A New Definition of Success: Finding Fulfillment in Life Transitions

Did you know that nearly half of successful people reconsider their career paths after a major life event? In an age of transformation, discover how personal stories of triumph over adversity are reshaping our understanding of true achievement.

As you may know, I am in the process of redesigning my retreats, combining my variously themed 5-day retreats into one 7-day retreat focusing on life changes, challenges and transitions coaching, and incorporating the mindfulness meditation with my horses, walking a section of the Camino de Santiago and explorative and experiential writing and reading.

Redefining the Definition of Success as I Create a Transformational Retreat

Obviously, I want it to be a transformational experience for my guests, whether it is their first, second or twentieth retreat. This has made me think about success, in general, and more specifically about how I will know whether my new retreats are successful in transforming my guests’ lives.

Success has long been synonymous with wealth, status, and power. Yet, in an evolving world marked by shifting values and unforeseen challenges, I think it is time that the definition of success is re-examined. This redefinition is often initiated by life transitions, changes or challenges that force people to reassess their priorities.

The reason my new retreat is focused on assisting my guests through life changes is not only because I have lived through several of these myself, more than once, but also because the majority of my guests attend retreats here while going through life transitions themselves.

I suspect it’s the call of the Camino de Santiago that draws them here.

Redefining Success

Success has become an increasingly complex and personalised concept, far removed from the one-dimensional definitions of previous generations. Where once success might have been simply measured by a stable job, a house, and a family, today’s landscape presents us with a multitude of competing values, opportunities, and pressures that make defining success both more challenging and more essential than ever before.

A Shifting Paradigm

In contemporary society, success has evolved from a fixed destination to a fluid journey. The traditional markers—climbing the corporate ladder, accumulating wealth, achieving status—still hold weight for many, but they’re no longer the only benchmarks that matter. Today’s definition encompasses a broader spectrum of human experience, including mental health, work-life balance, personal fulfillment, and meaningful relationships. This shift reflects a growing understanding that a life focused solely on external achievements often comes at the cost of internal wellbeing.

The Digital Age Paradox

The digital revolution has fundamentally altered how we perceive and pursue success. Social media platforms create a constant stream of others’ accomplishments, curated highlight reels that can make our own progress feel inadequate by comparison. This phenomenon has given rise to what many psychologists call “compare and despair” syndrome. Yet paradoxically, the same technology that fuels comparison anxiety also provides unprecedented access to diverse definitions of success. We can now witness people thriving in unconventional careers, living nomadic lifestyles, or finding fulfillment in minimalism—paths that challenge conventional narratives and expand our understanding of what a successful life might look like.

Aligned Success

Perhaps the most significant evolution in modern success thinking is the emphasis on alignment between values and actions. Today’s most satisfied individuals often describe success not as achieving specific milestones, but as living in accordance with their authentic values. This might mean prioritising time with family over a promotion, choosing a lower-paying job that offers greater purpose, or declining opportunities that don’t align with personal ethics. This values-based approach recognises that success without authenticity often feels hollow, regardless of how impressive it appears from the outside.

The Health Revolution

Modern definitions of success increasingly incorporate holistic wellbeing. Mental health awareness has brought emotional intelligence, stress management, and psychological resilience into the conversation about what it means to thrive. Physical health, once taken for granted in the pursuit of career goals, is now recognised as foundational to sustainable success. People are asking not just “Am I successful?” but “Am I healthy, happy, and whole?” This integration acknowledges that achievements built on burnout and sacrifice are ultimately unsustainable and unfulfilling.

Impactful Success

Another defining characteristic of modern success is the emphasis on contribution and impact. Younger generations particularly are redefining success to include positive influence on their communities and the world at large. This might manifest as environmental consciousness in business decisions, choosing careers in social impact sectors, or leveraging skills for volunteer work. Success, in this framework, isn’t just about personal gain but about leaving things better than you found them. This shift represents a maturation of our collective understanding—recognising that individual success exists within larger social and environmental contexts.

Linda the Corporate Lawyer’s Story

Consider the journey of my guest Linda, a corporate lawyer who spent a decade climbing the ladder in a prestigious firm. Her high-paying job and impressive title painted a picture of success. However, the long hours and constant pressure left her feeling unfulfilled. Linda’s turning point came when she faced a severe health scare, prompting a reassessment of her life’s direction. She volunteered at a local legal aid clinic, where helping individuals navigate their legal troubles brought her a deep sense of purpose. The gratitude of those she helped contrasted sharply with the impersonal nature of corporate law. After her retreat, Linda left her lucrative job to work full-time in public interest law. Her new career path, while not as financially rewarding, brought her profound satisfaction and a sense of accomplishment. Linda’s story suggests that success is not merely about external achievements but about finding work that resonates with one’s values, especially when life’s challenges push us to reconsider our paths.

Sylvie, the Successful Entrepreneur’s Story

“Success is not the key to happiness. Happiness is the key to success. If you love what you are doing, you will be successful,” said Albert Schweitzer. This quote mirrors the experience of Sylvie, an entrepreneur who founded a tech startup in her twenties. Initially, Sylvie’s measure of success was revenue and market share. Her startup grew rapidly, but the relentless pursuit of growth soon led to burnout and seriously strained relationships. As her marriage started to disintegrate, Sylvie attended a retreat here and, during the retreat, decided to reassess her priorities. She began to focus on creating a work culture that valued mental well-being and personal growth. Sylvie’s company started offering flexible work hours, mental health support, and opportunities for employees to pursue their own dreams. This shift resulted not only in a happier, more productive team but also in sustainable business growth. Sylvie is now convinced that success lies in nurturing a fulfilling work environment.

