How to Write About Tough Topics, with Jennifer Risher

Tough topics come in all shapes and sizes, but mostly when we talk about them we are talking about grief or loss of some kind. But those are not the only tough topics out there. Jennifer Risher is the author of We Need to Talk, A Memoir About Wealth, and she and I had  along, textured conversation about how to write about tough topics since hers is one of toughest topics there is – money. I met Jennifer online when she consulted me about her manuscript a few years ago and was fascinated by the complexity to telling this tale. Jennifer joined Microsoft in 1991, and with her husband experienced the financial upswing of the dot-com boom. By their early 30s, they had tens of millions of dollars. What you may not know is that there are millions of people like them. So, in terms of marketing to a group of book buyers, this book could have been written solely for those people, but it’s not. It’s written for us all, since she definitely takes on the taboo of talking about money. Listen in and read along as we talk about how to talk about how to write about tough topics.

Jennifer: Hi, Marion. Nice to be here.

Marion: I’m delighted. So didn’t an earlier draft of your book have the word “taboo” in the title?

Jennifer: It did. Yes. When I started out to write this book, it was 14 years ago and I thought I’d write a book in a year. Actually my first title was “Embarrassment of Riches.” I worked on that title for many, many years. Then the book became “The Tiniest Violin.” From there it was, “It’s Not About the Money.” And then it became “Confessions of a Rich Woman.” Then when I was lucky enough to work with you, it was “The Last Taboo.” And from there, it turned into “What We Don’t Talk About When We Don’t Talk About Money.” And then finally landed on, We Need to Talk, A Memoir About Wealth.

Marion: I love you telling us that. The honesty there suggests to the listeners that we’re going to get lots more of such honesty and you are because I know from working with you, that’s how you are. So the acceptance that this took a long time and that it morphed during that time, is that part of talking about this tough topic? This one is taboo, is part of why it’s so hard to talk about money. Is that part of why it took 14 or so years to write this book, is you learning along the way what you were really talking about?

Jennifer: Yes, absolutely. I guess it really started out me trying to figure things out for myself, sort of a form of therapy to start writing. It is a tricky topic. How do you write about money in a way that isn’t off-putting or offensive, especially when you’re writing about having a lot of it. It’s tricky. So, yeah, it took time. Part of the time it took me to write was really me teaching myself to write. So in addition to kind of grappling with how to talk about money, it was, how do I piece together my experiences in a way that’s compelling. It felt like a puzzle to me and it was a puzzle that I loved. So I hear writers worrying about like, I have to sit at my desk for X number of hours, or I have to force myself into everyday at three. I really woke up and ran to my computer to try and fit this puzzle together.

Marion: That’s wonderful to know because I run into all matters of writers, writing about all matters of tough topics in my editing and coaching world. And whether it be addictions, abuse, bad decision-making, it runs the gamut of human behavior. But sometimes knowing we’re taking on a tough topic can color the reporting and the writing. But what you’re saying in your case is it actually got you to dig down and figure out what you thought about it. I think that’s a wonderful thing for people to know. I always tell people that memoir is the single greatest portal to self discovery, but you’re kind of testifying to that effect. So that’s fascinating. But why is money so hard to write about?

Jennifer: Well it’s an emotional topic. We don’t tend to think we think of numbers as being not emotional, but actually it’s a lot more than numbers. Yeah, the more I kind of dug into it, the more I realized I need to get to those emotions. With memoir, I guess the more you can really touch on your own truth and share that, the more universal it ends up being. So I really worked hard to be honest with myself about my experiences and figure out what it meant to me, what I really felt about things. Money is very, very emotional.

All of us have a money story and it starts in childhood and we learn all sorts of approaches and perspectives and expectations around money. The emotions we have, I mean, it’s pretty universal. When it comes to trying to talk about money, I think we have a lot of fear, a fear of being rejected, of hurting other people’s feelings, of not measuring up, sounding unknowledgeable. I’m hoping that my book will help all of us move through those fears and get a little bit uncomfortable and examine our own relationships with money so that we can communicate and connect with each other in ways that we’re not right now.

Marion: Yeah. The truth that you tell, the truths that you tell are so important to the story. You published a piece, a pre-publication piece in Psychology Today about wrestling with wealth, in which you reveal that you were a child who grew up in a home where teabags were used three times. You talked about how saving gave you a sense of self worth and value as a responsible daughter, and it made you feel worthy of your parents love, saving. And that as you gained worth in your adulthood, nothing less than your identity became at stake. So that is a fascinating amount of truth to come to.

