Charting Your Retirement Journey
A roadmap to create meaning, joy, and purpose in your new chapter
Retirement isn’t the end of the road—it’s the beginning of your greatest expedition.
This practical and playful guide helps you design a meaningful next chapter filled with discovery, creativity, and connection.
Your Retirement Journey
After decades of work, responsibilities, and routines, it’s easy to lose sight of who you are beyond your career. Charting Your Retirement Journey is your invitation to pause, look around, and imagine what comes next.
Through stories, reflection prompts, and playful exercises inspired by design thinking and life-planning, you’ll:
- Discover what energizes you (and what doesn’t)
- Explore new directions and possibilities
- Design prototypes for your next life chapter
- Build confidence in your choices
- Adopt an agile, adventurous mindset
Whether you dream of new projects, travel, creativity, or contribution—this book gives you the tools and courage to make it real.
Who This Journey Is For
This book is for you if you’re:
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Approaching retirement and wondering, “What’s next?”
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Recently retired but missing purpose or direction
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Balancing freedom with a need for structure
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Curious, creative, and ready to explore new horizons
You don’t have to have all the answers—you just need the courage to start.
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From Base Camp to Your Next Summit
Your transformation unfolds step by step — just like any great adventure.
Each stage helps you explore, align, and design your next chapter with more clarity, purpose, and joy.
1) Who are you today?
Before you design your future, you need a clear picture of the present.
In this chapter, you’ll take stock of your health, work, play, and love, explore your personality and motivations, and create a snapshot of who you really are right now.
This self-portrait becomes the foundation for everything that follows.
Example exercises:
Base Camp Check-In — assess your readiness and satisfaction across life areas.
Explorer’s Profile — uncover your natural instincts and preferred ways of exploring.
Aligning the stars — align your direction with your core values.
2) What is important to you?
Sometimes the way you see a problem is the real problem.
Here you’ll learn to step back, remove your blinders, and reframe challenges from new angles—turning roadblocks into design opportunities.
Example exercises:
Adventure Style — define the kind of journey that fits you.
Route Options — explore multiple paths and prototypes.
Quest Map — clarify what your journey is really about.
3) You have more possibilities than you think
Your life isn’t limited to a single path.
In this chapter, you’ll brainstorm bold options, explore “what ifs,” and design three radically different Adventures—so you can see just how many futures are open to you.
Example exercises:
Explorer’s Diary — track your “good time” moments.
Travel Miles Record — take inventory of your past experiences.
Campfire Culture Map — identify the team and environments where you thrive.
4) Role-play your future life
Don’t just imagine your future—try it on for size.
You’ll prototype your ideas through interviews, networking, storytelling, and visioning, so you can test what excites you and what really fits before you commit.
Key exercises:
Explorer’s Superpowers — recognize your unique mix of talents.
Expedition Strengths — pinpoint your support network and allies.
Survival Skills — prepare for what’s ahead with confidence.
5) How do you know if you should jump?
Big decisions can feel overwhelming.
Here you’ll stress-test your plans with practical tools: mapping enthusiasm and confidence, spotting biases in decision-making, and adopting an agile mindset.
Key exercises:
Epic Journey Map — sketch three possible futures.
Next Summit Plan — pick one and take your first real step.
Reflection Checkpoint — stay agile and adapt as you go.
By the End of the Journey…
You’ll have more than a plan — you’ll have momentum.
A renewed sense of curiosity, direction, and the tools to keep exploring — one joyful step at a time.
Meet the authors
John Elbing
Life Architect • Storybuilder • Strategy Coach
I’m passionate about one thing: helping people understand themselves—and then figure out what comes next.
Born in the U.S., raised in Switzerland, I’ve zigged and zagged through careers—from coding and finance to marketing and startup life—always building new skills and refining my map of what’s possible. I hold an MS in Computer Science, an MBA in Finance, and certifications in Design Thinking and the StoryBrand storytelling framework.
Over the years, I’ve coached dozens of entrepreneurs, executives, and creatives—not by handing them a blueprint, but by helping them build their own. I’ve launched two startups, managed complex projects, and learned that life design is not a luxury; it’s a daily practice.
This book is a distillation of everything I’ve learned: the tools, the mindset, the joy of experimenting, failing, adjusting—and building a life that fits. I’ve been designing my life for decades—now I’m inviting you to build yours, too.
Luisa Colombo
People & Organizational Developer, Agile HR Practitioner.
I am passionate about people, their development and the mechanics of human being interactions. Curious and enthusiastic by nature, I like exploring new options and opportunities and my life-view looks like an exciting learning journey. I enjoy constantly asking myself and my coachees: “What do you want to grow into next?”
With a solid background in economics, I have more than 15 years’ experience working within organizations, mainly in HR functions. I combine my background in human resources, coaching and organizational development, with innovative Agile practices.
I have coached leaders and teams to unlock their potential, learn new skills and find innovative ways to boost their performance. I have helped executives and professionals to take ownership, design their career and shape their future.
