I've really enjoyed reading this thread. There are so many interesting stories.
I guess I'm a little outside the box. I've only seen someone else's signature on my paycheck for 5 of the 46 years since I finished school.
Right out of college I took over my parents' small-town hobby and craft shop (where I'd started out sweeping floors and washing windows in my elementary school years) and I began buying them out. That formed the basis of their retirement fund, as they couldn't have gotten nearly as much for the shop had they tried to sell it in the marketplace.
Over the years my wife and I added and deleted departments as the markets changed, opened a mail-order sales channel, a second store in another city, and in 1995 built a site on this new "world wide web" thing and began taking web orders.
It was all a struggle, done on a shoestring. We couldn't afford order-processing software that worked well enough, so I taught myself to write my own. When we needed to track inventory in two stores we couldn't afford the commercial software for that, so I wrote my own POS/inventory system. Same with the web site. I hand-coded HTML in a text editor.
I'm proud of what we accomplished, but those years were a roller-coaster of pain and triumph as, after about 1980, the hobby industry inexorably shrank.
As the web-based channel grew it made sense to shut down the brick-and-mortar stores. Those years of web-only sales were the most efficient, profitable, and fun of my decades in retail. But 30+ years is a long time to do anything, and I got the itch to do something different. My wife took control of the web business while I started exploring other options.
It was now the height of the housing boom, so I became a real estate broker for a few years. I did OK, but when I saw the craziness of the lenders and the buyers (No loan was too risky, no price was too high) I knew it couldn't go on. I found myself trying to talk buyers out of bidding on overpriced properties that they couldn't afford to pay off, to no avail. So I decided to get out. That was just before the bubble burst. I left with a clear conscience and a huge sigh of relief.
Since I'd enjoyed developing the business?s computer applications so much, I started taking classes to fill in the gaps in my knowledge and get some official-type credentials. My first job was a 6-month contract obtained through a recruiting firm. After that I spent the next 18 months with a large travel/hospitality company, managing Linux servers and websites and co-developing an email drip marketing application. That was the worst job I ever had. Unpleasant boss, miserable daily commute, high pressure, and the environment was a windowless room with black walls and workstations lined up on a counter. I couldn't find another employer fast enough.
The next job was much better, a stint managing customer acquisition software for a small marketing company. That was my first experience with a virtual company. There were up to 20 of us spread across the US. I only ever met a handful of my colleagues in person yet we formed some great "virtual" friendships. I learned a lot, got to craft inventive solutions to lots of problems, and loved working from home.
Then I opened my consulting business, where for the last 8 years I've been helping companies configure and maintain their customer acquisition software, and training their people to use it. I've also been doing some technical writing, UAT (User acceptance testing), and employee and customer training for a SASS startup in the customer-acquisition space.
This is by far the best job I've ever had. Every day brings a new challenge and new people. I get to formulate creative solutions. I can work from anywhere (I was beach-side yesterday), and my hours are reasonably flexible. I'm not "always on-call".
I don't think much about retiring. I'm healthy and enjoy my work too much to want to quit completely. But I have been careful to limit my at-work time. Work is fun, but it?s far from the only fun in my life.