In the process of your writing this, it seems like you figured that out. Did the figuring out lead you to do reporting outside? I mean, I know it did. So let’s talk about figuring it out in the large sense. You did a lot of reporting for this book. So why don’t you give people a sense of who you talk to, to build this sense of this argument you have about identity and self-worth and how you can find a new genuine home to live in, vis-a-vis one’s worth. Who did you talk to? Who did you interview?

Jennifer: The interviews came really towards the end of my writing process. A lot of it was me and me and thinking these things through and really grappling. Grappling with this issue of identity, because yeah, I got a lot of my sense of purpose and meaning from circling the block until I could find a free parking spot, and not paying too much for raspberries because they were out of season, and not paying an ATM fee. Even when I suddenly no longer had to worry about those things, I was worried about those things because it was just so part of who I was, and in many ways the values I grew up with, many of them have served me very well and they continue to serve me well, but there’s that sort of existential question when all of a sudden you’ve had this fantasy come true and you’re still living as though you were barely able to kind of get your bank account in order.

The other piece there I guess, is growing up believing a little bit like those people who have a lot of money are different than us who don’t and confronting that actually eight out of 10 people with wealth grew up middle class or poor. So they are you, and they’ve gotten lucky and they’re still human beings. One of my worries was, is all this money going to make me obnoxious or aloof because those were the images I had in my head. So I had to grapple with that too and realize actually, I’m not. You can ask my friends, we’ll see. But I don’t think that money has made me obnoxious. Actually what I’ve learned is that money doesn’t change you as much as you might expect. In fact, I feel like money reveals more of who you are.

Marion: Yeah. That’s what I love about the book. To me, the book it absolutely is a conversation about money, but for me, even in its earliest version that I read, I remember specifically saying there’s a real hero’s tale here, specifically with you trying to get to your own true home, that state of comfort with what you had gotten in life. You can achieve things and never be comfortable with it. We know this, particularly with women. We can say yes, but. Yes, but I still have that five pounds. Yes, but I still don’t like my, fill in the blank, my ass, my hair, my whatever. Yes, but. So the idea of developing comfort with that when the comfort of your life is so abundant, to me seemed like a real hero’s adventure.

People might think, well, that can’t be so hard. Let me try that. That must be great, but try writing about it. I say to people, because what you do is to describe and define some real identity challenges, and they only work because of what we mentioned before, that honesty. So those identity challenges, did you identify them as you were writing, did you know going into that, that this is where you’re going to have to go? They can be really huge obstacles to writers writing about challenges to one’s identity. Can you just give us some sense about how you identified those and then how you assigned yourself the task of reporting on how they were challenged and changed?

Jennifer: Yeah. So one of the things that happened to me while I was writing is, and I’ve heard this happens to people, but it’s sort of like the story was guiding me and telling me things. I was learning from my own writing, which seems very strange.

Marion: No, not to me.

Jennifer: Yeah. You know this. Actually, you were helpful in helping me make sure that the character that I was writing about, which is me, had this nice arc. So that was very helpful when we worked together. But one of the things, for example, my husband joined this small unknown bookstore that was selling books on the internet that ended up being Amazon and the company went public. This is the same moment really, that our first child was born. I remember this curtain lifted for me as I entered motherhood. I thought, this is amazing and incredible. I can’t believe how much I love this baby.

I joined a mother’s group and all of us new moms really bonded over all these ups and downs and experiences of like, should we let our baby cry it out? Or should we use a pacifier and how’s breastfeeding and how are your in-laws? There are so many issues that we had common and that we shared. I was in this amazing connected world. And at the same time I realized there’s this other curtain that’s lifted. Suddenly we have more money than we can wrap our heads around and that world is kind of a lonely, silent space where I wasn’t talking to anybody about all these things that were coming up for me. I mean, I think a lot of people think, “Oh, the wealthy only worry about people liking them for their money.” But I wasn’t worried about being liked for what we had.

I was worried about being hated for it. I didn’t want anyone to know and sort of diving into the realizing, wow, how difficult that was for me at that time. I write about this in the book, that experience of being part of that mother’s group and wanting to share and feeling so connected, but then also worrying that people wouldn’t think that I could relate to their experiences when I felt just like them. I still was my same self. The most important thing to me was that baby and our connection. I wanted to be part of the group, but when they were talking about what stroller to buy and how expensive it was, I felt like I couldn’t join in because I was worried about being judged and having people look at me different. I mean, I tried to keep our money a secret at that time. When you have something in your life that you’re trying to hide and keep secret, that’s not a good place to be.

