Designing Life from the Inside Out

I remember the excitement of my first day in the office at a big bank in New York - a new career direction (HR), in a big corporate office in Manhattan, in a leadership program.  But after the initial sparkle and honeymoon of my new job, I started to see the reality of my experience.  My manager did not care about me or my development; I felt anonymous at work; the work was repetitive and boring; and I was being asked to be in the office more days than originally communicated. 

Most of my colleagues were perfectly okay staying at Citi, though, which made me realize:

I had certain needs and priorities that my colleagues didn’t.  Which means...I could have done more thinking about what I really wanted as it related to my career.

I realized after my separation from the company that I valued certain things in the workplace that wouldn't be my experience at a big bank: innovation and creativity, freedom, challenge, genuine sense of mission.

Over and over, I asked the same questions when I was making my career decisions: what industry? what company? what role?

But I later realized I was thinking from a limited, incomplete frame. Enter: Design Thinking.

Why Design Thinking Should Be Applied to Our Lives

Design thinking is a process usually reserved for innovation—companies like IDEO use it to tackle complex problems. But it also works beautifully for designing how we want our lives to look. Instead of rushing to a perfect plan, you experiment with prototypes. Instead of staying stuck in analysis, you move into action.

At its core, design thinking is just structured creativity. We can summarize it in five steps:

1. Empathize – Understand the human side of the problem. Who are you designing for, and what do they feel, need, or struggle with?

2. Define – Get clear on the challenge. Turn vague frustration into a specific design question.

3. Ideate – Brainstorm widely, without judgment. Generate as many ideas as possible.

4. Prototype – Build quick, scrappy versions of possible solutions. Don’t wait for perfect.

5. Test – Try the prototypes, gather feedback, and refine. Then cycle back through as needed.

For reference, here is IDEO's actual process (although this is geared towards products/services):

When designing for your life, you’re doing the same thing—but you’re both the designer and the user.  You get to be present to who you are and what matters to you, including the emotions you want to feel, and ideate ways to bring them to life.  Prototype, test, and iterate - it’s that simple!  Jk.  But it is an iterative process where you are continuously learning and improving.

Research at Stanford’s d.school shows that design thinking helps people approach “wicked problems” (messy, ambiguous challenges like “What should I do with my life?”) with creativity and resilience. Professors Bill Burnett and Dave Evans turned this into the wildly popular Designing Your Life course, where students discovered that treating their future like a design problem made them more energized, hopeful, and flexible when life threw curveballs.

The secret is that design thinking isn’t about the “thing” itself—it’s about who you’re designing for, so that means…getting to know…YOU!

Why Start with Emotions?

Here’s the twist: instead of starting with what you what in life…start with how you want to feel in life.

Why? Neuroscience gives us the answer. Antonio Damasio, a leading researcher on decision-making, found that people with impaired emotional centers in the brain could still calculate rationally—but couldn’t make even the simplest decisions. Emotions are not fluff; they’re the compass we use to navigate life.

Positive psychology research by Barbara Fredrickson shows that emotions like joy, curiosity, and love expand our thinking and help us build resilience over time. And motivation research (Deci & Ryan’s Self-Determination Theory) proves that our drive is fueled by emotional needs—autonomy, competence, and connection. When those aren’t met, achievements ring hollow. 

So ask: How do I want to feel? That question unlocks far more possibilities than What do I want?  Not that we don’t ask both questions.

An Emotion-First Design Process

Here’s how you can start experimenting with life design using emotions as your North Star:

1. Empathize with yourself – Remember who you are: your values, strengths, quirks. Write your own “user persona.”

2. Define core emotions – List 10–15 emotions you want in your life, then narrow to the 5–7 that matter most.

3. Ideate possibilities – Brainstorm activities, places, people, or work that reliably give you those feelings.

4. Prototype experiences – Don’t wait for a five-year plan. Run small experiments: join that art class, try living in Colorado for a month, test a new role at work.

5. Test and refine – Pay attention to how these experiments actually make you feel. Adjust as you go. This is an iterative process, not a one-shot bet.

A Real Example: My Own Emotional Blueprint

When I applied this process to my own life, I started with a bit of my values and personality traits - I’m very extroverted, a positive, optimistic, ambitious person, who loves new experiences, is very active, and very expressive.  

I realized the emotions I wanted to feel most were: fulfilled, relaxed, joyful, grateful, freedom, challenged, love/d, and excited.

With those as my compass, my brainstorm shifted from questions of where I wanted to live and what activities I wanted to do to: What brings me fulfillment? What/who makes me feel silly? What challenges do I want to take on?

• Fulfilled comes from building community, having meaningful conversations with coaching clients, and being my best for my partner, family, and friends.

• Relaxed shows up when I spend an unhurried morning with a book and coffee, no rushing, staying in bed with my partner, and having financial security

• Joyful is dancing, being silly and laughing with friends, going to performances, traveling to new places, enjoying the sun, park, and ocean, having interesting conversations with people

• Grateful often surfaces when I journal at night or take in a sunset, am with the people I love, or even after having tough experiences

• Freedom is felt when I have autonomy over my time and work, not having to drive, expressing myself, and feeling safe

• Challenged comes alive when I’m building something new or solving a messy problem

• Excited sparks when I build and create things, when I form new relationships, or when I’m curating experiences for other people

As you see in the above, some of the answers are in the mundane of our lives - how we live day to day, which is great because you can craft days that you love.  On the other hand, some of the responses help me think through bigger life decisions - where to live, whether to have a stable job or go entrepreneurial, and what friends to keep around.

I can then create prototypes for my life: 

1. The International Portfolio Career

2. The New York Consulting Partner

3. The Bi-Coastal Coaching Entrepreneur

I won’t go into each of them in detail, but you can see that the options have distinctions about where I live and what career direction I go in. And now, I am currently testing prototype #1 🙂.

By making clear the emotions you want to center, you are expanding your thinking and reframing how you design your life around the emotions you want to feel.  We’re feeling creatures!

Bringing It Home

Our lives are more than a gigantic checklist. Imagine your life as a canvas, painted with emotions you’ve chosen as your palette. The job, the relationships, the travels—they’re just brushstrokes. The picture comes alive when the feelings behind it are clear.

Life isn’t designed from the outside in. It’s designed from the inside out - starting with feelings.

Give this process a shot! If you’re interested in this emotions design thinking approach, you can access our “Good Life” design guide by sharing your email HERE, and offer a free 30-minute review of your vision with you!

For Learning and With Love,

Chris