So your company’s In-N-Out reimbursement policy is a taxable benefit. But how do you tax a burger that's already in your belly? In payroll, this problem is solved with what’s called an “in-and-out.”

Employer health plans tend to be pretty strong. Strong coverage costs a lot. You probably just didn’t notice when your employer was paying for part of it. Now that you’re on your own, you can probably find a Marketplace plan for cheaper. Definitely check. But how much progress have you made toward your deductible so far?

Your fate lies behind these walls of text. This, my friends, is what it’s like to choose your health insurance. And your choices are hidden in a page that’s black with small print, written in a language you don’t understand, and littered with numbers that frighten you. So let’s demystify your SBC (summary of benefits and coverage) so you can make good decisions.

If your company covers most or all of dependents’ premiums, there’s no downside to adding your spouse to your plan. If both partners are in that position, why not both add each other to the other’s plan? You can see ALL the doctors and just pay whichever bills less, right? It doesn’t work that way.

COBRA isn’t real, like Santa Claus and the Tooth Fairy. I’m not saying that companies don’t have to follow the law. I’m just saying that there isn’t a basket of COBRA snakes in Washington, DC administering your health insurance like the IRS administers taxes.

The metal tiers are more about risk tolerance than coverage: Lower tier = pay less monthly, but pay more when you go to the doctor Higher tier = pay more monthly, but pay less when you go to the doctor

Life and AD&D is one of the last benefits that small businesses and startups add to their offerings. It’s a real bummer to talk about. And unlike short-term disability, the people who need it don’t complain if you don’t have it. But here are some reasons you should care about life and AD&D insurance.

A health savings account (HSA) is an interest-bearing bank account where you can put pre-tax dollars in and use them for healthcare costs. But to be eligible to contribute to an HSA, you need a special high-deductible, high-premium health (HDHP) health plan.

I’m talking about the small business where an employee is on their spouse’s insurance or a Marketplace plan and the company just reimburses them for all or part of the premium like a regular business expense. You're not supposed to do that.

A non-birth parent who was born in Argentina, had French citizenship, but was on a work visa in the UK sponsored by a US-based company.

The One Big Beautiful Bill Act (OBBBA) increased your health insurance premiums in two meaningful ways: It cut pandemic-era premium tax credits (which help the working poor get healthcare) and it cut funding for Medicaid (which pays for healthcare for the very poor).

White collar work is also more likely to lead to burn-out and mental health disability, which leads to longer and more expensive claims than many physical injuries. 

Let’s be real: Insurance isn’t there to protect you. It's is a financial product made to maximize shareholder value.

Did you know that your spouse needs to sign off if you designate anyone else as your life insurance beneficiary? Because if you croak, life insurance doesn’t want to get in the middle of your family drama. 

Since employer group plans need to offer the same coverage to everyone, employer-sponsored plans are sometimes the only way that people with serious or chronic health conditions can get any disability or life insurance at all. 

To state the obvious: When you mess with people’s rights, sh*t gets real. And there are IRL consequences when you get the balance wrong.

Most states have regulations that fall into a few easy categories: Do you protect 12 weeks of leave, even if the company isn’t covered by FMLA? Do you have a state-paid program?

Every law tells a story. Something happened to make the legislature need to put a law in writing. This labor poster from Georgia is no exception. And the story it tells is pretty grim.

Managing all of this takes time and brain power. You’re contacting the employee, looking up policy details, doing unconfident math, and trying to figure out payroll work-arounds. The lost productivity cancels out the amount you’re saving by relying on these outside subsidies. Meanwhile, the new parent thinks it’s all your fault and blames you for the terrible experience you’re putting them through.

I get that it’s expensive to pay someone not to work for several months, but there are strong business reasons why you should do it anyway.