So it's been 2 months and I feel like we're not getting anywhere. I feel like crying. I've canceled some items, tried to be more mindful about food, doing some shopping at Aldi but outside of a $150 decrease in food last month, we are not getting anywhere in overall total $$.
First, congratulations on making some changes. It's a good start! I recommend tracking the changes you've made -- it's so easy to keep moving the goalposts, and forget to celebrate the progress we're actually making. So write them down and give yourself a pat on the back for what IS working!
This is a long process, and what works for one person doesn't always click with another -- for instance, I have to laugh at the idea of switching to cash, which would utterly ruin my tracking system, and lead me to burn through all my cash like monopoly money. Glad it works for others, it's just not a fit for me! But once you find things that work
for you, hang onto them! Also, if your family members are on board, it might be worth talking about doing something like an Uber Frugal month (via the frugalwoods.com blog). Not a permanent thing, more like a 30 day "detox" from spending, which I think is a really useful tool. But not necessarily the right tool for every person, or every moment in life.
It does sound like you need to be tracking much better. There's just no way to effectively change our spending until we actually have a clear picture of it. I am a big fan of anything that tracks your spending automatically; second-best would be a system that you can turn into such a routine that you eventually just do it with minimal thought/effort. Instead of trying to figure out All The Things at once, maybe focus on getting a really good handle on tracking first, then start working on your next-biggest priority.
The single easiest way for me to save $$ is to change (renegotiate or simply cancel) automatic payments. For instance, when I started figuring out our finances, I cancelled a bunch of small, recurring subscriptions (Audible, Netflix, Amazon Prime, local newspaper, etc.). Individually, they didn't add up to much, altogether, they amounted to around $1000 of annual expenses, which is now going straight into our savings...it's a big difference.
So I would look at something like your cable bill (also amounting to over $1000/yr) and just cancel that. If it hurts to cancel -- if someone is your household absolutely loves some aspect of subscribing to cable -- then it might be worth brainstorming together about alternate ways to meet that same need. For example, my partner and I unsubscribed from all our video subscription services, but found we missed watching movies/mini-series together, especially on rainy weekends. So we first looked into free ways to do that (borrowing things from the library, free online sources), and eventually opted to add just one $10/month subscription back.
The fact that human beings tend to adapt so well is kind of our secret power here. It's
really hard to cut a luxury that you've gotten used to (cable, swimming pool, eating out, etc.). It actually hurts, sometimes. But once you adapt to a new baseline, you adjust to a remarkable degree. So for us, once we cut out the endless entertainment subscriptions, we had a couple of months to try a new reality, one where we had to find our entertainment via the local library or our own creativity. When we finally decided to add that Netflix subscription back, it felt like a massive luxury...while still saving 90% over our previous entertainment spending.
My second step, after cancelling a bunch of things, was to renegotiate or find better deals for "necessary" recurring bills. New cell phone plan, called the internet company to get a lower rate, shopped for car insurance, etc.. It's more labor-intensive than just cancelling crap, but because the savings are automatic, you just do the work once and then reap monthly benefits. I'm guessing you've already done some of this, so make sure to celebrate those as you keep working on your tracking tools.
As far as shopping, being mindful doesn't work for me, on its own. It's exhausting, and frankly, better habits do not come down to willpower. I need a system, and systems/habits take a lot of work to develop. It's worth it, because once I have a system that really works, it takes no more effort (sometimes even less!) than my current disorganized approach, but the up-front effort is sometimes really frustrating. It took me about three months to get our grocery spending, meal planning, etc. sorted out. They were not fun months, and there were some costly mistakes (because some of my experiments really did not pan out!). And then it took probably another 2-3 months for it to really start to feel natural, and be robust enough to hold up even when I was having a bad week. But now, it's actually much, much simpler than what I was doing before, as well as being cheaper and less wasteful (and still not perfect, and that's okay too!).
The thing about grocery shopping is that -- like almost ALL spending -- it feels a lot more complicated than it actually is. Most frugalizing just comes down to an ability to plan ahead and anticipate our needs. Tracking helps you understand your behavior now. Then you, and your family, can decide what you'd like your (collective) behavior to be. A plan/system/budget is what you use to close the difference. You can get this dialed in, it just takes work, and trying new things, until it comes together.