How a 1913 allegorical cartoon became my North Star through bouncer jobs, 3:45 AM dial-up sessions, and the obsessive journey from broke to consultant.
I’ve carried this image with me for 25 years. “The Road to Success” - an allegorical cartoon published by the National Cash Register Company in 1913, printed in Theodore Presser Company’s October issue of The Etude.
I found it somewhere on the early internet, probably buried in a Gopher site or an FTP directory I had no business being in. It spoke to me then. It still does now.
Why? Because I was on that road, and I could see every obstacle, detour, and dead-end waiting for me.
The Starting Line: Broke, Obsessed, and Naive
Mid-1990s. San Diego. I was broke, working as a bouncer at a bar in Ocean Beach at night so I could sell websites door-to-door during the day. I hated driving 2+ hours each way in traffic for day jobs that went nowhere. I needed something different.
The internet was just starting out. I saw it. I felt it. This was the future.
But explaining it to people? Impossible. Making money at it? Even harder.
So I did what you do when you have no money for school, no connections in the industry, and no safety net: I consumed everything.
The Grind: 3:45 AM and Dial-Up Dreams
I’d get home from the bar at 3:45 AM, fire up the dial-up modem, and stay online until the sun came up. Then I’d go knock on doors trying to convince business owners they needed a website.
Most days, nobody cared. Some days, someone would bite. Those days kept me going.
At night, while most people were asleep, I was deep in:
FreeBSD 3 - because Linux was still figuring itself out
Perl - the duct tape of the early web
MiniVend - e-commerce before anyone called it that
mSQL, then MySQL - when databases were things you compiled yourself
I had no roadmap. No bootcamp. No mentor. Just this image reminding me that the road was supposed to be hard.
You Can’t Learn “The Entire Internet” (But I Tried)
Looking back, I was too young, too naive, or too stupid to know I couldn’t just learn the entire internet.
But I tried.
Before work. After work. During work if I had a book hidden (shout-out to Unix System V). Anything I could find, I consumed:
Gang of Four - design patterns before I understood why they mattered
The Pragmatic Programmer - changed how I thought about code
LOTY (Language of the Year) - learning a new language every year because curiosity beats comfort
I worked jobs that had nothing to do with tech:
Bouncer at a bar
Body shop manager (twice)
Digging ditches for my dad’s electrical contracting business
Through it all, I was driven. Obsessed. Highly motivated to make this “internet thing” mine.
The Road Had No Shortcuts
The image kept me honest. Every time I wanted to quit, every time I wondered if I was wasting my life learning obscure Unix commands or debugging Perl regex at 4 AM, I’d look at it.
The road to success isn’t a straight line. It’s filled with:
Obstacles - technologies that die, clients who don’t pay, projects that fail
Detours - career pivots, skill pivots, entire industry pivots
False summits - thinking you’ve “made it” only to realize there’s more mountain ahead
But here’s the thing: Every obstacle taught me something. Every detour forced me to learn a new skill. Every false summit made me more adaptable.
25 Years Later: Still On The Road
Fast forward to today. I’ve spent 28 years in this industry. I’ve worked with 200+ clients. I’ve deployed thousands of hours of e-commerce and marketing technology. I’ve sent over a billion marketing messages (yes, with a B).
And that image? Still relevant.
Because the road to success hasn’t changed. The tools are different - we’ve gone from FreeBSD and Perl to Docker and Python, from dial-up to cloud infrastructure, from static HTML to AI-augmented development.
But the journey? Still hard. Still full of obstacles. Still requiring obsessive learning and adaptation.
Why I Still Show This Image
When clients ask me how I approach complex migrations or why I’m comfortable with technologies I’ve never touched, I think about this image.
I’ve been on this road long enough to know:
The swamps are temporary - every project has its mess, you just push through
The detours teach you - the “wrong” path often shows you something valuable
The summit keeps moving - which is fine, because the climb is the point
That 1913 cartoon from National Cash Register Company - pioneers of business technology - became my reminder that there’s a long tradition of people figuring out how to make commerce and technology work together.
I’m just continuing that tradition, one implementation at a time.
The Road Continues
I’m still learning. Still adapting. Still obsessed with making this “internet thing” work for the people who need it.
The difference now? I can show others the map. I’ve walked enough of this road to know where the solid ground is, where the shortcuts lead nowhere, and which obstacles are worth the detour.
That bouncer from Ocean Beach who couldn’t afford college but could afford dial-up? He’s still here. Still grinding. Still carrying that 1913 image as a reminder that the road to success has always been hard.
And that’s exactly how it should be.
If you’re on your own road - whether it’s learning a new stack, migrating platforms, or building something from nothing - remember: the obstacles aren’t blocking your path. They are the path.
