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?

Your personal growth philosophy


What is a personal growth philosophy? It’s a set of core principles that you turn into habit which guide your physical, mental, and financial growth. I won’t pretend to be able to help you make the leap to your own personal growth philosophy, but I can share what I’ve come to follow over the years in hopes it can get you started in the right direction.

Compound interest is the greatest force in the universe. What does this mean besides being an overused quote? Small steps add up! While some of the rules below may seem out of reach today, understand you can get there by starting small and sticking with it. No matter what your thoughts are on my own personal growth philosophy, I urge you to create a your own so that, whether you dive in head-first or you start small and work up to step by step, you will ultimately lead yourself to success.

  • Get to a healthy weight and body composition (muscle vs fat) for your height and then eat to maintain. You don’t have to look like Scooby, but your body is the only one you have in this life and investing in your physical health has well-researched and proven positive effects on your happiness, personal and business relationships, life span, and more.
  • As long as you are physically able to do so, lift weights or run 3-or-more times per week for at least 30 minutes. Again, check out Scooby above if you’ve never been “into that stuff”. If I were 20 again I’d lift 7 days a week as an over-investment in this area – the benefits are that powerful.
  • As long as you are physically able to do so, sit up straight, shoulders back. See any older folks at work or in your family who are permanently hunched over? You’ll thank me later. Search for “how to sit up straight” or “proper posture” online for images, videos, etc.
  • Provided you can do so without foregoing the basic needs of food, water, clothing, and shelter:
    • Chop 10% of all income right off the top and put it into a 401k with low fees. Plan to leave it alone until retirement (whether that’s 30, 40, 50, 65, whatever, just leave it alone). Remember to use the 10% rule – so as your income grows your investment grows.
    • Chop another 10% of all income right off the top and throw it into a diversified investment portfolio. Simple approaches available right now are available through companies like Wealthfront or Betterment – just set up auto-deposits and take advantage of their expertise and algorithms. And remember the 10% rule again. As this fund grows consider shifting some of the gains off to commercial “investment-grade” real estate: rental properties, a RV park, a parking lot, a strip mall, etc. and really putting the money to work in other ways.
    • Keep an “emergency fund” that will cover the basic needs for 6 months. Don’t touch it unless absolutely necessary (unemployment, illness, etc), and then replenish it as soon as you’re able. If and when the costs for basic needs grow, the emergency fund should grow to always be able to cover 6 months worth of time.
  • As a core principle, avoid debt. Get a great “rewards” credit card like Chase Amazon (if you use Amazon a lot) or one of the airline cards (if you fly a lot), but pay off the full balance each month. If you can’t, then unless you’re bootstrapping a startup you are overspending (and even then, you’re probably overspending).
  • Enjoy life and be social, but don’t drink your income. A case of wine for home is significantly cheaper than the same wine at a night out. In addition you can slowly build a wonderful collection of wines that are inexpensive today and will taste that much better in your 30s or 40s (and some will age longer), when drank with your future family and/or the good friends you make over the years ahead.
  • Read for 30 minutes a day or more – if you prefer to listen then consider Audible instead. Read books written by titans of industry and by prisoners of war. Learn from great philosophers across time. Specifically read either Seneca or Epictetus, or both: you don’t have to buy into Stoicism but their writings have been considered highly-applicable to the real world across centuries by some of the most accomplished humans through history and they are timeless works for good reason.
  • Simplify your food and clothing options. Figure out some standard healthful meals, ones that are inexpensive while still nutritious and that you can eat repeatedly throughout the week, and do so. Make a wardrobe and stick with it. Slacks with basic button-downs, jeans with t-shirts, the options largely depend on your personal and professional needs but whatever you do keep it basic. You’re doing this for three reasons:
    • Consistency in the cost of basic needs.
    • Frees up decision-making power, which you can now use on more important things. Greater decision-making capacity is an investment in your personal and professional future.
    • Reducing or eliminating these simple choices from your life means less stress. Less stress is an investment in both your mental and physical health.
  • Learn the art of goal setting and execution and apply it everywhere. See “How Google sets goals: OKRs – GV Library”.

In summary:

  • Take care of your body through nutrition and exercise.
  • Sit up straight!
  • Dedicate a portion of your income to each of a 401k, a diversified investment portfolio that can grow into larger investments in the future, and an emergency fund.
  • Avoid debt but don’t make the mistake of thinking it’s universally bad.
  • Don’t drink your income.
  • Read great non-fiction written across history.
  • Eliminate needless choice in the simple things.
  • Learn how to make goals and execute on your plans.


Originally taken from my answer at Quora.com to the question: What are the best investments you’ve made?

The time I was asked to resign

It was the Spring of 2007. I wanted to move to Oregon for personal reasons. My employer at the time asked me to come up with a 12-month plan for them to continue operations in the event it took a while to find my replacement. We set my last date of employment, at which point I’d be laid off from the company and given a severance package.

As a normal part of my approach to IT I had already:

  • Documented all of our infrastructure, applications, and processes (whether manual or automated)
  • Automated a lot of our processes
  • Managed all of our vendor agreements
  • Tagged and cataloged our physical and logical assets
  • Created an emergency response plan in case of my sudden illness, absence, or death and sent a digital copy and hardcopy to our primary services vendor

I spent a week building an index for all of that information and re-negotiating some services agreements. I also negotiated a couple of vendor proposals for monthly services contracts for IT maintenance and outsourced technical support. I bundled everything together into a digital archive and printed a hard copy organized in a 4″ D-ring binder.

But… there was a problem.

OK, two problems.

First, I really loved this place and the people. Second, frankly, I wasn’t having any luck finding a new job out in Oregon. I had to come up with a new exit strategy.

On the last day, my boss called me in to formalize the layoff. I said I have a better idea – instead of a layoff that involves paperwork, severance pay, unemployment and so on, how about I resign and I contract with you on a monthly retainer to perform a set of services and provide X deliverables on Y schedule? This was a win-win: I’d get to move across the country and keep a steady income, they’d get my expertise and experience until a replacement could be found. We spent the afternoon and went into the early evening working out the deliverables and schedule, the financials, the contract and getting it signed by legal, and otherwise finalizing everything.

Finally, my boss says with a smile, “So it’s almost 7 pm. I’m beat. Are you going to resign or what?”

I handed my boss an envelope and said, “Yup, here you go, I’m officially resigning.”

“Good. Have a safe trip and call me Tuesday morning once you’re settled in and back to work.”

“You got it, boss.”

“I’m not your boss now. I’m your customer!”

“Not until Tuesday, you aren’t!”




For those wondering, the envelope contained two letters. One was a short, signed statement of resignation. The other was a personal note to say thanks and express my gratitude for having such a great manager and mentor.

I wound up on retainer for nearly a year. When we finally found my replacement, my boss joked “I can’t believe it took so long to get rid of you!” I flew back for a day to officially say goodbye to everyone, closed out that chapter of my life, and moved on to the next one…