I was sitting at the V&A waterfront of Cape Town, one evening last week, enjoying Thai take-away while trying to stay warm against the growing winter cape wind. I had again forgotten my wind breaker as it was stowed in the easy-to-forget top pocket of my backpack. The fog rolled in, broken by the strong lamps of a Coast Guard bay patrol ship, red and blue to either side, white on a spindle for search and rescue.

I was just cleaning the last of the noodles from the inside of the waxed cardboard box with my split wood chopsticks when a young man, likely in his early twenties, walked up to the end of the bench adjacent to the one I occupied.

He spoke quietly, as though an apology were in order, hesitant with his words “Excuse me. Sir. Would you happen to have–”

While I could not hear the individual words against the blasts of wind, I knew the intent. He would be asking for money. I didn’t mind, as I wanted to hear his story, “I am sorry, but I can’t hear you.” I finished another bite of the last remnants of my food.

He started again, “Excuse me sir. I have a baby girl. She needs food. Could you spare some change for milk and cereal?”

There was something about him that felt quite genuine. He was well dressed for a homeless guy, relatively new shoes, each of which had laces. They were apparently the correct size too. Jeans with a belt, clean, and his inner shirt tucked in. He wore a baseball cap with the brim set high, his entire forehead visible from where I was sitting.

He was black African, speaking English with the subtle accent of Afrikaans, double beats given to otherwise forgotten vowels, melodic in their intonation.

I motioned for him to sit next to me, and asked if he wanted some food, “I will be pleased to buy food for you, if you are hungry.”

“Thank you sir. But it is my girl, she needs food, not me.” He remained standing, now by my side.

“Sit with me. It’s ok.” He looked quite uncomfortable at my request and declined. Not for disdain but for simple lack of having someone ask this of him. His body moved in the direction of sitting but his brain held him back, uncertain what would come next.

“Where do you live?”

“At the shelter,” he motioned behind me to what I assumed as beyond the water front shopping center, “we stay there.”

“Is it safe? For you and your girl?”

“Yes sir, it is safe.”

“Where is your daughter now?”

“She is there.”

“At the shelter? Alone? Who is caring for her?”

“At the shelter sir, she is there.”

“Yes, I understand. But who is watching her?”

“They are … the …” he struggled with the words and so I filled in a few for him, “Child care?”

“Yes. Child care. They take care of her while I am away.”

It seemed unlikely that a single man would be raising a young girl at a shelter or that a shelter would offer child care, but I do not know the South African system. I liked him. He was not too bold, in fact he was humble in his approach. Given my extensive interaction with the homeless population, he seemed authentic to me.

Inside, however, I found that familiar pressure against the inside of my ribcage, the one that says, “This guy is just taking me for a ride. He’s making a quick buck. I don’t need to support his bad habits. Why can’t he just get a job!?” It is natural for this to rise in us. We are open to a certain degree, yes, but also protective of our resources and ourselves. If experience has provided a correlation between one who asks for something of us only to find that the person asking was not authentic, it is a kind of stove-top burn not to be repeated.

What’s more, we can use a certain self-righteous mode of communication which appears to be supportive when in fact it is little more than a wall around ourselves, justification for why we could not provide what is requested by a total stranger. We keep ourselves safely hid from authentic engagement for a lifetime, believing we are not responsible in any way for their situation. These people, the ones at the bottom, should simply try harder.

“Where is there a grocery?” I asked.

“A what sir?”

“Sorry. A supermarket. Where is there a supermarket?”

He pointed over my shoulder to the Pick-n-Save I had not noticed, less than one hundred meters distance.

“Ok. Let’s go shopping and get what you need.”

“Oh!? Thank you sir. Thank you. Just milk and cereal is all.”

“What is your name?”

“William. My name is William.” Again, his Afrikaans foundation came through, the ‘w’ in William given a breathy ‘v’ and ‘h’ at the same time.

I extended my hand and shook his as I introduced myself, “I am Kai.”

“Where are you from?”

“From the United States. Colorado.”

“I hear it is beautiful there.”

“Indeed. It is. Stunning.”

We arrived to the front of the store. He hesitated as though he was to wait outside. I placed my hand on his shoulder as a subtle insistence that he continue inside with me. I got the impression he had not been in a supermarket often, or perhaps the last time he exited he had not paid for all that he carried. He was uncomfortable.

“Tell me again what you need?”

“Just milk and cereal, sir.”

My decision to spend this time with William was reinforced as he had ample opportunity to take advantage of my generosity but each time refused. If this was a scam, at any level, he was not much of a scam artist.

“You need food too. Bread? Cheese? Meat?”

“You don’t have to do that,” he responded.

“I don’t have to purchase milk and cereal for your daughter either, but I have already chosen to do this for you. So what will it be?”

As we walked through the store, grabbing various items which eventually, with some prodding, included fresh fruit and a bar of dark chocolate (which he had never enjoyed before), I made a point of making physical contact as often as possible, the way I would with an old friend or family member. I would hold the upper portion of his arm as we spoke or make certain that when we chose food I gave it to him to add to the basket in order that it was his act of shopping, not my own.