Lila, the Committed High School Teacher’s Story

Lila’s story further illustrates this redefinition. As a high school teacher, she found joy in inspiring her students. Despite pressure from her partner to pursue higher-paying jobs, Lila remained committed to teaching. A significant life transition occurred when her mother fell ill, requiring Lila to balance caregiving with her professional responsibilities. This period of dual roles underscored the importance of her impact on young minds and the lasting influence she had on their lives. Exhausted from her caregiving duties, Lila attended a retreat here. She realised that she does not measure success in monetary terms but in the pride she felt in her students’ achievements and the positive changes she brought to their lives. Her story demonstrates that success can be found in dedication to one’s calling and the positive change one brings to others, particularly when life’s challenges demand a deeper commitment to one’s true calling.

Essential Reading: Five Books on Modern Success

1. “The Success Myth” by Emma Gannon

I chose this book because Gannon directly confronts the outdated narratives around success that many of us inherited. She explores how the traditional career ladder has crumbled in the digital age and why that’s actually liberating. Through interviews with diverse professionals who’ve redefined success on their own terms, she provides practical frameworks for questioning inherited assumptions and building a personalized vision of achievement. Her writing resonates particularly with those feeling the pressure of conventional expectations while sensing there might be alternative paths worth exploring.

2. “Four Thousand Weeks: Time Management for Mortals” by Oliver Burkeman

Burkeman’s book makes the list because it fundamentally challenges productivity-obsessed definitions of success. By confronting the reality that we have roughly four thousand weeks in a human lifetime, he shifts the conversation from doing more to choosing wisely. This book addresses the modern epidemic of busyness mistaken for success and offers a philosophical yet practical approach to prioritisation. It’s essential reading for anyone who’s achieved traditional markers of success but still feels unfulfilled, helping readers understand that limitations aren’t obstacles to success but the very context that makes meaningful success possible.

3. “The Second Mountain” by David Brooks

Brooks distinguishes between first-mountain success (career, wealth, status) and second-mountain success (relationships, community, moral commitment). I included this because it captures the journey many people experience—achieving conventional success only to realise something crucial is missing. His framework helps readers understand why traditional achievement often feels hollow and provides language for the deeper fulfillment that comes from contribution and connection. This book is particularly valuable for those in mid-life or mid-career transitions, questioning whether there’s more to success than they’ve been pursuing.

4. “Designing Your Life” by Bill Burnett and Dave Evans

This book applies design thinking principles to life planning, which makes it invaluable for modern success seekers. Rather than prescribing what success should look like, Burnett and Evans provide tools for prototyping different versions of your life and testing what truly brings satisfaction. I chose it because it acknowledges that success isn’t one-size-fits-all and provides actionable methods for discovering your unique definition. The emphasis on iteration and experimentation reflects the reality that our definition of success may evolve throughout our lives, and that’s not only normal but healthy.

5. “Range: Why Generalists Triumph in a Specialised World” by David Epstein

Epstein’s book challenges the conventional wisdom that early specialization leads to success. I included it because it validates diverse career paths, career changes, and interdisciplinary thinking—all increasingly common in modern professional life. In an era where people are expected to have clear, linear career trajectories, Range provides evidence that wandering paths often lead to more innovation, satisfaction, and ultimately success. It’s particularly relevant for those who feel behind because they haven’t followed a traditional route, or for anyone considering a significant career pivot. The book reframes what might look like detours as actually being competitive advantages in our complex, rapidly changing world.

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The definition of success in modern life is ultimately personal, contextual, and ever-evolving. It requires each person to look inward, identify their core values, and build a life that reflects those priorities. While this lack of a universal standard can feel overwhelming, it also offers unprecedented freedom. We’re no longer confined to following predetermined paths but can instead craft definitions of success that honour our unique gifts, circumstances, and aspirations. The question is no longer “Am I successful?” but rather “Am I successful on my own terms?”

A New Definition of Success

Reflecting on these stories, it became clear to me that success today is a multi-dimensional concept, deeply personal and often unquantifiable. It is about fulfilment, purpose, and the well-being of oneself and others. Ralph Waldo Emerson aptly stated, “To laugh often and much; to win the respect of intelligent people and the affection of children; to earn the appreciation of honest critics and endure the betrayal of false friends; to appreciate beauty, to find the best in others; to leave the world a bit better, whether by a healthy child, a garden patch, or a redeemed social condition; to know even one life has breathed easier because you have lived. This is to have succeeded.”

I will know that my retreats are successful if they assist my guests in redefining success, particularly during life transitions, changes or challenges, to embrace a holistic view that values happiness, impact, and personal growth over traditional metrics.

Stories like those of Linda, Sylvie, and Lila, prove that true success is a journey, not a destination, and it is as diverse as the people who pursue it.

And it’s back to the “retreat redesign” drawing board for me!

(Names changed and stories altered to protect my guests’ identities.)

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