Marion: It’s not. The idea of it being bounty is particularly complicated. What I found fascinating, one of the things I love about this story is how charity helped shape this acceptance and change. Not that you just found a place to dump a lot of money and feel good about it, but that it gave you a place to reflect that it helped meld a more nuanced personality and character with the acceptance and responsibility of what money can do. You and your husband have done some really magnificent things with your money these days, in terms of giving back that I found as much a part of the story as anything else.

So can you just talk a little bit about how you write about charity and with that kind of truthfulness? You really write in it about it in a very nuanced way. It’s not just, “And then we gave away half our money and we feel much better.” It’s not that at all. It was really a reflection point and a learning place.

Jennifer: Just as we all have a money story that sort of starts in our childhood, I think we learn about giving and charity in our childhood, or we don’t learn about it. I didn’t really learn about it growing up. My mom and I took canned peaches to food drives and we took clothes to the Goodwill, but I didn’t ever learn about giving financial donations. That didn’t start until I was part of Microsoft and gave a percentage of my paycheck to United Way. Then I began to give back to places that had given to me, like we gave to NPR, we gave to my mother’s group that was organized by a nonprofit. There was a period of time where I really wanted to do more.

I felt a responsibility and an obligation and a desire to do more, but I was overwhelmed because I thought I had to do it right. I had to do it perfectly. I wasn’t sure where to give, how to give, who to give to. I felt like I needed to plan. It was more overwhelming than people might guess. I came to realize how, as you can sit in a sense of gratitude, it becomes easy to just give from the heart really and to realize that giving is very expressive. It’s expressive of who you are, it’s expressing your values. It doesn’t matter how much you give in terms of money. I think if we open our hearts to each other and give from the heart and do our best to help each other, we can all feel that sense of gratitude and generosity.

It’s been sort of a evolution. I mean, at first, the thought of giving $5,000 felt like so much. But then just as I learned to spend and be okay paying for parking in a lot or buying the raspberries, I also learned about giving. As I gave, I gave more and more. It just feels like part of my life. It’s something I feel very privileged to be able to do.

Marion: I couldn’t help but notice in your recent letter to The New York Times, you had a letter to the editor published in which you do a wonderful thing. You make a really good, solid criticism of the publishing industry. I thought, she’s got a book out, she’s got a dog in this fight at this point. Yet you clearly had a good look at what you were reading about the publishing industry in America. You realized that one of the major publishers, 79% of the workforce was white and that the diversity wasn’t there and you teed up and wrote a piece and said what you had to say.

So there seems to be a development of voice here that I don’t know if you always had. Did writing the book make you feel that you had more of a right, a privilege, a responsibility to comment on the injustices of life? You certainly could have left publishing out of this and just let them publish your book. But I was kind of fascinated by teeing up that criticism accurate as it is, but not everybody would have done that with a book coming out.

Jennifer: Thank you, I think. Yeah, it’s interesting because as a writer, the writing process is one thing. It’s very internal and contemplative and you’re alone, and you’re spending time by yourself. Then when the book was released, you have to put on this very different hat. Suddenly you are a voice and you have to be present and you have to be out there talking to people and figuring out what your message is. It’s really just been in the last few weeks that the book has been out, or the leading up to it and thinking about, I’m going to be on a book tour and what am I going to say and how am I going to present myself and what are my goals?

So, it’s been the process of thinking through, okay, I am getting published, that I have found my voice in a way that feels more powerful than I would have guessed six months ago. I mean, my goal really is to help us talk about a subject that all of us need to be talking about. Part of that is to help the millions of Americans like me, who have more money than they had growing up or more money than others in their extended family, or than their friends, help them talk to each other and learn from each other. But I also, and this may sound far-reaching, I also really hope that these conversations can help us fight income inequality.

I’m not happy with where we are as a society. I hate that there are so many people in our country going without, without healthcare, without housing, without food. There’s an education crisis. I mean, we need to start talking to each other and I’m hoping to shake things up. I mean, our silence kind of keeps the status quo in place.

Marion: Absolutely.

