This story still makes me laugh... and haunts me to this day. Is a boundary still a boundary if only one person asserts it? Or is it rebellion?

We’ve all been there. You dust off the old resume and break out in a cold sweat. You write what you think you’re supposed to. Two days or minutes later, the rejection comes. Or your boss tells you you haven’t demonstrated the skills yet. Not because you’re underqualified. Because you’re too specific and you’re expecting people to see the same depth behind the words as you do.

“Everything is broken and I hate it here.” Have you ever worked at one of those places where the work-arounds become the job? 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.

Let's get one thing straight: It's perfectly fine for your company to reimburse people for having a life. But if there's no business purpose or tax-preferred program for it (like an HRA, commuter benefit, or 401k), it has to be taxed as income. 

Did you know: Payroll doesn’t update tax settings automatically when someone moves. If you live somewhere where it’s common to commute across state lines, having different settings for where someone lives and works seems natural.

Somewhere between two weeks and thirty years, it has to become something else. 

Most teams treat FLSA salary exemptions as a payroll hack. But you need to do more than pay someone a flat rate for them to be exempt from overtime.

Parental leave combines the most complicated parts of HR into one policy: protected classes, disability, paid time off and sick time, obscure payroll esoterica, employees who are "active" but not "working" (and sometimes don't come back when you expect), insurance (policy details, deductions, and a qualifying event), onboarding and offboarding (maybe more than once per person), a bajillionty federal, state, and local laws, many of which conflict

People often confuse their job being 𝗽𝗿𝗼𝘁𝗲𝗰𝘁𝗲𝗱 (by FMLA, etc.) with getting 𝗽𝗮𝗶𝗱. It's a common mistake. I'm sorry. I really am. I know you're going through a lot. I hate delivering this message when it's already too late. 

It feels “leaderful” to manage policies, approve exceptions, or update payroll. That’s how power shows up for managers at big companies. But when founders take on those tasks, they lose sight of the strategic decisions that compound long-term.

Just like us, dogs align themselves with power. Oscar intuitively knows who the pack follows. Once he knows who’s the boss, he tries to win them over just like everyone else does. 

I forgot. I’d asked the new office manager to grab “breakfast” for the VIP meeting. I forgot “breakfast” was code for something different around here.

People Ops doesn’t have to be in-house. It doesn’t have to be full time. It doesn’t even have to “feel” like HR. But it does have to be done right.

Everywhere I went, I saw the same thing: Employees didn’t understand what they signed up for. Brokers didn’t really understand either. HR didn’t want to touch it. Claims were denied. People thought their plans sucked.

Termination isn't just a button in your HRIS. It's a tightly regulated event. It's the kind of process where everyone is watching. That’s why HR and managers feel so much pressure to keep it confidential. But too much confidentiality means the people responsible for execution don’t have enough time to get it right. 

If you're thinking, "But wait, that sounds like my company..."  That's the point.  These situations come up in all kinds of companies. They're as common as meetings that could have been emails. 

I don't know who needs to hear this, but Qualifying Life Events (QLEs) aren't written in stone.

Putting words to those operating principles won’t just help someone ramp faster. It gives your whole team a shared language to spot and fix misalignments.

Ops drag isn’t obvious at first, but it compounds quickly. Fortunately, small systems create big leverage. And a few smart fixes now can save you from spending your days scrambling as you grow.

Meanwhile, mistrust over the final paycheck was just one in a list of disagreements leading to a quickly deteriorating relationship