"Open to Work"

Like over 800,000 people in the tech industry, I find myself between roles. This is new ground to me because my last role was an executive one, and because I hadn't even been in the "job market" or decades, because I was running my own company. What I've come to learn so far is that the process seems pretty mucked up.

This is not a letter to you to complain. It's a bunch of observations.

Matchmaking is Quite Broken

Imagine two piles. On the left are "work that needs doing." On the right are "people who can do the work." There's nothing more obvious and simple on the surface. Matchmaking between these two piles is broken for some reasons. I have thoughts.

But first, let me tell you about an experience I had in a little diner in Lewiston, Maine, if you'll indulge me in a story.

I sat at the counter of a busy Maine diner slinging breakfast to a crowd of mostly locals, it seemed. One guy a few seats away from me did roof work. I know this because over the course of my meal, maybe eight different people interrupted him to ask him to check out a job they had in mind for him.

I couldn't ignore any of this, so I asked, "I don't want to interrupt, but you sure are getting a lot of business just sitting here at the counter. You don't advertise or anything, do you?"

"Nope," he said, pushing some eggs into his mouth and chewing for a little. "I come here for breakfast and lunch every single day they're open. And every day, someone asks me if I can look at a job. Easy as that."

Work Needs Doing

Recruiter types will say that without their AI-driven application systems, they'd be flooded with CVs/résumés. I've seen it. We'd put up a job req and then 1000 people would apply within the first fifteen minutes.

And I know (and advocate) for "hire slowly, fire fast." It's really risky to put someone in that isn't a skill fit, or a cultural fit, and so on. You can't just slam people into a role without some tire kicking and chat.

But does anyone feel like the system works as designed right now?

I keep going back to the two piles: work that needs doing, people that need work. One part of entrepreneurship that seems to resonate with this moment is the whole "disaggregating the middle man" part.

Think about ride sharing apps. Aeons ago, I was in San Francisco, and I couldn't hail a cab to save myself. Finally, some nice soul told me there was an app to request cabs. And even that was annoying. Is there any wonder that Uber came along to match the need of "person needs a ride" with "person who is willing to drive you somewhere?" I think not.

Yes, there are jobbing apps out there. Sites like Fiverr and Indeed and I'm even on one for executives to do short stints (though so far, the jobs there are often quite intense).

Should there be an easier way?

I don't know. It's something I'm musing over while I continue to refuse to put on the "green ring of sorrow." I'm open to work. So are millions of talented people. And there's work that needs doing.

What's in the way?

Chris...