Hey there!
Had a great Substack chat with , author of the Healthy Rich Substack (money talk for misfits) and the book You Don't Need a Budget. Our conversation covered her path from freelance writer to personal finance expert, the development of her concept of "budget culture," and her practical approach to maintaining a newsletter while writing a book.
We talk about how her working-class background gave her a different perspective than her colleagues in financial media and the story behind her essay for Culture Study that unexpectedly led to a book deal.
Dana generously shared straightforward strategies for managing newsletter content while tackling a book project.
This interview has tangible, practical wisdom for writers juggling multiple creative commitments.
For the reading-over-watching crowd (I see you and respect your choice), I've included the complete transcript below so you can get all the details about what she’s up to. And for those of you not on Substack, you don’t have to leave your inbox to enjoy our conversation.
Over the next few months, you'll see 1-2 of these interviews in your inbox. If you'd rather catch them live (and perhaps witness my occasional camera awkwardness in real-time), you can download the Substack app using the button at the bottom of this email.
Happy reading,
Dana's journey into personal finance writing
Jen: Let's start with your background. How did you get into personal finance writing?
Dana: I started writing about personal finance accidentally. I was working as a freelance writer for four or five years, just scraping by without a niche. A job opportunity came up with a team I really wanted to work with—an editor, Alexis Grant, was building a team for a personal finance media startup called the Penny Hoarder. I applied, thinking I would just put up with the personal finance topic, assuming it would be pretty boring.
But I ended up staying in that job for four years, and 10 years later, I'm still writing about personal finance. I enjoyed learning about the topic because it had felt so obscure and inaccessible to me growing up working class. Financial education wasn't something we focused on in my family.
When I started at the Penny Hoarder, most financial information online was about turning money into more money through investing. I enjoyed what we were doing—writing about personal finance for everyday people, explaining basic concepts and demystifying money management.
Jen: I think I read somewhere that when you were part of that editorial team, you realized you had grown up with a whole different set of money beliefs than the rest of the team.
Dana: Yes, that started to plant a seed. I worked with wonderful people who inspired me in their commitment to social justice and environmentalism. But when we talked about money, I realized most of them had come from middle-class backgrounds, while I came from a working-class background.
That difference showed up when we discussed what would be accessible for our readers. It was great because my colleagues were open to feedback, and I could offer that perspective.
I realize now how useful it was to have me in that room because I could speak to situations our working-class readers were experiencing that middle-class journalists probably couldn't.
Over the years, noticing how much of a minority I was in the space helped me understand where the advice was coming from and why it didn't seem to be working for so many people.
A newsletter for the rest of us
Jen: When you started Healthy Rich, even before it was on Substack, I read that you started with other people's stories about their relationships with money to give a voice to more marginalized groups.
Dana: Yes. I've always worked as a writer, but in my full-time job, I had several years of experience as an editor, and I enjoyed working with other people's writing.
When I started Healthy Rich, I was writing full-time as a freelancer, but I also wanted to invite more voices than just my own because that diversity is what I saw missing in the personal finance space.
I started with a writing contest to publish other people's essays. I did two of those and later did more pitch-based calls for contributors.
I asked people specifically to talk about their experiences with money based on their identity—the first contest was women and money, then I did the Black experience and money, disability, LGBTQ+.
Starting with other people's voices let me quickly see the diversity I had been missing in the publications I was writing for. It also taught me about other people's experiences.
Instead of starting with just one perspective, I heard many personal stories from different perspectives all at once.
I learned a lot about what was missing in the personal finance space, what wasn't working for people, and what I could add to the conversation.
Jen: From there, you started writing your own point of view and personal essays and moved over to Substack. Talk about how that evolved and your essay for Anne Helen Petersen's Culture Study.
Dana: I moved to Substack pretty quickly. I was on Kajabi initially for Healthy Rich because I was going to build something around courses and resources for educators. I had this idea of what an online entrepreneur was supposed to be.
I love creating that kind of content—building websites, conceiving courses, putting information together. But ultimately, I realized what I enjoyed most was the writing part. I thought, "Why don't I just make a content-based business? Substack is growing as a platform. We have this opportunity to build an audience there and make money there."