Jennifer: When there is a large and influential segment of our population that isn’t talking to each other, you might think, oh, all wealthy people are just talking. No, we’re not talking to each other. We feel isolated because wealth can be isolating. We feel estranged. We’re probably not at our most empathetic or generous, and we’re not necessarily holding ourselves accountable or inspired to make change. I really hope that my book becomes a catalyst for a conversation that sparks much needed change in our country.

Marion: Me too, and I think it can. I think you did everything right. When the book first came out, I wrote a piece in one of my newsletters about here’s a writer that did everything right. You did. Well, you did. I mean, I tell people all the time, write a short piece, write it in some place like Psychology Today, write something in the New York Times, write an op ed, write a letter to the editor, write, write, write, write, write. Get your platform out there.

Let’s talk about that for a minute because you have a website, which is very lovely. It’s very trim. It’s not filled with extra stuff. It sells the book and it’s JenniferRisher.com, which I advise people to do. Get your name, make it clear what you’re here to do, make sure I can get in touch with you, have a good regularized response to when people try to contact you. But you’re also set out to write some pieces. I want to talk to you about that, that decision to write a piece for Psychology Today on wrestling with wealth. That was published in May 2020. So how did you decide what to pick from the book and when to deploy it in the run-up to the publication?

Jennifer: All right. So, I’ll be honest with you. First of all, my book was supposed to launch in May. So that piece was supposed to be timed to the release of the book. We changed the release date because of COVID, which I’m very glad we did. So Psychology Today, I hired a publicist and she started working on getting me out there and getting me to write articles because you’re right. You need to start that conversation before the book is out. So they approached me and they made the suggestion of doing an excerpt in that chapter two, where I talk about my family and background.

So, they started it out and then it was actually a great process because I really felt I wrote and I sent it in and they gave me suggestions. So it went back and forth several times and I think it turned out nicely. It ended up being really great to have that piece out there. Maybe a little bit longer than I might’ve chosen. I thought the book would come right out, but having that out there and being able to kind of point to it as I was talking about the book was helpful.

Marion: Yeah. I always advise people to test your ideas on the public. So in terms of your publisher jumping back the publication date of your book but having that piece out there, I think was deeply helpful. Many people do hire a publicist for either a limited run or a more substantial run for help and contacts so that we can start to pepper the publications with your work. Then we can build some interest for the book.

I also like the fact that you told it short. It was a two-minute memoir. It’s one of Psychology Today’s signature things, and it got it all in there. It suggested to the reader that there was more, that you got all of my interest in there, but it suggested to the reader there’s more, which is exactly what you want to do is to tee up the reader for the interest in the book. So nicely done.

The platform that you’ve created for yourself again, it’s very tight. It’s not a big website. You’re not blogging. It’s pretty, it’s smart. You’ve got the book cover. Did you get advice from a pro? I’m assuming you got just professional advice on that. Just give people, young writers, maybe first book, this is your first book. Just give somebody a little bit of sense of what the advice was you got on how to represent yourself online, please.

Jennifer: That was me. So, I like simple. I like direct.

Marion: Oh, good.

Jennifer: Yeah, simple and direct. I looked at a ton of websites. I just went to all sorts of author websites and I could see what I didn’t like and what I did like. The simpler, the better, and the more straightforward, cleaner. Then I went through the process of hiring a website designer. Again, I talked to the people, I interviewed people and found one that I would highly recommend. I loved working with her and she has been a great relationship. I’m really happy with my website. Yes, I really focused on, I want the book upfront. I want to give people links to how to buy it, give a brief summary of the book. I included some of the endorsements on that.

Then I have a page for press, a page for events, and just really kept it simple. Everyone will tell you that you have to have this social media presence. I’m not a big fan of social media. I am now putting up with Facebook just because I have this book out, but I don’t like it. I mean, I thought it was wonderful when I first got on Facebook and I could connect with people, but I don’t think it’s a healthy space to be in. I certainly don’t like Twitter. I think that’s very aggressive and I’m certainly not going to say anything about wealth and money on Twitter because that’s a no-win place to be.

So I tell people and I guess I maybe did get this advice because I thought, oh my gosh, do I have to get on Instagram? Do I have to build all my friends and all this? Someone said, if it doesn’t feel in sync with who you are, no, you don’t have to do it. I think that is my recommendation to people is, stay true to who you are. If it doesn’t feel right, it’s not right for you. Listen to your intuition. Trust it.

