Every writer needs to have an honest conversation with themselves about their own tolerance for risk. For Josh Levin, that conversation lasted twenty years.

@emilynemens.bsky.social left The Paris Review to write her own novels. In this interview, she breaks down the financial reality: 📺 Why TV rights > book advances 🖊️ The humbling shift from "power" to freelance 🗓️ Her 6-month budgeting rule howimakemoneywriting.substack.com/p/interview-...

for our latest HIMMW interview: @joshuablevin.bsky.social left a 20-year "forever job" at Slate to go independent. We break down the finances of the jump: 🎙️ The cost of self-funding narrative podcasts 📖 Negotiating unpaid sabbaticals to write books 💸 Adjusting to a "TBD" income

For HIMMW, @jenlouden.bsky.social breaks down the reality of a 35-year career, selling 1M+ books, and generating $230k/year. She talks about: 📧 Why email lists > social media (advice she got in 1999) 🛑 The "80% Marketing" Rule most creators ignore 🔄 Pivoting from self-help to fiction

"I am not rich. I am struggling, like everyone else. I’ve had feast years and famine years." Alisa Lynn Valdes talks about: 💰 The real math behind her $475k advance 🌵 Leaving the city to run a pecan farm on her ancestral land 🚫 Rejecting Hollywood stereotypes

Novelist & playwright @alicejolly.bsky.social has the kind of resume most writers dream of. She is an O. Henry Prize winner, a PEN Ackerley nominee, and she teaches creative writing at Oxford. But in our recent interview, she was clear that critical prestige does not equal financial security.

When you look at @author-mjs.bsky.social's career, the headline number is usually the 2.5 million books sold. It’s an incredible milestone, but digging into his spreadsheets reveals something even more telling about the current state of publishing.

“I don’t think I’ll ever break into the middle class, but I live like a king most of the time.” A conversation with @adamgnade.bsky.social about how he makes money writing. howimakemoneywriting.substack.com/p/interview-...

I really appreciated this moment in my chat with @otroedgargomez.bsky.social. We often assume that choosing a creative life means accepting financial chaos, but Edgar pushed back on that.

I’m really looking forward to sharing my interview with @hamiltonnolan.bsky.social. He's a veteran labor reporter with a very grounded take on why so many journalists are moving to Substack right now.

When I first reached out to @richardscottlarson.com (The Long Hallway) for an interview, he hesitated. He actually wrote back wondering if his perspective would be valuable to the newsletter because, unlike the full-time dream we’re often sold, he relies heavily on a day job.

@mikebsacks.bsky.social had a really honest take on the danger of writing just for the paycheck in our interview. He warned that "if you’re forced to write pieces just for the money, it can be a very heavy slog."

I really appreciated this breakdown from @philippaeast.bsky.social in our interview. She's spent seven years balancing two careers—one as a clinical psychologist and one as a suspense novelist—and she was incredibly open about how the math actually works.

We often hear stories about writers quitting their day jobs to take the leap, but we rarely hear about the financial logistics that actually make that landing possible.

Aram Mrjoian (author and managing editor of Michigan Quarterly Review) once told me that he worries that too many writers are waiting for "one lucky break" to make everything fall into place.

When you see "Pulitzer Prize Finalist" next to an author's name, it’s easy to assume they have reached a level of financial security that the rest of us are chasing. We tend to think that kind of critical acclaim automatically translates into financial freedom.

I’m so grateful to Edgar Gomez (author of Alligator Tears) for breaking down his income in our interview. It is such an illuminating look at what life as a full-time writer actually entails.

I spoke with novelist, playwright, and memoirist @alicejolly.bsky.social, who has spent 28 years navigating the brutal economics of literary fiction: howimakemoneywriting.substack.com/p/interview-...

In this upcoming interview with @davidwbrown.com (The New Yorker, The New York Times, author of The Mission), he offers a reality check that every freelancer needs to hear.

I spoke with culture writer & author @carriesnotscary.bsky.social on the economics of her 14-year media career: 💸 The transparency of spousal support as a safety net 📉 Why name recognition no longer guarantees better rates ✍️ Writing "bullshit" clickbait to fund the work you actually love

"I chose a life where I could still do the meaningful work of journalism and my novel writing would be free of financial and professional pressure. And I have no regrets about that decision." — @knguyen.bsky.social

I spoke with comedy-horror author @jeffstrand.bsky.social on quitting his day job & going indie: 💸Trading traditional advances for indie 🎥Why Hollywood rights pay peanuts unless you write the script 🧟How a 50-book backlist creates stability howimakemoneywriting.substack.com/p/interview-...

“Have a partner who makes more money than you do. There is no viable business model for non-topical, freelance, slowform journalism.” — Elon Green (Interview #4: How Elon Green Makes Money Writing)

“Keep your expectations in hell, because that's where writers live. Enjoy the act of writing. Enjoy what you write. Do it for yourself first. Be grateful for whatever opportunities or monies come from it. The crumbs are few, and the mouths are many.” — Ashley Hutson (HIMMW #43)

Love this advice from @nickbowlin.bsky.social for journalists: "Go to where the other reporters aren’t, find the stories that haven’t been told. It’s the only way I know to consistently get responses from editors."

I spoke with Verge reporter @miasato.bsky.social on navigating the volatile economics of the internet: 🏆The reality of journalism awards: prestige vs. paycheck 📱Why she posts on TikTok 💼Why she chose a staff role over the "freedom" of freelancing howimakemoneywriting.substack.com/p/interview-...