Pain of Paying

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Imagine this…

You’re burnt out and in desperate need of a vacation.

The plan? Spend a week lying in the sun with a Pina Colada in one hand and a book in the other.

You have two options:

  1. Get an Airbnb on the beach somewhere tropical
  2. Go to an all-inclusive resort

The Airbnb would allow for more privacy and a bigger space. But, it also means you’ll have to grocery shop, find good restaurants, and be your own bartender.

The all-inclusive resort would feel effortless.

Simply pay the fee upfront and then settle in to relax for a week of pampering

You make your choice and book your stay.

Feeling excited, you close your laptop and breathe a sigh of relief—you really need this break.

Which option did you pick?

In today’s edition of Why We Buy , we’re exploring the Pain of Paying — why paying upfront removes the pain of playing down the line.

Let’s get into it…

“Top Marketing Newsletters You Need to Subscribe To”

The Psychology of the Pain of Paying 🧠

Each time you spend your hard-earned money, you feel a slight twinge of pain.

Even if you’re 100% certain about the purchase, the part of your brain wired for loss aversion feels a little bit like this: 😬

That feeling gets heightened when we spend cash versus using a credit card.

An MIT study of 64 students bidding on baseball cards found that students paying with a credit card would bid more than double ($61) the amount students using cash would ($29).

When you stay at an all-inclusive resort, you swipe your card before departing—oftentimes weeks or months in advance of the trip—and only go through the pain of paying once.

Each time you get a new Pina Colada or hit the buffet for some tacos, you get to feel the excitement of the experience without the nagging emotion of having spent money.

Instead of getting hits of 😬 your entire trip, you feel like this 🤩

And 🤩 is exactly the experience you want to create for your buyers, right?

Inside Your Buyer’s Mind🧐

Research shows that people judge their experiences based on how they felt at the peak and at the end. Behavior scientists call this the Peak-End Rule.

Embrace delegation

Even if the whole experience was fantastic—like enjoying a meal at a Micheline Star rated restaurant—coughing up cash for the big bill at the end of it can leave a bad taste in their mouth.

When people pay for your products, as excited as they are, the loss aversion part of their brain rings a quiet alarm when they go to pay. 

To get this alarm to ring a little quieter, create a buying journey that makes your customers feel less pain each time they buy your products.

How To Apply This 🤑

Alright, so how can we apply this right now to sell more?


Break up big payments into smaller increments

Big ticket items can come with less pain when divided into multiple payments. Smart companies like Apple offer financing options to make purchasing less painful and quiet the nagging loss aversion alarm.


How to reactivate churned subscribers

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Offering past customers an incentive or free gift if they resubscribe can win them back. And because their credit card is already on file, you can streamline the checkout process and reduce the pain of payment.

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Embrace delegation

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Retail & Hospitality

Reimagine what payment feels like

Businesses that prioritize fun, like casinos or Disney theme parks, understand that paying is painful. That’s why they encourage guests to pay with chips or a pre-paid MagicBand. Losing a stack of chips still stings, but it’s less painful than losing a stack of bills.

And Disney’s MagicBand reduces the pain of paying since swiping a bracelet doesn’t feel like paying, allowing theme park goers to stay in the moment rather than stressing about each purchase.

Embrace delegation
Service Business

Get people to pay in advance

Many service businesses wait until the work is done to charge customers. Asking customers to pay in advance moves the pain of paying to the beginning of their experience, giving you the opportunity to wow them at the end.

I recently hired an at-home car detailing service. I paid in advance and they did the job while I worked at home. When I got in my sparkling clean car later that day, I found a candy on the seat and a free air freshener. It was such a delightful experience that I felt obliged to write a Facebook post about them.

Embrace delegation

The Short of It 💥

Loss aversion is very real and even exciting purchases can be slightly dampened when it’s time to pay.

Be purposeful about your buying experience to make people feel less loss aversion and more joy from their purchase.

And as Jay Abraham would say, feel free to steal loss aversion techniques from other industries.

Until next time, happy selling.



Wanna really get inside your buyer’s head?

There are a few ways we can help:

Written By Katelyn

Katelyn Bourgoin is the CEO of Customer Camp, a 4X founder, and a cheese lover. She lives by a simple mantra: whoever gets closer to the customer wins.

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