“The web looks different today.”
That was a cancellation reason from an agency customer recently. At first I thought… what does that even mean?
But the more I considered it, the more it’s been stuck in my head ever since.
For years, our target buyer at PMPro was a developer helping someone without tech skills build a membership site. At least that’s what the minimal customer research told us. A couple surveys and interviews with the people that said yes.
The person with the idea needed the person with the skills.
In 2025, we realized how much that had changed. Our buyer became the person without tech skills, or with very low tech skills, building the site themselves.
The middle got cut.
I’m seeing this everywhere now. So many people in their 40s and 50s are on the job market. People who did everything right. Took strategic jumps in their 20s and 30s. Landed at product companies or agencies. Built the systems. Trained the teams. Became the institutional knowledge.
Then “AI happened” and products got acquired and the marketplace shifted right out from underneath them.
Here’s the pattern:
- PE or VC buys the company and things trickle along for 3 years, maybe 5.
- Finance someone decides it’s not turning out as planned.
- Time to trim.
- Who goes? The middle.
The people who built the successful systems. Because now, those systems mean more junior people can run things with a skeleton crew of senior folks at the top.
I say this not because I know much about career progression, interviewing, proving my value, being relevant in today’s job market. I’ve literally never had a career that was someone else’s to control.
I say it because it’s here. I see it.
And I think the best thing someone in their 40s who’s been interviewing for way too long can do is this: turn the discomfort of not having a job into the discomfort of starting a business.
Call it a side hustle so it doesn’t feel like a huge commitment… and just keep interviewing.
But start building something. It doesn’t have to be a digital or physical product. It can be a service business. It can be an association of peers with a shared interest.
You know more about how businesses actually run than most 20-somethings vibe coding their way to million-dollar valuations. You’ve watched systems work and fail. You’ve managed people. You’ve been the one holding things together when leadership had no idea what was happening on the ground.
How many times have you thought, “If they would just listen to us. We know what we’re doing!”
You do know what you’re doing. So listen to yourself.
Maybe this doesn’t have to turn into a gap on your resume. Maybe it turns into a whole heckuva lot more.