What I learned quickly in writing a newsletter is that people want to hear from the creator.
They want to build a connection with you. Email is like a conversation with a friend, and that's why people like it.
Even on Substack, where we're treating it kind of like a publication, what people really like is that individual connection with the creator.
I started writing more essays from my own perspective to connect with readers.
Once I got the book deal, I realized how important it was to put myself out there, own my ideas, and be a leader in this conversation rather than staying behind the scenes because people were going to buy the book for my point of view.
I still do Q&As with people and occasionally invite guest essays. I want to make sure there's space for diverse perspectives.
In the book, I made a point to talk to many people, not just use them as examples of why my method works (which is what you see a lot in self-help books), but to learn from them and write about what I learned.
The essay that changed everything
Jen: So Anne Helen Petersen put out a call for essays. You were obviously a fan of Culture Study.
Dana: Yes, it's a great Substack. It's kind of an ideal situation where you're pitching a story to something you actually read. I had been reading Culture Study for years when she put out a call for takeovers.
I pitched an essay about budget culture, an idea I had just started conceiving and defining myself based on what I had learned about diet culture. I was seeing parallels in how we relate to money culturally.
So I named it "budget culture" and searched to see if anyone else had coined that term because it seemed so obvious in the way we talk about diet culture. No one else was talking about it.
The timing was great. I was ready to test this idea with a bigger audience, and the Culture Study audience was perfect—thoughtful, smart people interested in digging into new ideas.
I pitched it, got it accepted, and a few months later, the essay was published. It did really well, with lots of comments because people have feelings about money.
Jen: It was Budget Culture and the Dave Ramsification of Money, right?
Dana: Yep, that's my fun headline from years of writing online. It defined our default cultural relationship with money as one that focuses on restriction, shame, perfectionism, and individual responsibility.
The Dave Ramsification part is about how personal finance gurus came into play.
For a long time, nobody talked to people about money. Then when they did, it was about stock picks and CNBC—for people who had a lot of money.
Dave Ramsey came along and created this personal finance space about managing money as an average person, changing the conversation. But it became very budget-focused, restriction-focused, and shame-based. That's what I'm trying to move away from.
From essay to book deal
Jen: After Culture Study published that, did you have an agent and an editor reach out to you separately?
Dana: Yes, that was very exciting. As a writer, I always imagined I would write a book someday. With Healthy Rich, I knew I was onto something—this different way of talking about money. I thought, "This is probably what I'll write a book about one day in 10 years or something."
After that essay, a literary agent reached out first and said, "I really enjoyed your essay. Have you ever thought about writing a book?"
I said, "Of course I have. Let's talk about it!" I had no ideas at the time. I scheduled a call for about a week later, and in the meantime, an editor from Little Brown Spark also reached out and asked the same question. That's when I knew I was really onto something.
I worked with the agent to write a book proposal, which took about three months. I'm grateful for that time and for my agent, who's with Aevitas Creative Management. They focus on developing new writers and first-time authors. He guided me through the process, what goes in a book proposal, and the shape of a book.
He asked a lot of questions, like an editor would, about the process and the content. That helped me flesh out the ideas because I had to sell the concept in more than the couple thousand words I had in that one essay. We had to show that it had legs and that I had more to say about it.
Jen: At this stage, Healthy Rich was still a relatively small list, a fairly small community?
Dana: Yes, when we were doing the proposal, I was probably at around 2,500 subscribers. Over the years, I had been blogging for about 10 years at that point, mostly about writing, content, or editing specifics.
I had built a list of about 1,000 people who stuck around as I tried different projects. That grew to maybe 1,500 when I first started Healthy Rich. By the time I was writing the proposal, about a year after moving to Substack, it was probably around 2,000-2,500.
How the community shaped the book
Jen: How did your community shape your idea for the book? And how did you balance keeping the newsletter going while writing the book?
Dana: The influence came a lot from people's responses to what I wrote—the kinds of questions they had and the pushback I would get for new ideas like "you don't have to pay off debt" or "you don't need a budget." The ways people would protest against that let me know what I needed to answer in the book.
