OP UpdateBoy did this thread take off. Thank you all for the 100+ posts, it's greatly appreciated--there's a ton of great posts about how best to approach this. I've been slammed at work and haven't been able to reply to a lot of these, so here's my best effort to respond to a few of the posts.
If you want to help them, be ready for a long journey. Currently they don't want a budget, they don't want to sell their bikes, they will grudgingly sell their pricey vehicles. You need to find out why they want these items, what problems they're trying to mask (insecurity, personal expectations of themselves), and offer advice to guide them towards what makes them truly happy - while knowing that the ultimate decisions still belong to them.
This post was really, really spot on. We laid everything out at Christmas--you make x, you are spending y (line for line), this is unsustainable--and the only positive thing they have done is sell my older brother's truck (still not complete yet, though).
I can't figure out the why. I honestly think they have this hardcore blue collar mentality that this is the struggle that everyone faces, this is normal, etc. Having cable, cell phones, high car payments--it's all normal for middle class America in 2015.
I have a sibling who lives exactly like this. The problem is she is 40 years old and still financially dependent on my father. You cannot reason with some people. I told my father to give her the boot many years ago and let her learn to live a financially responsible life. But he wouldn't and now he is stuck working himself to death to support her. This is someone who owes tens of thousands of dollars to family members and she's never ever made good on any "loan"--not to family nor to banks/credit lines. Who knows how many friends have been stung.
And yet, to this day, there is always a ready excuse as to why she still needs to buy a newer car rather than using public transportation or riding a bike or even driving an older car. There's every excuse as why she has the full cable package rather than an antenna. I gave up a long time ago trying to reason with her. As she's family, I haven't cut her out of my life--but I've made it clear that the ATM here is closed for business.
So...let your brother and his GF learn their lesson. It may or may not work, but helping them constantly will almost guarantee they will never learn to fend for themselves. Put it in black and white--data in an spreadsheet of how much they can save by deleting/decreasing the bikes, gym memberships, etc. If the hundreds of dollars difference each month doesn't wake them up--then it's their fucking problem. Sorry, if that's harsh, but let's just say I've had an adult lifetime enough of financial idiotic siblings.
Harsh words greatly appreciated.
I am more worried about your Mom than the people of your generation.
Keep reassuring your Mom. Listen to what she says patiently so she can express her concerns to you but be very firm that she needs to save as much as she can for her own retirement and not enable these two. Tell her the truth: that they will never ever learn to manage their money if she ever gives them any. No matter how pathetic their story, she needs to tell them "I'm proud of you and I know you are smart, and so I'm sure you will figure it out." That's what she should say whenever they say they can't pay a bill, have no food, or need money for this or that.
100% agree that I need to work on my mom having boundaries before approaching brother and SIL. Right now they have her to lean on. It's a very minor safety net (she gives them $20 after dinner or something), but it's something they rely on and they'll never learn.
Something missing from all of this, make sure you acknowledge their frustrations if you do approach them.
Understand, that even though they might be completely financially retarded, they still feel the feelings they have. Those are very real to them RIGHT NOW. If you approach them and dismiss these as being whiney or stupid or lame or even just don't acknowledge them you are going to immediately put them in a defensive mode which will make meaningful advice impossible.
You don't have to condone the feelings, but you can acknowledge them as being real.
"That must feel hopeless" or "you must be so frustrated" can cause a lot of relational empathy in a situation like this.
I think this is the best post in this thread about the psychology of what's going on with them.
My older brother worked 23 hours in a day--twenty three fucking hours. I wanted to call him Sunday morning and ask, "Aren't you tired? Aren't you frustrated? Are all your toys worth it? You realize the only reason you have to work this much is because of your toys, right?"
Careful when telling people to stop doing crossfit. "You'll get the whole it's for my health and I don't care what the cost is I'm paying for it" shpeal. You might infuriate them and not be able to talk about other areas. Although I'm sure the same could go for some people and there harleys.
I think this has been manifested in this thread, haha. The whole Crossfit movement is fine with me, but in my SIL's position, it's not financially viable when the pavement is free and Planet Fitness is $11 per month.
Another way of framing it when it comes to enabling family members is drawing the parallel with drug users.
You can tell YOURSELF that you are giving them money for food or rent or whatever but at the end of the day - whatever money you give them enables them to feed their addiction.
It is the same with money. Would your mom feel better cutting them off if she looked at the big picture beyond the "butter and pasta" and realized that she is basically paying for their motorbikes/gas guzzlers and other expensive things she wouldn't even buy for herself?
Are you okay subsidizing their expensive lifestyle? Working through the idea that you are doing something like "helping with food" and realize in the bigger picture - you directly funding their big wasteful purchases.
Really good post. I will use that language with my mom when I speak with her--you aren't giving them money for food, you are giving them money for their bikes, their cable, etc.