My dad made a ton of money and barely spent a dime on me, so your son doesn’t care about your success, he cares that you care about him and his well-being.

Kid loves you because you’re still there for him, for better or worse. If he doesn’t feel abandoned or less important than material things, then he’ll keep on loving you just the same.

Still, long-term, you need to plan for building him an independent life while getting one for yourself. It’s a tough gig but you have experience. Your work ain’t done yet pops, so good luck!

You basically have to change how you calculate your worth.

You are the one who set the standards that you are failing to meet.

People with depression often fall into this trap. You set a standard you can’t possibly reach and then get upset you aren’t reaching said impossible standard.

When I get thoughts like this i try to look past my thoughts and feelings and look at the evidence.

Is your son happy? Have they done anything that leads you to believe they feel let down? Etc.

Because it sounds like the only thing making him unhappy is you being unhappy.

Kids generally just want attention and love more than anything. Things are nice but they are no substitute.

Rich people go bankrupt all the time and it doesn’t make their quality of life any worse.

Trump has been bankrupt at least six times.

The problem isn’t that you went bankrupt, the problem is that you can only do it once before losing everything. The problem isn’t you, it’s the system that’s fucked up.

The only thing that will ever matter is what kind of Human being you are. If you are a kind, compassionate, honest person who shows, love, respect and gratitude, that’s all that matters. Your behavior tells the rest of the world who you are. That’s how we actually judge people. Money is a terrible way to measure your “worth” in the world. There are billionaires who are utter trash. The only reason anyone wants anything to do with them is to get some of their money. Without that money, they are invisible.

I don’t believe I’m a failure. I believe civilization as a whole is.

Teach your kid how the world works so they’re prepared for it and don’t go through the same thing. Most of us didn’t have parents that cared enough to bother and it’s a huge advantage to know in advance that everything in this country is predatory and precarious.

Damn dude if you owned a business and had a car or a house you’re way ahead of basically everyone I know. Most of us just struggling to pay rent.

Vocabulary is loaded. The words “rich” and “poor” conflate munificence with success or happiness. When we see an injured animal and say, “That poor creature!”, we are obviously not talking about its bank account. By the same token, being short of money is a problem but it absolutely does not make you a “failure”.

I’ve been laid off 3 times since 2018. The first time was from my job of 6 years that I was pretty set in making my career. I was making money, I was getting promotions, it was looking like I’d have a nice long tenure there. Then came the corporate restructuring.

I got into a really weak job after a few months of unemployment cause the job market was rough. It gave me flexibility but the job itself was low pay and low responsibility.

Then Covid came and I got laid off again. Company stopped doing business in that field.

Found ANOTHER company that was similar but paid better and kept my flexibility. Was good for about 4 years then came corporate restructuring.

Now I’m back at the business from 2018 but under a new product lineup.

Point of all this is: I learned a valuable lesson in having less “successful” work. I learned how to actually value my time and the people who I provide for. At my career gig, I put in so many hours and really pushed myself, in the jobs after, I’ve been able to put my mental health first and take care of my family better. Sure it’s less money, but it’s more attention.

Money isn’t what kids need, they need you to be there for them first and foremost. Money just makes it easier to do things.

Good luck, and I hope your situation gets better.

After having gone through a number of setbacks in my life that challenged my self-identity, I realized that I needed to reassess both what I considered to be what made me “me”, and what made me worthwhile, which is similar but not the same.

You are not your job or your salary, and you are worth more than your salary. Find new target for what makes self-worth for you. It will give you better rewards than cash when you strive for them, and will give you a better perspective about money than if you tie your identity and self-worth to how much you can make.

Being poor isn’t a failure. You had bad luck and didn’t have things in place to protect yourself, which was a mistake. Learn from it. You’ve been up there before and know the path to it. Try and do better and you might make it again.

I bet your son will remember more about how you being there for him than the failure - regardless of whether you’re poor or not in the future.

As someone who’s had multiple failed companies you have to learn how the rich people do things and protect your personal assets from your business ones (& even your business from your business ones). Once you’ve got better advice from a lawyer then maybe try it again, especially construction, unless it’s now a wellness reason. Your business should be able to absorb a lawsuit and reform under a new s-corp with most of your assets intact. It’s super hard work pulling yourself out of the pit and starting over again but the extra income is worth it. You could try moonlighting for a while until your expenses get balanced.

Remember you are not a failure, you are still trying everyday, and you have seen the method to your success before. It takes a real motivated and hardworking person to make a business grow and you’ve proven you could do it once. Work towards that financial independence again, take it slow and keep yourself free of the liabilities this time.

Money is a carrot on a stick. It’s not fulfillment.

We find lasting fulfillment and self-worth through our connections with each other. With your kid, with your co-workers. With other people in your life.

Try consciously putting your attention on the things that are actually fulfilling. Money doesn’t buy happiness. It does make life easier. But happiness is the time you spend with your kid, not the money you spend on him.

I had a stroke two years ago and have been living on $30 a week ever since. You just keep going.