How Giving $150 To Strangers Didn’t Go As Planned: 5 Lessons Learned

Generosity; the readiness or act of giving more of something, like money or time, than is necessary or required.

I would be nowhere without the generosity of others. Truly, I've had moments in my life where I've felt totally alone. I struggled with wanting to live when friends would drop off food or mixed tapes just to remind me they were thinking of me. I've cried on the beach and had a stranger sit down willing to listen and offer a hug. People have held space for me emotionally, given me their time, and even their money to help me navigate life.

If not for the generosity of people I know and strangers, I have no idea if I'd be the woman I am today. People always ask me how I stay so optimistic and positive, which always makes me laugh. I've been through some very dark times so I don't always see myself that way. But whenever someone says it to me, I ask my husband, “can you believe they think I'm like that?!” He always reminds me, “but you are. It's how you've gotten to where you are today.”

True optimism is a mindset of determination, resilience, and grit.

Today's post is sponsored by Frost Bank. Frost is a financial institution that believes in holistic financial well-being, spurred by the idea that optimism positively impacts emotional, mental and financial health. They gave me a $100 giftcard to go out into my community and do random acts of generosity, and 5 $10 gift cards to give out to strangers for them to pay it forward (or #FrostItForward) too. In fact, you can participate too by sharing how you would pay kindness forward to a stranger. Frost will review all entries and share additional Frost It Forward gift cards at their discretion for you to do your own act of generosity! Click here to learn more!


When I first heard Frost was giving me $150 to do random acts of generosity, I was SO excited! I mean, hello, how amazing is that?! It's in alignment with how I already live my life so it felt like the perfect fit. No way in a million years did I anticipate the struggle that would actually ensue. What actually ended up playing out was very unexpected and eye opening; and even more beautiful than I could've imagined.

How I Typically Have Done Random Acts Of Generosity:

I have always done random acts of generosity and kindness. However, when it comes to strangers, I do them quickly and quietly. For instance, I remember checking out in a store once with my husband, and spastically searching the line for the perfect person. He asked me, “what are you doing?” I said, “nothing.” Then walked up to someone and handed them the stack of coupons and the gift card in my hand saying, “here these are for you,” then walked out of the store. No explanation to the person or my husband; totally awkward in retrospect. I just never wanted to receive praise or acknowledgement. I've struggled with receiving. A reaction, I realized throughout this experience, I'm not alone in.

What I Initially Tried To Do With the $100…

I felt like I needed to do this big grand gesture. You know, find some wildly “deserving” person and totally surprise them with Christmas gifts they couldn't afford or something. So I texted a few people to ask if they knew of anyone who had recently fallen on hard times that I could do something for. For the most part, I was met with a lot of digital fundraiser suggestions.

And while donations are great, the moments I remember helping me the most are when a stranger sat down next to me while I cried. Or gave me money unexpectedly during my waitressing days. Those are the moments that have inspired me to do the same for others over the years. I realized in that moment that a lot of us have forgotten to reach out and just help the person in front of us. So I decided to drop the idea of some big surprise and keep my eyes open in my community…

Getting out into my community to do random acts of generosity…

So my first attempt at doing a random act of generosity for a stranger went pretty similar. On Christmas Eve I went out to the grocery store, intent on doing a random act of generosity. I felt like a total spaz watching everyone in the store – still so focused on finding someone who looked “deserving” – when it hit me. This cashier was working on Christmas Eve evening! Instead of being bitter, she was bringing all of the cheer to the people she was checking out.

As she handed me my receipt, I handed her a $10 gift card and said, “this is for you, it's a $10 gift card. Buy yourself and the stranger behind you a cup of coffee or something.” On the sleeve of the giftcard it explained to #FrostItForward. Her reaction was priceless!

How it felt afterwards:

She screamed with joy, and you could just see the pure shock and bliss in her face. I awkwardly darted out of the store and as I walked out, I could still hear her cheering. Honestly, it's something I'll probably never forget.

As we walked home, and I recounted the event to my husband (he'd been waiting outside the store with our dog), I kept saying I couldn't believe how big and joyous her response was. He pointed out to me that $10 is equal to about an hour's worth of work for her and it really hit me. Even though I spent 7 years working similar jobs (I was a cashier and have worked many a waitress shift where no one came in earning less than $10 for the hour); I had honestly forgotten what it was like to calculate money in terms of “this equals one hour of work.” I was immediately brought back to my younger days and wanting a $60 sweatshirt and realizing it would take me about 7-8 hours of work to buy it.

My next random acts:

A couple of days later, I went to a busy shopping plaza. I witnessed this young man get out of line and go out of his way to help some of the workers move a table. So when he stepped up to the register, I offered to buy his hat. He looked at me stunned and said, “No, no, I'm good.” And so I pressed on, “No seriously, I would love to buy you your hat.” He asked, “why?” I explained what I was doing with Frost and that I saw him go out of his way to help the women, and that it inspired me. He thanked me but said he really was good and he's got it.

Meanwhile, the cashier was in shock and awe over the entire exchange, so I asked her if I could go to the grocery store in the plaza and buy her some lunch. Initially her reaction was “no thank you” as well, but I pressed and said, “don't let me get rejected twice here!” She laughed and told me to get her some fresh cut pineapple.

