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How I Landed the Worst Best Job

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The Early Days

Note: As usual, much of the below is from decades ago and my memory isn’t perfect. In the unlikely event you are mentioned here, it’s possible your memory will be different from mine.

I am often asked how I got into writing software for a living. This is the story of my first real programming job and the strange path that took me there.

In 1982 I was attending Keystone School in San Antonio, Texas. It was a very dark time in my life and my geometry teacher recognized that I was in trouble, so she allowed me to play in the computer room that was reserved for older students. I learned BASIC programming and discovered something in school that I loved. After I left that school to go back to a public school, I started writing (bad) games in BASIC and laboriously typing in programs I found in magazines.

I had begun with Commodore PET computers and moved on to the technological marvel that was the TRS-80 (called the “trash 80”). By 1985, I already written a fully-featured lo-res graphics program for the TRS-80 that allowed users to create images, saved across multiple files (I didn’t understand data compression back then) and stitch those files together to print the images on a dot matrix printer.

Those were the days. I had demo images with that, including a nice, but pixelated minotaur’s head, dragon’s head, and other AD&D images.

One would think that after I graduated high school in ‘85 that I would go on to college and do something with my life, but one would be wrong. We were dirt poor and at the time, to qualify for financial aid for college, I had to first apply for a Pell Grant. That required that my parents provide several years of past tax returns to show what level of financial support they could provide. My mother explained to me that my step father did the taxes. He had failed to file them for years, so no Pell Grant for me. No financial aid for me. No college for me.

The next several years were me bouncing around from odd job to odd job, mostly fast food. At one point I had worked at Wendy’s restaurant in Anchorage, Alaska, Kingsville, Texas, Universal City, Texas, Longview, Washington, and Honolulu, Hawaii. I was a pathetic peripatetic, wandering from state to state, deeply embarrassed that the “Most Intelligent of the Class of ‘85” of Marion High School was an itinerant burger flipper.

Years later, I eventually went to a community college in Portland, Oregon and managed to get an Associate of Science degree with a 4.0 GPA , having taken every economics class they offered with a specialization in international relations.

An Associate’s Degree is a two-year degree and unless you use it to go on to a four-year college, it’s worthless for many jobs.


Which is how I found myself working as a barista (espresso bartender) when a young, pretty lady walked up and placed her order, leaving a large tip in my tip jar. I was proud of the fact that I was the highest tipped male barista in our chain of stores and I accomplished this by flirting. So I flirted with her, in my naïveté thinking it was innocent fun. I had known her and her boyfriend as regular customers, but that’s all. And that’s when she made me a rather curious offer.

I declined, pointing out I had a girlfriend, to which she replied that my girlfriend could join us.

Er, no. So when her boyfriend arrived later to place an order, I apologized, explaining that through I didn’t know him well, he should know what happened.

He swore, thanked me, and explained that their lifestyle was a bit different. However, they agreed not to proposition people without the other’s knowledge. I still wasn’t going there, but he and I started talking more and eventually we became friends. Turns out he was a software developer and when he found out I used to write software, we started talking about this frequently.

One day he came in to place an order and said he was quitting his job and he’d be happy to recommend me. The software was written in something called UniBasic and he was sure I could handle it. He would stay on for three months to train me.

I got the job and it got my foot in the door, but to my surprise, it was often less professional than the fast food restaurants I had worked at.

My First Test

My friend was leaving his job on the last day of December. I had been on the job for just three months, learning their software, but only being allowed to work on it part-time. Otherwise, I made sure all of the employees were turning in their paperwork correctly. On that last day, the controller called me into his office. He explained that they needed to increase the price of everything by X%, varying per category, and have it ready for tomorrow.

This wasn’t just running a bunch of SQL. We were using a UniData multivalue database , prices were scattered all over the place, and I wasn’t very good with their query language. Worse, our license allowed us to write code to read the data, but not change it. Updating this data was done through software running on a terminal and it created audit trails for everything. I needed audit trails, too.

This was a bad idea on many fronts. First, my friend made it clear how much he despised the place and he was leaving at 5PM because he had a New Year’s Eve party to attend. He explained to me how to do the job and I knew enough about the design of our database to figure it out, but it should not have been a rush job.

