say to you, they have their reward. But when you do a charitable deed, do not let your left hand know what your right hand is doing, that your charitable deed may be in secret; and your Father who sees in secret will Himself reward you openly.”

Matthew 6:1-4

Several years ago, I was in New York City doing short-term missions work. It was this time of year – cold, crisp, and full of the expectation of Thanksgiving. During the grueling 14-day trip facilitating worship, outreach, and ministry to the homeless, I had one 10-hour break to enjoy the city. A few subway stops later, I was strolling through Central Park with a friend, on our way to gawk at 5th avenue and the finest that New York had to offer. Everything was full of lights and color, and overwhelmingly decadent. We strolled, carefree, and I’ll admit I was a little taken in by it all.

Ahead of us, a light turned red, and we stopped.

Beneath the cold street sign that boldly proclaimed “5th Avenue” was a homeless woman. She was lying on the sidewalk, wrapped in a dirty, gray cotton sheet. Her dark hair was matted into dreadlocks; her lips were crusted yellow with dehydration. Tears flowed freely across her beautiful cheeks as she stared at the ground in desolation. The glamour of 5th Avenue disappeared with a sort of violence, and my heart broke in two.

Her shoulders were shaking in agony as she wept. I placed a dollar in her plastic solo cup full of pennies and nickels. My friend knelt down and tenderly asked if she could pray for her. The woman nodded. We prayed.

Hundreds of people were passing by without a second glance, and who could blame them? Sometimes the need is so great that it is too much for our hearts to feel. We have to shut it out just to avoid despair, but I think we all can relate to getting it wrong sometimes. In that moment I was repenting for forgetting compassion. 

As my friend prayed, the woman raised her eyes. Slowly, afraid of what she might see, she looked up into my face. Surprise registered as she saw that I was crying too. She held my gaze for a long time, like a thirsty man drinking water. She tentatively held my hand with two of her bony fingers. There was not enough space in my heart to contain what I felt in that moment.

Suddenly another woman, in cashmere and leather, aggressively came marching up from a restaurant a few feet away and angrily spat at me, “I just want you to know, we decided to buy her dinner, and they’ll bring it out to her.”

I had to smile. As reluctant as that woman was, our choice to see this child of God in the street, had allowed her to see also. Our conviction begat more conviction. Our tiny, almost insignificant, generosity begat more generosity.


When I was a child (a very legalistic, perfectionist, pastor’s-kid of a child), I would read Matthew 6 with horror. How could I possibly keep every act of charity a secret? Would God be angry with me if someone else knew I was tithing from my $6 allowance? Once I even went so far as to sneak into the office after service with my dad’s key and add my tithe. It makes me laugh now; I imagine I may have caused the accountant some frustration over 60¢.

I didn’t understand the heart of it. I didn’t understand that it was about heart motivation, not a legalistic practice of physically hiding. I didn’t understand that generosity done for accolades receives its reward in the moment. It’s still generosity, it still has value to the one who receives it, but there is something higher to strive for. Generosity done out of care for the other, out of compassion, out of conviction, out of the love of Christ produces not only eternal rewards, but also produces joy.

In the famous soliloquy, Shakespeare penned Portia’s words:

“The quality of mercy is not strained.
It droppeth as the gentle rain from heaven
Upon the place beneath. It is twice blest:
It blesseth him that gives and him that takes.”

Like mercy, real generosity blesses “him that gives and him that takes.” Or more appropriately from scripture:

“In everything I did, I showed you that by this kind of hard work 
we must help the weak, remembering the words the Lord Jesus
himself said: ‘It is more blessed to give than to receive’.”
Acts 20:35

One day we will all stand before the Judgment Seat of Christ. Our selfish deeds will burn away like chaff, and we will have to make an account for our actions. In Matthew 25, Christ admonishes us that whatever we do or don’t do for the least of these, we do unto Him. 

I like to imagine that I will be taken aback by the deeds that Christ honors in that hour: that woman who provided a dinner on the street in New York; a mother turning the other cheek as her son angrily rejects her; a man struggling against the temptation of pornography and choosing holiness; a husband quietly caring for his ailing wife without thanks or praise; an overcomer of sexual sin silently enduring slander from our culture and loving beyond the accusations and hatred. 

I like to imagine that as the Bride of Christ, we will have the opportunity to celebrate powerful acts of unseen love and generosity.

Culture, and so much of the Western Church, has turned its back on people who are struggling with unwanted same-sex attractions and sexual brokenness. These are a people “thirsty” and “given nothing to drink.” Someday, all of the agendas, the rhetoric, and the arguments will fade away, and Christ will bring right judgments about the way that the Church has responded to this sexual crisis. You are part of a different company of people. You see the need, and you believe in healing and transformation. You have poured out incredible generosity to help us bring hope and healing. You have helped bring living water to those in need.

As we enter into Give to the Max 2019 and this season of generosity, would you consider giving a gift to Outpost to help us continue in ministry? Your generosity begets so much more generosity, and your generosity brings joy.

Thank you for standing with us.

Donations can be given online at GiveMN.org on the TCJHOP organizational page, which will be directed to the Outpost General fund.

About Alissa H.

Alissa Holmes is the Development Director and Executive Pastor of Outpost and TCJHOP.