And speaking of equal opportunity, pirates welcomed escaped sailors from marginalized identities, giving them opportunities for advancement that they never would have had in the navy or merchant marines. Lady-pirates could even become captains, like Ching Shih, who led a fleet of 1,200 ships and a workforce the size of Morgan Stanley. You could call it D-E-Aye-aye-matey.

The game begins. You have one calendar year to spend the money. The company has a year to collect it back from you. If you both follow the plan, you’ll both walk away scot-free, with the taxes you didn’t spend still in your pocket.

Maybe you’ve had this experience: You’re in crisis. You can’t work, so you call in. A well-meaning person you hardly know sends you information about the Employee Assistance Program (EAP). You look into what it covers and wonder how this could possibly help. The minimum CYA measure to guard against the wild things that people in crisis do.

What if, instead of inflating wages with cash, the company offered to pay for something even more valuable than cash? The health of workers and their families. 

Did you know that if your company has more than 50 employees (100 in CA, CO, NY, and VT), the employer sees all the prescriptions people take?  They don’t know who, but if there are fewer than 100 people it’s pretty easy to guess who needed a prescription to control their excessive underarm sweating. Or who's on Lithium.

The many layers of humans and technology that go into insurance deductions can make it hard to track down where the problem is. And because of the old school systems insurance companies still use, it can be like traveling back in time. 

For years, health insurance costs have already been increasing at more than double the rate of inflation. But even factoring in that trend, next year’s numbers seem like a prank. 

Both of these tools are available to companies for less than a dollar per employee per month. They can transform someone’s exit from cold paperwork to meaningful support.  If it rips your heart out to see what’s happening in the job market, Callings and Kept are two things you can offer right now that make a real difference.

You’re probably sleeping on the biggest company perk just because you think it isn’t free. You may think you’re maximizing the company perks, but if you aren’t maxing out your 401(k), you’re playing like an amateur. 

Insurance premiums have been increasing at more than double the rate of inflation for the past 3 years. In 2026, employer group plans are expected to increase nearly 8%. 

Employers have discretion about what's covered in their HRA plan, which is what makes them so useful. The company decides the annual limit, as well as specifications like whether to cover deductible expenses, post-deductible expenses, and/or over-the-counter expenses and services.

A PEO is an insurance broker, a guardrail, and a payroll provider. But it’s not a brain. Some people need a PEO. Some need a person. Most don’t know which they are.

What we’re really seeing is misaligned incentives disguised as authority. They have no reason to follow through, just respond. We wouldn’t put up with this in any other business service.

Even the fancy ben admin tools. Somewhere behind the curtain, someone is downloading a form and forwarding it to a carrier. Often using unsecured email.

"Is this because I said I wasn't pregnant?" He scratched his beard. He was the first non-birth parent to use the policy. And it wasn’t working as planned. And yes, his claim was denied because he wasn't pregnant.

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.

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

These problems don’t show up right away. They lie in wait until someone balances the books and notices thousands of dollars missing. 

A man claiming to represent the New York Workers' Comp Board had shown up at my client's home in upstate New York, demanding proof of coverage. It would have been laughable, except that it was real.

Running the People side of your business takes a lot of work, but hiring a PEO comes with trade-offs that you may regret later.