Dave Ramsey: Holidays and family

Dear Dave: I work as a software developer, and recently a co-worker approached me about starting a side business together. We would create apps for the legal community with advice from my wife, who is a lawyer. The only problem is that we're in the middle of Baby Step 2 of your plan, and we still have some debt to pay off. Do you think starting a business would be too risky at this point? — Jeremy

Dear Jeremy: It sounds to me like this is the kind of idea that would require more in the way of brain sweat and time than money. I would just think of it as a part-time side job and go for it. However, make sure you have a clear understanding of exactly how much — if any — financial support would be required. Set these financial boundaries, and also be clear on when you expect the business to make money.

One thing I would warn against is ending up in a partnership if this thing becomes a success. Partnerships are bad news in the business world, so I'd advise you to figure out a way to structure things where you each own different parts — something more along the lines of a joint venture.

But in terms of doing some side deals, creating some cool new apps, and making money in the process? Absolutely, I would do that. Just figure out an intelligent way to structure the business and finances so you don't get pinched!

Dear Dave: I haven't spoken to my mom and sister in more than six months. Over time, I realized we have a real clash of moral values that has led to arguments and hard feelings. Lately, with it being Christmas season and a new year just around the corner, I've found myself wanting to navigate things a little better and stop avoiding them. It's been mostly just between myself and them, so my wife and kids are pretty insulated from the ugliness. Do you have any advice for handling situations such as these? — Dave


Dear Dave: Well, the good news is it doesn't sound like you've had to spend a lot of time with them. So their influence over you and your household has been minimal. Still, things like this are painful. These are people you love, even if they are hard to get along with or understand.

I'm not a family counselor, but my initial advice would be don't try to change them. And don't take discussions too deep. If you get together, just keep things simple and on the surface. To the extent they try to invade your family, that's where you have to put up a good solid boundary. You have to protect your family and try your best to keep bad influences at a distance. But I don't think you're going to fix them. Probably the best thing you can do is model sanity and reason in front of them.

A friend of mine who has some crazy in-laws says he adopts the bobblehead deal. He just sits there like a bobblehead and smiles and nods, no matter what craziness is swirling around. And that's not a bad idea when you think about it. You don't want things getting ugly if you can help it, plus the chances of you changing a lifetime of toxic behaviors in one brief interaction are very small.

Pray for them, too, Dave. Then, if they ask for help, maybe you could insert some gentle wisdom. Don't tell them what they're doing is wrong or that they're bad people. Just describe things you and your family have done and how you've handled similar situations. But until they bring it up, I wouldn't go there.

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