Those who aspire but never attain—midlife questions in the seasons of achievement

Have you ever been told you're going to do "great things" but left wondering what exactly someone saw in you that you can't see in yourself? Perhaps teachers, coaches, or mentors were early champions of your potential, speaking words of destiny over your future. Yet decades later, despite external success, you carry an elusive sense that you've never quite met the mark of that potential, never fully measured up to what others believed you could become.

As an act of vulnerability, I'll share my own story of chasing success in pursuit of someone else's expectations, only to feel as if I fell short, disappointing them and myself. For years, I hid behind the regret of not completing what I set out to do, holding onto the shame of not finishing what I started.

My years as a Boy Scout were filled with summer camps, weekend adventures, and multiple 50-mile treks. I earned dozens of merit badges, filling my sash, moving through the ranks to Senior Patrol Leader. Ironically, I arrived at the rank of Life—one step before Eagle Scout—with only the service project requirement remaining. Then our family moved to a new area. I rejoined another troop, yet never took that final step to Eagle Scout.

This became a mark of regret that has, at times, created an unhealthy drive toward my goals, as if achieving other things could somehow compensate for that unfinished chapter. Yet in hindsight, to say I "failed" as a Boy Scout isn't true. Those experiences shaped countless characteristics during my coming of age, influencing my love and lifestyle of the outdoors that continues today.

This pursuit of success to satisfy internal questions reveals something profound about how we measure achievement. Our criteria for success evolve dramatically with each decade and season of life. Reflecting on this evolution can be a transformative and empowering experience.

Markers of Success by Decade:

Twenties: Landing the right job, hitting income targets, establishing independence, proving competence Thirties: Career advancement, recognition, building something significant, accumulating achievements Forties: Making a meaningful difference, leaving a mark, questioning legacy, deeper relationship connections Fifties: Wisdom over achievement, mentoring others, authenticity over image, enjoying the fruits of earlier labor Sixties and Beyond: Relationships over accomplishments, leaving something valuable behind, peace with the journey

What remains constant is the human tendency to place our sense of worth in external validation rather than internal clarity about what matters to us. The Boy Scout trail taught preparation and perseverance. Still, life teaches us that our deepest satisfaction comes not from completing every badge, but from how the journey shapes our character and values.

The executive who measures success only by revenue growth misses the satisfaction of developing team members. The leader focused solely on the next promotion, overlooking the daily opportunities to solve problems, build relationships, and create positive change. The parent obsessed with their children's achievements might miss the simple joy of being present in ordinary moments.

Reflective Questions for Your Season:

Before rushing toward the next goal, consider these questions:

What were you told you'd accomplish that still haunts you today?
How has your definition of success evolved over the past decade?
What external achievements are you pursuing to answer internal questions?
When did you last feel genuinely satisfied with your daily work, regardless of outcomes?

Next Steps to Define Success for Your Season:

Start with Values: Identify your top five core values. Not what you think they should be, but what actually drives your sense of meaning and satisfaction. These become your TrueNorth when external pressures try to redefine success for you.

Find Joy in Small Wins: Begin noticing and celebrating micro-achievements daily. The difficult conversation handled well, the moment of genuine connection with a colleague, the problem solved creatively—these matter.

Practice Gratitude: Dedicate five minutes each morning to a gratitude journal. Write down what brought you satisfaction the previous day, what you enjoyed, and what felt meaningful. This isn't toxic positivity; it's emotional fitness.

Look for Themes: After a few weeks or months, review your entries. What patterns emerge? What consistently brings you joy or satisfaction? These themes reveal your authentic criteria for success in this season.

Find a Guide: After your reflection, seek out a trusted friend or mentor to walk with you. Share your discoveries and invite accountability. Success in any season is rarely a solo journey. Having a mentor can provide you with the support and guidance you need to navigate your personal journey.

The Challenge and Encouragement:

Where you've faced regrets from the past, I challenge you to reframe success. Disappointments can lead to life's most significant appointments. Consider how those 'incomplete' experiences shaped who you've become. Define success for today based on your current values and season, not yesterday's unfinished business. This is not about compensating for past regrets, but about honoring what matters most in this chapter of your life.