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- Sunday Postcards: Plot Twist..You Didn’t See That Coming!
Sunday Postcards: Plot Twist..You Didn’t See That Coming!
Hiiiii homies!
Another week, another dollar? Amiright or Amiright?
I hope you all have been spending the weekend getting rested, being mindful and prepping your demure for the week.
I’ve spent most of my weekend doing personal things like…wedding planning. Only a couple short months and the big day will be here. I’ve spent most of the wedding planning this year obsessing over small details because I have a fear that if the napkin colors aren’t right, the whole thing is ruined. It’s called…delulu bride.
But…you didn’t come for napkin talk, you came to learn the thangs of the trade!
The last couple of months, I have been working with a creator brand that caters to a particular generation. (I’d name names, but I want you remain unbiased in this conversation).
Just like other brands, they have been facing a tough challenge: standing out in a saturated market where consumers are overwhelmed with choices.
Despite having a strong product and an engaged audience, their sales were plateauing. The creator themselves is a huge part of the brand’s identity, but customers were treating it like just another product on the shelf, instead of feeling the connection that was originally so powerful.
So we dug deep into their brand strategy, aiming to tap into something more emotional, more personal.
Here’s where Hindsight Bias has come in.
We realized that customers had long followed and loved the creator but, with so many choices, they felt unsure about why they should choose this brand over others. If we reemphasized the emotional connection they’d always had with the creator, it allowed them to feel like they knew all along that this was the right brand for them.
We rewrote their brand identity and crafted the right messaging that tapped into those past experiences and the creator’s journey. By doing so, we created a compelling narrative that made the brand feel like the obvious choice—a decision they were always meant to make. This strategy doesn’t just sell a product; it is meant to reignite the emotional bond, making the purchase feel like a natural and inevitable choice all along.
By framing the decision in a way that connects with customers’ past experiences, they feel more confident in their purchase, aligning perfectly with how Hindsight Bias leads people to believe they always knew it was the right fit.
Let’s get into how this can apply for you…
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Plot Twist..You Didn’t See That Coming!
Hindsight Bias, also known as the “knew-it-all-along effect,” is the tendency for people to perceive past events as having been more predictable than they actually were. After an event occurs, individuals often believe they had foreseen the outcome, even though they may not have had the evidence to predict it beforehand.
A Psychological Glimpse into How We Reframe the Past
In 2015, the Seattle Seahawks were on the brink of winning the Super Bowl.
With seconds left and just one yard to go, they chose to pass the ball instead of running it.
The result? A game-losing interception by the New England Patriots.
But here’s where it gets interesting and why this is relevant.
After the game, many fans and commentators said they “knew all along” the Seahawks should have run the ball.
But in reality, before the play, few thought it was a clear mistake.
This happens because Hindsight Bias makes the outcome seem obvious only after the fact. It skews how we perceive past events, making us think we predicted them—when we didn’t.
In marketing, this bias can lead to overconfidence. That’s why it’s crucial to present clear facts to help buyers make informed decisions, avoiding the illusion that “everyone knew it all along.”
Your customers don’t know all of the facts about your brand the way YOU think they do.
You have to train them, you have to remind them and you have to trigger their Bias.
Give Your Customers a Clear Reason to Buy.
Going back to the creator brand that I was mentioning earlier.
They improved their product quality, but with that came higher prices.
The issue? Customers didn’t understand why the price had gone up, and as a result, sales plateaued.
When brands fail to communicate the reasoning behind changes, such as higher pricing—or better materials or ethical production—customers lose sight of the value they’re getting. Clear messaging that explains the “why” gives customers a concrete reason to pay more.
Once our client started highlighting the value of these improvements, sales trended in the right direction.
Simply put, when people understand the reason behind your positioning, they’re far more likely to make the purchase.
Convincing A Customer The Product is Right For Them.
Often, people have tried multiple solutions to solve a problem without success. This leads to Hindsight Bias, making them feel like failure is inevitable. (my napkins story 😉 )
As a result, they’re reluctant to invest in yet another product.
Let’s take Sephora as an example. Idk about you, but when I walk into their store or shop online…I am overwhelmed af. What if I make the wrong choices? What if I buy things that aren’t right for my skin?
Enter…beauty quizzes (as seen on literally EVERY other beauty brand too).
They address this by providing personalized recommendations and tools like their Color IQ system, which helps customers find the perfect foundation shade based on their skin tone.
This eliminates the fear of purchasing the wrong product—especially for items that can’t be tried before buying online.
Sephora also uses customer reviews, detailed descriptions, and tutorial videos to give shoppers confidence. Seeing how others with similar skin have had success eases the fear of post-purchase regret. ← People influencing people.
This strategy kills objections early and builds trust. When customers feel informed, they’re more likely to feel confident in their choice, sidestepping the “failure is inevitable” mindset.
That’s that on influencing your purchaser to buy from you. It might seem like something you already know, but I am here to meet everyone where they are. Whether operator, or founder, understanding WHY we buy can help you influence and deliver a dope brand experience.
But as always, if you have any questions or things you want answers to in this newsletter, please hit the “reply” button and send them over or hit that link below for my form!
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Same time, same place next week?
Jess

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UPCOMING EVENTS
Nancy and I are hosting a Customer Service Appreciation week dinner! If you are a CX operator and in NYC, this one is for you on October 8th. RSVP HERE
A FUN AF Shoptalk party. Casino Night for Shoptalk Fall in Chicago on October 16, 2024! RSVP HERE
Come to NYC on November 14th for SheInnovates 2! If you are a women in ecommerce, this one is for you. Snag your tickets here.
I will be hosting a new and improved AfterHours LIVE on Monday, Sept 16th at 530pm CST on Linkedin. RSVP HERE
BEST PIECE OF CONTENT I’VE SEEN THIS WEEK…
Spotify is launching Countdown To, a video series where artists discuss their new projects with fellow performers, family, and friends.
👐 BONUS CONTENT 👐
This week, I released an epi with my mentee Mark Galvez of Taste Salud.
Let me just tell you…they don’t make em like Mark! The nicest, kindest and most hardworking person I know. I am honored to have mentored him and I love watching this kid succeed.
Be sure to follow along on my YouTube, Spotify and Apple Podcasts.
Interested in working together for consulting, events or content?