Why Achievement Without Alignment Leaves Leaders Empty at the Top

My joy and heartache as a mentor, coach, and friend come from listening to stories of peaks and valleys in life and work. I've sat with leaders who strived to succeed in their businesses, going all in with their time and resources, only to be left in failure—validating the statistical reality that 90% of start-ups fail. The primary contributors to the failure of any venture are stark and often unforgiving: lack of financing or investors, running out of cash, lack of market demand or poor timing, and people problems. Success more often lies in factors beyond our control.

Yet, I also have the privilege of partnering with a few courageous souls who venture and succeed toward their dreams. Whether in corporate environments or entrepreneurial start-ups, we tend to climb the ladder of success only to often arrive at the top with the sobering reality that we were climbing the wrong ladder all along. Such sobriety at pivotal moments in our lives and work gives us pause to redefine our success criteria, a courageous act that inspires and empowers us all.

After 15 years of running a business, I have experienced firsthand the highs and lows of success and failure while trying to make sense of defining my success between wins and losses, victory and setbacks, and success and failure. Over the last decade, after thousands of hours spent in one-on-one coaching partnerships with leaders across industries, a central question has emerged at the core of nearly every leadership challenge: What is success? This deceptively simple question often proves the most difficult for leaders to answer authentically.

5 Criteria for Navigating what is success:

Seasonality of Success: Success in our twenties looks fundamentally different from success in our forties or fifties. Recognizing your current season and adjusting your definition of success accordingly acknowledges that our values, core beliefs, and priorities naturally shift throughout our professional journey.

From Success to Significance: As Bob Buford powerfully explored in his influential book "Halftime," true leadership growth often requires moving beyond conventional achievement metrics toward what creates lasting meaning and value. This transition invites leaders to identify what is genuinely significant in their current season and understand why it matters to them personally.

Sustainability vs. Sprinting: Many leaders operate in perpetual sprint mode, moving from deadline to deadline, only to find themselves exhausted and questioning their path. Developing sustainable models across all dimensions—financial, emotional, mental, and relational—transforms survival mode into thriving leadership.

Support Systems: The myth of the self-made leader crumbles under scrutiny. We're all standing on someone's shoulders or have been sponsored or supported by others throughout our life and work. Building and nurturing support networks provides assistance and accountability throughout your leadership journey.

Sage Wisdom: Drawing from the experiences of those who have navigated similar challenges can provide invaluable shortcuts to sustainable leadership. While no mentor leader is perfect, learning from others' patterns of success offers practical guidance for your journey, making you feel guided and supported.

Practical Next Steps for Redefining Success

Conduct a Season Assessment: Take an honest inventory of your current life stage. How have your priorities shifted from five years ago? What values now take precedence that didn't before?
Define Your Significance: Write down three legacies you hope to leave through your work and leadership. How do these align with your current focus and time allocation?
Audit Your Sustainability: Identify areas where you're running a sprint when you need marathon endurance. Create boundaries that protect your physical, emotional, and relational well-being.
Select Your Sages and Support: Identify 2-3 mentor leaders and friends whose trajectory you admire and respect. Contact at least one to discuss their definition of success.
Schedule Reflection Time: Block time; start with 30 minutes weekly to assess your progress, adjust your approach, and reconnect with what truly matters this season.

Chasing success can feel like chasing the wind; it's always changing and elusive. If we're honest, we may be chasing someone else's definition of success. Whatever ladder you may be climbing, take pause. Reflect on these steps to offer a renewed perspective of your success criteria and strategies to attain it, then count the cost. Then, take a few steps of faith that align with your deepest values and most significant priorities.