I didn't exactly blog the book as far as publishing the actual content to the newsletter. But as I explored ideas or things I found in research, I would work through them in the newsletter. I also used the newsletter to connect with sources for the book and cited ideas from published essays.
I was able to engage with people's ideas and do research and interviews that way. Instead of just getting on the phone with 100 people throughout the writing process, I connected with people through the content in the newsletter, which worked well for my energy and work style.
Jen: That's a new source, isn't it? If you'd done a book five years ago with a MailChimp list, you wouldn't have really thought about that.
Dana: Yes, the community aspect of writing a newsletter on Substack is a really new thing. With a newsletter previously just being in people's inboxes, that community didn't exist in the same way before Substack.
Now that it's this whole platform and community of creators, there's a lot more fluidity among Substack writers. I'm discovering people I never would have connected with, and I get to dive deep into their writing, which is what I like most as a writer myself.
Balancing newsletter and book writing
Jen: Once you had the book deal and knew you had a year to write it, how did you balance that with your newsletter and paid subscriptions?
Dana: The newsletter wasn't a big source of income for me at the time, which helped because it wasn't necessarily part of my job.
It was more of a creative outlet, a side gig. It was a way to work through ideas I was developing for the book and continue building the audience I knew I would eventually sell the book to.
At the time, I was only publishing once a week. For a long time, I never published more than that on any platform to protect my energy. I was either working a full-time job or, in this case, writing freelance.
I got an advance for the book, but not enough to stop working for the entire year I was writing. I was still freelancing to earn money.
That's tricky to balance because I always feel pulled to prioritize paying clients and immediate deadlines.
When a book deadline is eight months away, it's hard to dedicate time to it. But I've followed enough authors to know I couldn't leave it all to the last two months. I made a schedule for myself to stay on track.
I gave myself the first three months mostly for research, interviews, and refining the outline. I ended up changing the outline quite a bit from what was in the proposal. Then I started writing with deadlines for chapters each week.
To keep the newsletter going, I relied on contributors. Over that summer, I republished many of the early essays from the writing contests. Those had reached a small audience initially and hadn't been sent through Substack yet, so I could republish them as new newsletters. I let people know they were originally written a couple of years earlier.
I like doing that because it gives new life to content that would otherwise sit in the archives. Especially when it's written by other people, I want to make sure it gets as much exposure as possible.
That approach was really helpful during summer in Wisconsin, which is packed with activities. Between that and writing a book, it was nice to just schedule the newsletter each week without putting creative energy into something new.
Jen: That's so smart. I talk to people about that a lot—pulling older pieces that many people haven't seen, especially if you're growing on Substack.
Dana: Yes, I come from the world of blogging and online media where we did a lot of repurposing for SEO. Just look at your numbers—if you have twice the subscribers you had when something was published, that's people missing out.
And as a reader, even if you read something two years ago, you might not remember it. If you do remember it, it must have been really good, so you'll want to read it again.
Just make sure to give context. I've seen this as a freelancer and don't like it when something gets republished without noting that it was originally published years ago.
I always give that context, especially when it was written by someone else, and update any references and links. It's a much lighter lift than writing a whole new essay.
Dana's business today
Jen: When you started on Kajabi, you were thinking about the online entrepreneur life. Now you've written a book, and I know from chatting that you want to write another one. As a freelance writer, published author, and with a solid career in content marketing, what does your business look like now?
Dana: I thought about that a lot, especially after the book was written, and I was starting to think about promotion. What did I want my career to look like after the book came out?
I had this model of online entrepreneurship where a book is your “business card” to get other work. Should I use this to get coaching clients? Do corporate training? Keynote speaking?
We all know you don't just make money from a book unless you're publishing frequently, which I don't have the energy for.
I realized I don't want to be constantly hustling for coaching clients or traveling for speaking engagements. I don't want my career to hinge on these things. I do some training and speaking at conferences, but I don't want to need a keynote every couple of months to survive.
I realized that as much as possible, I want a career focused on writing.
My business now has three pillars: the newsletter, freelance writing for other publications, and the book. The book isn't an income stream yet because I haven't earned out my advance. Eventually, that might earn royalties, or I might get advances for future books.
