A few months ago I went to a local cafe in my smallish town, to air out my head.

The WiFi wasn’t working for me so I got to chatting with the person behind the counter to see if they could help me troubleshoot it. They proved non-technical, so I walked them through identifying which box behind the counter was the router, if it had a power button and which wire was the power supply so they could reset it for me. It didn’t work, I resigned myself.

There was a gent there having a coffee who made technical noises at me, something a bit more esoteric sounding than I am familiar with so I asked him if he knows networking and if he had any advice. It’s been a while since and I didn’t take notes, so my recollection is spotty, but he said something about packet sniffing and WireGuard which perked up my cybersec nerd ears so I asked him about himself and his work.

He disclosed that he runs a cybersecurity company locally, has a “few guys” working with him, his wife used to be a teacher at a private school. He complimented me on my troubleshooting ability, said I had a rare talent for methodically working through a problem (I’m not a hot young thing, I strongly doubt he was hitting on me) and intimated that it’s hard to find people with that ability. “Technical skills and tools I can teach, but it’s hard to find what you have.”

Well, I thought, this sounds like an opportunity for me.

See, I’m in the middle of a protracted career switch, this guy sounds like he sees something in me that I know I’m good at and he’s in a field that I find interesting. Time to build some bridges.

I do the offer to help, he starts to backtrack, dropping that his company does offensive cybersecurity that skirts the edge of law (!) and that I wouldn’t be able to work with them because NDAs and he doesn’t want turnover in his staff etc etc. Now I’m puzzled. He’s going all hot and cold on me.

So I counter with “happy to help with non-NDA related items so you can get a feel for me” and mention that I’ve worked with sensitive, private information for 15+ years. He gives me his email, says he and “his guys” are at the cafe “all the time” and we leave it at that.

Wrote a nice “great to meet you” email and didn’t hear back. The name and email he gave me don’t get any hits in public searches. The name is generic, WASP, and used to belong to a dead Canadian politician. The domain name of the email is a private domain with a blank home page and a “Registration Private, Domains by Proxy LLC”. Cool, cool, understandable.

But why not write back if you’re enthused about what I can do? Why go hot and cold?

Is this something peculiar to infosec guys in their late 40s, early 50s – they’re keen on talent they spot and they feel the need to talk about their work and how it makes them feel important, doing cool spy stuff in the background, being all clandestine and shit? Because I can completely understand that.

What I don’t get is expressing and interest in another professional, valuing something that person can bring to your organisation and then not following up on mutually expressed interest.

What are your stories of missed connections and what might have been?