I wanted to know more about William, to receive his story.

“How many years of school did you attend?”

“I completed the sixth grade.”

“Ah. Good. What were your favorite subjects?”

“Mmmm, the one with numbers, what is it called?”


“Yes, mathematics.”

“Are you good with numbers?”

“Yes, I like numbers.”

We walked down a few more isles, eventually finding the original two items he had requested.

“Do you know how to write?”

“Yes. I can write.”

“Do you enjoy writing?”

“Yes, very much.” He lit up a bit, making eye contact with me again.

An idea jumped into my head in full form. I moved on it immediately.

“Do you write poems?”

“No, but I write songs.”


“Yes sir.”

“Are they original?”

“Yes, original songs.”

We had just walked past the office products isle. I stopped abruptly, grabbing William by the arm. “I have an idea. I am going to help you start a business.”

He was intrigued, but didn’t respond.

I grabbed two bound notebooks, the kind whose pages can be removed; two ball point pens (blue at William’s request) and two packs of twenty envelopes.

I handed the collection to William and then explained my concept. “When you approach someone asking for money, you are a beggar. No matter how well you dress, no matter how good you smell, even if your story is completely legitimate, you are still asking for something without giving anything in return. As you likely well know, this usually doesn’t go over so well.”

He agreed, knowing all too well the challenges of this affair, “Yes, that is right.”

I continued, “If you sell something, magazines or books or fruit, people assume you stole it.”

He nodded his head again. His eyes widened as he caught on.

“But if you can sell something that could not possibly be stolen, an authentic, originally part of you, well, then you are no longer begging. You are a proper business man.”

I waited. He looked at me, his hands, and back to me again, smiling. “You mean I sell songs?”

“Yes. Exactly.”

He appeared perplexed, “I never thought of that.”

“You said you like math, so let’s run the numbers, ok?”

We quickly added the total cost of the books, pens, and envelopes which offered more than enough pages for him to scribble, write draft songs, and practice his penmanship and signature. In summary I concluded, “You sell each song, handwritten, signed with a title and date, placed neatly inside an envelope. Don’t seal the envelope as your potential customers may desire to inspect the goods, or even pick their favorite song from your portfolio.”

He nodded, listening with intent.

“We have a total cost of forty rand for the whole package. If you sell each song for just ten rand, and there are forty envelopes, that is four hundred rand. Forty from four hundred leaves you with a profit of thee hundred and sixty.”

William looked at the goods in his hands again, and then back to me. These basic things were no longer just paper and pen, but a source of income for him. He had a huge smile on his face and that look of having discovered something totally new.

He shook his head and said, “I never thought of that. I just never thought about this before.”

“If you sell just one or two a day, at least it is some cash flow. As you get better at writing and presenting yourself, your sales will grow.”

We turned toward the cashier and he asked, “How did you think of this?”

“It’s what I do. I help people build their business.”

“Then I am so lucky to have met you.”

We added diapers to the shopping list, which was a bit of a chore as he did not know which size was the correct one for his daughter. Again, doubt returned to my mind as I wondered if he really did have a daughter back at the shelter. But if it was his goal to sell or trade the diapers, even some of the food, then at least he would be building upon his entrepreneurial experience and learning how to barter. I encouraged him to keep the receipt in case he had to return anything. Clearly, he was not aware of this process, and so I explained it to him.

We sat outside the supermarket for another ten minutes. On the inside cover of one of the two notebooks we built a simple amortization schedule to determine the real cost of each song sold. The profit per song was of course far better than my rough estimate which assumed the total volume of both notebooks and the ballpoint pens would be consumed with the sale of just forty songs. William’s math was rusty. I encouraged him to practice his basic tables using one of the notebooks in order that he could easily present change to his customers. He seemed eager to do this, soon.

We parted ways, shaking hands. He offered a Christian blessing and I reciprocated in good form, having learned that even if this is not something I usually do, it means a lot to those who offer.

I walked only a block from the water front when my emotions caught up with me, rising in my chest like expanding air. I sobbed.

Having been in this situation many times before, I knew what had happened. I had disabled that the part of me that would otherwise keep William on the outside, a safe box for me and another in which I define this homeless man. Instead, I chose to recognize him as an old friend with whom I was simply catching up, and in so doing, I automatically recognized how similar he is to me. All barriers were down. I saw him as a complete human being, no different than me or any other. His chemistry, his needs and desires identical to my own.

In that place, he could have easy been me and I could have been him.

Therein lies the true source of fear, the reason we choose to not engage. It is not because homeless people and beggars are poorly dressed or speak with a limited vocabulary. Outside of those who do present a danger, it is not truly for our own safety. No. We maintain our boundaries because to truly engage someone less fortunate than ourselves is to see ourselves in their place.

And that is something we are not readily willing to do.