A few days ago, after a disappointing email and a very ill-advised lunch involving leftover Chinese food, I decided to go for a run.

Tuesday Triage

December 23, 2025

Hi there,

 

A few days ago, after a disappointing email and a very ill-advised lunch involving leftover Chinese food, I decided to go for a run.

 

I bundled up our smallest dog in his red winter coat and assumed that movement would solve everything, including his hatred of the cold. It did not. He hates walking in the cold and, it turns out, he hates running in the cold, too. So there I was, jogging backwards, very slowly, while gently encouraging what looked like a miniature dog Santa to run towards me, discovering once again that good intentions don’t guarantee good results.

 

Good intentions and desired outcomes don’t always line up when it comes to holiday gifts either.

 

A lot of people like to give money—sometimes to family, sometimes to employees. And many people assume those gifts aren’t taxable to the person receiving them.

 

If you’ve been listening for a while, this might sound familiar. You may remember Episode 46, How to Give Money Without Triggering Gift Tax. That episode was about gifts to family members.

Today’s episode is different.

 

Today, I’m talking about what happens when cash gifts are given in the context of work, and why the tax rules are very different. We’re not talking about gift tax here. We’re talking about income tax. And that distinction matters.

 

I walk through:

And one more thing, especially as we head into the holidays.

 

The Death Readiness Playbook connects the everyday details of your life with legal insight and the personal choices that matter most. It’s designed so that if something unexpected happens, your people aren’t left guessing—they have answers.

 

The digital version is just $27.

Because clarity is a gift the IRS doesn’t tax.

Thanks for being here.