What I Thought Success Would Look Like
When I was younger, I figured success meant financial security, maybe a nice car, and the freedom to buy whatever I wanted. Now, years later, I’m still living paycheck to paycheck, cycling to work instead of driving that car I imagined.
But somehow, I don’t feel like a failure. Which has me thinking: what does success actually mean once you hit your 50s and beyond?
Table of Contents
The Money Thing: Where I “Failed”
Society mostly measures success through money. Using that measure, I haven’t made it. I still watch my budget. Unexpected expenses still stress me out. I don’t have investments or a retirement plan that would impress anyone.
Let me be clear—I’m not some guru pretending money doesn’t matter. I’d love to be richer than I am. I wish I were more ambitious, and especially more confident that I actually deserve financial success. Those doubts have probably held me back as much as anything else.
Here’s something I rarely admit: I feel intimidated around wealth. When I walk into a computer store to check out the latest gadgets, I feel like a fake even talking to the salespeople. Back when I was learning to fly helicopters in my 20s, I met people who could actually buy helicopters—and that intimidation has never quite left me. I avoid window shopping for things I can’t afford because the experience just reminds me it’s still out of reach.
Some Law of Attraction people might say that’s my fundamental problem, and maybe they’re right. If you want something, you should invite it into your reality however you can. But there’s a gap between understanding that concept and actually feeling worthy of wealth.
Do you feel intimidated by wealth, or comfortable around it?
What Wealthy People Actually Have
Before I go further, let me be clear: I’m not dismissing financial success or the people who’ve achieved it. There are plenty of wealthy people who worked incredibly hard, who provide for loved ones, who donate to charity. Self-made success deserves respect, especially when those people are also kind.
This isn’t about wealthy people being bad or my lack of wealth making me virtuous. It’s just honest reflection on where I am and what I have instead of what I don’t.
Who do you actually admire for how they handle their success?
What I Do Have: People Who Show Up
What I actually have is a small but solid group of colleague-friends, something I mention in The Unexpected Gifts of Growing Older.. We’ve worked alongside each other for years. We help each other through hard times and celebrate the good ones. I’ve built a reputation for being supportive and reliable—things that don’t show up on a bank statement but definitely make life richer.
Which makes me wonder: do wealthy people have the same? I imagine many do—people who worked hard AND maintained real relationships. But I also wonder if some traded relationships for achievement and now find themselves wealthy but uncertain who’d actually be there if things went sideways.
Who would you call at 3 AM if you really needed help?
The Body Keeping Score
My mirror definitely shows 56 years of living. But I’m still the same waist size I was decades ago. There’s a small victory in not “letting myself go” physically, especially when aging often means expanding waistlines.
I don’t take this health for granted. Each day of being able to move and work is a gift. I know how fast health can change.
What physical thing are you actually proud of maintaining as you age?
When Changing Direction Counts as Success
Five years ago, one of my bosses closed his English school after his father died. He invited me to join his family’s farming team. Suddenly I was outdoors, working with my hands, getting therapy from nature instead of sitting in classrooms and at computers all day.
Success isn’t always climbing higher. Sometimes it’s changing direction into something that brings more balance, more peace. This farming chapter has been successful by that measure.
When has changing direction actually been the right move for you?
When Endings Count as Success
When my wife left last year, it felt like the opposite of success. The first seven months were brutal. But looking back, our years together served their purpose—I supported her when she needed it, and that chapter ended naturally. I’m still there for her if she ever needs me.
Sometimes success is just finishing what you started, even when the ending isn’t what you imagined. Sometimes it’s surviving the storm and finding yourself still standing—maybe weathered, but wiser.
What ending in your life turned out to matter more than you realized at the time?
What God Might Think
I’d love to ask God if He considers me a success. Not by the world’s standards, but by whatever I was actually supposed to be doing here.
