It is not your job to assist others financially, in a way that rewards good habits.

It is not your job to train them in good financial habits.

And even if you did try, more than likely, you're not going to change any bad habits that they have picked up over a lifetime.

With that said, for 12+ years I have been contributing to the support of a cousin whose husband is blind. I send 6 checks per year so that if so inclined, they can't blow through a lump sum all at once. Beyond that I have no control nor do I want any. I have determined that they warrant the support and once the check is cut, the money is theirs to do with as they please, regardless of whether I like what they are doing with it or not.

And as suggested in a comment by Jammin4CO:

• Give without remembering; take without forgetting

Never, ever, ever, ever, ever give money to any able-bodied person unless you want to destroy them.

capital to an asset

Something you could do is (1) use your capital to assist someone in purchasing a house (or conceivably another asset).

So for example, your relative R has income but has not yet bought a home, so they're wasting rent and not exposed to gains. You could organize something where you put in the initial capital, and R pays the loan.

Naturally in the future when the home is sold, you take back your share plus the share of the increase; the second part of the equation is if they miss one payment or flake out in anyway they're out. (And you've lost little or no capital.)

buy a job, the "franchize not handout" solution

A second thing you can do is (2) "buy a job" for your relative R. So, if you have substantial money laying around, you buy and build a Dunkin' Donuts franchize and make R the manager. This will set them incredibly ahead by skipping many steps on the career ladder, and, putting them "inside" business. If they flake you fire them and hire a normal manager - no harm done.

pay for skool

The third and only other possibility - there's the (3) "pay for school" option. Say R has small children, as the "grandpa" you may wish to pay for the children to go to a fancy-ass school. Similarly you could contribute to higher education costs (college/similar). However, I'd be extremely careful about that: it would have to be an absolutely money-making-focussed educational path. Obviously, phrase it only as a generous interest-free loan until they qualify as a physician / HVAC tech / similar.

1+2+3 ... try a scratch business

Best of all is a combination of 1+2+3 which is: (4) "provide capital for ideally non-depreciating assets so they can start a business". R believes the BobaTea fad has legs in your area; you pay to buy a shop, with easy rental terms for them, and they try their hand. R has some idea that renting out a crane would work in your market; you pay for the crane (note however the ideally non-depreciating part) and they get renting.

(2) is of the most practical benefit for most people, pushing them ahead by years or decades in the learning curve

(4) is by far the best, but, obviously 99.999% of business ideas are total crap

(3) is traditional but beware of the first sentence in this post

(1) is probably the most sure-fire, low-risk

Here's some tenets I follow when helping others:

• Don't support bad habits

  Don't give money to someone to pay gambling debts, or to pay rent because they've spent all of their money on less important things (drugs, alcohol, electronics, etc.)

• Give them what they need, not what they ask for

  I do this a lot with "panhandlers" that solicit me in a parking lot. If they "need gas to get to the next state", I offer to fill their gas tank instead. If they need food, I offer to bring them back sandwiches. 99% of the time they refuse and walk away.

• Ensure you're not making a bad situation worse

  If I give someone money, I talk to them about their financial situation first. How did they get into this position? Are they working as much as they can to support their spending? Are they willing to cut expenses to a manageable level? Are they using credit cards too much? I'm willing to help with budgeting, finding a job, etc. as much as I can to help get them going in the right direction before I give money.

So for "creative" ways it probably depends on the situation.

Have someone with gambling/drugs/alcohol problems? Help them get to a recovery program and make it a condition of your "gift".

Someone need money for food or rent? Find out why they're short to make sure they're getting enough income or aren't wasting money on other things. Help them put together a rough budget to control spending.

Someone need a car? Rather than cosigning for a loan, help them shop for a cheap used car that they (with your help) can pay for in cash. Teach them how to change their own oil (or just do it for them) to save on maintenance.

It's very hard for most people (myself included) to actually invest in someone's life and help them make good decisions, but it's much more effective than just writing a check.

Kudos to you to wanting to make the world a better place!

Maybe ask yourself, what is the best use of the extra money that you don't need?

$100 that you don't need could provide enormous benefits to people in poor countries (or very poor people in your own country) but only modest benefit to your friends and family who are presumably doing ok.

Consider donating more money to charity in a way that satisfies the proverb in your question instead of giving to friends and family.

Money doesn't fix money problems. Someone earning 50k a year and spending 50k a year has just the same problems as someone earning 500k a year and spending 500k a year.

Give away resources (books, podcasts, fixed fee advisors, etc) and tell people that you're available for them if they need guidance or pointers of other valuable resources they can find for themselves.

