💡 Every Way I've Made Money as a Writer, Ranked by Difficulty

The 9 income streams behind my 7-figure writing career, ranked from 'start this weekend' to 'statistically, please don't.'

On Wednesdays, I try very hard to be unemployable.

Novel pages in the morning while the light comes up over Sutro Tower, dusted in morning fog. A matcha roughly the size of my ambition. Then my husband Kyle and I disappear into San Francisco for the rest of the day (a ferry, or a restaurant we’ve been circling for weeks) while the rest of this city sits in standup meetings.

Sounds dreamy, right? It is, but I’ve spent a lot of time, energy, and strategy to get here.

I’ve been a working writer for a decade now: a TV writers’ room, six-figure memoir projects, a seven-figure freelancing career, a newsletter business that hit $267,537 in gross annualized revenue, four published books and a fifth serializing on this very Substack. When people find out I write fiction every morning in one of the most expensive cities in the world, they usually want the one answer. The secret unlock.

Here’s the truth: there is no one thing. There’s a stack. Nine income streams, built in order, each one funding the next. And they are NOT equally hard.

So today I’m ranking every way I’ve ever made money as a writer, from “you could start this weekend” to “statistically, please don’t.” For each one: how hard it really is, how long until the first paycheck, how high the ceiling goes, and what it costs you in the only currency I actually budget these days (energy).

Two disclaimers, because I always tell you the truth here. Every number in this post is revenue, not take-home profit. And I’m a writer, not a financial advisor — run your money decisions past a real CPA.

Let’s dive in.

The Ranking, at a Glance

The tool is cheap. That was never the hard part.

From easiest to hardest:

1. Content writing & copywriting: 2/10

2. Freelancing on platforms (Upwork, Contra): 3/10

3. Digital products & courses: 4/10

4. Consulting & coaching: 5/10

5. Self-publishing books: 6/10

6. Ghostwriting memoirs & books: 7/10

7. A paid newsletter: 8/10

8. Serialized fiction: 8/10 for the money, 2/10 for the joy

9. Writing for television: 10/10

The first two are free for everyone today, strategy included. The other seven live below the paywall, and they’re where the numbers get bigger and stranger.

1. Content Writing & Copywriting (Difficulty: 2/10)

Time to first paycheck: days to weeks
Estimated ceiling: $1,000–$2,000+ per article once you specialize
What it costs you: almost nothing to start, your soul if you price too low

This is the on-ramp: blog posts, email campaigns, landing pages, product copy. Businesses have an infinite appetite for words that sell things, and most founders would rather pay you than write a single sentence themselves. If you can hit a deadline and absorb a brand-voice doc, you’re ahead of half the market already.

The low barrier is the good news and the bad news. The bottom of this market is content mills paying $5–$20 an article, and I need you to walk past them like they’re handing out flyers on a street corner.

The way up is specificity: pick a niche where the words are attached to revenue and become the person who writes THAT. Email flows for skincare brands. Case studies for B2B software. Greeting cards for houseplants with googly eyes. (Okay, maybe not that last one. But if the googly-eyed houseplant industry calls, you answer.)

Specialists get hired faster and paid more, because “generalist” reads as cheapest option in a client’s head, and “specialist” reads as insurance policy.

Where to start looking: my guides to content writing jobs that pay fairly and where to find freelance copywriting jobs. And if you’re choosing a lane, I broke down ghostwriting vs. copywriting vs. content writing (and which pays more) on the blog.

2. Freelancing on Platforms (Difficulty: 3/10)

Time to first paycheck: a few weeks of unglamorous proposal grind
Ceiling: $300,000+ (my lifetime Upwork number, plus $25K+ on Contra) but there are other freelancers with $1,000,000+ on these platforms (but they do pay boatloads in platform fees)
What it costs you: platform fees, and one small ego death per proposal

I made my first $10K on Upwork in 2018 while everyone around me insisted the platform was a race to the bottom. It’s only a race to the bottom if you line up at the bottom.

What actually worked, in order: a profile positioned around one expensive problem instead of “I write anything!” Proposals that open with the client’s problem instead of my biography. Raising my rate after every successful contract. And when the pandemic closed my TV writers’ room in 2020 and I went all-in on freelancing, I got ruthless. Fewer clients. Higher rates. Clearer boundaries. My income tripled.

Platforms are training wheels with a toll booth. You pay fees for the privilege of a deal-flow firehose, and it’s worth it exactly as long as it’s teaching you what clients pay premiums for. Then you graduate to referrals and repeat business, where the real margins live.

My comparison posts if you’re picking a starting point: Upwork vs. Contra and the 5 best writing job boards for freelance writers, plus how to price your writing services so you don’t anchor yourself in the clearance bin.

And if freelancing is the stream you want to build for real, that’s the entire mission of my other newsletter, Make Writing Your Job: step-by-step playbooks, live classes, and a community of working writers, for $19/month (or $135/year, which works out to three months free).

What’s Behind the Paywall Today

The seven remaining streams are for paid subscribers. Below the line:

• The consulting rate ladder ($90 to $350 to $750 to $1,000 an hour), including the client who answered my quote with silence, then “send the invoice.”

• How my 2023 book pulled roughly $110K of client work to my inbox, and why the new one costs $0.99 on purpose.

• Six-figure memoir math: the $150K quote a client called undercharging, and the async system that means I take zero calls.

• The real paid-newsletter timeline: $0 to $267,537 gross annualized, the version with the boring parts left in (three years, I ran basically no ads, fees disclosed).

• What serializing a romantic thriller chapter by chapter actually pays. (And why I’d do it for free. Don’t tell my accountant.)

• Why television, the “real” writing career, is ranked dead last by someone who held a winning lottery stub.

• The calendar architecture that bought my Wednesdays back, and the energy budget that keeps the novel first in line.

If this newsletter has ever made you money or made you braver, today is a very good day to upgrade. Paid subscribers get every essay in full, plus my romantic thriller Let Me Be Your Ghost as it serializes (the first chapters are free here).