How to Pay It Forward

How to Pay It Forward
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After the election, I’ve been trying to find ways to channel my grief into positive action, so this past week seemed like the perfect time to “pay it forward,” or show kindness to strangers. Don’t worry, I don’t have grand illusions that my tiny acts of kindness will prevent the dismantling of our country, but any good deed is better than no good deed. That’s a saying, right? This week I made a list of concrete actions I could take to “pay it forward” and show love and kindness to strangers.

  1. Pay for coffee for the next person in line.
  2. Introduce myself warmly to new colleagues.
  3. Let someone cut me in line at the grocery store.
  4. Donate to a few charities.
  5. Tell a restaurant manager that I received excellent service and tip very generously.
  6. Give my boss recognition for her hard work.
  7. Buy a few umbrellas on a rainy day and give them out to strangers in need.

Most of these acts of kindness were relatively easy and don’t merit further discussion here. But the last act on my list definitely deserves a deep dive.

Shared these with my coworkers = paying it forward

Shared this with myself = also paying it forward

Day 2 of my week arrives and it is the perfect day to hand out umbrellas to strangers because it’s raining furiously. Living in New York City, a city in which everyone walks everywhere, having an umbrella on a rainy day is critical. As I remind myself of this fact, I begin to imagine all of the grateful smiles I am going to see when I give out free umbrellas. I haven’t even begun to pay it forward, yet my ego is ballooning.

I buy four umbrellas from a corner umbrella man. For those of you who don’t live in NYC, a “corner umbrella man” is a man who stands on the street corner and sells umbrellas, usually only on rainy days, and often by yelling “umbrella, umbrella, umbrella!” not unlike Rihanna. I opt to buy my umbrellas here because (1) they are much cheaper than buying them at the store, and (2) I’m always in favor of supporting someone’s hustle.

I happily set out on my mission, naive about how difficult it will be. I encounter my first obstacle when I inadvertently become one of the four beneficiaries of my own act of charity. I am carrying a useless, pocket-sized umbrella that’s built to weather light sunshowers, and within seconds, the oppressively windy New York City downpour tears my tiny umbrella to shreds.

Umbrella Beneficiary #1: myself

With a sturdier umbrella protecting my head, I start seeking out my next beneficiaries. I am beginning to realize how awkward this project will be. Each time I get ready to approach someone without an umbrella to ask if they’d like one, I nervously back down. As I back down, I make up the following excuses for my behavior:

  • Woman who is visibly wet: But her friend has a big umbrella. Surely, she’ll share with her. Right?
  • Guy in business suit: Too privileged.
  • 14-year old boys walking home from school: They seem happy. Also, they’re wearing shorts. Who dresses them? Where are their parents??
  • Resting bitch face: Too scared she’ll yell at me.
  • Girl carrying two grocery bags: She doesn’t even have the hand space to carry an umbrella. Honestly, she’d probably be annoyed and feel inconvenienced if I gave her one.
  • Everyone wearing headphones: I don’t want to disturb them. Quiet time is very important.  
  • People huddled under doorway of Starbucks: I don’t have enough umbrellas for all of you, so none of you gets one. It’s really about fairness.

I approach my first target, a middle-aged woman without an umbrella or a coat. She definitely must want an umbrella, I smugly say to myself. I politely ask her, “Want an umbrella?” She barely mutters no thanks and hurries away. What just happened? Does she think I’m akin to a used car salesman and that I’m going to trap her into usurious monthly payments to pay off the $5 umbrella?

While nursing my rejection, I begin to understand why some men are shy about asking women. The rejection is painful! And I’m a good samaritan offering a very useful gift to a complete stranger out of the pure goodness of my heart. Not some creep who wants to get in your pants.

After feeling dejected, I become even more selective about who will get an umbrella. I pass several people by who probably could use an umbrella out of fear that they too will reject me. Finally, I spot a man who is literally drenched and appears to be shivering. Yes, shivering! I nonchalantly sprint his way and ask him if he wants an umbrella. He smiles but says, “Oh, no, it’s okay.” Not accepting no for an answer, I reply, “It’s free. And you look like you could use one.” He nods and accepts the umbrella. I feel the heavens parting.

Umbrella Beneficiary #2: shivering man guilt-tripped into accepting an umbrella  

Shortly thereafter, I spot a golden target: an elderly woman with a cane. First shivering, now a cane! This couldn’t be easier. Just as I’m about to approach her, a black car pulls up to the sidewalk and picks her up. Granny knows what’s up with Uber? Impressive.

Luckily, my next victim (target) is not far off: a mother with her young son. The boy has an umbrella, but mom--being the selfless badass that she is--braves the storm alone. Feeling strangely cheeky, I ask, “Want an umbrella to match your son?” She appears confused, unsurprisingly, as I’ve made her think that I’m a magician who can make an umbrella identical to her son’s appear out of thin air. Recognizing my awkwardness, I add, “I have an extra umbrella, would you like it?” Eventually, she smiles and thanks me.

Umbrella Beneficiary #3: mom of the month  

With one umbrella left, and the rain slowing down, I am a Nervous Nelly. Giving an umbrella to a stranger is hard enough already, but giving an umbrella to a stranger when it’s barely raining? Impossible. Carrying an umbrella when it’s barely raining is like being stuck in a relationship with a person who sucks but whom you can’t dump because it’s their birthday or their dog died.

But I’m just in time! A young woman is throwing her own useless, pocket-sized umbrella on the floor after it bends in half. I swoop in and say, “It’s your lucky day. How about a new umbrella?” I notice that my opening lines are becoming increasingly bizarre, which means I’m becoming increasingly desperate to get rid of the umbrellas. She eyes me suspiciously, as any good New Yorker would do, and says in a thick Staten Island accent, “For free??” I say yes, and she runs off with the umbrella as if she’s just won the lottery but doesn’t want anyone to find out.

Umbrella Beneficiary #4: Snooki's twin 

As the rain continues to lighten, I sigh with a sense of relief. Paying it forward with umbrellas is much more difficult than it seems. Frankly, it’s exhausting work. Or maybe I’m just a mildly crazy person who should stop over-analyzing every person I see on the street. I suppose we’ll never know the answer to that though.

But, in all seriousness, isn't that the point of paying it forward? Doing real work that takes commitment, energy, and love in order to bestow kindness on others? Yes, it's hard and sometimes uncomfortable, but nothing good ever comes easy. That's a saying as well, right? (I'm terrible with sayings, phrases, and idioms).

Have you ever "paid it forward"? Would love to hear from you!

Yours Truly,

Your Awkward But Well-Meaning Friend