Jennifer is a CEO Coach & founder of Kamara Life Design. She helps founders go from good to world-class while designing well-lived lives.
"So, what do you want to do with your life?"
Few questions trigger more sweaty hairlines than this one. Whether you're 18 or 48, the expectation that you should have a perfectly mapped route from here to retirement is as common as it is unrealistic.
What if, instead of treating your life like you came with a blueprint at birth, you approached it as a series of thoughtful experiments?
This is the genius of applying design thinking to your life. Design thinking is a methodology pioneered by David Kelley of IDEO and expanded at Stanford's d.school, which Kelley helped grow. Since 2007, when Stanford professors Bill Burnett and Dave Evans first adapted these principles for life planning in their "Designing Your Life" course, thousands have discovered a more dynamic approach to navigating life's big decisions.
The Problem With Traditional Life Planning, And What Design Thinking Solves
Traditional life planning follows a "prediction model"—pick a goal, plot the path, then execute. The problem? Research shows we consistently misjudge what will bring long-term satisfaction.
Harvard psychologist Daniel Gilbert's research reveals we are terrible at forecasting our own feelings. We overestimate how happy achievements will make us, underestimate our resilience after setbacks and fail to account for how we'll change over time.
The design thinking approach offers a refreshing alternative—"wayfinding" – where each step reveals information that informs the next move. Rather than betting everything on unreliable predictions, you build toward your future through constant learning and adjustment.
Curiosity Over Certainty
Traditional planning prioritizes certainty, while design thinking cultivates curiosity. Yet when we seek certainty, we become rigid and less creative. When we stay curious, on the other hand, our brains light up with excitement, helping us discover fresh solutions.
Replace absolute questions ("What should I do with my life?") with exploratory ones ("What makes me feel fulfilled?"). Track what energizes versus depletes you for two weeks and look for patterns.
True North: The Ups And Downs
Another life design framework emphasizes examining both your peak experiences (moments of high fulfillment) and your valley experiences (periods of dissatisfaction).
Think back on at least three peak and three valley experiences. For peaks, list what elements created fulfillment. For valleys, list what was missing. These contrasting experiences act as powerful signposts: Peak moments often contain elements aligned with your core values, while valleys typically indicate where important values are being compromised.
A Room With Two Views
The misalignment between work and personal values is one of the strongest predictors of career dissatisfaction.
Draft separate "Work View" and "Life View" statements articulating what good work means to you and what matters most to you in life. Identify points of harmony and tension between these perspectives.
Prototypes
One of the most powerful aspects of design thinking is the concept of low-cost experimentation. Traditional career exploration often focuses on things like "informational interviews," but design thinking emphasizes what Stanford's Life Design Lab calls "prototype experiences"—brief, immersive exposures to potential futures. Like trying on outfits in a fitting room.
Create small, practical experiments to test elements of your possible futures. Rather than jumping into a complete career change from running a restaurant to nursing, volunteer at a hospital for three weeks first. Instead of wondering if you'd enjoy living in another city, arrange a two-week home exchange. The experiential data from brief immersion provides more accurate information than unlimited hypothesizing (a.k.a. overthinking).
The Drawing Board: Designing Better Together
Design thinking is inherently collaborative. Research published in Psychological Science in the Public Interest demonstrates that we consistently overestimate our ability to accurately evaluate our own strengths, limitations and patterns.
Form your own "design team" of diverse individuals who can offer different perspectives. Welcome feedback around specific prototypes rather than seeking general advice.
Making It Real: Turning Ideas Into Action
The beauty of design thinking lies in its bias toward action. Unlike conventional self-improvement approaches that can emphasize extended analysis before action, design thinking reverses this sequence: Take small steps, learn quickly, refine continuously.
Gravity Versus Design
Distinguish between "gravity problems" (unavoidable forces you cannot change) versus "design problems" (constraints that can be worked around creatively). Design problems are invitations to find alternative paths.
Odyssey Plans
Next, generate multiple "Odyssey Plans"—three distinctly different five-year visions for your future. The goal isn't to choose one perfect plan but to expand your thinking of what's possible. Then identify the common themes or components across different scenarios.
Go Wayfinding
After each new experience, ask: "What did I learn?" and "Does this feel right for me?" These check-ins provide clues about whether you're heading in the right direction. The more experiences you try, the better your map becomes, helping you find your way with growing confidence.
Know Your Ideal End State
The Ideal End State Exercise, developed by successful entrepreneur Kevin Dahlstrom, invites you to design your perfect life by getting remarkably specific about your daily existence.
Write down the smallest details that make your life meaningful. Examine how your current choices align with these specifics and look for disconnects. This granular level of detail forces honest reflection about whether you’re acting in concert with what truly matters to you.
The Mindset Shift: Life By Compass
Perhaps the most profound contribution of design thinking to life planning is the shift from viewing your future as a blueprint to seeing it as a compass. A blueprint assumes perfect foresight and stable conditions, while a compass offers direction while allowing for adaptation to changing landscapes.
In applying design principles to life planning, we transform uncertainty from a threat to an opportunity. By embracing iterative prototyping, we discover that the path to meaningful work and life emerges not from perfect planning but from purposeful exploration.
Whether you're considering a career pivot, relationship change or geographic move, you don't need to have all the answers before taking the first step. You just need enough curiosity to prototype your way toward a future that feels increasingly right for you.
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