It seems like every year or two, somebody asks me how to get my job. Given the way the last year or so has gone, I can’t believe anyone’s asking me that question, but it’s been coming back up again. I’ve made some mistakes in my career–obviously–but since I’m still in the field, I must have done a few things right too.
I guess it makes sense to trace my career and see what I would do differently.1984: Yes, it all started when I was 10. I’d wanted a computer for as long as I could remember, and that year, Mom and Dad finally bought one. I spent as much time messing with that old Commodore as I could. And when I wasn’t messing with that Commodore, I was reading about it. It was an obsession. It bordered on unhealthy. Or maybe it was unhealthy.
In high school, if you’d offered me a choice between a date with the best-looking girl in the school or a new Amiga 1200 or 3000, I might very well have taken the computer. Sure, I was interested in girls, but the computer wouldn’t break up with me, right?
I bring this up for one reason: If you’re wanting to get into the field for money, find something else to do. Go into sales or something. If you don’t absolutely love this stuff, you won’t last, so there’s no point in wasting your time.
1994: I started my career in sales. When polite company isn’t around, I say I whored myself out for a large consumer electronics chain. That might be a bit more accurate. In a way it was a good move. A lot of IT people my age started their careers the way I did. It’s better than fast food, at least in regards that IT recruiters use it as a scouting ground. Work there and do well, and it’s just a matter of time before recruiters will want to talk to you.
What I did right: I started filling in for the store’s technician, who frequently had problems showing up for work.
What I’d do differently: First, I’d find out who the best salesperson was, and really learn how to sell. I’ve worked with IT management people who couldn’t figure out how to make their computer play solitaire, but they know a little bit about selling, so their jobs are safe, even though they had no qualifications.
The other thing I’d do differently is to get A+ certification. It’s not strictly necessary to get a better job, but it opens more doors. A lot of jobs require A+ certification just because some idiot in HR (and yes, most of them are idiots) decided it’s a good idea.
1995: I caught a break because I knew both Macintosh and IBM hardware, I knew OS/2, and I had connections at the journalism school at the University of Missouri. A professor mentioned the job opening to me and handed me a phone number. After class I called the number. The guy on the other end asked me what I knew how to do. I told him, he told me he’d pay me $7 an hour, and asked when I could start.
It was supposed to be a temporary gig. But it turned out I knew how to do a lot more than just the grunt work that needed to be done, so they found money to keep me. And when I was about to graduate, they offered me a full-time job.
What I did right: I showed up for work, I did everything they asked me to do, and whenever somebody else was sick and they asked me to try to fill in, I filled in and actually managed to do a decent job.
What I’d do differently: It wasn’t a bad gig, until Yoko Ono came along. Actually she was from Pittsburgh and she was Scottish-American. But the relationship interfered with the job and the job interfered with the relationship. And when something went wrong with one, it messed up the other too. I’d have done well to learn how to separate the two. That’s a lot to ask of someone who’s 23. Now I’m 31 and don’t know how now either. Neither does my 40-year-old boss.
1998: I moved to St. Louis to take another job in IT. This was also the year I re-discovered God and religion. This was a dream job, working for my church. I took a demotion and a pay cut to do it. Of course I didn’t know until I’d already quit my other job that it was a demotion.
I’ll get off track if I talk about it much more than that, so let’s just talk about what went right and wrong.
What I did right: I racked up a lot of impressive statistics and I learned how to do everything they asked me to do. I usually wasn’t happy about it, but I always did as well or better than the person who replaced me. The guy I replaced was a legend and I don’t think anyone would have been able to replace him adequately.
What I did wrong: I shouldn’t have taken the demotion. Not at 23. If you’re married and have kids, I can see taking a demotion so you can work better hours to spend more time with your family. When you’re 23 and single, you can’t waste time climbing a ladder you already climbed once. A banker in Columbia offered me a job as a systems administrator when he found out I knew OS/2. I should have taken it and called St. Louis and told them I wasn’t coming.
This job really went downhill as another relationship was coming to an end too. No need to re-hash that.
I made one other mistake. I won’t elaborate on it. But if you see upper management doing something unethical, LEAVE.
2005: Mercenary time. My first contract was with a very large and very nearly bankrupt cable company. The work wasn’t nearly as interesting or challenging as my previous job, and my coworkers were at either extreme: Some were among the very best people I’d ever worked with, and some of them were just overgrown high school bullies. But it was work, and the pay was fair, which was nice after working for seven years at anywhere from $15,000-$20,000 less than I was worth. Making a double mortgage payment and still having more money left over at the end of the month than I’d had a year before was very nice.
What I did right: I came in, learned quickly, took things seriously, was very professional and very effective.
What I did wrong: I didn’t press in. I did what I was asked, and that was it. That’s what a hired gun does. And the result was I was treated like a hired gun. As soon as the money got tough, I was the first one out the door.
I had coworkers who didn’t want me to learn more about the system. Since they didn’t want to show me, I should have found another way to learn it. And I should have loosened up.
2006: I won’t tell you who I’m working for now, other than to say it’s someone you’ve definitely heard of.
This time, I made an effort to go to lunch with my coworkers. I didn’t do that at the cable company because I was trying to save money. I’d gone without enough money for a couple of months and was deathly afraid of having to do it again. I’m still a tightwad and everyone knows it, but I’m willing to spend $7 to bond with my coworkers once a week. The theory is it’s a lot harder to show the door to someone you like than to someone you barely know.
The other thing I did this time was to steal some responsibility. I volunteer for everything. Sometimes they end up giving it to someone else anyway. But I’m always willing. When people give me some of their old responsibilities, I take them, and I figure out how to do them faster and smarter. After about two months, now my boss is surprised when I do something his way.
My path isn’t the only path. There are two previous bosses I wouldn’t hesitate to work for again. One is a retired U.S. Marine. He went into the Marine Corps as a technician, fixing teletype machines. When teletypes became less important, he moved on to computers. When he retired, he kept on working for the military as a contractor.
Most of my coworkers today took a similar path. Some enjoyed very long careers as defense contractors after their military days came to an end.
That seems to me to be a good route to take if you don’t have a lot of connections. And the upside to the military approach is that you know your job won’t be outsourced to India. That’s a real danger and that danger is going to get a lot bigger before it gets any smaller.
The other previous boss has a degree in psychology. He started working with computers because he found them interesting. I don’t know how he got started in the field, but during the time I worked for him, he was the epitome of connections. He knew everybody, and whenever something goofy came up, he knew how to get in touch with them to get the answer. The result? He’s every bit as entrenched as a tenured professor would be. The difference is there’s no question as to whether that’s a good thing.
David Farquhar is a computer security professional, entrepreneur, and author. He started his career as a part-time computer technician in 1994, worked his way up to system administrator by 1997, and has specialized in vulnerability management since 2013. He invests in real estate on the side and his hobbies include O gauge trains, baseball cards, and retro computers and video games. A University of Missouri graduate, he holds CISSP and Security+ certifications. He lives in St. Louis with his family.