Dear Grade 8 Guidance Counsellor

Dear Grade 8 Guidance Counsellor,

First off, your 1970’s career punch card computer program was right. I should have been a tug boat pilot. In retrospect, it’s the job that would have optimized my strong needs to be outside, to be moving and to be on the water. But just because your computer was right doesn’t mean you were.

You said lots of things about maximizing potential, but you never once mentioned the value of portability. Lots of people I know have trades, professions and skills that let them pick up and move from place to place, finding work as they go. But my career is a big city kinda thing that doesn’t lend itself to foreign seaports. You knew I liked sailing. You should have emphasized the importance of selecting a skill that I could capitalize on while sailing.

Here, on this rally, we have with us an awesome array of talents. We have rally members that are electricians, diesel mechanics, outboard mechanics, nurses, certified captains, diving instructors, security experts, aerospace engineers and canvas workers and other skills I’ve momentarily forgotten. And then we have me:

Me: Hi, I’m Thom. I’m a a leader of product innovation for emerging payment and security technologies.

Another human: A whose-a-what-again??

Me: Umm, I may be able to help you with a computer problem…or build you a website?

Other Human: Oh, good to know, I guess. Let’s talk about [insert far more pragmatic topic here].

It’s excellent to have so many great skills with us on the rally. But it really makes me feel like I should have picked something less niche and something more re-package-able a long time ago. While I’m getting better at some of the many skills that a good sailor has in their ditty bag – (Sailor talk for “duffle bag”. Yup, we’ve got our own word for that too!) – I’m years away from being able to charge money for any of them.

It’s certainly not an issue in the short term, and I’m confident in my ability to learn new things and spin old skills in new directions as needed. But as we consider our long-range future, I think of how many of the people we know could simply hang a shingle in any port and pick up work. My shingle would read something like “Stymied over which product strategy is best for your new payment innovation???” And really, no one needs to read that shingle.

So why am I sharing this with you? I dunno. It’s not to evoke sympathy. Please don’t tell me not to worry, or that I’m smart and will think of something. I’m smart enough to know that I’m getting dumber by the day. That’s okay, With any luck, I’m also getting wise enough to know that it’s time to trade in being clever for being something else. The question is, what?


  1. I thought computer skills is a portable job. As long as you have good internet you should be able to work from anywhere? Don’t forget you’ve got mad pizza-making skills too!


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