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Once I’ve paid rent, bills, petrol, food, etc. I have a relatively small amount of money left over each month. I would get by just fine on this, if it wasn’t for spending the money on other people.

A lot of my family/friends are in a similar or worse financial situation than me. I’ve gotten into a bad habit of paying for things: ‘don’t worry, I'll get it’ kind of thing. Which obviously I can afford to do once in a while, but I’m doing it so regularly that I can’t build up savings which is what I need to do.

Also many have had big events like babies and weddings and expensive events which naturally carries an expectation of a gift.

To add to this, a lot of people don’t drive, so aside from paying for petrol because we’re in my car, I’m always picking people up and dropping them off. I’m getting tired of doing it. It sounds awful but I’m rushing about all harassed, looking a mess, making a journey out early to collect someone and they roll out of their house all chill, looking great, etc.

People are grateful, and I do care about these people and when it comes to covering costs it’s me who is instigating it not them. But it’s very hard if they’ve just been telling me all their money troubles to resist paying for things, especially if it’s something I wanted to do.. e.g. somewhere I wanted to go for lunch.

In short, I want to disengage from the constant giving but I don’t know how to convey this to the people around me.

How do I convey to these people that I want to stop paying for them when I'm the one that wants to go somewhere for lunch and I know my friend has financial issues, or plan an outing that's only affordable when everyone pays their share, or that they need to pay for petrol?

Edit: Thank you so much everyone! Great bits of advice all round.

I experienced this too, in addition to the charities that I wanted to make donations to. I am adding this because it is very similar to you.

I learned to allocate a percentage of my income to a fund that I labelled "Donations".

When the donation budget was empty, I would tell people just that, but that I would add their name/cause to my next months one. I was amazed how many people would plead, to which I would reply that I can not make money out of thin air. Often they would tell me not to worry about it. I was quite surprised to see the ways in which they coped fine without my help.

Something else that I did try, was to offer (family) the chance to earn the $25 (for example) by doing a gardening or cleaning chore that I didn't want to do. I made a rule that I would not pay until the job had been done - "I'm going to pay whoever does this job $25 when it's done.") I was astounded at how often I was told they would be back to do it, and never arrive.

Because I would never ask someone for something unless I was truly desperate, I was under the impression that others were the same. I have learned that not everyone has the same definition of desperate.
I hope this helps.

"Pay yourself first", my grandfather used to tell us. That was and still is great advice.

Make your savings deposit, pay your bills, etc. Do that, and you can truthfully tell them that you don't have anything to help them, sorry.

Those two books changed my life! And they can help you to overcome this worry and fear of people's reactions too.

I've been the one benefiting from wealthier friend's generosity, and the one helping more needing person (friend or family member). It's really important to understand that people's minds are the core of the problem:

1. they realize that you help them and:
   
   
   • will take advantage of it as long as they can pull the rope.
   
   
   • will not take advantage and [ feel bad / grateful / a bit embarrassed ]
   
   


2. they don't realize you help them and will only realize when the source will dry up.

As the one who could help once in a while, I'd do that "as much as I could". You know how much you can afford, spend, and how much you can help. Others may not know, you'll then have to let them know. From your question, it appears that you set their expectations (I've got into a bad habit...). Now, you'll have to "explain" why you change things, and switch behaviour. I would do that smoothly, in order to not hurt them, but still, set boundaries. Draw the line, and don't cross it.¹

When I wanted to let people know/understand I couldn't pay for them, I'd use a little trick. For instance, you plan on going to the mall + movie + dinner. Cost is roughly $50 each. I'd just call/text/ask friends if they're willing to go:

Hi folks, I thought we could go to mall + movie + dinner on saturday. It's the new "any blockbuster". Cost would be roughly $50 each, who wants to come?

This way, you give them a chance to understand that you care for them (because you want to hang out with them), but (even if you're the leader of the pack) you can't afford paying for the whole "wolf pack", because you give the price each and everyone will have to pay. And it gives them a chance to step out without being seen as broke or cheap.

When it comes to family, I'd let them understand that I need my money for something else. Again, softly speaking, but clearly setting boundaries.² I used to say that I needed to save. Period. And if they ask why and what for, tell them about [ holidays / retirement plan / furnitures / car / ... ]. Which is always true, you'll need the money for this sooner or later, it's not even a white lie.

