That's a non-compliant plan, I'm pretty sure. You can't just expense an all-alcohol trip to a bar because you're stressed. You're not personally in violation but the organization is violating the IRS rules for letting you do it. They'll get away with it usually, and if a tax auditor sees it there'll be modest fines unless it was systematic approach to dodge taxes.

As for "why" it's a personal benefit, that's just how we've decided as a society. We want people to pay tax on personal income irrespective of how it's spent and we want to allow businesses to pay tax on net income because to create economic value you sometimes have to spend a lot on inputs.

So we have rules for what income is taxed on gross and what income is taxed on net. For the most part, personal income is taxed on gross and business income is taxed on net. And then, to compensate for the gross taxation, a standard income deduction is offered.

Because of this difference between the way personal and business income are taxed, the classification of things into one and the other matters. A logical way for a company to restructure things given just the naïve implementation is to transfer all payment to payment in kind: the company buys your groceries, pays your rent, and so on. You love this, your taxes are lower and you still get the same benefit of the money. The IRS, therefore, qualifies what is personal and what is business. Your company cannot buy you your groceries and pretend they aren't paying you.

However, it is true that the company sometimes sends you on assignment where your costs would be higher than if you were to stay at home. In these cases, it is reasonable for them to pay for your expenses. Well, ideally, your company then always sends you on a one-day trip every month but sends you back with a Costco-haul. This would let them pay you more (you both win, the tax man[0] loses) so long as they appropriately redirect pay into in-kind. So the IRS says "you can either be careful or you can have a fixed amount for travel that works for these categories"[1].

So, "why" is it a personal benefit? It's because we have taxation, and because business and personal income are differently taxed, and because business spending has to therefore be defined. That's the broad strokes of it though there's nuance, and a lot of "well, actually" to get it out but that's the picture for the most part.

In the end, the lines have to be drawn somewhere. If you eat the office catering that's not a taxable benefit. But if you were to drive home to pick up and eat the Doordashed sandwich from the same place there and return to work, you would have eaten identical food and perhaps done identical work, but the treatment is different. Such is life at scale.

0: That's us, this society. We collectively are the tax man.

1: https://www.irs.gov/pub/irs-drop/n-25-54.pdf

> For the most part, personal income is taxed on gross and business income is taxed on net

This bothers me a lot.

So basically a wealthy billionaire can take one company that makes profits and acquire a large loss making company that he also owns and Viola suddenly the profit making company doesn't need to pay as much in taxes anymore.

Or Google takes out huge ads on its own properties but it doesn't have to pay anyone and therefore doesn't have to pay any sales tax on those ads.

It feels like we are structurally encouraging vertical integration and bigger businesses.

We need to have some kind of alternative minimum global tax for companies based on gross receipts rather than net.