Ruth Olson’s parents had reached a point in life where they had everything they needed, or could buy it themselves. So the Minneapolis woman was baffled about what to get them for Christmas.

Then Olson thought back to the holidays of her childhood. Frugal throughout the rest of the year, her parents had always gone all out at Christmas — honoring the special requests of her and her five siblings.

Olson decided to carry on this tradition by giving to other kids. She bought a cartload of toys and donated them to Toys for Tots. Then she wrote a heartfelt letter to her parents, wrapped it and put it under the tree.

“I was nervous on Christmas morning for them to open it — what if they didn’t like it?” Olson recalled. “But I knew immediately that I had made the right choice when my mother got no more than two sentences into the letter and started crying.”

Her father read the rest of the letter aloud, spurring a conversation about the family’s memories and how they were being carried into the next generation.

That was 23 years ago. Every Christmas since then, Olson has honored her parents by donating to a charity significant to their lives. Her siblings joined in and made donations of their own. As her own children move into adulthood, Olson’s parents have started contributing to important organizations on their behalf.

“All throughout this, my children have seen and participated in being part of the larger world community and recognizing that a little help can go a long way,” Olson said.

How hard can it be, giving money to a charitable cause?

Making charitable choices

You probably encounter almost daily opportunities to make handouts — clipboard-clutching volunteers at your front door, or a neighbor’s kid selling wrapping paper for a school fundraiser, or a page someone posted on Facebook, or a guy at the stoplight holding a hand-scrawled cardboard sign.

It’s tougher, though, if you’d rather your giving be planned rather than spur-of-the-moment or guilt-induced. There are so many worthy causes in need of financial support: anti-poverty campaigns, associations fighting various diseases, environmental groups, arts institutions, animal welfare organizations, education projects ... the list goes on. And of course each of those activities can be subdivided: Advocacy or research? Local, national or international? Large and well-established or small but spirited?

At least there’s no shortage of possibilities. In the United States, you can choose from more than 1.5 million charitable organizations.

But where do you start?

Searching the heart

Some experts who work with nonprofits and donors suggest making decisions using both the heart and the head. Find a cause that closely aligns with your values (heart), then research organizations devoted to that cause to select an effective one (head).

Start by figuring out what you care most about, perhaps by examining your experiences and values. Did a loved one suffer from a disease you’d like to see eradicated, or receive help from an organization in a time of need? Are you distressed about families in poverty or damage to the environment? Do you feel passionate about animals or art or literacy?

“I really encourage people to think about things like, what are the values that they have that drive them to want to make a difference in the world?” said Robyn L. Schein, director of the Family Philanthropy Resource Center at the Minneapolis Foundation.

Enlisting the head

Once you’ve selected a cause (or causes) to support, it’s time to research. Google can guide you to organizations focused on your issue. Check their legitimacy through the Better Business Bureau and the Minnesota attorney general’s office. If a tax deduction is important to you, make sure it’s registered with the IRS as a 501(c)(3) nonprofit organization (unless you’re getting a product or service in return, in which case your donation is not deductible).

Narrow the list and dig further. Make sure the organizations are what you think they are (beware of sound-alike names). Go to websites that break down their budgets, and check how much they spent on overhead and fundraising relative to programs directly addressing their issue. Evaluate their transparency, governance, leadership and effectiveness. Don’t hesitate to call the organizations themselves and talk to staffers; good charities welcome your questions. You can immerse yourself even further by visiting the headquarters or even volunteering your time if opportunities are available.

The more involved you are with an organization, the better you’re likely to feel about supporting it.

Involving the family

Schein encourages parents to discuss their charitable giving choices with their children — the organizations, if not necessarily the dollar amounts — and even, when possible, to involve the kids in the process. She knows of families that require children to donate part of their allowances, letting the kids choose the causes.

Schein enlists her own children to give to an annual food drive. “Instead of raiding [our] own home pantry, I take them shopping. They pick out the food they want to donate. I have the kids think about, ‘What if you didn’t have a whole pantry to pack your lunch every day? Others don’t.’ It’s very relatable to them.”

Planning for spontaneity

Kris Kewitsch, executive director of the Charities Review Council in St. Paul, suggests setting aside some of your donation budget to requests that pop up throughout the year — the neighbor kid’s wrapping paper, the GoFundMe plea, even the guy with the cardboard sign.

Some experts might say donating to an organization helping the homeless would be more effective than slipping a stranger a $20 through your car window. But there are no wrong answers, Kewitsch said.

“Philanthropy is an art and a science,” she said. Return on investment is not everybody’s top priority.

On the other hand, Kewitsch said, if you’ve already determined your priorities, you can feel equally comfortable keeping the window closed, scrolling past the Facebook post, maybe even politely turning away the neighbor kid.

“It’s about using your head in order to feel good about saying yes to an organization — and saying no.”