“You should send donuts – make your proposal stand out.”

That was the advice of my friend Margo, who is a master at public relations and generous and kind with her time and talent as I stretch my career into new places.

“Love it. Yes.” I wrote back. But the idea was already evolving in my mind.

I know what I’ll do, I said to myself. I’ll send hera treat instead and make it a surprise! 

And that’s how I ended up spending $100 on pie. Yes, pie.

The plan started off sound enough. Margo’s idea of giving gifts as a part of my client development was genius because it was so antithetical to the values and business practices of my career path. 

Gift giving in the nonprofit sector is uncommon because budgets are tight. And, well, the IRS doesn’t approve of spending donations on gifts, either. It’s, like, a thing with them.

But even before I worked in nonprofits, as a journalist, we thought of gifts as manipulation. The giver was swaying someone’s opinion or making it tough for them to think objectively. 

So to reconsider giving gifts as a positive thing – and as something available to me– was blowing my mind. Suddenly, I had permission to see gifts as a symbol of shared values like generosity, pleasure, and surprise. 

Gift giving can be a way to balance the scales, and human beings like our scales balanced. That feels healthy and fair to us. And gift giving can be an act of empathy because we can demonstrate that we understand what matters to the other person in the perfect gift selection. All of this. 

I know that I cannot buy gifts for everyone, of course. That’s not wise business development. But at that moment, the idea felt so liberating and fun that I could not resist.

When I settled on my idea, I clamped down on it like a Gila Monster gripping an arm in its jaws. After trying to find a unique and totally inspiring gift, I landed on the Milk Bar website. Milk Bar is a bakery and ice creamery with a shop in The Cosmopolitan. Then I discovered that there was free shipping on the Crack Piebecause it was March 14, or Pi Day. 

I was sold. Pie! This was sure to make Margo and her team feel special and excited, like a little surprise delivered right to their door in the middle of the doldrums of a long day at work. 

I imagined the delivery man dropping the package and knocking twice. They open the door. There, on the step, is a delicious, fresh, gooey and buttery Crack Pie. Everyone is addicted and they’re all like, “Who is this Stephanie????” 

But, as you can guess, that’s not exactly how the story unfolds.

The first thing you’re probably wondering is, “Who spends $48 on a pie?” The girl who is so excited about the liberation of buying a gift as client development that she just does it, that’s who. 

The website was so alluring. The pie looked delicious. I’m a sucker for good branding.

I entered my information online to make the purchase, but I was no match for website ordering form and, in the seconds after the order was placed, I had a realization: I DIDN’T ENTER A SHIPPING ADDRESS HOW DO THEY KNOW WHERE IT’S GOING?

That’s right, the pie was scheduled to be delivered to my house because the auto-populated fields made the shipping and billing address the same. And, due to the tight turn-around of the delivery, it was impossible to make a correction. 

I was getting a pie, too, and that could have been the end of the story: Great! Delicious! Pie! But my heart was set on the gift and I wasn’t giving up. So I ordered another pie, albeit this time with slightly less enthusiasm.

I’m filling out the online form. I’m careful. Intentional. Closely paying attention to the order form. And then there’s this field: email address. 

I thought through the scenarios of why they were asking for the email: The delivery person cannot deliver the pie. It’s getting late. They don’t want to leave it at the front door so they send an email to the recipient: “Hey, just checking when you’ll be around . . . I have your package and it smells sooooo goooood. I think it’s a pie.”

Yes. That’s totally what would happen. That’s entirely feasible. Put Margo’s email address in the field.


Wait two hours. 

Then an email from Margo: It’s the receipt for the order and a generous, loving note of gratitude: “You didn’t have to do this!”

OMG. The receipt was sent to her because I entered her email on the form.

So there you have it. The surprise was ruined, the price tag was publicized. The entire project felt beyond my capacity. I’d spent $100 on two pies and was defeated by online order forms. 

My initial enthusiasm for the wonder of the gifting culture was starting to give way to my rational, prudent self. What was I trying to accomplish, anyway? 

“Sometimes messy is way better,” a friend texted. “Human. They’ll love it.”

The thing is, if we’re truly growing and thinking with creativity, we’re working outside of our zone of familiarity and we’re bound to make mistakes, small and large. 

Sometimes, in all the talk of being “strategic” and “effective” and “impressive,” we forget that in the end we’re all just people doing jobs. We want to be the best representations of ourselves that we can be, and strive for excellence, and achieve greatness, but at the end of the day, all of us is a work-in-progress and that means we make mistakes.

Let life be a little messy and go with the flow. Sometimes ordering super expensive pies is part of the learning curve. 

Plus . . . it was a delicious mistake.

About Me

I’m Stephanie. I’m a writer, coach, and facilitator. I work with individuals, teams and leaders in creative, entrepreneurial, and nonprofit fields to improve communication, find a true purpose, and deepen connection and meaning. If you enjoyed this post, share it with a friend! And I’d love it if you would subscribe to my email list, below.