The bulk of my income still comes from freelance writing, similar to before I wrote the book, except now there's a lot of press scattered in—podcast recordings, events like this—because I'm talking about the book.
But because of the book promotion, my newsletter has grown significantly, from around 3,000-3,500 subscribers before promotion to 10,000 by January.
I can now make a couple thousand dollars a month from the newsletter, which is the first time I've had a substantial amount of paid subscribers.
That was exciting—a long-term goal after the book came out that happened quickly. Now, I'm publishing three times a week, and the newsletter has replaced a client or two. I can really put time into growing it.
That's always the tricky place when something doesn't make money—you have to put time into growing it so it will make money, but you need to earn money elsewhere. The book promotion helped tip this into viability.
I'm proud that the newsletter is now a chunk of my business. I want to build that to be a bigger piece because, especially in the personal finance space, my message is often counter to what other publications want to publish. As a freelancer, I'm not always able to dig into that message the way I want.
The more I can make from Healthy Rich and focus on writing there, the more I can share the message I want.
But I like having diversified income. I like having variety with the book, newsletter, and freelancing so that they can shift as my interests change over the years.
If Substack pulls the rug out from under us in a couple of years, I have freelance clients to fall back on. I've learned enough being online for 15 years not to put all my eggs in one basket.
Navigating Substack's evolution
Jen: Let's talk about where you put your attention on Substack. It's interesting, especially having worked with someone like Alexis Grant, who's such a brilliant writer, content marketer, and entrepreneur.
You studied all the strategies for Facebook and Twitter, and then you got to Substack and realized you needed a different approach.
Dana: Yes, and Substack still has a lot of good that's better than other social media platforms since it's not ad-supported.
And like any tech company, they're experimenting with new features, and a lot is getting thrown at us. It's noisier now.
But it requires a lot of labor on our end as writers and readers to not get overwhelmed. I told you before we went live that I spent years reading about how to succeed on Facebook and Twitter, but I never really built a following on social media the way I have through my newsletter. So, I continue to double down on the newsletter. It's what I enjoy, and it's what's working.
Some of what we love about having a place to read great writers is getting diluted. There are benefits too—I discover many new people through Notes, which is cool. Having an algorithmic platform rather than only seeing people you follow helps you discover things you wouldn't have otherwise.
I try not to think too much about what I'm posting on Notes and how often. I just engage organically because I see good content and want to respond to it. That's the experience I want to have on this app.
It's tough not to get sucked into what people are engaging with on the app.
I did switch my strategy from only having other people write to writing more myself because I saw more responses there. Part of that is chasing engagement, but part of it is giving people what they want. It's always about finding that balance and allowing myself to indulge my own creativity.
Dana's advice for Substack writers
Dana: I try not to get caught up in the mechanics of what works on Notes or overthink my strategy. What I've learned is to engage organically with content I genuinely find interesting.
For newsletter writers trying to balance it all, I recommend:
💡 Republish older content, especially when you're busy with other projects. Most of your newer subscribers haven't seen it, and it gives valuable work a second life.
💡 Focus on what you enjoy creating. For me, that's the newsletter rather than trying to be on every platform. The thing that's working is where I put my energy.
💡 Listen to your readers' questions and pushback—they tell you exactly what you need to address in your work.
💡 Build in sustainability from the start. Publishing once a week worked for me for years, and I only increased frequency after I had financial stability from the newsletter.
💡 Remember that growing anything new requires patience. The hardest phase is when you're trying to grow something to the point of viability while still doing other things that already generate income.
The most important thing I've learned after 15 years online is not to put all your eggs in one basket.
Platforms change, and algorithms shift, but quality writing and authentic connection with your audience are always valuable.
Links We Mentioned
📚 You Don’t Need a Budget – Buy the book
✍️ Dana’s Newsletter – Healthy Rich on Substack
🔥 Viral Essay – Budget Culture and the Dave Ramsification of Money
🎙️ Healthy Rich Podcast – Listen on Substack
💰The Penny Hoarder – Read The Penny Hoarder
📚 Helen Anne Peterson - Culture Study
What resonated most with you from Dana's story? I'd love to hear your thoughts in the comments.
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