✍️ How I Made $300,000+ on Upwork — And Why We’re Adding Upwork Jobs to the Writing Job Board

A love letter (and warning) about the world’s most polarizing freelance platform — plus: a gift for paid subscribers!

Hey writers —

Big heads-up: this will be our last “Sunday Post.” But don’t panic — we’re not going anywhere. In fact, we’re expanding. You’ll see what I mean soon: the job board is getting an upgrade, which will roll out in a bit.

We’ll still have long-form articles here on Make Writing Your Job, just not on a rigid Sunday schedule. And for those of you who like the behind-the-scenes, personal essays, and the messy reality of building a seven-figure writing business — I’m moving all of my personal takes and tips over to my new Substack, Sutoscience. If you want the unvarnished dispatches about life as an author, working writer, and “creator CEO,” you can join me over there.

Nothing else is going away. ClassStack continues. Subscriber Chat stays. Founding Members will get even more perks with our new quarterly mastermind and 24-hour advance access to featured jobs.

I’m excited for you to see it all roll out.

Now, for today’s main topic: the most love-it-or-hate-it platform in the freelance world — Upwork.

💰 Plus: how I made over $300,000 on the platform and where I think it can fit into your freelancing journey.

🎁 And: a gift for paid subscribers at the bottom of this email!

✍️ Missed This Past Week’s Writing Jobs?

Did you miss it? Here are the writing jobs on the most recent job board:

• A fast-growing history YouTube channel (361K+ subs) is paying $250–$300 for sharp, funny scripts on historical topics.

• A major U.S. arts org is offering a $60,000 grant to authors working on nonfiction books in the humanities

• Five authors are seeking developmental and copy editors for speculative, dark romance, and time travel manuscripts.

Apply to these jobs — and unlock 100+ hand-selected freelance writing opportunities, contests, residencies, grants, and pitch calls below at the latest edition of the writing job board:

🙌 Writing Community Wins!

Here’s what some of your fellow writers in the community have been up to lately:

• Hailey Amare
  shared her wins in her writing business: “I landed two book coaching clients this week! 🥳 And I’m talking to 5 more ghostwriting & editing potential clients!”

• Shayla Elizabeth
  shared her awesome writing momentu: “Today and yesterday, I was inspired to write 2 Flash Fictions, after a long dry time, to enter in a contest found on Amy's Make Writing Your Job thread 🤩”

• Sara Hussein
  shared this great piece she wrote about learning how to fight in a Thai fight camp: “Not a win per se but I finally got around to writing about the time I dabbled in professional fighting in Thailand. sarahusseinwrites.substack.com/p/what-getting-punched-in-the-fa…”

• Julia Lauzon
  shard her fiction book accomplishment: “I finished my 95,000 word dark fantasy manuscript this week and sent it to the editor! A personal win, as im looking to start querying it next month 💫🏆”

Share your writing wins in the chat below:

🎓 Amy’s Favorites: The Freelance-Friendly Credit Card That Pays You Back

If you’re self-employed, every dollar is an investment. Make sure your card treats it that way.

This week’s pick: Robinhood Gold Credit Card.

✅ 3% cash back on everything

✅ No annual fee

✅ Simple rewards, no confusing categories

Most cards give 1.5%–2% on groceries or gas. But freelancers don’t live in categories. Software, flights, coffee with clients — all fair game at 3% back.

Spend $2,000/month? That’s $720/year back in your pocket.

💳 My take? If you’re going to swipe, get paid for it.

🔗 Sign up to get the Robinhood Gold Card*

*FYI, these are affiliate codes, which means I may earn a small reward at no extra cost to you.

🫖 Sunday Tea: How I Made $300,000 on Upwork — And Why We’re Adding Upwork Jobs to the Writing Job Board

Upwork.

That single word can start a brawl in any group of freelancers. Some think it’s a race to the bottom. Some treat it like their personal ATM. I’ve been both.

