The Hidden Cost of the ”Perfect” Journey (and how to avoid it) / Kendra Shimmell / Ep. #244

2026-01-01

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Sorry, but I have to say it...We are optimizing our way to boredom.Measure everything, test every variation, and optimize the customer journey until it’s "perfect". That seems to be the mantra of modern business today.But in this first episode of 2026, our guest Kendra Shimmell throws a big wrench in this machinery.Kendra argues that while things like A/B testing validate what works right now, they often come at a steep cost. Because if we rely solely on reacting to quantitative data to make small, incre...

Sorry, but I have to say it...

We are optimizing our way to boredom.

Measure everything, test every variation, and optimize the customer journey until it’s "perfect".

That seems to be the mantra of modern business today.

But in this first episode of 2026, our guest Kendra Shimmell throws a big wrench in this machinery.

Kendra argues that while things like A/B testing validate what works right now, they often come at a steep cost.

Because if we rely solely on reacting to quantitative data to make small, incremental improvements, we eventually, you guessed it, optimize our way to mediocrity and boredom.

We lose the soul in our services.

Kendra shares a painful example of this phenomenon in action: social media algorithms.

You click on a cool backpack once, and the system thinks it has you figured out. Suddenly, your entire feed is just backpacks. A lot of backpacks.

The algorithm is "optimized," sure.

But it has stripped away all the serendipity, turning a place of discovery into a repetitive, boring experience.

As Kendra put it, just because you can keep a user clicking doesn't mean you aren't exhausting them.

So, the question is: Why do organizations default to this?

Why are we so focused on squeezing out efficiency rather than exploring new avenues?

When I asked Kendra, her answer was blunt: "Greed, Fear, and Confusion." Ouch.

The greed to squeeze out the last 1% of revenue.

The fear that if they try something new, they won't find product-market fit again. And the confusion that comes from ignoring the fact that humans are wildly irrational beings driven by feelings, not spreadsheets.

This conversation is a wake-up call to stop treating our customers like subjects in a scientific experiment and start treating them as people to co-create with.

And if your organization isn't ready to hear that? Well, Kendra has some advice on how to be a little "sneaky" to get the work done anyway!

The conversation ends with a question that pairs perfectly with a long walk, somewhere where you can let a little serendipity back into your day: "When, where, and how is it most important to be human?".

Happy New Year and keep making a positive impact!

Be well,

~ Marc

--- [ 1. GUIDE ] ---

00:00 Welcome to Episode 244

04:30 Why We Need Co-Creation Over Experimentation

08:30 The Twitch Lesson

14:30 Why Excessive Optimization Leads to "Beige"

16:03 Social Media & the Algorithm

23:45 Backpack Rabbit Hole

25:30 3 Forces of Stagnation

32:30 Funding Analogous Thinking