On Generosity

Generosity has always mattered to me, and I’ve been lucky to have it modeled so clearly by my family of origin.

As a kid, I knew that each holiday included a cookie-baking-and-decorating session that concluded with my mom driving us around to the homes of friends and family to doorbell ditch them with sweet, seasonal treats.

I knew that we carefully considered the types of presents we’d get for loved ones at Christmas and birthdays, and that they were wrapped, including card or tag.

I knew that my dad would pay for the meals of friends and family when he could, and that he always, ALWAYS left a good tip. Service was bad? Good tip. Service was good?  Great tip.

I knew that rather than throwing things away or trying to sell them, we donated anything we no longer used or needed.

If our teammates needed rides or an extra water or to share some snacks, it wasn’t even a thought.

If a kid in the ward was fundraising for football or an Eagle scout project, check written.

If any of us was invited anywhere, we came bearing gifts or side dishes or assistance or supplies.

This isn’t a financial flex; it never was. In fact, I observed that the flavor of generosity I liked best wasn’t broadcasted OR sneaky.

The flavor of generosity I liked best was WARM generosity. The kind that is visible to the recipient in a way that communicates love.

To me, generosity is giving whatever you can, when you can. Whether it’s money, time, attention, materials, friendship, the benefit of the doubt, wisdom, space, forgiveness, or the truth.

Generosity is an abundance mentality executed with an acts of service love language.

I was attracted to see this in Ryan, even in our earliest interactions. He, too, came from a family where generosity wasn’t just valued—it was practiced daily. My in-laws capacity for giving has been a source of awe and profound gratitude for me throughout my time as a Holdaway.

I want to be careful that what I say next isn’t classist or privileged or gross. Because I have seen with my own eyes some incredible examples of stingy selfishness from people far richer than I, and the most heartwarming generosity from people in dire financial circumstances. Generosity can be so quickly tied to financial success, privilege. And while I certainly value financial success and plan to pursue it my entire life, that’s not the central focus of this value.

I really cringe and find myself losing respect for individuals who lack generosity. Someone ruining a group dinner by getting really weird about the check. Someone refusing to contribute to something, always choosing the lightest lift, and constantly benefitting from the larger contributions of others. Someone who has a hard time feeling happy for others, or who turns everything into a zero sum game—where THEY are more deserving than others, THEY must be the recipient.

I think, at its core, my generosity value is anti-competition. It’s the belief and the practice of mutual winning. Whenever possible, helping one another win is the choice that will make all of us happier, all of us better. I didn’t get here without the boundless generosity of so many in my life: parents, grandparents, aunts, uncles, teachers, coaches, church leaders, friends, coworkers. And there are people who will need my generosity to get where they want to go.

Of course, generosity is a value that, if unchecked, can become dangerous quicksand. In Radical Candor, Kim Scott explains the concept of Ruinous Empathy, which is basically toxic niceness. Born and raised as a female in a high-demand patriarchal religion, I’m familiar with the give-give-GIVE expectation. We should always give. And do. And care. And say yes. And give some more.

The Giving Tree made flesh. The Little Stream, running tired and dry.

I don’t think it’s a coincidence that birth rates, marriage rates, and “traditional” female gender roles are in decline. I think giving without boundaries, without a sense of WHY or SELF within that generosity, is cancerous. It’s unsustainable, and it leads to resentment (the opposite of the energy we’re trying to create).

So how will I practice generosity without burning out or becoming selfish and miserly? I’m not sure there is a line in the sand that makes sense to me. Sometimes giving when we don’t want to is meaningful, so “If it’s not a HELL YES then it’s a HELL NO!” doesn’t work for me. Sometimes we have some form abundance that someone could use, but it will change the relationship and their abilities to grow if we give to solve a problem that isn’t ours to solve.

How can I instill this value in my kids, knowing that some of the magic of generosity is lost if forced or sanitized into an equation?

I don’t know.

Against my more orderly inclinations, I’m gonna try to lead with feelings. If I have time, money, effort, supplies, encouragement, or a bucket of popcorn that I can share, I am going to err on the side of sharing whenever possible. If it feels good to give, I’ll give. If I feel sus, I can pause. I won’t extend generosity that hurts my family or my life, no matter how much it would mean to someone beyond that tight circle. I won’t live life as a zero-sum game, but I do understand opportunity cost, and my generosity needs to create opportunity—not sacrifice it.

If I can’t give with no strings attached, with no expectation or judgment or need for reciprocity, then I’ll set a boundary for my generosity or decide it’s not my role to give in that moment.

I will be generous, for others have been so generous with me.

And because generosity makes the pie bigger for everyone. It just feels good.

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