The Time Hack

28 Notes

Day 18: Have dinner with a homeless person

*Note: The events described below, including quotes, have been pulled from memory and may not necessarily be accurate. Please refer to the audio recording linked to under the “ACTUAL EVENTS” heading.

A short time into my first reporting gig, I found myself ducking in and out of tunnels in an impoverished area of Harlem just after dusk. It was late fall in 2006, and my newly purchased trench coat and leather bag filled the neighborhood with a scene of naivety and inexperience.

I was hired to work for The Tokyo Shimbun, a large Japanese newspaper, in their New York foreign bureau. At the time it was lined with aged, yellow newspapers and adorned with a thick coat of worldliness only newsrooms can offer. A 23-year-old new arrival to the city, I knew practically nothing of reporting and even less of the city.

Armed with a digital recorder that produced audio quality equal to that of a home answering machine, I had one task: to interview those living on the streets of Harlem for a series on the city’s homeless.

My naive, obnoxious questions about “what it’s like living on the streets” were greeted by a receptive group of tightly-wrapped, warm-eyed individuals who, to say the least, had fallen on hard times.

I hunched over them as they rested on sidewalks, trapping them in a swell of white puffs of air from my mouth. I explained the reason for my visit to each, and they were enlivened to speak to me, jumping at the chance to tell their stories.

Chris was evicted from his apartment after losing his job, Jada suffered from mental illness and could not hold a job, and Keith was, as he put it, born into a life of poverty.

But as much as their stories differed, they all had the same question for me: Do you have something to eat?

I didn’t aside from a decaying Snickers bar, which I kept in my bag for the times when my stomach would growl during interviews.

I offered it up, but the five or six individuals I spoke with politely declined, citing diabetes as the reason.

“Had it for years,” one said.

On day 18 of The Time Hack, the task was having dinner with a homeless person. This time, I came prepared with two sandwiches, Cracker Jacks and apples. A man named Raymond greeted me in Washington DC with the same enthusiasm as those I spoke with five years ago.

Upon offering the food, Raymond politely asked if he could save the meal for later that night, as he had just eaten. He then gently agreed to allow me to gulp down my bag lunch while we talked.

Dressed in tan cargo pants, a ripped winter hat and two stained coats, Raymond seemed pleased to have a set of open ears at his disposal. His lower jaw furiously smashed his brown beard into itself as he tripped and stumbled over his words with excitement. Unlike my experiences five years ago, Raymond dug a bit deeper into his past – and fast.

He described snapshots of his life in a fragmented way, periodically stopping to open the glass doors of a McDonald’s restaurant on M Street for customers scuffling in and out.

He was released from jail in 2001 after being convicted on two counts of murder and one count of burglary. 

“Yep, it was a drug deal gone bad,” he said, adding that he shot a man at pointblank range in the head during the incident.

“Na, I don’t regret it,” he said, explaining that after that night he zigzagged across the United States for 44 months while on the run from police. 

“I was on America’s Most wanted. Right down there, right down M Street – that’s where the show is filmed,” he said pointing to his left.

 Raymond turned back toward me with a look of accomplishment and continued his story, while another homeless man teetered past us squinting suspiciously at my interviewee. It was apparent, as the conversation moved on, that Raymond believed himself to be significantly more intelligent than the other homeless in Washington.

He continued with a convincing degree of warmheartedness. Raymond was pleased with his life and boasted that he’d seen a “bunch’a prisons” across the US, from Miami to Oklahoma to Virginia. 

I stopped him eventually, and asked if he would at least consider having some of the Cracker Jacks while we chatted about his life. He politely declined.

“Can’t. Diabetes, had it for years.”


  1. Aside from the remembered details I listed above, I recall Raymond said he went to high school in Anacostia (a neighborhood in DC).
  2. He was excited for the opening of a new nearby furniture store. This meant he would have somewhere permanent to live – for some reason.
  3. He had a bottle of Coke sitting on the ground next to him, which made his claims about being a diabetic all the more strange.
  4. He said he was 57 years old, but looked much younger.
  5. He said a police officer bought him his shoes and cargo pants.
  6. His teeth were all separated from each other by a significant amount of space.
  7. He explained that he made his way across the US by robbing pedestrians he met on the sidewalk, but that was “all over now”. He’d been clean for 13 years and the police around the neighborhood liked him.
  8. His family was dead, Raymond said, and it was the medicine that made him stay awake in order to “keep it all going.”
  9. Halfway into a story about how he once was rushed to the hospital after a DC police officer bought him “the biggest steak you’d ever see,” he spotted a man hobbling down the street.
  10. He peered at the man, who was hunched over and had a sparkly strand of drool stretching from the edge of his lower lip to past his knees. Teetering from one foot to the other, the passerby kept his brow pointed toward the wet sidewalk as he slipped past Raymond, who flexed his muscles.
  11. Toward the end of the interview Raymond opened the door for a girl who attempted to put money in a thick plastic cup he was holding. She missed and responded by telling Raymond he had to work for his money. Her friends laughed.


What actually happened on day 18? Listen to the audio of the event here. Video was not recorded of this event.


  • I estimate that I spoke to Raymond for 19 minutes.


How long did it take? Find out here. I had a problem with my stopwatch and feel that it may be around one minute short of the actual time it should have recorded.

Why don’t videos or recorded times appear on this site?



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