It can be really difficult to watch someone you care about repeat the same mistakes in life over and over again.
Maybe they're failing to overcome an addiction. Maybe they're having difficulty keeping a job. Maybe they can't pay the rent because they spend money far too loosely. Maybe it's all of these things - and more.
Whatever it is, you're left sitting there watching that person fail and fail again.
You offer help, but it often feels like you're just throwing money and time down a black hole. Yet, when that person is down in the dumps, you're there offering help once again, hoping that this time is different.
It almost never is.
Having someone like this in your life is draining. It drains your money. It drains your time. It drains your emotions. I use the word "drain" here because that's what it honestly feels like - you give your time and money and energy and emotion and nothing ever really changes. The things you give simply seem to disappear.
Turning your back on this person seems cold and empty, yet offering help to that person seems to go nowhere at all.
What do you do?
Here are a few things you can do to start turning this ship around and, ideally, put that person in a better place and end the "drain" on your life.
First, check yourself. Does this person really need your help? Are you injecting yourself into a situation that you've judged to be "wrong" in some fashion? Is this person really asking for your help, or are you jumping in to promote what you think is the "right way" of doing things? Often, people think they're helping when they're really just trying to push the other person's life into the form that they want. Is this what you're doing? If you are, back away. Put yourself in check.
The worst thing you can do is find yourself getting emotionally attached to their choices. If they make a good decision, it should not bring you elation beyond a general sense of being happy that their life is going better. Similarly, if they make a bad decision, it shouldn't drag you down into depression. Separate yourself emotionally from their choices.
Second, focus on encouraging the good steps. When you see that person doing something right, tell them that they're doing something right. When you see that person making a good move, give them praise. This not only feels really good, it also makes it clear that you're paying attention to what they're actually doing.
At the same time, dial back on the criticism. When people make mistakes, they often realize it for themselves. It doesn't really help when someone else piles on, particularly someone they love and trust. If they need help resolving their mistakes, they'll talk to you about it. If they don't, it's none of your business.
You should also strictly avoid the bad decisions they're making in your own life. It's pretty hard to accept advice on alcoholism from someone who drinks. It's also pretty hard to accept spending advice from someone who throws money around all the time. When your actions go against your advice, it makes your advice seem hollow. In other words, be a role model through actions, not words.
You should also give, not lend. Never, ever "lend" money or resources to someone who is struggling. This creates a lender-borrower relationship between you and, for a lot of people, that's a ticket to poison. If you want to help, do it with zero strings attached.
When you do choose to give, give them a path to better choices. Don't enable the same old mistakes. It is extremely rare that handing someone cash will make their situation better. Most of the time, it just enables them to make the same errors again and again. Instead, give compliments for good moves. Give an ear to listen to troubles and a shoulder to cry on. Give them a ride to a job interview or to a rehab clinic. Give them contact information for resources you trust. Don't just hand out cash.
Remember also that handing out cash destabilizes your own situation, making it harder for you to provide the other kinds of help that you might offer.
It can be very hard to say "no" to a request for cash, but nothing changes (except in extremely rare situations) when you simply say "yes" and open your wallet.
In the end, seeing someone continually make the same mistakes in their life is difficult, particularly when it leads them down a long and painful road. Helping people in that situation is never easy, particularly when the most obvious and straightforward ways to help don't really help at all.