Gary first off, thank you for your service. I actually thought very seriously about joining the Air Force myself. I was 17 years old with a baby on the way, and it seemed like a solid option, but in the end I decided to work and go to college instead.

My first job was at Radio Shack when I was 16. I think I was making $3.65 an hour, which was like 30 cents an hour over minimum wage in 1988 - so I was a baller. LOL. After dropping out of college (I was bored learning Pascal), I got a job doing phone-based tech support. I have mentioned this in a few of my videos. At that time it was still possible to know pretty much everything about computer software. It was all still relatively straightforward, even before Windows 95 came along and complicated things.

When I was first hired, the company had maybe a dozen employees in tech support. They grew fast and started hiring new people left and right. Since I had done some presentations before and showed an aptitude for teaching, they tasked me with training the new hires. So for about a year I was teaching people how to help customers on the phones. That is where I really learned how to explain things clearly, and how to train people to figure things out for themselves. This is when they stamped "training manager" on my job description and expected me to work the same crazy hours with no overtime. Ha!

Of course once the company got bigger and I had developed all the training materials, they decided they no longer needed me. They promoted someone under me and told me "buh bye." After that I went through a temp agency and bounced around a bit. One assignment had me programming accelerometers and reading data from crash test machines. I had to plug the sensors into the computer and use Visual Basic to capture the data. That's when I really started learning how to use VB (version 4, if memory serves). That was fun work, but it was one of those jobs where they would hand me a list of tasks on Monday morning that was supposed to take all week. I would usually finish it by Monday afternoon, and then spend the rest of the week alone in a room playing solitaire.

Around that same time I moved into an apartment above a vacant retail space. A few months later a computer shop opened downstairs. I went down, introduced myself as the resident computer nerd, and ended up helping them out with all sorts of projects. I was not an employee, just doing side work with them. Eventually their business folded due to questionable management decisions by the owner, but it gave me the idea that I could do the same thing myself... only better.

So I started selling computers and related services out of my apartment. I would run ads in the newspaper, build custom systems, and I even started a fax newsletter that got pretty popular.

The big break that really gave me the confidence to go full-time was when a friend tipped me off that a local company was looking for an IT service contract. They did not want a full-time IT guy, but they wanted someone to handle problems as they came up. I put in a bid for something like a 100-hour contract for $3,000. Even then it was not a lot, but this was 1994 and it covered several months of my rent. In reality the company only needed me a few hours a week, fixing printers or helping someone log into the network. That contract gave me the financial cushion and flexibility to go out and find more business.

So I went full steam ahead with my computer business. I started hiring friends, and eventually had 12 employees. I moved into a "real" office.

A lot of times when I sold a company some computers, they would say things like "We hate QuickBooks, can you recommend some better software?" or "Who's going to teach us how to use all this?" That is how I drifted into building custom Access databases and training. At first it was on-site, but demand grew enough that I eventually set up my own training room.

But that is what really launched me into self-employment. It is tough, especially when you are young with a family to support. I always tried to keep six months of expenses in the bank, just in case. But I always preferred the idea that if I worked harder (and smarter), I could earn more and shape my own future... and never be reliant on working for "The Man."

And honestly, I do not think traditional jobs are all that secure either. Unless you are in a union or a government position, there's no such thing as job security (well, unless your government position is a political appointment, as we've seen recently). I have seen plenty of people get laid off after 15 or 20 years with nothing to show for it. That is why I have always believed there is no real job security unless you make it yourself.

Richard , Your last paragraph nails it.  Even Union and government employees are not immune, as government employees are finding out today.  In union construction, virtually everybody gets laid off sometime.  It is up to me to make sure I am not high on the lay-off list.

My career path has taken several turns and I never thought I would be a union employee.  I just looked for places pay well and provide the opportunity to learn something new while leveraging what I know to get in the door.

The responsibility of providing for the family made self employment daunting and I have earned enough to dissuade me from taking a stab at it.  Like Gary, I have much respect for those who do.