As I walked to the store, I felt like I was on cloud 9 honestly.

Despite getting rejected and the entire awkward exchange, it was truly amazing to see how lit up and inspired she was that I acknowledge the young man's kindness.

As I checked out of the grocery store and began to leave, I saw another young man about to swipe his credit card for a couple of groceries. In what was probably one of the smoothest moments of my life, I said, “let me get that for you” and swiped my card.

It took him a minute to even process what just happened. He looked at me with an ear to ear grin and was like, “are you serious?” To which I replied, “yes, it's done. You're good.” He looked at the cashier in shock and disbelief who confirmed, “Yep, it's paid for.” And you could see the joy in her eyes too.

It was one of those moments that I envision him going home and telling whoever, “Some girl just went up and paid for my stuff! Can you believe it!” Honestly, if I thought that I felt on cloud 9 walking to the grocery store, then I had just busted through the Universe. My entire body was buzzing with pure joy and I could not stop smiling for the rest of the day.

In the days that followed…

I bought the entire line behind me at a coffee shop their coffees. People were suspicious and couldn't believe I was serious as I kept going down the line saying, “and what do you want? Coffee is on me!” One of the women asked me, “why?” So I said I had woken up in a not so great mood and wanted to get out of my stuff by doing things for other people. It was so great, as we picked up our drink, she said to me, “Thank you so much, next time I get coffee, I'm going to pay it forward.”

I bought groceries for strangers and handed out more gift cards.

I bought some teenagers lunch who were talking in quotes from my current favorite social media platform. On this platform, another teenager has risen to meteoric fame in months (like 15 million followers in 4 or 5 months), and as a result, has faced a lot of bullying from peers. So I asked them what they thought of her. One of the girls scrunched her nose and made a face/gesture of disgust, the other girl (after realizing I was a fan) said she shadily watches and likes the content. I told them I liked this “famous” girl because she's been lifting other people up with her and giving back to charities.

Despite the initial girl turning her nose up and passing judgement (which was my entire fear, that these girls were part of the “bullying” camp), I offered to buy them both lunch. I realized at that moment, it doesn't matter if people are “deserving.” We all need to show more kindness and compassion.

Here's what I learned through all these acts of generosity:

No act is too big or too small.

I was so fixated initially on some grand gesture and honestly felt defeated by the “donate online” suggestions. In another situation, I may have abandoned it all together. But after doing the acts, I realize there is no gesture too small. Like I said, that $10 was like an hour of work. The groceries I bought for the young man were like $5. Not huge amounts of money, yet a big impact in their eyes still.

It's alright if it's awkward at first.

I'll be the first to admit, we've fallen into such a digital age that it is easier to donate online than to look people in the eye. The first act I could only manage with the gift card because it was quick and I could get out fast. It still felt amazing.

But as I did more of these, and became less awkward, they felt better and better. I no longer feared people thinking I was weird or rejecting me. I no longer thought it needed to be this “perfect” thing. With each gesture, I felt more at ease… which leads me to…

It's okay to receive.

I struggled with actually doing the gesture – not just giving a gift card – because it meant interacting and opened up the doorway to receiving more on my end too. It felt scary. I wanted to do these things out of true altruism and didn't want anyone to think anything else – so before this exercise, I thought giving needed to be quick and anonymous with no personal gain.

Through this, especially witnessing others struggle to receive, I learned that in order to heal, we all need to open ourselves up to receive. We all grew up hearing “it takes a village” – and somehow we've forgotten that. Because we receive good feelings for doing something good, it doesn't make it any less okay. Because we accept a coffee, or a hat, or pineapple from a stranger, doesn't make you any less you. Which leads me to…

Everyone is deserving.

Every person walking this planet has experienced hurt and pain and trauma. Just because you can afford to buy yourself a coffee, doesn't mean you don't deserve a stranger doing it for you. We are a community and we all deserve to be seen and supported; even if we aren't asking for it or don't seem to “need” it.

Every person – no matter how different they are – deserves our love and generosity. We are all healing from stuff, and you never know what will be the act of generosity or kindness that can shift someone towards optimism.

Generosity and optimism go hand in hand.

Frost borrows their definition of optimism from psychology with the belief that optimists feel they have the tools to create a positive outcome for themselves. Optimists expectations have been verified by their own experience. Optimists view their habits and behaviors as the why and how behind making good happen in their lives.
In fact, being generous can have a big impact on your sense of optimism.

Here's a list of some benefits of generosity:

  • It improves your overall health by reducing blood pressure and lowering the risk of depression and anxiety.
  • Generosity lowers stress levels by reducing cortisol, a steroid hormone that drives your stress response.
  • Science has also shown that generously volunteering can actually reduce mortality rates and extend our lives!
  • It also triggers feel-good chemicals like endorphins, dopamine, and oxytocin to make us happy.
  • Lastly, generosity can improve your relationships by creating an environment of reciprocity and mutual impact.

That last one is so important; especially for people like me who have struggled with receiving. When we receive more, we have a fuller cup to give from. We acknowledge our own worth and “deservingness.”

Frost It Forward

Frost has been in business for over 150 years and believes they can be a force for good in everyday life. It has sparked a mission for optimism and what drives them to do better every day. Let's take a page out of their book, and do the same and #OptForOptimism.


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