Sure, you might want to help some close people to buy some food and meds and doing that in a limited scale isn't necessarily a bad thing but it's important that it's rare enough so that the person doesn't become dependent on it.

Once someone is financially savvy enough to be relatively independent you can start helping them to escalate their runway by lending money or giving away small chunks that are not being used to promote consumerism (instead helping them with small businesses, entrepreneurship, buying smart low cost housings, investing in smart assets, etc) -- but old habits die hard so be prepared to forgive loans you make to people whose relationships you value more than the money, you might have to forgive it if they slip and are unable to pay.

Again, find a way to help people when they are making financially wise steps in their journey. Don't lend money that are meant to fix money holes related to money problems. You might have to make some exceptions to this in your lifetime to help a loved one avoid foreclosure or defaults but be fully aware of what you're doing and make it an educational moment for the person being helped out if it happens.

The most important thing is to keep enough for yourself so that when we go through the next financial crisis or a medical incident occurs for you or anything that could happen to you then you need to be able to get through that.

Just write a check

There's pretty good research that points to just giving money as an effect way to lift people out of poverty.

Bonus - you aren't going to harm your relationship with anyone by trying to manage their life.

"Invest" your time

Think of this as leading by example. If you spend quality time with people, you will rub off on them. They'll learn your good habits by watching you live them.

I would ask the people that you are giving money to...

What will you do to help others?

If the person is of good character I would allow a great amount of flexibility. "I would like to give you $4k each year for the next few years but would like to know that this is cascading. Whether that is helping a school, a charity, coaching kids, whatever.

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Now if this person has had issues with money, drugs, dealing with others I would handle this very differently. It isn't about paying their rent or basic things - as other have mentioned. I don't agree with this. They will just funnel the money that they don't have to pay for rent or food, to their bad habits.

Therefore the only way to deal with this type...

Make them work for the money. It is the same as above but you are assigning and requiring this.

I try to give money in a mutually beneficial way: this can be buying me and a friend video games we can play together. Paying for dinner. Or buying a new phone and giving away my working one. This way the recipient doesn't feel like a burden(I spent the money for my own enjoyment)

I just want to start by saying I absolutely love this question!

Note that you did not specify a monetary range, so I have provided suggestions that span the gamut.

Investing

Are you talking about adults only, or including children in your target help group?

For minors, setting up a UTMA/UGMA and buying them an investment can work, provided you're willing to use it as a tool to help them learn about saving and investing for the long term. If you're not close enough to get a full fledged investing account opened, there are services like stockpile.com that let you do it easily. This allows you to give money that isn't touchable until they've learned good habits and/or it's really needed (college age).

Matching

Another option is matching of some form.

For younger kids, consider matching a 429 account, to help them go to college. Or for teens consider matching funds for their first car. - Per Tracy Cramer's comment

For college students, offering to help pay for school by matching any cash money (not loans) they can put up at the time will encourage a strong work ethic. I would couple this with a requirement of a certain GPA, so they don't just let the schoolwork suffer in order to work. As a bonus, this makes post-school full-time work seem like a vacation.

You could also match earnings for someone who has a poor work ethic and difficulty keeping jobs. This provides an incentive for them to maintain financial stability, especially if they're having trouble finding good paying jobs and feel like their earnings are insufficient for the amount of work the jobs they can get provide. This would need a structured tapering system so that them earning more money doesn't mean an equal reduction in your help; otherwise there is no incentive to professionally grow.

You could match 401k / IRA investing to encourage saving for retirement. Even if they learn nothing, you may save them from poverty in old age when it's too late for them to do much about it.

Something They Can Use

Consider focusing on something that they can and will really use; buy them potential instead of a physical item.

For instance, a hard worker supporting a growing family can often hardly afford a used $50 P&S camera. If they love capturing memories with their kids buy them a nice dSLR that suits their needs; You're buying memories instead of buying a thing.

Know someone who always wanted to raise chickens for 'home-made' eggs? Maybe you can buy them the coop and chickens? Give them the potential to do something valuable that they couldn't otherwise afford the initial investment for.

Know someone with a large family that supports themselves well enough, but doesn't have a whole lot of 'extras'? How about buying them a pool, or a membership to a private pool?

Frivolities

You can avoid the money being wasted by giving them the kind of thing they might waste the money on. :)

If you know someone who works hard and is just managing to support their family, it could help quite a bit to send them on an all-expenses-paid vacation. Long-term stress can have serious health effects (physical and mental) that you could help alleviate.

Paying for an extravagant holiday dinner for those who couldn't afford it would be helpful in a similar way.

