Setting out on our journey


Anthony and me on the first day of the project (photo: Reed Sandridge)

This story begins on February 19th, 2010. I was out of work – I was laid off at the end of September of 2009. The country was spiraling into the deepest depression since the thirties. Anthony was homeless. He sold the Street Sense newspaper to make enough money to get by each month – but not enough to leave his small patch of frozen sidewalk behind and get into an apartment.

Our lives crossed paths that day because of a personal project that I had embarked on. After being unemployed for about two and half months, I did something that most people would consider crazy. I started giving away money every day to a stranger. I wasn’t giving a lot of money away, heck, I didn’t have a lot of money to start with, but I did the math and had just enough money to make it a year (in case I couldn’t land a job) and still have a bit left over to fund a $10 a day project I called the Year of Giving.

The concept was born largely out of inspiration from my mother. She had passed away three years earlier and was one of the most generous people I have ever known – not in the sense that she ever had enough money to be philanthropic – but just in the simplistic way of thinking about others before herself. I believed the Year of Giving would honor her while at the same time free me from this idea that I was at the whim of the mighty dollar.

So I started on December 15, 2009 – the three-year anniversary of her passing. I gave away $10 that day – no strings attached – and did it every day for the next 364 days. You can check out the journey for yourself – here’s a link to Day 1.

So, back to February 19th, 2010. I was two months into my year-long journey when I met Anthony pacing back and forth atop a crackling layer of snow at the corner of 19th and M in DC. I didn’t know it then, but Anthony and I were just getting started.

After our chance encounter, which you can read about here, we stayed in touch. Often times just meeting up for coffee or lunch and I’d try to help him with some of the challenges that are all too common for the homeless.

Recently I found myself at odds though. I realized that my treating him to lunch now and then, while I’m sure it was appreciated, was doing very little to get Anthony off the streets. But what could I really do to help affect tangible change. I mean, I have no background in this. I am not a social worker nor have I ever been in his shoes (which reminds me – there’s a good story about Anthony’s shoes!)

Earlier this month he and I were having coffee at the Au Bon Pain just south of the spot where we originally met.

“A year from now – where do you want to be?” I asked him feeling as though I might come off a bit too preachy.

Anthony’s eyes were locked in on mine. “I want to be in an apartment – my own apartment,” he said peering through those big thick spectacles of his.

We parted ways and I headed up to Dupont to nest in the Starbucks that’s just north of the circle. I’ve been drifting from coffee shop to coffee shop lately finding free office space to work on my book – it’s a book about my journey of giving away the $10 every day. Anyway, it’s been almost two years since I finished the project and I haven’t even finished the book proposal. Sure, I have spent a lot of time writing and have a few chapters partially written, 25-30 pages of the proposal done, etc. but some how I’m just not making the kind of progress I want.


Sign outside of a tucked away cafe where Anthony and I had lunch today. When he told me he wanted to take me to the “The Works Cafe” I thought he said “Worst Cafe” – it turned out to be anything but that! Great little greasy spoon smack in the center of the city! (photo: Reed Sandridge)

What I need is a coach…someone to hold my feet to the fire. I need someone who cares about my project and who I wouldn’t want to let down. And then it hit me. Why not ask Anthony to be my coach. I’ve been so focused on helping him I didn’t see it – he could be the answer! “But he doesn’t know the first thing about writing a book,” I thought. And I guess that makes him the perfect coach given that I don’t know the first thing about how to really help someone pull themself out of the black hole of homelessness. We could create our own mini Mastermind group.

The next week we met up for lunch and I shared my idea with Anthony. He was excited about the possibility of getting off the streets – but frankly I think he was just as excited about helping me do something that was important to me. So here we are on November 27, 2012. This morning was our first meeting. We met for a couple of hours, started mapping out what we needed to accomplish to reach our goal and then setting up some basic working parameters for our project and defining some SMART goals (I can’t help it – I’m a businessman at the core) for each of us over the next year to help keep us on track. We agreed to meet every other Tuesday to review each other’s work.


Some of our to do list from Nov. 27, 2012

Part of a successful formula for making change is building a strong support base – and that’s where you come in. I figured it couldn’t hurt to open the door to the rest of the world to watch this experiment. You can provide guidance and encouragement – but more importantly we are now publicly accountable to you for our goals – a key element in my success plan for personal change.

So stay tuned, drop me an email, go visit Anthony at the corner of 19th and M (he’s in front of the Wells Fargo bank) and say hello. Give him some encouragement – tell him that you believe in him and what we are doing. Who knows – maybe you have some advice that will be the difference in us succeeding in this journey.

Tagged , , , , , ,

Leave a Reply

Your email address will not be published. Required fields are marked *