Marion: Good. I think that’s exactly right. Because so many people, especially some of the people that I know that are a bit older, the idea of going off on Instagram is uncomfortable. You’re right. A conversation about wealth on Twitter could be certainly defined as unproductive right now. So as we start to turn for home on this, one of the things that I love that came out of your life and that we get from reading your stuff is that you and your husband David have founded, or your husband is a CEO of World Reader, a nonprofit he co-founded with a mission to create a world where everyone is a reader.

You and he launched Half My DAF. The book publicizes those, those publicize the book, the Psychology Today piece kind of starts it off, the letter to the editor. All of these are part of a piece, but they’re very interconnected to me. I would just like you to explain to people what Half my DAF, or maybe you say Half my DAF, maybe that’s it. It’s the rhyme. Half my DAF, what the DAF stands for and what it is that ultimately has come out of this new home that you find yourself in. What is that nonprofit?

Jennifer: Thank you. Yes. I will answer that question, but I do want to say, I’ve been asked, how do you use your wealth for good? I’ve thought a lot about that. I think the real question is, how do you use your life for good? We have wealth as a tool that is an amazing tool that has given us time and resources, but how do we build a life that’s meaningful and that does feel like it has purpose? So my husband, yeah, he co-founded and is the CEO and works full, full, full time on World Reader to get digital books into the hands of kids in the developing world. He’s coming to the United States and he’s spent the last 10 years of his life a hundred percent focused on this nonprofit.

I’ve spent a lot of time reading or writing and I’m now out talking about my book. So it’s living, it’s trying to be the best person you can be. So with Half my DAF, DAF stands for donor advised fund. And what a donor advised fund is, it’s a charitable vehicle. So let’s say you have some event in your life and you have some extra money or you want to put some money aside for giving. You can put it into a donor advised fund and you get a tax break up front. Then it allows you to organize your giving, so you can give over time.

It’s sort of like a charitable checking account. So in a way it’s a very nice vehicle, but what’s happened is that people are opening these donor advised funds, they’re putting their money in, they’re getting their tax break, but then they’re not moving the money through. They’re not putting that money to work to help people. A bunch of money is stuck in donor advised funds and actually $120 billion is stuck in donor advised funds.

Marion: That is a bunch of money.

Jennifer: It’s tragic. So actually when COVID struck and my husband and I were thinking, what can we do? We want to help people. We want to help nonprofits who are no longer able to raise the money they need. They’re working harder than ever. We want to give to nonprofits and we were going to give just ourselves. But we realized if we put up a million dollars as a way to inspire others to give with us, and we asked people to half their DAF, spend out at least half of the money that’s in their donor advised fund, we will match grants wherever people want to give. We don’t care. Give, give, give. That was our message.

So it was really rewarding because we got in five months, our million helped move $8.6 million into nonprofits and helping nonprofits in environmental, community, food banks, racial justice issues. It was everywhere. It was so wonderful to hear from donors, hear from nonprofits to feel a sense of community building. Donors told us this is the nudge I needed. They’d said, we’re sitting around the dinner table now talking with our adult kids about what we value, where we want to give. We’re having money conversations that we wouldn’t otherwise have had.

Nonprofits are also so grateful that we’re pushing more giving. The nice thing there is that nonprofits are starting to build better relationships with donors because in the end it really is all about building those relationships. So, thanks for asking. It’s been a really wonderful way to give back and to kind of help boost our community right now when there’s so much need.

Marion: It’s wonderful. I love that there’s a book at the center of it. I think that that says a great deal to everyone in terms of inspiring what books can do, what a writer can learn while she’s spending 14 years throwing titles around in her head, getting behind each of them, but really pushing into her own story. She may reveal many things and what may come out of them may surprise us. But one of the things that came out of all of this is this remarkable generosity and thoughtful purpose of life. Thank you. Thank you for spending the time with me today, Jennifer. I’m really grateful to hear from you again, and I’m just damn happy for the book. So congratulations.

Jennifer: Thank you so much.

Marion: You’re absolutely welcome. So that was Jennifer Rischer and her new book, We Need to Talk, A Memoir about Wealth. It was just published by Xeno Books and is available wherever books are sold. See more about her at Jennifer Risher dot com. I’m Marion, and you’ve been listening to QWERTY. Subscribe wherever podcasts are available. QWERTY is produced by Over It Studios in Albany, New York. Reach them at overit studios dot com. Our producer is Adam Claremont. Our assistant is Lorna Bailey. Want more on the art and work of writing? Visit MarionRoach.com and take a class with me. Thanks for listening. Don’t forget to subscribe to QWERTY and listen wherever you go.