How to tell if you're wasting your career at a crappy job

“Everything is broken and I hate it here.”

Have you ever worked at one of those places where the work-arounds become the job? 

It’s like your car in college, were the radio didn’t work if the headlights were on and the passenger seat was stuck fully reclined. 

Except it's not just the drive to class anymore, it's where you spend eight (probably more) hours per day. 

You weren’t hired to be the PTO police, but you spend two hours every other Tuesday chasing down managers to approve time off because no one can remember where the "Approve" button is.

You have a spreadsheet called “The Beast” to calculate all the edge cases that your payroll software doesn’t handle.

Or whatever the equivalent workflows are in your role.

Every time something breaks, you build a workaround. Then another. And pretty soon, the workarounds are the job.

Your playbook has more pages than Wikipedia. It's supposed to help, but there's so much there that you can't find what you need anymore. 

Onboarding someone new isn’t about learning your product or roadmap. It’s about learning where the landmines are, how to use The Beast and navigate the playbook.

New hires don’t learn the craft. They learn how to chase signatures, read Excel formulas, and hope they didn’t miss a step that lives in someone’s head. 

People who can’t navigate the dysfunction are asked to leave (or show themselves the door). 

“It wasn’t a good fit.” Sayonara suckah!

But this pattern isn’t a people problem. It’s a system design failure.

That feeling of “everything’s broken and I hate it here” comes from building scaffolding around dysfunction rather than digging down to the root issue. 

Implementing a different PTO tracker (for example) may seem like an unnecessary waste of resources until you realize that all the 3-minute searches for the "Approve" button and 2-hour PTO Police shifts add up to 800 person-hours per year. 

Or you’re paying out an average of 6 “unused” PTO days that were probably used per exit. But who can tell?

And then you realize that this kind of inefficiency is happening in everything else, too.

The “good jobs” are the ones that don't just patch the surface issues, but fix problems from the ground up. Those are the companies where people stay, and everyone contributes to growth.

Is managing your People processes taking so much time that every day feels like running on a treadmill?

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