I come from a somewhat wealthy family and I am completely financially handicapped as an adult.

My mom and dad both come from generational wealth that pretty much dried up in the last decade or so. I grew up in a modest house and our cars were always used but we were upper middle class. I received my inheritance and bought a restaurant in may, 2008, just before the economy tanked. I lost over $235k in the following two years just trying to keep it open (I signed a bad owner money management contract). I was 23 at the time and became a father of 2 sons in that same time frame and their mother basically left me to raise them on my own when they were babies. I have absolutely struggled since then to provide a stabile home for my boys and I am ashamed at my financial situation. I’m 38 now with no savings, no investments, and no resources besides an old beat up work truck. My borrowing isn’t terrible and I don’t really have any borrowing card debt but I’m a giant ball of anxiety pretty much daily when I think about money.
Thank god for my wife who was able to buy a house and put a down payment. I make our home loan and pay the utilities with the money I make as a contractor but it’s very much feast or famine in this very small midwestern American town. I work 50-60 hrs a week and I set my own rates but there’s just not ever enough money to actually start to save.
Now with the holidays here I know my kids will get lots of great presents from their grandparents and other wealthy family members but I feel like such a failure because yet again I am scraping up pennies to just get some stocking stuffers. My constant stress about money is starting to take a toll on my marriage and I’m beyond ready for a change.
To be completely honest, I’m just terrible with money. I get chunks of money and try to hide it from myself as a sort of “savings stash” but when a big job goes too long or a repair has to be made or a tool breaks, I inevitably end up depleting it to stay afloat. My power has been shut off 3 times this year, cell contact number twice, and ran out of propane this summer just because I forgot to pay the bills.
Is there some kind of service or professional I could hire to help me manage money or even just do it all for me and give me an allowance? My wife and I keep finances separate because I seemingly have a curse on me and she won’t help. I am in desperate need of an accountant but I don’t think I can afford one for the level of help I need. I know I need therapy but we don’t have coverage. I want to be better more than anything but it’s like my brain is broken when it comes to money.

Somebody please point me in the right direction.

Edit: thank you all for your time and generous advice. I’m grateful for this community and I look forward to implementing some new thinking first thing tomorrow morning. I’ll be seeking a mentor and creating a solid financial plan tomorrow as I re-read through all of this wonderful advice. Good night.

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