How to Enjoy Giving Money Away

People often talk about charitable giving as though it were mostly a question of generosity. But I think charitable giving is also a skill.

And like most skills, it tends to become more enjoyable as you get better at it.

Think about cooking. If you don't know how to cook, making dinner feels like a chore. Every part of it is stressful, from picking out a recipe, to tracking down each item in the store, to guessing blindly at substitutions when the store doesn't have exactly what the recipe calls for.

Then you bring everything home for still more guessing as you slog through the instructions. Is this what it's supposed to look like? How do I tell when the onions are done?

Even after all that work, sometimes the food just doesn't turn out very well. You might end up wishing you'd just ordered Domino's.

But as you get better, the experience changes. You start to understand the rules, what works and what doesn't. It doesn't take so much constant effort and attention. You can get creative and cook from first principles rather than following every recipe quite so verbatim.

And as you relax, it actually becomes kind of fun.

The same thing happens with most other hobbies, I think. Skiing is mostly about falling down a lot at first. Learning a new language is an exercise in embarrassing yourself over and over. Gardening means killing dozens of plants.

At first, there's a lot of effort and not much reward.

I think giving money away is no different.

Someone who is new to charitable giving might respond mostly to whatever happens to cross their path. They get a mailer around Thanksgiving or Christmas and send a check. They round up a few cents when the machine at the grocery store asks them to.

There is nothing wrong with that. But it can make giving feel random, reactive, and surprisingly unsatisfying.

One of the biggest problems people run into is giving money away without really knowing what happened afterward. They don't see the impact, so they wonder whether or not it helped. The money seems to vanish into the ether.

Meanwhile, they keep getting peppered with requests to give more. And, perversely, donating money only seems to lead to more requests.

So it's easy to feel discouraged.

But rather than treat this as a problem with generosity, I prefer to see it as a chance to develop the philanthropic "skill."

Skills develop with deliberate practice. New chefs start with simple, forgiving recipes, rather than a four-course meal. They learn what they like to cook, learn some patterns, and build expertise slowly. 

Similarly, someone learning to give well can start with relatively small gifts spread across a range of charities and causes. You can study different causes and service models and start to see how organizations use their money. Along the way, you learn what feels personally rewarding, which causes you actually care about, and which organizations foster a real sense of connection and purpose.

One test I look at is quite simple: Does the organization send a thank-you note after you donate?

This may sound like a small thing. It may even seem to have more to do with my ego than with the organization itself. But bear with me.

First, there's nothing wrong with wanting to be acknowledged for giving money. You shouldn't need a parade thrown in your honor, but a simple "thank you, here's how your money is helping" goes a long way toward making giving a positive experience.

Second, I see donor follow-up as a small test of operational discipline.

My grandfather often said, "If you want something done, give it to a busy person." An organization that reliably follows up with donors is demonstrating that it has systems for doing an important part of its job well.

Conversely, think about what it says when your donation disappears without any kind of note or acknowledgment. It doesn't feel very good as a donor, and it raises a reasonable question: If this organization depends on donations, why isn't it taking better care of the people who have already chosen to support it?

Sending a thank-you note is really inexpensive. Postage, a card, a couple minutes of someone's time. Those costs are minuscule compared with a hundred-dollar donation, let alone a multi-thousand-dollar gift.

Third, a thank-you note can open the door to a more personal relationship with the organization.

That relationship improves the donor experience, but it can also create opportunities for future involvement, volunteering, and connections with other people who care about the same causes.

It's one thing to know, "Hey, that organization is doing a great job for kids."

It's another thing to have a personal contact there who will take you on a tour, show you the day-to-day, tell you what they're working on this quarter, and explain what they hope to do with future donations.

So don't underestimate how much personal relationships matter to your satisfaction and involvement. It helps to know people by name, and maybe even make some friends. You may also discover ways to contribute beyond your finances. Volunteering can be a lot of fun, and sometimes your time or expertise may be just as useful as your money.

There are financial skills to giving, too.

An important part of this, in my opinion, is integrating charitable giving with the rest of your financial plan.

Ad hoc giving can leave you wondering whether you're overdoing it or whether you're going to miss the money later. But when giving is part of a larger framework, perhaps based on your income, cash flow, or net worth, it starts to feel less like a sacrifice and more like a natural part of what your money is for.

That's how it feels in my own life, anyway. 

There are also ways to make those dollars work harder. You can learn when it makes sense to donate appreciated investments instead of cash. You can bunch several years of gifts into a donor-advised fund. You can coordinate charitable giving with unusually high-income years, retirement distributions, or estate planning.

Within an organization, you may also find opportunities to direct your donation toward particular projects. These might be projects that speak more directly to your heart, or projects that simply wouldn't happen without private donors.

This is part of becoming good at giving.

Early attempts may be awkward. You may support organizations you later decide aren't as compelling. You may give to causes because you feel obligated rather than excited. You may discover that something you expected to care deeply about doesn't actually resonate with you.

That's okay.

No one becomes a great cook, gardener, or musician without making mistakes. There is no reason charitable giving should be different.

You learn by doing.

Eventually, you may find a few organizations, people, or problems where giving money feels extraordinarily satisfying because you understand what the money is doing and you genuinely want more of that work to exist.

And that's when it gets really fun.

Start small enough that you can experiment. Pick something you're genuinely curious about. Learn who's doing good work. Give some money, and look for that thank-you note.

And then see if there's a day when you can come visit and learn more.

That's how you get better at giving. And, like most things, getting better at it is part of what makes it fun.