know — that’s exactly how I jumped into the side-hustle game many years ago.
Many years ago, in the early days of my professional career, I was a U.S. Air Force computer systems officer. I was stationed at Cheyenne Mountain in Colorado Springs, Colorado, and was assigned to an office of about ten other officers and civilians who were responsible for writing software for the missile warning defense of the United States. Basically, our software received messages from sensor sites all around the world that detected missile launches and then used some head-spinning math to figure out if this alert was just a test launch by “the other side” or if (cue the ominous music) they had just started World War III.
A pretty cool-sounding job, right? This was in the early and mid-’80s, at the height of the Cold War, and you could say that business was good for the missile launch detection mission and expanding the functionality of our software to support new and upgraded sensor sites. Only one problem: Our software was written in an ancient programming language called JOVIAL that was already obsolete and was only used in certain military-oriented applications and systems. Well, make that two problems: Our JOVIAL-written software ran on antiquated UNIVAC mainframe computers from the ’60s and ’70s. (In fact, our UNIVAC was so out of date that the university where I went to school — Arizona State — had retired its UNIVAC two years earlier because it had become too obsolete for academia!)
The early and mid-’80s were also when so-called “microcomputers” — what we know as personal computers today — were hitting the market and quickly becoming wildly popular, not only for home use but also in business. Wouldn’t it be great to get some experience in this hot new area of computer technology, even if the hardware and software of my full-time job was light-years behind what was coming to market? I was almost certain that I wasn’t going to stay in the Air Force past the four years that I owed in exchange for my college scholarship, and when I reentered the civilian world, I would be four years behind so many other people in the tech field.
I bought my first personal computer and started a little application development and computer training side business, aimed at small businesses and not-for-profits in Colorado Springs and in Arizona, where I had gone to college and lived before going on active duty. And of course, I crammed and crammed and crammed, learning as much as I could about these new-fangled microcomputers and then-modern PC programming languages and software development frameworks.
Soon enough, I landed my first consulting project at a local tourism-oriented business. That first project was a doozy! I learned the hard way how packaged software development frameworks didn’t always work as advertised and were often full of bugs (as we refer to software problems in the programming trade). I had to program a lot of workarounds into the customer’s system to prevent the applications from blowing up, or to help them get back up and running if their application suddenly and abruptly terminated. I think I sized and priced the job at about 150 hours and wound up putting an extra 30 or 40 hours into the project that I didn’t bill for to handle all the complications.
But I learned a ton! And I learned even more on the next customer’s project, and the next one after that. Fast-forward to when I got ready to leave the Air Force and started looking for a job. Everything I learned during four years of doing software projects (and also some computer training) on the side — in other words, my first side hustle — really helped me get the perfect job and jump-start my civilian tech career.
Was I trying to make some extra money above and beyond my Air Force salary? Of course! Back in those days, junior officers didn’t make a whole lot of money. So, I was absolutely after money!
But even more than the additional income, my primary motivation was the knowledge and experience that I gained from my side-hustle consulting and software business. Could I have just bought a PC and taught myself modern programming skills and microcomputer administration without starting a side hustle? Sure. But my thinking at the time was — and still is, even with 40 years of hindsight — that if I didn’t force myself to spend all those hours behind a keyboard because I owed finished applications to my clients, I might not have had the motivation to do more than a perfunctory amount of self-learning. And I almost certainly wouldn’t have run into all the unforeseen software hiccups for which I had to find workarounds, which served me well even in my full-time Air Force job, not to mention when I became a software product developer after leaving the Air Force.
Jumping onto a different career track
Maybe you’ve been in your career field for 10 or even 20 years, but you’re at the point where going to work every day is starting to be harder and harder. True, you’re making decent money. But the days drag, and you can’t wait until the workday is over.
Or maybe you wound up with the job of your dreams, but those dreams turned out to be more of a fantasy. Sure, you knew about the crushing hours and the wearying travel, but you were actually looking forward to the fast-track lifestyle on the road toward that big-time paycheck. Now, after only a year or two, you’re asking yourself, “What in the world was I thinking?”
You’re not quite ready to hit the ejection seat without a new job. You could start interviewing for jobs with a better work–life balance. But one message that has come through loud and clear every time your boss tells you that you need to work all weekend and miss a family event: You really want to be your own boss.
Or, if something miraculously happens for the better in the realm of your full-time job — say, you wind up interviewing with and then accepting a new job in your current career with better hours and a much lower stress level — you can either keep your side hustle going or slowly unwind and stop doing your side gig (see Chapter 14).
Profiting from a hobby or passion
Todd started collecting baseball and other sports cards when he was a kid and collected them all through high school. When he went away to college, he tossed all his cards — carefully, of course! — into the closet of his old room at his parents’ house. Fortunately, Todd’s mother didn’t throw out all his sports cards when he moved away, as many of Todd’s friends’ mothers did. Almost 20 years later, Todd rediscovered his old cards during a Thanksgiving visit to his parents’ house.
What did Todd do next? Sure, he began buying current cards for his personal collection at the local big-box retailers and also at hobby shops. But he also discovered something interesting: Some of his childhood cards were now worth a fair bit of money! He began reading blogs and listening to podcasts about the investment and speculation side of sports cards. He began bargain-hunting on social media, at swap meets and flea markets and estate sales, and anywhere that he might find cards for sale. If he found a good bargain, he would buy cards — sometimes