I missed an opportunity to help – and I feel like a jerk


sharebuck A few weeks back I sat in a Chicago vegan restaurant sipping a frosty pinot grigio eating a braised kale, sauerkraut, and tempeh something or other. I looked up and saw a lanky man in old faded jeans take a seat just outside the window where I was sitting with a piece of cardboard and a pen.

I watched him work on his sign for a good 10 minutes while I ate lunch.

Poor guy was using a pen. You know how many times you have to go over text when you’re using a pen and you don’t have a sharpie? A GAZILLION.

It was clear enough that I could read most of what he was writing.

I read his intro, “Hi, my name is Shane. Fallen on hard times…if you donate, then thank you.”

I had an idea…

Maybe it was my suburbanite upbringing and not having any idea what it’s like to actually be hungry or want for much. I live in an abundant world that I have to consciously not eat like I have an abundance.

I thought, maybe I could help him.

I’m a mother-loving communications expert and all. My clients pay me to help them find the best words to communicate complicated, awkward, and sometimes downright scary things they have to say.

Could I help this guy? What if a well-written cardboard sign could get him an extra $20 today? What could he buy with that $20? Would he not worry about food for the next three days?

As soon as I saw his intro, I pushed my flavorless kale bowl aside, tore a sheet of lined paper out of my notebook and started writing.


What I wrote

I was writing attention-grabbing alternatives for Shane to include on his sign. Words that would get straight to the point, and get him more of what he needed. But first, he needed words that stand out – and didn’t read like every other cardboard sign on the streets of downtown Chicago.

Because you know what, every single person that walked by him looked directly at him while he sat here and wrote his sign. I could tell people were trying to read it as they passed. They saw him. But didn’t want him to see that they noticed.

What is wrong with us?


When self-doubt rears it’s ugly green head

I wanted to help him. I truly thought some cardboard-sign-sparkling would help him. But then self-doubt kicked in and I worried I’d be offending him by offering him some suggestions. I mean, I don’t go around submitting grammar corrections to all the terrible web copy and bad signage I read. (Sometimes I really really want to.) Doing this would definitely make me an asshole.


Would offering this man with the cardboard sign my unsolicited advice make me an asshole too?


I scribbled some ideas while ignoring the voice in my head…

  • I’m Shane, I’m human. I see you. Thank you.
  • I’m Shane. I’m here. Thank you for seeing me.
  • Thank you for believing in me.
  • Thank you for your generosity
  • …and a bunch more

I also planned to find the nearest CVS or Walgreens, buy him some posterboard, a few sharpies and give him the lone $20 bill from my wallet.

He started packing up – presumably to take his corner for the afternoon rush.

“Oh fuck”, I muttered, as I folded up the paper I was working on, tucked a $20 inside and ran out the door. I wandered down the same alley he traveled and came to the end. Left or right? Which way did he go? If I was a homeless guy who needed money would I go towards the Board of Trade building or towards Lake Michigan? I picked the Trade building. I stood there on each street corner looking for him. I couldn’t spot him and his cardboard sign anywhere.

Defeated, I tucked the paper holding the $20 into my pocket and headed towards the car. Hoping that I’d run into him on my way. I rehearsed in my head what I’d say, promising I didn’t mean to offend him when I handed him a list of 10 suggested signs for his cardboard sign.

But I didn’t see him.

A lesson in losery

I was too caught up in trying to be the most helpful, most amazing that I didn’t get to help him at all. The $20 is still in my wallet and I didn’t get to give it away that day.

I should have just ran outside and given him some money right away. Or maybe sat with him and helped him write some killer copy for his cardboard sign. What’s the worst that could have happened? In the least assholy way I know how, I could have really, genuinely helped him. Instead, I sat there, doing something he didn’t ask for.


Shane, next time, I’ll be ready.


PS - if you liked this, maybe you'll also like When I shut my laptop, went into the bathroom and cried and Which way to the arena?