Sometimes, you'll face some unpleasant reactions, something you can't really avoid, but nothing you shouldn't be able to deal with anyway...

^{1. this far you may come and no farther; Job 38:11}

^{2. The prettiest girl in the world can only give what she has...}

They do say that saying no is an art on itself, and I believe that your question has 2 parts to be answered.

The first one is how you say no to yourself, as you mention in the question as well in the comments, that you often offer to pay for something ("don't worry, I'll get it") or you dismiss somebody's offer to pay for something ("do I owe you anything?" "No, it is OK") because you are aware of their money troubles and don't want to add more into it. Unfortunately, we cannot help you with this part. You yourself have to draw the line.

The second part is how to say no to somebody after you said no to yourself. I've been to both sides of the coin, since I was often "the poor friend" when I was in middle / high school and now I'm often "the rich friend" after university and years of professional experience. A few tips for dealing with the situation, from what I do to others and it works well, or what was done to me and worked well:

1. Create a recognizable pattern, as this helps to manage expectations.

I have a very dear friend that earns a significantly lower salary and has chronic money problems. Our agreement is whomever names the place pays the bill. Since we live in different cities, when I'm around I drop a message and from there we have two options:

• Hey, I'll be around "Friend's City" on Tuesday and Wednesday, do you want to go to "Restaurant"? (between the lines, it means "Hey I'll be around and I want to check this place, I really want you to join, so I'm paying.")




• Hey, I'll be around "Friend's City" on Tuesday and Wednesday, do you wanna catch up? (between the lines, it means "Hey, I'll be around and want to catch up, but I'm not up for footing the bill for 2 people, can you choose somewhere you can afford?" - most of the time it means he'll cook something or we'll meet at somewhere cheap)

The second example is my boyfriend, I am the one with the higher income and we live 150km / 2h30 / 30 euro (after discounts) train journey apart. Our arrangement is whomever comes to visit pays only the train ticket and the "host" bears the cost of outings and meals.

2. Be upfront about payment expectations (arrangements AND value), let them make a conscious / planned decision and be ok with it.

I mentioned that I was the poor friend growing up, so many times when we had an outing in which sharing expenses was needed, my friends told me upfront that it we would split the bill and the expected value was X. That allowed me to either plan for it or decide if I wanted to go or not. If I could not go, they were perfectly fine with it and would also often offer to postpone it for a later date when I could afford to go.

In your example from the comments, the next time you and your sibling are hosting something, you can say that you looked into X takeout and it will be 30 bucks each, and either offer a cheaper alternative or let they come up with an alternative that fits their budget.

3. If there is an offer of payment, accept it without fuss.

Make it sound like casual, as it is a natural expectation - because that's exactly what you want it to become - natural expectation.

Many times people offer to do something because it is the polite thing to do, not expecting the offer to be accepted (usually the case with sharing food, but it can also be with other stuff, like a ride home or paying half of something). Once the offer is accepted, it makes them think twice about offering something without intending on carrying on that promise, and also stops them from expecting you to pay fully for something.

Back to the sibling example, if they ask "do I owe you something?", just say how much they owe you. Sometimes they'll say they don't have that much money on them, just go "ok, how much can you give me? We'll settle the rest later." Whether or not you'll collect, it is your decision, but get them used to having you accepting payment offers.

4. When somebody asks you for a favor, ask for a small payment. They don't need to pay you in full, but at least get them used to paying you something.

Especially for rides, if somebody asks you for a ride or asks to join in into a ride you've already planned (and that will most likely make you detour), ask for a small payment.

Following #3, make it as natural as possible or use the detour as an excuse for them to "help you pay for the petrol".

You don't have to ask for the full payment of the gas, just a small payment, mostly to convey the message that it is not for free. Then they'll either stop asking or start paying.

5. Ask for contributions in a subtle way

As sugggested by Mike in the comments to the answer, you can also put a contribution box in your car as a way of asking for people to at least give something back. It is less direct than #4, but it can still be effective.

In summary, this is all about breaking habits and building new ones. The first part (the one you need to solve yourself) is the most important one as your decision will be the trigger for when you start asking for payment and when you let it slide. Do not be afraid of asking for a little bit back, you're not being selfish and it will help both sides on the long run.