I made over $300,000 on Upwork before I built better client pipelines in other areas for clients to find me in other areas of the Internet.

Today I want to tell you why we’re adding Upwork listings to our job board — and how you can use it to land serious work.

Because, yes — there are $5 jobs on Upwork. And yes — I’ve turned a job with a $500 posted budget into a $25,000 contract.

The first lesson? Every budget is negotiable. (Even all the posted budgets for the jobs here on our job board!)

🎯 Why Use Upwork at All?

Upwork is a middleman. They take a cut (used to be 10–20%, and it seems like they keep changing the amount). It’s easy to hate them for that.

But let’s be real:

✅ If you’re just starting out, they handle contracts, payments, invoicing, and dispute resolution.

✅ You get access to clients who don’t know where else to look.

✅ It’s a warm lead engine. Someone is already shopping for a writer.

Yes, you pay for that. But you’d also pay for ads. Or your website. Or your newsletter. Lead generation always costs something — time or money.

💸 But What About the Low-Paying Jobs?

You’ll see them. The $10 blog posts. The $100 “novel.” Laugh, keep scrolling.

Here’s the secret: the posted budget is almost meaningless.

If they want you — the right writer — they will come up. I routinely sold work at $350/hour and $750/hour on Upwork to clients who posted that they were only willing to spend $200 on a freelance writer.

Budgets are just a starting point. Your skill is in negotiation.

🔑 5 Tips for Winning on Upwork

1️⃣ Have a Killer Portfolio

Upwork is a portfolio-first platform. Your profile is your storefront. Invest in it.

We have an entire portfolio class in ClassStack that translates perfectly here. Build a clean PDF portfolio. Link it in proposals. And yes — you can make money while you’re building it out. And no, you don’t need experience or paying clients to build out your portfolio.

2️⃣ Nail Your Cover Letters

Your proposal is your audition. I’m sharing my exact cover letter template that I’ve used at the end of this email — exclusively for paid subscribers. This is the cover letter that helped me win over $300,000 worth of work on Upwork.

3️⃣ Be Ruthlessly Persistent

Upwork charges for Connects (their system to apply to jobs). You will spend money. At my peak, I spent hundreds monthly on Connects — but earned 100x that back, sometimes banking $20,000 or $30,000 from Upwork alone in a month.

So yes, Upwork is pay-to-play. Don’t like it? Totally fair. But for the right freelancers, Upwork can be a cash printing machine.

4️⃣ Obey Their Rules

They’re strict. You have to keep messaging on-platform until a contract is in place, so read up on how to work on Upwork before you start freelancing with them. Break the rules and get booted. Play nice and get rewarded.

5️⃣ Optimize for Search

Upwork is a search engine. Use keywords in your headline and profile. If you’re a memoir ghostwriter? Say so. Use it repeatedly. Make it easy to be found.

🗂️ My Honest Take

Can you become a six-figure writer on Upwork? Absolutely.

Can you become a seven-figure writer just on Upwork? Doubt it.

It’s a great launchpad. It’s a great supplemental funnel. But build your own systems too.

✅ Why We’re Adding Upwork Jobs to Our Board

Because they’re real, they’re plentiful, and they move fast.

A lot of Upwork clients hire immediately. If you want those jobs, you need to see them fast. That’s why we’re adding them to the board.

You can spend hours scrolling. Or you can let us do it for you for $8/month. If you think even 1 hour of your time is worth more than $8, then consider signing up for a paid subscription so we can do the heavy lifting for you.

You’ll need an Upwork account to apply. But we’ll find the leads. You jump on them.

If you have questions about Upwork — drop them in the comments.

If you want my exact $300,000-winning cover letter template? It’s waiting below for paid subscribers.

Let’s go make writing your job.

🎁 Gift for Paid Subscribers: My Upwork Cover Letter Template

As promised, below is a link to the exact cover letter template I’ve used to make over $300,000 on Upwork, just for paid subscribers: