Back in the days when I worked at Planned Parenthood, I would joke that as a sex educator I was great at oral sex. In other words, I could talk about sex all day. I would sometimes tell teens that they should get better at oral sex, talking about it more and doing the deed later. I have told university classes of mine for years that I had a very specific rule about having sex with anyone. If I don’t know your middle name, we will not be having sex. I suspect that sounds really basic, but it precludes very many common mistakes people make.

Students would sometimes say, “Do mean I should just ask someone her middle name?” Hmmm. It seems like a good alternative to just going for it. When we find asking someone’s name is too embarrassing, then having sex with them is too thoughtless.

But think about my point: When you are a sex educator you need to be fluent in the language of sex. You should be able to say penis, labia, vagina, clitoris, anus, condom, oral penetration, and frottage without flinching. Doing so is awkward at first, but you get used to it with practice. During my first weeks at Planned Parenthood, I would stand at a mirror and for minutes on end say, “Penis, vagina, penis, vagina, penis, vagina…”

I have been experimenting this past week with communicating about another taboo topic. I have invited over 100 people who subscribe to this blog to comment on the topic. Through social media, I have invited more than 500 more to do so. Thus far, fewer than 10 have taken me up on the challenge. In some ways, this is not surprising. After all, we don’t know each other’s middle names.

The topic this week has been generosity. Giving.

I personally want to get as comfortable talking about philanthropy as I am at talking about sex. For some, that is not a high enough bar. Parents of infants and dog owners might want to get as comfortable talking about generosity as they are at talking about poop. Each person will need to set their own higher bar.

Wouldn’t it be great if we could all get smarter about giving? For example, long ago my parents told me what tithing meant, encouraging me to give 10% of my $.50 allowance in the collection basket on Sunday. There was an expectation in our church that we should aim at giving 10% of our income to the church. I recall how silent and irritated they became when I asked if they tithed, if that 7was before or after taxes (gross or net), and so on. Today, I might have included the notion of earned income and investments. And what about net worth?

The guidance of tithing is flawed in many ways, but at least it is a relatively clear concept. For some time now, I have been contributing a minimum of 10% my net income in charitable giving annually. More recently, I have managed 20% of my gross. I say this not to suggest a standard, to brag, or to offer a challenge. I am writing about this to become comfortable talking about philanthropy.

Penis, vagina, penis, vagina, penis, vagina.

For me, part of the conversation depends on why I give. I do so because I want to support movement on the things about which I care. I give because I am passionate about people and our common good. I give in appreciation for what I have received. For example, I had a lifeline at ages seven through 10 in the Boys’ Club of Milwaukee, now the Boys and Girls Club of Milwaukee. In 1955, the Franklin Place club was my Saturday respite from school, my neighborhood, and my family. Clubs like the one my buddy, Gatlin Dresidan manages today are far different than the one I went to sixty years ago. But some stuff has not changed: staff are still augmenting budgets with their own resources and fund-raising so that youth will enjoy safe spaces for social and emotional skill development outside of school time.

The conversation about philanthropy for me also relates to qualities of the organizations to which I give. I have worked in public schools and non-profits my entire adult life. Following stints in manufacturing, technology, and hospitality, I knew that these were not for me. But I also recognized that the workers in the Midwest are amazing for our industry and loyalty. Many places I worked prior to landing in Milwaukee Public Schools seemed to make money despite themselves. I would argue that their products were really good because of their workers, not their management structures or their relationships with their workers. So now when I give to organizations, I am very interested in learning how workers are supported in doing their work. I prefer those where workers have what they need to do well. So I generally give to general operating expenses instead of to a new building fund or specific program.

My talking about philanthropy has also required me to look at leadership, mine and others’. I have mentioned in an earlier blog post the extraordinary leadership team Ray Crossman and Joy MacPhail have assembled at Adler University. I would be remiss if I failed to note similarly the leaders of After School Matters, Boys and Girls Clubs of Chicago, Diablo Ballet, Diverse and Resilient, Heartland Housing, Heartland Human Care Services, Milwaukee Ballet, Planned Parenthood of Wisconsin, United Way of Greater Milwaukee and Waukesha County, and YWCA of Southeast Wisconsin.

Valentine card from Paul Mandracchia, 1957-2014

Ultimately, however, philanthropy for me comes down to love. How do we sufficiently express the joy, awe, appreciation, and wonder of living, for the world, and for the billions of us who share this life? When I feel the challenges of my life today and in the past, I confess I am not comforted by the advice of Mary Poppins to whistle a happy tune. While I do like brown paper packages wrapped up with string, they do not assuage my feelings of fear, hopelessness, resignation, or futility. I do not believe in silver linings. I find that continuing to lean into the wind, building muscle, resolving a challenge, noticing my passions, showing myself, engaging deeply with others, and resolving to stick with things beyond the point of reason — these give me comfort. This is my philanthropy.

I resolve this year to keep practicing my communication skills in philanthropy. I will likely do so in front of a mirror, with a friend or two, or with smaller groups of people. I hope you will join me.