Living Out Loud

Freelancing in the Old Days

A technician's hands working on a laptop

When I bought my first computer in 1993, they cost about 50% more for an entry-level machine than they cost now without adjusting for inflation. It was a lot of money. At the time, I was working two jobs through a temp agency, unloading trucks for Burger King during the day and working at a Westinghouse factory at night. Within a couple of years, I'd learned enough about DOS 6.22 and Windows 3.1 to be dangerous, and when Windows 95 came out, I decided to market myself as The Computer Buddy through the classified ads in the local newspaper to see if I could make a few bucks helping people get started on their own technology journey. I decided to charge twenty-five dollars an hour for the first hour and fifteen dollars for subsequent hours. I was willing to drive anywhere in the surrounding area.

Some of the first appointments were challenging, especially because I had little to no idea how this kind of enterprise was supposed to work. A family-run brick mason's business asked me to come install QuickBooks for them, which I did easily enough. Then they asked me to teach them how to use it. I knew nothing about accounting, business management, or brick masonry, but I gamely went to Barnes and Noble, bought a book on the program, stayed up all night reading it, and went back and gave it my best shot.

Back in those days, when people were just starting to get online, Walmart ran a special on 14.4 modems, complete with an AOL disk and a phone cord. On the box, it said, "Everything You Need to Get on the Internet." Someone bought one and called me to help them set it up. When I showed up, they handed me the box and looked at me expectantly. I asked them where their computer was, and they looked confused. They pointed at the box: "Everything you need to get on the Internet." They didn't own a computer.

I got a call from a lady who managed her family's sheetrock business. When I asked her what kind of computer she had, she didn't know. I asked her about the operating system. She didn't know that either. I went ahead and made an appointment anyway, and as it turned out, I developed a relationship with the family that lasted well over a decade. Long after I stopped doing any kind of side work, I was still making the drive to the next county to help her run her annual reports. She went through about three computers while I was helping her and went from not knowing how to save or open a file to mastering a specialty accounting program and using business-class tax software.

I had a few embarrassing moments. A local man contacted me to help train the staff at his synagogue on basic office skills. He sat in on the lessons and seemed interested in computers. Later, he called me and said that someone had pawned one at his shop and not picked it up. He wanted me to come to his home, in the oldest and wealthiest part of town, to help him use it better. I obliged, and when the night came, we were going over the system when the phone rang. He answered and began talking to his son, a medical student. His wife came in and began asking me questions about Internet speed.

"How come some sites load really quickly and others take forever?" she wanted to know. I explained to her that Netscape had a cache where it downloaded graphics and if you visited a page a second time, instead of downloading the images again, it would just read them from the disk. I went to demonstrate by opening a random file from the temporary Internet files, expecting to see a CNN logo or something like that. Instead, I found porn. Raunchy porn at that. Her husband was still on the phone, and his eyes were bugging out. Of course, she wanted to know how THAT got on their computer, and I assured her that it was definitely something left over from the previous owner. It was not, but there is a Bro Code, you know? When I went to settle up with the gentleman at the end of the appointment, I really expected a tip, but he was still too shaken up to appreciate me saving him, so I didn't get one.

I continued the business for about five years, doing everything from building custom computers to clearing viruses, setting up printers, tutoring a millionaire's six kids to setting up the first satellite-connected computer in the area. People thought nothing of calling me on a Saturday night in the middle of a movie to ask me random computer questions because I'd been to their house one time months before. Others would have a floppy drive fail sometime after I'd installed AOL for them and insist the problem was my fault because I was the last one who touched it. By this time, I'd started working professionally in IT support, making decent pay, and I decided that the hassle was no longer worth it. For a long time, I wouldn't even disclose to people what I did for a living for fear that they'd hit me up for free computer help.

These days, people tend to know a little more than they did back then because computers aren't just for hobbyists anymore. I don't mind having a conversation with someone who has a problem, but I definitely don't offer to drop by their house to look at it. That's reserved for family, most recently my grandson who forgot the pin to his iPad. I learned a lot about customer service in the old days, lessons that still profit me today. The money I earned came in handy, even if it looks pitiful by today's standards. Given the chance, I'd probably do it again.

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