When I was younger, I imagined success would look like financial security, perhaps a fancy car, and the freedom to buy whatever caught my eye. Now, years later, I find myself still living paycheck to paycheck, cycling to work instead of driving that imagined car.
Yet somehow, I don’t feel like a failure. This has me wondering: what does success really mean as we journey through our 50s and beyond?
The Financial Measure: My Supposed “Failure”
Society tends to measure success primarily through financial achievement. By that narrow definition, and looking at my finances, I haven’t quite made it. I still watch my budget and occasionally feel the pinch when unexpected expenses arise. I don’t have hefty investments or a retirement plan that would impress a financial advisor.
Let me be clear – I’m no guru offering wisdom from a mountain of achievement. I’d absolutely prefer to be richer than I am. I wish I were more ambitious and especially more confident that I actually deserve some form of financial success. These doubts have probably held me back as much as any external circumstance.
Yet the universe (or God, if you prefer) has consistently provided what I’ve needed when I’ve needed it. Not always what I’ve wanted, but what was necessary. There’s a certain success in that flow, in trusting and receiving, even if it doesn’t translate to wealth.
Beyond Money: The Wealth of Connections
What I do have is a small but reliable network of colleague-friends built over years of working alongside the same teams, something I mention in The Unexpected Gifts of Growing Older. We rely on each other, support each other through life’s challenges, and celebrate each other’s joys. I’ve earned a reputation for being supportive, reliable, and faithful—qualities that don’t show up on a bank statement but certainly enrich our lives.
I wonder how many “financially successful” people can say the same about their relationships? How many traded connection for achievement and now find themselves wealthy but wondering who would stand beside them in troubled times?
The Physical Scorecard
While my mirror definitely shows my 56 years, I take some pride in maintaining physical health. I’m still wearing the same waist size I did decades ago. There’s a certain victory in not “letting myself go” physically, especially in a culture where aging often means expanding.
I don’t take this health for granted, not for a moment. Each day of mobility and strength is a gift, and I know how quickly circumstances can change.
New Chapters as Success Markers
Five years ago, when one of my bosses closed his English school after his father died, he invited me to join his family’s farming team. This unexpected pivot brought me outdoors, into nature’s therapy, with informal work rhythms and physical activity that balanced my classroom and computer time.
Success isn’t always climbing higher—sometimes it’s moving sideways into new chapters that bring small wins, more balance, more peace. By that measure, this chapter has been tremendously successful.
Relationship Endings as Milestones
When my wife left last year—see It’s Okay to Be Broken, it felt like anything but success. The first seven months were a heart-wrenching challenge. Yet in reflection, I realized our years together served an important purpose—I supported her as she needed, and that chapter reached its natural conclusion.
Sometimes success is completing what you started, even if the ending isn’t what you imagined. Sometimes it’s simply surviving the storm and finding yourself still standing, perhaps a bit weathered but wiser.
Success Through God’s Eyes
Ultimately, I’d love to ask God if He considers me worthy of being labeled a success. Not by the world’s metrics, but by whatever divine purpose I was meant to fulfill.
Have I been kind? Have I eased suffering where I could? Have I appreciated the gifts I’ve been given? Have I grown through my challenges rather than becoming bitter? These seem like measures of success that might matter more in the grand scheme.
New Horizons later in life
I’m currently learning about AI, absorbing content and building skills that might help me create online income. The daily Duolingo is still going strong. There’s something successful about continuing to learn, to adapt, to try new things even as many my age are settling into familiar routines.
The motorcycle I dream of buying represents more than transportation—it symbolizes freedom, exploration, and new experiences. Perhaps success later in life is still having dreams, still believing in possibilities, still taking steps forward.
What About You?
This isn’t just my story—it’s a pause for thought, an invitation for you to join the discussion.
I wonder what you think about your own success journey. Would your younger self approve of where you are now, or shake their head in disappointment? If you don’t see yourself as successful, can you identify what’s holding you back? Are you still working toward bigger goals, or have you found peace in your current circumstances?
Does it make sense to measure success by social media standards, comparing ourselves to carefully curated highlights of others’ lives? Or should we define it more personally, more spiritually—like happiness, contentment, peace?
I’ve read “The Seven Spiritual Laws of Success” many times. While its principles resonate deeply, I sometimes think Deepak Chopra should rename it “The Seven Spiritual Laws of Happiness” to reflect my experience better.
Perhaps that’s the ultimate redefining of success—recognizing that happiness, connection, growth, and peace matter more than the size of your paycheck or your possessions.
What do you think? How do you measure success at your age?
