The Illusion of Our Boxes
Better Question: What day do you want to live every day?
When I was a kid, I wanted to be a lawyer. With one exception: for a few years in middle school, I thought I wanted to be an interior designer.
It didn’t last. I returned to my original idea until my sophomore year of high school.
While it’s tempting to write this story as if I’d given great thought to either path, alas, that was not the case. I had no lawyers or interior designers in my family. In fact, I’m not sure I knew any lawyers in real life. I’m certain I didn’t know any interior designers.
But I felt I needed a good answer to the question, What do you want to be when you grow up?
So, I tried to find a good answer. I found law in the never-ending episodes of Law & Order. Interior design stemmed from my penchant for redesigning my room as a child (which I did quite a few times including one unfortunate version that rendered my room the equivalent of living inside a Pepto Bismol bottle).
It’s unsurprising that as adults we ask strangers, “What do you do?” right after we ask, “What’s your name?”
.
What day do I want to live every day?
When we ask someone what they do, we’re actually trying to understand them quickly. We use their answer to put them in a box. It’s an example of the representativeness heuristic. This cognitive shortcut involves judging something by comparing it to a mental stereotype.
We lean on boxes like this one because it’s mentally faster. Oh, you’re a doctor? I’ve watched Grey’s Anatomy so I now have a sense of you. Oh, you run a marketing company? I bet you offer X and Y services because that’s what marketing companies do.
The speed feels great. The certainty, even better. But for those of us looking to understand the world deeply, boxes obscure essential details.
Here’s how to put it into practice →
One way to bridge the gap between representative boxes and reality is to ask the question, “What day do I want to live every day?”
When we ask someone else, “What does an average day look like for you?” we get richer stories. Asking ourselves, “What day do I want to live every day?” helps us better understand how we want to exist in the world. It reveals the daily practices that serve as the fabric for your life. Do you want to get up early? Do you want to work closely with others? Do you want to remain allergic to sitting at a desk?
Whatever you determine, you can compare your current reality to the life you actually want to live — and adjust accordingly.
In business, this question reminds us to seek out the details boxes overlook.
It’s easy to get attached to the silver bullet — the clean, optimized final outcome where we adopt a technology and everything runs smoothly, or we launch a product and sales roll in.
What’s missing is the reality of using that technology, and what building — and more importantly maintaining — that new product actually looks like. These realities may be in total misalignment with your current capabilities or culture. They may create more work than they’re worth in the end.1 They may also be a pain in the ass no one wants to deal with.
Asking, “What day do we want to live every day?” brings those patterns into focus so you can consider them.
Before you’re stuck with them.
.
Hi! I’m Katie
In addition to writing this newsletter, I speak, cultivate a community, and work directly with teams. Here’s how you can work with me:
Speaking: Bring me in to challenge assumptions and explore frameworks to think more strategically.
Community: Join The Glaede, a space for those who find deep thinking fun.
Direct: Work with me 1-on-1 at Point:Value to ask the right questions and evolve your value.
A reminder that “What’s the point?” is a great early question.+




