When I was in high school, I made a new group of friends. The first time we hung out we were going out to dinner. This is right after school and I didn’t have any money.

So, they decide they were going out to dinner and I told them, “I can’t go with you guys, I’m sorry.  I don’t have any money.”

One of them said, “That’s okay. I’ll pay for you.”

I grew up pretty poor. We didn’t have much. My parents didn’t have a way to give me money. Between my workload in school (which was really heavy) and sports, there was no way I could work. There wasn’t time.

The next time I went out with them, I said I didn’t have money for dinner tonight. They were like, “It’s okay, we’ll pay for you.”

That became a thing. At some point, I asked that friend, “why do you pay for me?”

He said, “Well, my parents spoil me so I want to spoil my friends.”

Recently I had a conversation with my daughter because keeps billing this friend in Venmo for small things. Like, “Pay me $4 on Venmo.”

So I told my daughter my story about my friends in high school and I said, “Stop doing this to your friends. Stop billing your friends.”

Here’s a question about billing and OFS from Anjali:

Does your OFS handle billing? I have a consulting business, and charge high ticket prices for large packages. I’m very hesitant to have my OFS get involved with the billing or even know how much I am charging because I feel that if they do, the discrepancy between their salary and these fees will be shocking for them and awkward for me.

We don’t have billing in our business.  However, yes, I would definitely have them handle it. They have no idea what other expenses go into the business.  They don’t know what’s involved.

Even if they do, it doesn’t really matter. They know they’re an employee. It won’t be awkward for them and it shouldn’t be awkward for you. In fact, it may give them some security. If they know your business is profitable they’ll feel like their job is secure.

If you trust them, let them do it.

Also, with very little going on right now (in most businesses), now’s a good time to get your OFS started working on a.new project for you. Start creating training (a video with Snagit is a great start), think through what they’ll need and what they’ll need to do.  Get an early jump on your New Years resolutions.