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In 1991, David Kelley — founder of IDEO, a pioneering and innovative design consultancy, and the legendary d. school at Stanford — was asked to redesign a shopping cart. Instead of sketching better wheels or a sturdier basket, he assembled a team and sent them to grocery stores with one instruction: watch people shop.

They discovered that shopping carts weren't really a product problem.

The problem was people.

People abandoned carts in parking lots because returning them was annoying (guilty, sorry!) They chose broken carts because they couldn't tell which ones worked. They crashed into displays because the carts handled like drunk elephants.

IDEO redesigned the cart entirely, making it modular, maneuverable, and impossible to steal. But the cart wasn’t the real innovation, it was the method:

This is called design thinking, and it works on lives as well as shopping carts.

The Problem with How We Approach Change

When we address our stuckness, and seek to redesign our lives, we often treat the endeavor to change like filling out a form.

We identify the problem: I hate my job, my relationship feels stale, I'm anxious all the time…then jump straight to solutions: quit, break up, up my dosage of Lexapro.

We skip the most important step: understanding what's actually happening.

Psychologist Ellen Langer calls locking onto an explanation before you've gathered real data "premature cognitive commitment” (sexy, right?) You decide your anxiety is about work when it's actually about how you talk to yourself. You think you need a new relationship when you need new relational patterns. You believe the problem is what you're doing when the problem is how you're doing it.

Design thinking forces you to slow down and observe first. To treat your life like a prototype, not a finished product.

Added perk of design thinking: it instills creative confidence.

How to Use the IDEO Method on Yourself

1. Empathy (Not Introspection)

Designers don't start by asking "What do I think users want?" They watch users interact with the world. They look for friction points: where does the experience break down?

Apply this to yourself: Don't ask "Why am I unhappy?" Ask "Where does my day feel most difficult?" Notice when you feel worst. What triggers it? What makes it better? Track it like data, not drama.

For instance, maybe the problem isn’t too much work, but what part of the day you prioritize creative work. If responding to emails first thing in the morning seems to drain you for later work, maybe the problem is that you’re doing your creative work after the work that drains you.

Swap places and see what happens.

2. Define the Real Problem

IDEO calls this "reframing." A shopping cart problem becomes a human behavior problem. A coffee maker problem becomes a morning ritual problem.

What if your "I need to be less anxious" problem is actually an "I need to feel less afraid of my own anxiety" problem? What if "I need a better relationship" is actually "I need to stop over-performing in my relationship"?

Our friends, loved ones, and TikTok influencers offer solutions to problems we haven't properly defined. This is why most answers don’t work.

Design thinking insists you get the problem right first.

3. Ideate Without Censoring

Designers generate hundreds of ideas, most of them terrible. The goal isn't to find the answer, it's to get your brain out of its default grooves.

Try this: Set a timer for 10 minutes. Write down every possible way you could address your problem, no matter how absurd.

Want to feel less lonely? Ideas might include: join a kickboxing gym, host a monthly salon, adopt a dog, become a regular at a coffee shop, text three people per day, volunteer at a library, take a class in something intimidating.

The bad ideas often contain fragments of good ones. The ridiculous ideas reveal what you actually value.

4. Prototype Small

Design thinking diverges from traditional goal-setting because you don't commit to a five-year plan. You build a prototype: a small, testable version of the change, and see what happens.

Want to try out a different career? Don't quit your job. Spend two hours a week doing the work. Want a different social life? Don't move cities. Host one dinner party. Want to be "less anxious"? Don't overhaul your entire life. Pick one anxiety-producing situation and try a single new response.

Prototypes let you fail without real world consequences, or catastrophe. Instead, they offer useful information.

5. Iterate Based on What You Learn

The first prototype usually reveals something you didn't expect. Maybe hosting that dinner party showed you that you don't actually want more friends, you want deeper friendships with the people you already know.

Maybe trying the new work revealed that you love the content but hate the structure.

Most people try something once, it doesn't work perfectly, and they conclude they were wrong. Designers assume the first version won't work. That's the point. You iterate based on data, not disappointment.

What This Actually Looks Like

Let’s say you feel stuck in your life. Same job, same apartment, same routines for a decade. Maybe you’ve tried making big changes (applied for new jobs, considered moving cities) but nothing felt right.

Ask yourself: Where in my days do I feel most alive?

Let’s say you answered, “During conversations.”

Which sort of conversations?

“Conversations where I’m helping someone think through a problem.”

Have you accidentally designed a life with too little conversation?

If so, prototype: start hosting a monthly dinner, or a monthly breakfast at a local diner, where you invite the people you find most interesting. Ask everyone to bring a problem.

Maybe the first few gatherings will be awkward, but maybe by the third, you’ll have accidentally created something you love: a space where people think out loud together. You don’t need to change jobs or move. You just need to redesign one night a month to change how you feel about life.

You don't figure out what you want by thinking harder. You figure it out by trying things and paying attention to what happens.

Your life isn't a problem to solve. It's a prototype to test.

So, what will you prototype first? Let me know in the comments!

Until next week, I will remain…