Next, since software I wrote could only read data, not change it, we had a huge risk. If we changed the data and were caught, we’d have to pay $25,000 (almost $50,000 in today’s money) to buy a copy of the software outright. We were a small company and that would have hurt us. We’d also lose all technical support from the company that “designed” this software. and we’d no longer get free upgrades. Having a few hours heads-up on New Year’s Eve that I needed to risk destroying the company’s business wasn’t fun, but this was how the company worked. So I worked.

After writing the software to update the prices, I ran it. If it worked, it would look like people had spent days manually updating all of the prices, complete with audit logs. I had done it in hours. But if I—a junior developer—corrupted the data, I might be fired. Happy F’ing New Year.

It was getting late in the evening and I was tired and stressed. I ran the software. I corrupted the data.

The only reason I didn’t get fired is that I wrote the software to terminate after the first change and I had printed out all of the data that would be altered by the first run (this seeming much easier than the alternatives in those early days of software development). The controller and I manually fixed the data, I figured out what I did wrong, and ran my software again. This time it worked.

I went over all of the data carefully. I double-checked everything I could. The database was complex and prices for different kinds of goods were stored in different ways, but I couldn’t see anything wrong with what I did. I explained everything to the controller (who, to be fair, had become a friend of mine. He was also surprised by this last minute request). I told him I could remove the code that caused the software to halt after the first change. The software would run overnight and we wouldn’t know until the morning if it worked. The controller told me to do it and get to my party.

January 1st, I get a phone call early in the morning. I’m hung over and not looking forward to this call. It seems they had been checking all of the data they could.

The software worked.

How I Became a Bill Collector

This was a small, family-owned business, with several stores offering a variety of products, many of which had to be ordered months in advance to be handmade in Europe and shipped to the US. The business wasn’t struggling financially, but as far as I could tell, they weren’t getting rich. They needed more money. In fact, I needed more money. I asked for a raise.

At the time, I was paid $x dollars an hour for my administrative role and a couple of dollars an hour more for when I wrote software, capped at 15 hours a week. This wasn’t legal, but I wasn’t slinging espresso or burgers. I never complained, but I still asked for that raise.

We had a new office manager who was not well-liked, was a rubbish manager, but knew our products like the back of his hand, having recently been promoted from warehouse manager. He listened to me, nodded, and explained that they were having trouble with customers ordering goods and not paying, leaving the company with a huge accounts receivable (AR) balance. The company simply didn’t have the money to pay me.

Oh. That’s interesting. In my prior life, I had also worked in car sales. I knew exactly what this was: a negotiation. The manager probably thought he had told me “no,” but I heard his objection and I isolated it .

Me: “You don’t think I deserve a raise?”

Him: “Yes, you do, but we can’t afford it.”

Me: “And this is all because of the outstanding accounts receivable?”

Him: “Yup, sorry about that.”

Me: “So if I can get those people to pay, you can afford to pay me.”

He was trapped by his own words, but to get out of that, he made me an offer I couldn’t refuse, but couldn’t win. If I could get AR to zero by a certain date, I’d get a raise. He wouldn’t budge from zero. We had a lot of outstanding accounts, but not an insurmountable number. However, the goods we sold weren’t cheap and getting people to pay wasn’t going to be easy. I was allowed to take any reasonable steps to enforce this.

That’s how I became a bill collector.

The first thing I did was, of course, write software to produce daily reports for me on the next accounts I would go after, and the steps I had taken to collect on those accounts.

I sent email to everyone I could, and called the others (all customers gave us phone numbers). An astonishingly large number of those people had no idea they owed money and paid up. No one had bothered to contact them! I was surprised at how easy it was. But a large number of them simply didn’t answer.

My next step: I received permission to contract with an actual bill collector. They would buy the debt from us, paying a fraction, and then it was their problem. That’s when I discovered the world of potential clients wining and dining you to win your business. I only accepted lunch from them, but now I realize that even that is dubious.

I chose a bill collector, the company signed the contract, and another large subset of accounts were cleared. But there will still more.

