Whose version of success are you living?

The evolution of success

As a high performance psychologist working with high-achieving founders, executives, and changemakers, I've observed a fascinating pattern: our definition of success isn't static, it can evolve over time. The most fulfilled individuals are flexible and willing to reassess what success looks like on a regular basis. Yet many people remain trapped in outdated definitions that no longer serve their deeper purpose or values, leaving them feeling frustrated and lacking purpose. 

We can identify three very distinct phases in this process.

Success 1.0: The Achievement Phase

Early in our careers, success often looks like traditional markers of achievement:

• The prestigious job title

• The impressive salary

• The external validation from peers and mentors

• The visible symbols of "making it"

This phase is natural and often necessary. These external benchmarks provide us with structure, direction, and feedback about our capabilities. The drive to prove ourselves can be a powerful motivator.

For entrepreneurs, Success 1.0 might manifest as funding milestones, user growth metrics, or industry recognition. For executives, it often appears as promotions, expanding responsibilities, or performance bonuses.

But for many high-performers I work with, a moment arrives when they reach these goals only to think: "Is this it? Why doesn't this feel like enough?"

Reflection Question: What were your early career definitions of success? Which of these metrics are you still measuring yourself against today?

Success 2.0: The Meaning Phase

As we mature in our careers and lives, success typically begins to incorporate deeper dimensions:

• Creating impact that aligns with personal values

• Building meaningful relationships and connections

• Developing mastery in areas that genuinely engage us

• Finding purpose beyond achievement alone

This evolution often comes after experiencing the limitations of Success 1.0. Promotions, raises, and accolades create diminishing returns on fulfillment. The high-achievers I coach frequently describe reaching significant milestones only to feel a sense of emptiness rather than satisfaction.

For executives, this phase often emerges after reaching a long-pursued leadership position, only to discover the role itself doesn't deliver the anticipated fulfillment. For entrepreneurs, it might surface after a successful exit, or significant company growth that fails to bring the expected sense of accomplishment.

Success 2.0 asks different questions: "Does this work matter to me? Am I making a difference I care about? Am I growing in ways that feel meaningful?"

Reflection Question: Where are you seeking meaning beyond achievement in your work and life? What impact feels genuinely fulfilling?

Success 3.0: The Legacy Phase

The most evolved version of success transcends both personal achievement and immediate impact. Success 3.0 considers:

• Contribution that outlasts your direct involvement

• Development of others who will carry forward important work

• Creation of systems, ideas, or organizations with lasting value

• Integration of all life domains into a coherent whole

This phase isn't about retirement or slowing down, many leaders find their greatest energy when operating from this expanded definition. Instead, it's about extending your vision beyond immediate results to consider the ripple effects of your choices and contributions.

For executives, this might manifest as mentoring the next generation of leaders or steering organizational culture toward greater purpose and sustainability. For entrepreneurs, it often emerges as building companies with meaningful missions, creating products that solve significant problems, or investing in other founders with aligned values.

Success 3.0 isn't limited to later career stages. I've worked with young founders who naturally think in legacy terms and senior executives still operating primarily in Success 1.0 paradigms.

Reflection question: What would it mean to create value that continues beyond your direct involvement? What legacy are you building, intentionally or otherwise?

The cost of not evolving: Why we get stuck

Many high-achievers find themselves trapped in outdated success paradigms that no longer serve them. The costs of this stagnation can be substantial:

Identity entrenchment

When you've built your identity around specific achievements or roles, evolving beyond them can feel threatening. The executive who defines herself primarily as, "the youngest VP in company history", or the entrepreneur who sees himself as, "the founder who disrupted industry X", may unconsciously resist expanding their definition of success because it requires identity reconstruction.

The Hedonic Treadmill

Success 1.0 in particular is vulnerable to adaptation, what psychologists call the ‘hedonic treadmill’. Yesterday's exciting achievement quickly becomes today's baseline expectation. Without evolution toward meaning and legacy, high-performers often find themselves chasing increasingly elusive satisfaction through the same achievement patterns.

Organisational inertia

Both executives and entrepreneurs can become constrained by the success metrics valued by their organisations or investors. Quarterly targets, growth expectations, and industry benchmarks can create powerful incentives to maintain outdated success definitions, even when they no longer resonate personally.

Fear of reinvention

Evolving your definition of success often requires brave reinvention. I've worked with many executives who know their current path no longer fulfills them but fear the uncertainty of change. Similarly, entrepreneurs who have succeeded with one model may resist evolving their approach despite diminishing personal returns.

Breaking free: How leaders successfully evolve

Those who successfully navigate these success evolutions typically share certain approaches:

Regular values recalibration

Successful executives and entrepreneurs create intentional space to revisit and realign with their core values. One entrepreneur I work with schedules a quarterly "values audit", to ensure her definition of success remains connected to what truly matters to her.

Community upgrade

Our communities powerfully shape our definitions of success. Leaders who successfully evolve intentionally diversify their circles to include people operating from different success paradigms. For example, deliberately building relationships with social entrepreneurs, artists, and academics to expand your success lens.

Metrics expansion

Rather than abandoning measurement, evolved leaders expand their metrics beyond traditional KPIs. Could you develop a "fulfillment dashboard", tracking not only business outcomes but also team development, personal learning, and impact alignment. This allows for creating accountability for your evolving definition of success.

Legacy thinking

Incorporating regular reflection on longer time horizons helps break the immediacy bias that keeps many stuck in Success 1.0. Questions like, "What will matter in five years?" and, "How would I want to be remembered?", help both executives and entrepreneurs transcend short-term achievement fixation.

Identifying your current success definition

Take a moment to consider these questions:

1. When you feel disappointed or frustrated despite "checking all the boxes," what deeper values might be unaddressed?

2. What would success look like if no one would ever know about your achievements? What would still matter?

3. Which accomplishments from the past three years have brought lasting satisfaction, versus temporary relief?

4. What aspect of your work would you continue even without recognition or compensation?

5. How has your definition of success changed from five years ago? What triggered these evolutions?

Your answers reveal which success definition currently drives your choices and satisfaction.

Creating your evolved success template

The most fulfilled leaders I work with have consciously evolved their success definitions rather than unconsciously inheriting or maintaining outdated ones.

This doesn't mean abandoning achievement, it means enriching it with meaning and legacy. It means defining success in ways that energise rather than deplete you. It means creating a personalised roadmap that grows with you.

Ask yourself:

• What elements of each success phase resonate most deeply with my authentic self?

• What outdated metrics am I ready to release?

• How can I integrate achievement, meaning, and legacy in ways that feel aligned?

• What would make me proud when looking back at this period of my career and life?

For executives, this might mean redefining leadership success beyond organisational hierarchy, to include team development, cultural impact, or industry influence. For entrepreneurs, it might involve expanding beyond valuation and growth metrics to consider the quality of relationships built, problems solved, or lives improved.

Remember, there's no universal definition of success. The only "right" version is the one that honours your values, leverages your strengths, and contributes to a life you find deeply fulfilling.

Are you ready to evolve your definition of success?