I've given this guy so many "second chances" it's unreal. He's caused me more stress, more grief in a year than all of my past and present employees combined. He has a stinking attitude, he has no idea how to show the guy who signs his paychecks basic respect (I'm not talking about boot-licking respect here, just the bare minimum), he screws up again and again, he becomes abusive and argumentative if you try to take him to task over anything, he's constantly late, he's just bad for business man. But I'm a soft touch (see: idiot) and I've given him so many chances to turn things around, stop being late, stop being lippy, stop screwing up. Within a couple of weeks he's back to his old self again. I've had friends, family, the girlfriend absolutely horrified that I wouldn't fire this guy. I've had so much stress and tension over him and I've been constantly worried how he's going to f-up next. 
 
Well this evening he went off on one of his trademark rants via text - even after I asked him to stop texting me - and I just fired him on the spot. I should have done this ages ago. It's going to cause a lot of trouble because I don't have anyone to replace him straight away and I'm going to be running around like a headless chicken covering his work, but the main thing is that he's not going to be a part of my business any more and that's great. So why do I still feel like crap about it? I mean I actually feel sorry for the guy and worry about how he's going to live, even though he truly has been a nasty piece of work. How in the hell do these big honchos hire and fire at the drop of a hat? Am I going to have to start smoking cigars or something? 

sharke
How in the hell do these big honchos hire and fire at the drop of a hat? 

Start by buying a hat to drop? 

1) Hat
2) Cigar 

sharke
So why do I still feel like crap about it?

Because you're human, with the human capacity for compassion.

I've had to fire quite a few people too, and it never gets easier, at least not for me. I always feel like the biggest scumbag after it's done. I try to remind myself of all the reasons that it was necessary, but it doesn't help. You'll feel better in a couple weeks when it's not so fresh. For what it's worth, you did the right thing. Best wishes.

It just means...probably...that you're a decent guy who is loyal to his staff and wants the best possible outcomes for them, you and your business. Been there...done that. Likely to go again. But you did...finally...the right thing for you and him. It's one of the toughest things about owning and running your own business. Sounds like you gave him more than enough chances. Rock on, ol pal. Rock on.

Thanks for the nice comments.  I know I'll feel better about it in a few days. To tell you the truth he's only the second person I've ever fired. The first one was equally as depressing because it was a pregnant woman. But pregnant or not, she repeatedly displayed gross incompetence and dishonesty at a level which if tolerated for a second longer, would have put me out of business. Oh I felt crap about that one for weeks lol...
 
The worst part of being a boss is when you go out of your way to look after someone and they turn around and throw it back in your face. I employed a guy for two years one time and lent him money whenever he was short (hundreds of dollars) and gave him a laptop because he didn't have a computer (actually gave him a second one when he broke that one, lol). And then out of the blue he tells me he had to quit his job to go spend time with his sick father. When he quit, most of the clients he was servicing quit on me too. How strange! I subsequently found out that the sick father thing was BS and that he quit to start up in business himself, taking my clients with him (he even lifted parts of my website for his own). It's like being cheated on, you feel sick.
 
This guy tonight...he didn't have enough work on of late and since they're on a piecemeal pay structure, I was giving him a lot of money out of my own pocket every week to supplement his wage. And still the attitude! When I got ordered to garnish his wage for the child support he hadn't been paying, I felt bad about that so I started slipping him a little extra to make up for it (basically taking over his financial duties as a parent). Gratitude? Nil! When I had it out with him tonight he called me an a-hole, a bad boss, a bad person etc. And I realized how utterly futile it is to try and work with people like this. Like Jerry Seinfeld said, "You should just do it like a Band-Aid. One motion, right off!"

I don't know if this will help. If you care more about fixing him, solving his problems, and improving his quality of life than he does, you're making yourself responsible for his happiness. You can't win. Even if you give him more than he could ever wish, it's unlikely that it will ever be enough. Instead, he's likely to resent you for "meddling" in his life. 
 
Some people expect that the world owes them a prosperous, easy life and they'll be miserable until that happens. If they can make you clean up their mess, feed them, and give them toys just by throwing temper tantrums, why would they stop? Sometimes, the kindest thing you can do for someone is to let them suffer natural consequences. 
 
I've had to fire people at various times. Sometimes, people just can't/won't do the job. If they aren't capable, maybe they'd be happier in a different career where they could be competent. If they are capable but not willing, maybe they need to learn a difficult life lesson.
 
As the boss, it's not your job to parent your employees. It's the employee's job to be responsible for himself/herself. As the boss, you communicate your expectations to your employees. Either the employees will meet those expectation, or they can find a new job. It's not heartless, it's the way it is. If an employee has a good attitude and a solid work ethic, you can teach them to do almost anything. If not, they can have all the skill and experience in the world and still never meet expectations. It's not your job to make them better people. That's their job.
 
(No, I don't have a hat and I don't smoke cigars.)

(For the record, if anyone would like to give me more than I could ever wish for, I promise never to resent you.)

I hear you. With some people it's like trying to deal with a chronic heroin addict - fruitless. They'll say whatever it takes to get what they want, no matter how dishonest. It gets to the point where no matter how much they plead for another chance and promise they'll change, you've been burned too many times and you can't trust them any more.

Now this guy is screaming about his "worker's rights" and threatening to haul me up for unfair dismissal. I told him look, I have a record going back months of all of the texts you've sent me which make for some fairly fruity reading. Anyone reading them would wonder why I didn't fire him months ago. But he looks upon me as someone who is morally and legally obliged to provide him with a living, no matter how badly he's performing. He's one of these people who think jobs exist purely for their sake. I don't think it occurs to him that businesses, and therefore jobs, cannot exist without customers and that if my employees are screwing up then I lose revenue and hence can't pay their wages. It's amazing how many people don't understand that wages are paid for out of revenue and that without revenue there are no wages. They think the boss is paying them out of some secret stash somewhere.

I do wear hats, and I do smoke cigars.
 
But this is exactly why I've engineered my life and livelihood in such a way as to never be in a position to fire anyone. I find it very hard to do, and have to be pushed into it by conditions getting so bad that I had no choice.
 
My son, however, hires and fires people on a weekly basis as part of his job. Every time, it's agonizing for him. I think his boss makes him do it so the boss won't have to.
 
I truly believe that if you don't find it difficult then there's something seriously wrong with you - you might in fact be a psychopath. So take some comfort in the knowledge that you are probably not a psychopath.
 
UB's right: parenting your employees is not your job. Look out for them, sure. Have their back as you'd want them to have yours. But you will never have enough time or influence to substantially change a person's fundamental character.