I used to think 28 was a good stopping point in life, mostly because that’s when my mom passed away. Back then, it felt like enough, a safe milestone, a vision shaped by the only blueprint I had: her. But now, as I approach 50, my understanding of 'enough' has transformed. It’s no longer a single number or fixed destination. Wisdom has taught me that 'enough' evolves with experience, clarity, and intention.
When I first entered the workforce, my idea of success was earning $100,000. That felt like a magic number, the benchmark for financial security. What was your number? $50,000? $200,000? Most of us start with a number, but wisdom eventually teaches us it’s not about the number, it’s about understanding what truly matters.
Morgan Housel’s The Psychology of Money hit me hard. In one chapter, he talks about knowing your "enough", not chasing what others define as success, but understanding what fulfillment looks like for you. It challenged me to think about my own relationship with money. What if enough wasn’t about a number, but about freedom, freedom from worry, freedom to give, and freedom to live on your terms?
For me, enough boils down to three things:
- Enough to cover my bills, always.
I never want to experience the stress of owing money I can’t pay. Financial independence isn’t about luxury, it’s about peace of mind. - Enough to retire, if I choose.
While I love working and creating, the option to step back, if life requires it, is priceless. Retirement for me isn’t an exit, it’s a choice. And choice is power. - Enough to leave something for my family.
As someone who’s worked to change the trajectory of my family for generations, this goal is deeply personal. My enough includes creating opportunities for my children’s children. That’s how I measure success, by the seeds I plant for a better future.
It’s not just about my family, though. A crucial part of my mission is giving back to the causes I care deeply about, causes that provide a hand up, not just a handout. I want to support efforts that empower others to change the trajectory of their lives and their families’ lives for generations. Whether it’s through education, mentorship, or access to resources, contributing to this kind of change aligns with my purpose and values.
At the core of these goals is a simple litmus test: If I stopped working today, could I live worry-free without exchanging my time for a paycheck? Right now, I’m not there yet. If I stop working, every goal above is jeopardized. That reality drives me to think differently about achieving "enough." My strategy? To sow my talents and gifts in ways that create value. By doing so, I’ll not only provide for my family but also build a life rooted in purpose.
What about you? What does "enough" look like for you today? Is it freedom from debt? The ability to retire comfortably? Or maybe it’s as simple as knowing you can take care of the people you love. Whatever it is, define it. Write it down. And don’t let anyone else’s version of success distract you from building a life that’s yours.
In what ways have I been holding myself back because of the fear of what others might say? How can I focus on real impact instead of just appearances?
Reflection Question:
Hi, I’m Orvin Kimbrough, volunteer, board director, chairman, and CEO. I help professionals move from feeling stuck to being strengthened by reshaping how they think, lead, and live. My work focuses on confidence, leadership, and influence through mindset shifts, expanded networks, and bold, values-aligned action. My perspective is rooted in lived experience, from growing up in foster care to leading complex institutions as a CEO and shaped by faith, resilience, and a deep belief in human potential.
Books for Every Stage
A memoir often described as a leadership guide wrapped in an honest, relatable story of perseverance, healing, and growth. It explores how pain can be reframed into purpose and how ordinary people build meaningful lives through courage and clarity.
Written for teens and young adults, this book encourages confidence, resilience, and identity formation during the years when self-belief is being shaped.
A children’s book that gently introduces big ideas like belonging, courage, and hope, helping young readers see themselves as more than their circumstances
INTRODUCING: The Thriver’s Path™
This blog is part of The Thriver’s Path™—a growing ecosystem of writing, courses, reflections, and community designed to help people of all ages reframe their thinking, reclaim their agency, and take their next meaningful move.
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