What career opportunity have YOU passed on?

A Quora user asked, “What were your career alternatives to the one you have today?” I couldn’t resist the opportunity to go back through my (really) old resumes and reminisce a bit. What job or career have you declined in favor of your current path?

I’m grateful to have had an awful lot of job opportunities throughout my life. At the same time I suffered a great deal of wanderlust until around my early 30s which means I’ve had quite a few jobs. I’ll get to the careers in a moment. First I want to start with all the jobs I’ve held for actual pay/wage/salary, versus things I’ve just dabbled in as a hobby, because frankly I don’t think I’ve ever put the complete list down on paper. Feel free to jump to the bottom if you’re only interested in the career alternative to what I do today (for the latest on my career visit me on LinkedIn).

  • Farmer on one small farm in NH; collected eggs and gourds, milked cows, maintained tractors and all the tools, fed and cleaned all the animals, also where I first learned how to shoot.
  • Horse Groomer on another small farm in NH; got to ride and train as well although anyone who has done so will tell you the horses train you as much as you train them!
  • Printer Technician for big office printers and plotters; I once got to repair a laser engraving unit, the one fun/cool standout in a long list of maybe 1,000 office printers maintained or repaired.
  • Retail cashier. More than once.
  • Lineman for cable TV and Internet, not powerline.
  • Truck unloader in a Wal-Mart warehouse, never a loader though!
  • Administrator for the State of MA Board of Registration in Medicine. It’s true, the State at one time granted me the authority to sign off on whether candidates had fulfilled all regulatory requirements needed to become a licensed medical professional (specifically only dealt with MD licensing, not RNs, Dentists, etc).
  • Receptionist. More than once.
  • Graphic Designer, making business cards, logos, and print ads for area small businesses before the Internet started taking off, then I switched to…
  • Web Designer / Developer, helped get a lot of small companies take their first steps onto the World Wide Web, switched from print ads to banner ads (yes, I was one of those people… sorry!), and moved a bunch in-house systems to the web / Software-as-a-Service (SaaS) before that became “a thing”. I also won a bid to get a mid-size power distribution company on the Internet, so that was pretty cool.
  • Designer / Engineer of a small A/V company focusing on security systems. If your favorite bar or other hot spot in southern Mass or Rhode Island had cameras, keycards on the office doors, alarm systems, that might have been yours truly “back in the day”.
  • Partner in a small tech consultancy, quite literally doing full transformations of getting companies from paper-based processes to computer-based ones back before “digital transformation” that was “a thing”.
  • “Entrepreneur” fits for the above 4 roles. Since I was an owner-operator or partner, I also had to learn hard and fast how to outsource accounting, legal, administrative, and other functions so I could focus on getting new clients (sales), design, development, engineering, support, you name it.
  • Computer Technician, back then we were building desktops and servers from parts because it allowed much easier and cheaper customization for our clients than buying through companies such as Dell, Compaq, HP, etc. Oh MS-DOS, Windows for Workgroups, Novell… those were the days!
  • Project Manager & Technician with a smart home automation firm waaay back before SONOS, Alexa, Nest, and all this “smart home” stuff went mainstream.
  • Accountant, specifically a Jr Accountant, where I first got hands-on with business financials and bookkeeping, general ledgers, P&Ls, accounts payable & receivable, budgeting, cash flow, reconciliation, and of course all about depreciation & amortization — this is the job that really launched my longer-term career in high-tech, as it would combine with my technical experience to form a personal philosophy on delivering business value through IT and leading with TCO/ROI in my budget plans, as opposed to operating IT as a cost-center which was the leading IT/Ops mentality at the time.
  • …and then there is the laundry list of roles in the IT industry since that last one. Check out my LinkedIn profile if you’re interested in all the IT-related roles through the years.

OK, might have missed a few but let’s get back to the original question which was about careers not jobs. Given the above list I can confidently say that I’ve had a few of them! I’ve been a laborer, worked in operations, been a designer and programmer, done a bunch of technician jobs, owned or partnered in several companies – thus why I call myself “Wearer of One-Thousand Hats!”

What about that career alternative I left out?

In the Fall of 2003 I had the opportunity to go to the National Defense University at Fort McNair in Washington, D.C. to participate in cyber war games with a group of my peers. Little did I know that what I thought was just a field trip was actually a candidate selection process. Long story short, I won the games and was offered an entry-level role with a three-letter agency. While the career alternative of cyber defense for the United States of America was pretty compelling, alas, I was more interested in starting a broader “generalist IT” & IT Management career so I ultimately declined.

I wouldn’t change a thing!

Original answer at Quora.com: What were your career alternatives to the one you have today?

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