When people ask me for money, such as a homeless person, Girl/Boy Scout, checkout person asking about a donation to random charity, or whatever, I say "Sorry, not today". This implies that I've given in the past or will in the future, and am not interested in doing it again/right now. For most things not personal to you, they just want recognition of their question. Whether they accept this answer depends on how reasonable they are.

I realize that doesn't really work with friends and family, but in these situations, they should understand that you aren't "made of money". If they don't you can still answer with the same statement as above. If they are truly your friend or care, they'll understand. If not, then it might be time to rethink your relationship. It's not enough reason to let it go completely, but it might be an indication they aren't in your life for your benefit. There's always the possibility of turning that around, but it may not work. And this is getting off topic fast.

One thing you can try is "I know you're having a hard time too, but it would help me if you could help pay $X.XX for fill in the blank." You may have to remind them of this from time to time. A friend of mine was dating a girl that had more money than him. He wanted to pay for everything, but some of the things she wanted to do was outside of his budget, including eating out all the time. He finally asked her to help pay for things, which she agreed to, but after a while, it tapered off and stopped. When he reminded her, she started paying again, but it tapered off again, too.

Try to be consistent and eventually it should become a habit of people to help pay for things. It's great you want to help people, but it sounds like you need help, too. Just remember that you can't help others financially when you don't have anything to help with.

Also, you aren't a taxi/Uber/Lyft/etc. Even if you are, you should know those drivers get paid for what they do. Since you have a job and I would assume you want a life outside of ferrying people around, you should tell people that you can't help them all the time. It's hard to tell people "no", but it's something you need to learn. I used to be the proverbial "doormat", but I took control of that by saying "no". It took a while, but I eventually lost the guilt of not helping everyone all the time. Taking control of your life actually feels pretty good. Don't get me wrong, I still help when I can, and even when I should be doing something else, but I try to make that a conscious decision instead of an automatic reply.

Also note who you say to and how they react. I found that most people didn't think twice about me saying "no" and that the inevitable confrontation I thought was doing to happen never did. Well, at least with most people. There were problem people, and generally they didn't stick around long after I stopped helping them with "everything".

To help with this guilt and fear of a negative reaction, you can say "I'll help you in a little bit, but I need to finish what I'm doing right now." If they need immediate help, they'll look for someone else. Doing this also puts forward the expectation that you have other things to do, too, and they aren't the most important part of your life, while still being willing to help. This works especially well if they actually interrupt what you are doing to ask for help. What you can do to make this more prominent is to actually be doing something when people ask for your help. Whether it's reading/writing a book, doing homework/taking night classes, having a hobby, or whatever, just make sure you let them know they are interrupting, if it's not absolutely obvious.

Giving them a time frame of when you'll be ready will help them determine if they need to find someone else to help them. "I'll he there in a little bit" can mean 5 min or an hour, so try not to use this unless you really don't know how long you'll be. If you do use this, add in why you don't know how long you'll be, such as "I just started gluing something together and (I'm not sure how long it needs to set before I can let go) or (I need to do a bunch of things all at once before it fully dries and I'm not sure how long that's going to take)". If you do know or can make a time frame work, tell them. "I'll be there in X minutes." It doesn't even have to be too accurate. If it's a short period, you don't generally need to give a reason. If it's a longer period and not obvious why it'll be longer, give a simple reason why. "I'll be there in 45 min, since I just started something and (need to make some real progress before I stop again) or (need to find a good stopping point)." If you miss that target by several minutes, either let them bring it up and apologize, or bring it up right away. "Sorry, that took longer than expected," should suffice either way.

Once you get the hang of this and you start losing the guilt, you can move on to having a relaxing dinner out (either with someone or on your own), taking a long bath, watching a movie, or doing something else to let your mind & body relax. Most people don't understand this is really important. Humans aren't robots and need to rest. This counts as "doing something", just like a hobby, working, or studying. When someone interrupts these activities, they are still interrupting something important, so use the same reasoning as when they interrupt studying, work, or whatever. You are busy at keeping yourself sane and healthy.

Doing all this frees you up to doing the giving you actually want to do. FYI, gifts at baby or wedding showers is expected, but still not a requirement. If people have a problem with that, it's their problem, not yours, so don't make it your problem. This will likely take time to work through, as well.

Giving is great, but you have to learn restraint, otherwise it's sucking you dry, as you are learning. Reasonable friends, family, charities, etc. will understand you can't give your money and time to everyone and everything all the time. Remind them of that.