Every time you "help" them, you're telling them that you'll always bail them out. Time to have a sit down and tell them that you're done. Hard? You betcha! But in the long run you're doing them a favor. Help them first learn to budget; then help them find organizations in the community that help with short term assistance (although it doesn't sound like they'd qualify for that with two incomes). The best thing you can do for them and you is stop enabling. I have had to do something similar things with two of my sons; thankfully, we started when they were young to draw the hard line. They went through some tough times, but the oldest has been making his own way for years now and is very thankful that we were firm with him. The youngest--well, he's still learning. Your retirement should not be compromised because your sons are irresponsible or needy or budget-challenged. But the hard truth is that you have allowed them to be and actually helped them. It's not too late to make the change, but it will be very hard on many levels.

I think this is a great topic that you bring up. Would you be comfortable sitting down with your son, daughter-in-law, and husband to have a conversation about their financial situation going forward? I think this would really help to get everyone on the same page. My parents were always very forthcoming about financial conversations and set boundaries for my siblings and I as young adults. I say this because as being someone on the receiving end of financial boundaries from my parents, I never resented them for it and even found it helpful at times as it allowed us to have good conversations about money and budgeting. I hope this helps!

Hi! This isn't a direct answer to your question but I wanted to point something out. If you are self-employed, you have access to retirement plans like a SEP-IRA (which will reduce your business's taxable income.) It gives you the ability to save more money than say through a traditional or a Roth (Roths are great though because they're tax free in retirement.) If you have any questions about this, send me a message, happy to talk anytime.

Not enabling a kid nor being enabled, but have watched my grandmother do this with her step-kids (my step-aunts) thru the years. She complains about it, but secretly I know that she likes being needed in this way. Not saying this is the case for you, but you might think about what you personally are getting out of this arrangement. They benefit financially, but maybe you're getting emotional gratification knowing that you are still needed. If that's the case, that's totally ok! Nothing wrong with being needed, everyone wants to be needed. But if there's money concerns, maybe try to redefine your relationship with them so that you both still get what you want (they get help and you are needed), but your money is not involved.

I would suggest the course by Dave Ramsey. It’s online and it outlines how to manage money. It’s about taking care of your expenses and budgeting. A very valuable course !! I would set a time limit on giving them money. Maybe 6 months to figure out how to change their budget. And then tell them you won’t be able to help them after this 6 months. It gives them time to figure out how to make ends meet. We all need help a some point in our lives. Maybe they need a different budget. Or maybe they do take out too often.

You don't talk in your post about the other adult son. Have you ever considered what this other person might feel like? The reason I ask is that I am that person in my family. My sibling has been bailed out for twenty years by our parents, and I have never had that luxury--partly because I saw the strain and pain it put on my parents to not be able to say no. It ruined my relationship with my parents for many years because I thought that they loved my sibling more than they loved me. I still have trust issues with all of them because of this repeated behavior. You've enabled your son and his wife to have you in their back pocket financially. They know you can't say no, especially if you're doing it behind your husband's back. They have you wrapped around their finger. It doesn't matter if they are grateful--I'm sure that they are--but if you don't stop doing this, they will spend you dry. If you live close by and can offer help in non-financial ways, I encourage you to say that you're happy to watch the kids one afternoon per week, help clean the house, or something else that costs your time but not your money. Set firm boundaries that you are unable to be their backup plan any longer because you have your own priorities to attend to. Lastly, I encourage you to check in with your other child and ask if this arrangement has upset him--it could mean the world to him.

It sounds like your son and daughter in law need to sit down and have a hard look at their budget. Everyone gets into difficulty at times, and while I don't doubt that they are diligent and it appears they are not extravagant, that doesn't mean there are not ways they could reduce expenses to allow them to save for unexpected expenses. I know it's an awkward thing to try to raise that conversation, but the truth is that if you give them money now instead of saving for retirement, you run the risk of reversing the situation in your later years. When they asked for money from you, in particular because it is a repeated event, it put you in a position to start asking these hard questions of them. Perhaps you can use your greater experience to help them identify ways to get in better shape financially. I'm sorry you're in this situation, it must be frustrating. I wish you the best of luck!