One, in particular, was someone who told me on the phone that she owed nothing. But she did, and I had the paper to prove it. In fact, I often went back to the paper because if this went further, I wanted more than just ones and zeros on a hard disk. She clearly owed the money and it was a lot, so I tried to collect directly rather than hand her off to the bill collector.

Turns out she was a lawyer and immediately replied that we were going to be sued for harassment. The company agreed to write her debt off and the grounds that a trial would cause more pain than her debt. Another account cleared.

On the day of my deadline, the manager greeted me with a smile. He was very happy with the work that I had done but, unfortunately, I hadn’t reduced AR to zero. No raise.

I handed him the AR report. If the owners of the company paid their bills for the products they bought, our AR would actually be positive. Should I send them to collections?

The trap was sprung, the manager was caught. I got my raise.

Sexual Harassment

The worst nightmare at this job, though, was the sexual harassment.

Three people, Alice, Bob, and Charlie. All of them were nice people and friends of mine. I was still very young and not understanding how business was supposed to work, so I flirted with Alice. She flirted back. We liked each other, but she was also an extremely devout Christian, so my atheism was an issue.

Nonetheless, we continued to flirt. A little harmless fun, right? Bob didn’t flirt with her, but he cracked lots of jokes, was well-liked, and he and I started hanging out after work. He was a great guy; we’ll get back to him. I liked Charlie, too, but Alice didn’t. So when Charlie would make inappropriate comments to her, just like I did, she ignored them.

One day she came to me with a problem. The company was driven by testosterone-fueled cronyism and she didn’t trust upper management. She said she was being sexually harassed by Charlie and didn’t know what to do.

Oh, shit. I wasn’t entirely sure of the law, but a few thoughts crossed my mind.

  1. I stopped flirting instantly
  2. If I didn’t act, I could be culpable
  3. I had to talk to upper management
  4. She was about to be fired for being our worst salesperson

She reluctantly agreed to let me explain the issue to management, but wouldn’t tell me details. After speaking with management, they were incredibly pissed that they couldn’t fire her. However, they would take no action against Charlie because he was our number one salesperson. They eventually agreed that Alice and I would have meetings to work the situation out, with me being the intermediary between her and upper management. I was not happy about this, but that was that. So some evenings, Alice would leave the sales floor and have private meetings with me in a locked back office, trying to find a way forward. This was not professional, but I didn’t know that. And remember, I left the sales floor and locked myself in an office with a pretty woman who wasn’t selling anything but still kept her job.

Bad optics. Really bad. Bob, my new friend who I was hanging out with a lot, joked in front of Alice and myself that he hoped we were having a good time in the back office. He knew nothing about the sexual harassment allegations and I couldn’t tell him. I just turned to him and replied, “never say that again.”

I lost a friend that day. It hurt.

It was Charlie’s flirting with her that she objected to. She found him repulsive. At this point, I knew Alice well enough that I pointed out that I had said similar things (a phenomenally stupid thing to say), but she explained that she knew I didn’t mean anything. Charlie, in her eyes, was a creep.

In reality, Charlie was gay and had no interest in Alice, but he still liked to joke around. Of course, that in no way excused his behavior any more than I had an excuse for my behavior. Alice didn’t know Charlie was gay, but as a devout, conservative Christian, it certainly wouldn’t have made the situation better.

Eventually, Alice left the company (I don’t know the circumstances), and I learned a hard lesson about my personal behavior and what is and is not appropriate in the work place. I also began to get an understanding of how horribly women are often treated and realized that, even if she liked me, I had a hand in that treatment. It’s not a fun lesson to learn about oneself, but the most painful lessons are often the best.

My flirting played a role in my landing that job, and now it played a huge role in several people being hurt.


I started going back to college to take COBOL classes and after six months, leveraged that knowledge and my limited experience to get a full-time job at an insurance company. At the time, it was the best paying job in my life. I was a finally a professional software developer.

My first programming job is still my “best” worst job because it was the platform that launched my career, but it was a nightmare. Good people, bad people, and cronyism galore. And decades later, I still feel bad about my role in the mess.

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