Chasing Dreams vs. Chasing Money (And Why I’m Still Figuring It Out)

The 3 AM Confession of a Hope Addict

Last night, thanks to a persistent mosquito and my overactive mind, I managed about an hour of sleep. Instead of tossing and turning, my brain lit up with blog ideas: new posts to write, CSS tweaks to make, ways to improve OldDogZeroTricks.com. At nearly 60, lying there energized by possibility instead of exhausted by insomnia, I realized something: I’m addicted to hope. I’m still chasing dreams, still grinding for money.

But not the healthy kind of optimism that gets you through tough days. I’m talking about that restless, tinkering, “maybe this time” energy that has kept me building websites for two decades, most of which have quietly faded into digital dust.

Is this addiction serving me, or am I just avoiding the bigger question of what I’m actually trying to accomplish?

Have you ever felt energized by possibility at the most inconvenient times?

The Comfortable Drift of Dreams

I’ve drifted through life more than I’ve driven through it. Not particularly ambitious, some might say, and they probably wouldn’t be wrong. After achieving my one big dream (CPL (H)) at 28, I found myself in that strange territory of “what now?”

The money ran out before I could take my instructor’s practical exam, though I passed the written. But here’s the thing: I didn’t miss flying. So long as I have a worthy role or mission, I tend to be okay with wherever life takes me.

A wooden boat floating and drifting on a calm, misty lake.
A wooden boat floating and drifting on a calm, misty lake.

That drifting taught me things a linear path wouldn’t have: How to find meaning in unexpected places, serve others in classrooms and fields, and how to appreciate what I have while still nurturing quiet ambitions.

One of those quiet ambitions? The Yamaha Niken GT – a three-wheeled motorcycle I’ve been obsessing over for years. I even built a whole website researching it. The bike sits there in my dreams, waiting for the right timing. Probably once I know whether I’m staying in Japan or moving back to the UK to help my aging father. Some dreams wait patiently while life figures itself out.

But reaching this age has also reminded me of ambitions I haven’t reached. Specifically, the paycheck-to-paycheck grind when one of my loves is computers and being online, yet I have no online income or passive income to show for decades of digital passion.

Do you feel like you’ve drifted through life more than driven through it?

The Spiritual Challenge of Money

If we’re here to serve others, then maybe my hobby hope addiction has served a purpose. Filling gaps between work, taking my mind off the daily grind, or preventing that “why bother with anything?” feeling that can creep in. It’s allowed time to flow, given me enough alone time, and given others space too.

I have a natural faith for many things, yet I feel that putting money on a pedestal is my spiritual challenge to overcome. There’s something about chasing financial success that feels like it could taint the purity of creating something meaningful.

But let’s be honest. I’d like to have faith that I can be financially successful. Not for luxury, but for the freedom it represents, and especially to help those I care about.

What’s your relationship with money like?

When Tinkering Meets Purpose

My previous websites were mostly about computers or smartphone ROMs. Technical content that was more SEO challenge than meaningful communication. I enjoyed the tinkering more than needing people to visit, which gave me purpose but defeated the whole idea of having a blog.

The tinkering keeps my mind busy and analytical. Learning about APIs, CSS, fonts, and solving little digital puzzles. But now I’m older and living alone, I’d like to make a real go of this blog. For once, the content feels potentially evergreen and useful for people, as opposed to blogging about Microsoft Windows updates in the past.

There’s something different about writing for fellow travelers dealing with aging, loss, purpose, and the quiet victories of daily life. This isn’t just hobby tinkering. It feels like a mission. The thoughts we rarely admit is where I come into play.

What interest have you been tinkering with that could serve others?

What Success Actually Looks Like

What does “successful” mean for this blog? Having plenty of visitors and people who want to comment. The feeling that the content resonates and helps some people navigate age-related challenges. I’ve never had ads on a blog in over 20 years of building them, so even that small potential step feels significant. I expect it will be easier to setup in the UK.

Just having a platform for my thoughts passes time, but risks being a waste of time. The therapy of chatting with AI and working through ideas has value, but the end goal must be a fruitful and worthy blog that serves others.

Watercolor of an artist sitting at a desk with a blank canvas, surrounded by colorful paint splatters, exploring his creativity whilst chasing a dream.
An artist sitting at a desk exploring his creativity whilst chasing a dream.

Will focusing on success change my relationship with the writing? I don’t think so. What motivates my writing is expressing reality that others might identify with. I don’t mind if people think I’m weak or emotional with some of my anecdotes, so long as the overall message helps them somehow.

The Energy of Possibility

Here’s the strange part: when I’m sleep-deprived but my mind is racing with blog ideas, it’s 100% energizing. That restless hope, that “maybe this time” feeling, it might be addiction, but it’s also fuel. I’ve touched on this restless creative energy in How Do You Know You Are Mentally Healthy?.

Maybe the question isn’t whether to chase dreams or money, but how to chase both without losing the joy in either. How to build something meaningful that also sustains life practically.

At this stage, I’m still figuring it out. The helicopter dream is behind me (obviously), achieved and complete. This blog dream is different. It’s less about personal accomplishment, and more about connection and service.

Perhaps that’s the evolution of dreams as we age: from “what can I achieve?” to “what can I contribute?”

What gives you that energized “maybe this time” feeling despite past attempts?

The Honest Ledger

Some nights, lying awake with possibility buzzing through my mind, I wonder if I’m fooling myself. Is this authentic hope or just sophisticated procrastination? Am I building something worthwhile or just keeping busy?

But then morning comes, I get my coffee, and I start writing. The words flow naturally, honestly. I welcome comments from people that say “this resonates” or “I needed to read this today.”

Maybe the addiction to hope isn’t the problem. Maybe it’s the fuel that keeps us creating, contributing, and believing there’s still something meaningful to build, even when we can’t see the whole blueprint yet.

Are you chasing dreams, chasing money, or trying to find a balance?

dog paw print

Share your thoughts below. I respond to every comment, and your experience often helps others more than mine does.

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