💡 "it's cringey that you post about how much money you make from writing."

Let's break it down.

Every so often, I get unsubscribes like this one over on MakeWritingYourJob.com:

And listen — I get it. Talking about income as a writer can feel like standing up at Thanksgiving and announcing that you run an OnlyFans.

Money has been a taboo for a reason, especially in the writing world, where starving is part of the brand.

But here’s the thing.

Back when I was a minimum-wage assistant in Hollywood, sharing a sunless apartment with a roommate and barely scraping by, I stumbled across Lindy Alexander’s blog, The Freelancer’s Year.

Back in 2016, Lindy used to post monthly income reports. As in: “Hey, here’s how much I made this month as a freelance travel writer.”

And to my broke little brain, it was like discovering Narnia:

Writers. Getting. Paid. To. Write. And travel?

Everyone had told me writers were broke. Suddenly, the glass ceiling I’d internalized shattered — and a door cracked open.

That transparency changed my life.

So in 2018, I documented what it took to make my first $10k on Upwork as a freelance writer after being at it for two years. I was still in the struggle — piecing together freelance jobs between fraught assistant gigs and crashing on couches at friends’ places in NYC just to get out and see slices of the world — but I wanted to prove that making money as a freelance writer could be done. And no one called that blog post “cringey.”

Why? Because I wasn’t “there” yet.

Apparently, it’s only bragging if the numbers get big.

But sharing numbers matters.

Because back in 2021, I was also fighting my way out of tens of thousands of dollars in medical debt after being diagnosed with rheumatoid arthritis in my twenties. I needed to see that someone was making it work. I needed to believe that I wasn’t a fool for wanting to make writing my job.

And I did. Freelancing paid the bills — including the scary ones. It also bought me the time to rest, heal, and eventually put my autoimmune disease into remission.

So yeah, I post about money.

Not to brag. Not to posture. But to show what’s possible.

I want to be the proof for someone else.

When a subscriber recently emailed me to ask if freelance platforms like Upwork were still worth it in 2025, I didn’t just say “yes.” I wrote a whole post about how I made $300,000 on Upwork, gave away my go-to cover letter template to my paid community, and announced that we’d be adding Upwork jobs to the writing job board.

Could I have said all that without the dollar figure? Sure. But would it have landed? Probably not.

Because context matters. If I’d made $300 total on Upwork, you shouldn’t be listening to me. Just like you wouldn’t hire a personal trainer who’s never broken a sweat.

I’ve made it my mission to build credibility by sharing real numbers and real experiences. Yes, even when it makes some people uncomfortable.

And if you’re someone who needs that kind of role model — a writer who posts receipts — I’ve got you.

If not? That’s okay, too. The Internet is a buffet. You don’t have to like every dish. Swipe left and find a Substack that’s more your flavor.

I’m not offended. Genuinely. I wish you — and the subscriber who decided to move on! — well.

But let’s not confuse transparency with cringe.

Let’s not pretend that it’s more noble to suffer quietly than it is to share the roadmap that helped you get free.

Two years ago, I set a “big audacious goal”: $96,000 in ARR for my Substack. At the time, I had zero paid subscribers.

I made a whole YouTube series about it that I just reposted — and not because I thought I was hot shit, but because I wanted to document the weird, wobbly, often hilarious process of building something real.

(You can see many times I was unsure or pivoted or was like “welcome to the trough of sorrow!” in the YouTube series recorded over the past two years where I just nervously laughed through confusing metrics or periods of stagnation.)

I wanted to test what it meant to create value. To connect. To serve.

Money wasn’t the point — it was just the measuring stick.

If the number went up, that meant I was helping people.

If it didn’t? Time to iterate.

Eventually, I cracked the code. I built the writing job board. I figured out how to channel my freelance firehose into something sustainable.

Now? That $96k ARR goal? Hit it. Surpassed it.

Is that bragging?

Maybe.

But I’m proud — not just of the revenue, but of the community it reflects. Of the readers who show up week after week to make their own writing careers real. Of the writers who land their first freelance writing jobs, grow newsletters, publish books, and finally believe that they can make writing their job.

And if someone calls that “cringe”? Again — cool. I’m just not your cup of tea.

Or maybe — and hear me out — the discomfort comes from something deeper. Maybe it’s not about me. Maybe it’s about what we’ve been taught.

That writers should starve. That artists should grovel. That ambition is suspect. That money corrupts. That “real writers” don’t care about things like rent, or royalties, or eating three meals a day.

I reject all of that. Loudly.

Because the starving artist trope was never an option I could afford.

And because I’m writing a book about this very thing — and I’d love your help.

If you want to be a beta reader, I’m giving away advance copies in exchange for honest feedback. Sign up here and I’ll send it your way soon.

To the reader who unsubscribed: thank you. And I mean that with sincerity. You gave me a reason to write this.

To the rest of you: keep going.

You’re allowed to want money. You’re allowed to want power. You’re allowed to want joy.

You’re allowed to build a writing career that supports the life you actually want to live.

And when that happens — when you wake up and realize that this is the life you get to live?

It’s not cringe.

It’s freedom.

Let’s raise a glass —

To the writers who believe in what’s possible.

To the ones building empires out of words.

To you.

–Amy