This section works especially well for elders in your life. Know someone who is retired and did well, but dreamed their whole life of owning a Corvette that they could just never attain? Buy them a two year old Corvette. You're not teaching anything or supporting good habits, but they may not need that. Maybe they spent all their money on their kids, or helping others...give them a reward.

Since it's family and friends that you are familiar with, you might offer to hire them to help each other out. This probably wouldn't work with strangers or acquaintances.

If somebody is bad about cleaning their house, pay the person who needs the money to clean it for them. If someone's is healthy and the other not, hire one to do the yardwork. Childcare is another good service for people who trust each other.

It might go smoother if you ask the people you want to help to send you a list of tasks that would make their life easier, and then offer to pay for those tasks to be done. Not everyone is comfortable being paid, and not everyone is comfortable having things done for them.

Talk to the persons you want to give money to and see what their goals are.

Some ideas:

1. Pay for their schooling - college, trade school, etc, almost universally more education is equal to better financial future.
2. Help them start a business. This one is self-explanatory
3. Even something simple as buying them a car can extend their reach and will have positive long term financial effect.
4. If none of these apply, maybe you can start a retirement account for them. Even a modest sum can grow over the years and have significant effect in their later years.

Perhaps look into sponsoring and supporting https://www.banqer.co/ in your families kids /local school. Banqer is a financial literacy tool/teaching game for kids in school.

Far more important than the 'what' in this question is the 'who'. If you want to have satisfaction with an investment, choosing the correct investment for your expectations is paramount. So if you are expecting to help someone and see them grow or have a better life, then the individual needs to be prepared and willing to accept your assistance. Otherwise, you may feel that your investment was not worthwhile. It would be very unfortunate if you became disenfranchised with your current plan and decided to stop trying to help because it wasn't doing any good.

If you want money to grow, you choose the right things to invest in. If you want to see people grow, you choose the right people to invest in. Giving someone money who makes bad financial decisions currently will probably not make their lives better. Someone who cannot manage $50K, will also struggle to manage $100K or $1 million. If someone's financial struggles are the result of a lack of skills, no amount of money will fix their problem. You could consider education for individuals in that group, i.e. free classes or personal instruction. But you may be disappointed that basic financial principles which seem so straightforward to you are hard for many people to understand. I think you will be much happier choosing individuals and families that are 'ready' for some financial help.

How do you choose a good candidate?

• Selfless vs Selfish - pick someone who spends more time thinking about others than themselves. You will probably be impressed with how they receive and utilize your gift.
• Choose a saver - people who save a little bit when they have little will not waste the money you give them.
• Choose a giver - It's easy to say "If I was rich, I would be generous!" Most people who say that will never be rich. I would look for the widow who gives a mite instead.
• Choose a worker - someone who has a good work ethic and good work habits has the ability to make a small gift go a long way.
• Choose someone who serves - That cheerful young lady behind the counter at the soup kitchen may be a good option.
• Consider the disabled - If you know someone that is simply not capable of taking care of themselves, consider giving them an opportunity to live with greater dignity. Even if they can't work, allowing them to develop a skill or talent that they can share or an opportunity to go someplace or be a part of something can be life changing.

I would say I have known many 'poor' people who are money wise, but are not wealthy because they have chosen to work more to help others than to help themselves. A close family member is an elementary school teacher, for example. He was absolutely 'killing it' in sales, but realized he had a gift with children that had certain learning disabilities and made teaching his career. He left a lot of money on the table, but changed countless lives - adults who look back now and say, "I hated school until I was in his class." This would be an ideal candidate for financial assistance.

Once you have chosen who to help, it's simply a matter of seeing where the gaps are in their lives and using your resources to fill them. Helping good people is so rewarding. Good luck!

It totally depends on circumstances.

I'm in the comfortable position I'm in right now in my life because a fried just lent me 20k after hearing my grandiose plan of buying a suit, going to an interview in a different city and moving there if I got the project. Risky, but it paid off.

Small amounts here and there might take the edge off things, but to effect an actual change in circumstances often requires an investment, which includes the possibility for loss if it doesn't work out, and which needs to be looked at holistically rather than in the details.

I'm just spending a lot of money on a kitchen, with lots of frivolous little extras like getting the expensive surface finish that costs me 200 extra now, but will likely make it easier to sell the entire thing to the next renter, so I expect it to save me a few thousand in ten years.

Also, keep in mind that responsibility and decision power go together. You cannot teach someone to be responsible if they have no influence over the situation, so be prepared to discuss choices (and their outcomes) that you want to keep a bit of control over, and try to keep out of choices that you don't care about.