Have I been kind? Have I helped when I could? Have I appreciated what I’ve been given? Have I grown through challenges instead of getting bitter? Those feel like measures that might actually matter.
But here’s the uncomfortable truth: being a kind soul doesn’t seem to be enough to attract financial wealth. It’s as if there are other laws operating, and despite reading “The Seven Spiritual Laws of Success” and finding relatable aspects, the money side has escaped me. It’s all within reach—I believe that. I just wonder if my own thinking or some divine plan is delaying the timing. Or maybe believing in any one concept is my mistake.
What do you think matters more—being kind or being financially successful?
Still Dreaming at This Age
My Duolingo streak keeps going. I’m still learning new things when plenty of people my age have stopped. The motorcycle I want to buy someday isn’t just about transportation. It represents freedom, exploration, new experiences.
But here’s what I’m aware of: I’m older now. My reflexes are slower. My processing is slower. Being young and cool in a fast car is probably safer than trying to drive the same car fast when you’re much older. Maybe that’s why some of us don’t reach as high for certain things anymore—not because we don’t want them, but because we’re realistic about what makes sense at this age.
Maybe some older people feel successful because they have great memories, lots of grandchildren, successful kids. I don’t have a large family. My father and sister stay in touch, but I don’t have the family circle that makes some people feel complete. That’s not a complaint—just a different dynamic.
Maybe success later in life is still having dreams, still believing things are possible, still taking steps forward even when you’re realistic about your limitations.
What are you still dreaming about, even knowing the limitations?
The People You Surround Yourself With
Someone reached out on X recently. They might be trying to scam me—who knows—but just imagining they might be financially successful gave me a confidence boost. There’s truth in that saying about surrounding yourself with people you aspire to be like.
I’ve spent years around people who, like me, hoped someone would rescue us from lack of success. Maybe we held each other back instead of lifting each other up. It makes sense to welcome productivity-driven, successful people into your life so you can all inspire each other.
That’s how the helicopter thing started—just requesting a brochure in the mail. Maybe there’s a brochure on its way to me somehow. Maybe it’ll find me through this blog.
Who are you surrounding yourself with—people who lift you up or people stuck in the same place?
The Honest Truth About This Post
Look, I’m aware of how this sounds. An older guy analyzing his life, trying to justify his lack of financial success, searching for ways to feel okay about his insecurity around money. That’s exactly what this is.
But that’s also what this blog is about—honesty and admitting awkward truths. If I can put myself out there without rose-colored glasses, maybe other people will feel okay admitting their situations too. Maybe we can celebrate the dreams we have of improving our circumstances or becoming abundant, even while being honest about where we actually are right now.
Sometimes I look very much like that comically optimistic grey-bearded old guy in the featured image—raising his arm in success while wearing old-fashioned pilot goggles and homemade cardboard wings. Still hoping for that deserved payday. Still believing.
I’m rich in experience. I tend to think being a kind soul is important. A clear conscience is priceless. But I’d be lying if I said money doesn’t matter or that I’m completely at peace with not having it.
Nothing’s free in this life. My goal isn’t to get things for free—it’s to earn it, deserve it, work alongside others and help them succeed too. Your vibe attracts your tribe, as they say.
What’s your honest assessment of your own success right now?
Your Version of Success
So what do you think about your own success story? Would your younger self approve of where you are, or shake their head? If you don’t see yourself as successful, what’s holding you back?
Has aging made you give up on certain dreams, or has it made you finally reach for them before it’s too late? Do you settle for less because you’re not “young and cool enough” to enjoy certain things anymore, or are you still going for it despite the limitations?
Maybe success after 50 is recognizing that happiness, connection, growth, and peace matter more than your paycheck. Or maybe it’s being honest that you still want the paycheck too, and that’s okay to admit.
What does success actually look like for you at your age? Are you comfortable where you are, or still reaching for something more? Share your honest thoughts below—no rose-colored glasses required.
I respond to every comment, and your experience often helps others more than mine does.
