The $10 Printing Press
Confessions of a self-taught, accidental IT generalist.
The Keyhole Problem
All I wanted was an easy way to let people read what I write.
That remains true. Everything else that followed was entirely self-inflicted. Up until now, I’ve been sharing stories via text message—which is like trying to hand someone a novel through a keyhole. I’ve emailed PDFs that required a high level of commitment and decent eyesight. I tried WordPress, which felt like renting a massive warehouse when all I needed was a shelf. I even looked at Substack, which assumes you have a "brand identity" and strong opinions about marketing.
Somewhere in the middle of the confusion, I repeated a line from an earlier post and realized it still applied: I’m making a fine mess of my free time.
The Spreadsheet vs. The Pinup
The idea for a privately hosted blog came from my nephew, Jason. That alone should have been a warning sign.
Jason and his brother Eric both read a post I wrote called Handlebars and Heavy Things. Same post. Same words. Two completely different reactions.
Eric, ever the thoughtful one, zeroed in on the section about index funds and long-term investing. He agreed they were a solid, sensible, no-drama vehicle for growth. Reliable. Proven. On-brand.
Jason, on the other hand, really liked the Farrah Fawcett pinup. I could practically hear the wolf-whistle through the internet. They couldn’t be more different. One sees the spreadsheet; the other notices the poster on the garage wall. I love them both for exactly those reasons.
Plumbing the Internet
It was Jason who suggested the private blog. Not because it was easier, but because it would work the way I wanted it to. I registered the Lenny’s Confessions domain for ten dollars a year.
That price point immediately appealed to the part of me that is Ed’s son. I come from good stock—savvy shoppers who feel a deep sense of moral victory when something costs less than expected and actually works.
But then I had to learn the pipes:
- Cloudflare: The receptionist and security guard. It checks if visitors are legit and keeps the traffic moving.
- The Git Repository: My meticulously organized filing cabinet. It remembers every version of every sentence I’ve ever typed.
- Publii: My personal printing press. I write my posts offline, in plain English, and when I’m ready, I hit a button and it packages everything up in one clean move.
And then there are the plugins. They are like the little gadgets you keep adding to your workshop. You don’t strictly need them, but once you have them, you wonder how you ever lived without them.
A Blessing in a Technical Headache
Here’s the part I didn’t expect: This project turned into a blessing disguised as a mild technical headache. It has renewed relationships. Friends and family are reaching out with comments and memories that matter more than a "Like" button ever could. It’s given my retirement a shape.
When you slow down enough to write, you start noticing what actually mattered. You realize that many of the trials that once felt overwhelming were, on reflection, manageable.
Of course, a blog needs a machine to run it. And in true Lenny fashion, I couldn't just buy a laptop off a shelf. I ended up in a garage in Poinciana, navigating a giant pitbull and some very "aromatic" scenery to rescue a used Dell for two hundred bucks. You can read the full, slightly-hazardous story in my other post, The Poinciana Powerhouse.
Retirement gives you time; writing gives that time a purpose.
The Heir Apparent
Lately, Jason has been nudging me in other areas, too.
First, it was cruises: "Always upgrade to the balcony cabin, Uncle Len. Perspective matters." Then it was the domain name. Now, he’s pointing me toward luxury automobiles—the kind with seats that don't argue with your back and doors that close with a confident thud.
Naturally, I consulted Eric first. He ran the numbers, looked at the depreciation curves, and confirmed exactly what I suspected: a terrible investment.
But Jason isn't looking at the spreadsheet; he’s looking at the experience. He’s the reckless one, the "upgrade" guy, the one who reminds me that you can't take the index funds with you.
It’s becoming clear that I’ve accidentally trained a dual-purpose succession team for my sunset years. When the time comes for long-term care, I have a plan: I’ll let Eric handle the finances to ensure the check doesn't bounce, but I’m putting Jason in charge of the accommodations.
I can see it now: Eric will be in the corner meticulously auditing the pharmacy bills, while Jason makes sure I have a balcony suite, a staff of pretty nurses, and a fresh copy of that Farrah Fawcett poster taped firmly to the wall.
I might be the resident crackpot genius for now, but between the level-headed auditor and the reckless heir apparent, the workshop is in good hands.
The Good Kind of Mess
This blog has become more than a way to share stories. It’s a record. It’s a long walk back through a life that’s been richer than I sometimes remember.
Even if no one ever reads these posts, they still matter. They’re my version of journaling. Typed instead of handwritten. Hosted instead of hidden. I’ve once again turned a simple task into a complex project. I am still making a fine mess of my free time.
But it’s the good kind of mess.
I am not an expert. I am a generalist. I notice things.