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My 3rd year freelancing: An honest review

The 3 biggest wins (and losses)

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Hi there,

Three years ago this month, I made my first dollar from freelance writing. I’ll never forget that day — I was at a Halloween party, dressed as the Wish.com version of Ariana Grande (don’t ask how I pulled this off).

Amidst blood-red fruit punch, plastic skeletons, and cobwebs, Paypal’s email read: “$551.50 has been deposited into your account.” The freedom I’d always dreamt of was now becoming reality.

But fast-forward to today and there’s no denying it: This year was intense.

With the fear of AI, layoffs, and a recession, the freelancing landscape has been…tumultuous, to put it lightly. So, I want to give you an honest look into what happened during my third year as a freelancer. Let’s dive in. 🏃‍♀️

The 3 Big Wins

  1. Found a “Team”

My biggest client is Smooth Media (I write three weekly newsletters for them!). Over the past year, I’ve gotten to know the team, and spoiler — they’re absolutely wonderful. A good portion of them are based in NYC, so I’ve met them IRL and even co-worked with them in their WeWork building.

After spending the past three years freelancing alone, having a team of people to hang out with feels nourishing (corny, but true). Freelancing can be lonely AF, and I’m grateful to know these amazing people. 🫶


  1. Income Steadily Rising

Let’s have an honest chat about finances (I do write for Salary Transparent Street, after all).

  • Year 1: ~$47,000

  • Year 2:~$65,000

  • Year 3:~$85,000

Note: This is before tax and doesn’t factor in all business costs. I can share those details (as well as how I manage my money) in a separate newsletter if you’re interested.

For additional transparency:

  • I stash away 30% of every invoice for quarterly taxes.

  • I pay $400 a month for health insurance (which doesn’t include dental or vision…thanks, America).

  • I now have a VA for whom I pay $35 an hour (roughly ~$380 a month).

In short: My salary increased by ~30% from last year. Woo! It’s also important to note my hours: While I did work many weekends, work felt manageable. On average, I’m clocking in 3-5 hours a day, and get to do so from anywhere in the world. This past year, I traveled (solo!) to Guatemala, Brazil, and Croatia.

My setup in Lake Atitlan, Guatemala (eep)

  1. Started to Write Faster

I used to have the belief: “If I didn’t struggle and spend lots of time writing this, it’s not good.” That meant long working hours, grueling assignments, and wanting to bang my head against the keyboard 24/7.

This year I’ve been unlearning this and realizing writing can be “easy.”

I’ve had some of the same clients for 6-12 months now. That translates into days (even weeks) spent writing for them. I can now write their articles much faster, helping me boost my income without raising my rates.

For example, with one client I’ve spent a total of 144 hours (that’s 6 days straight) writing their newsletter. I’m telling myself that it’s normal for my brain to now know exactly what to do to get it done fast (without compromising on quality).

The 3 Big Losses

  1. Lots of Missed Opportunities

I’ve lost count of the number of times a call went great only to never hear from that person again. I’ve had clients ghost when they saw my rates, when I double-emailed them, or when I reached out to them six months later…the list goes on.

I also decided to break my “no unpaid trial assignments” rule for one startup. I “passed” their test, but when the client asked for my rates, I was 2x out of their budget. I had spent the weekend on this trial assignment and lost a lot of time.

But hey, at least I learned a valuable lesson – if you’re going to an unpaid assignment, know their rates beforehand.

  1. Terrible Timing on Gumroad Product

Earlier this year, I launched “The Freelance Writers Guide to Twitter.” I poured my heart into writing this guide to teach freelance writers how to use Twitter to land and pitch clients.

Despite a solid launch, right after posting, Twitter’s interface changed dramatically (thanks, Elon). Anyone who was on Twitter in 2020–2022 can tell you that the differences are vast. As a result, my guide lost relevancy, and I don’t feel comfortable promoting it today. So much for “passive income” (kidding, kidding).

  1. Many Stories Never Saw the Light of Day

This year wasn’t easy for a lot of companies.

That meant a bunch of publications closed down, and my clients were no exception.

First, I worked with a startup to create in-depth articles on AI tools for writers. After spending dozens of hours on each piece (GIFs and all) the client vanished. The pieces were never published. The startup never even got a website up.

Repeat after me: This is why you always get a deposit before working with a new client.


Next, I worked with Lens (a by-product of Stir) on a handful of personal essays. Unfortunately, the publication shut down and doesn’t seem as though it’ll return (fingers crossed it does!).

Last but not least, one of my goals this third year was to pitch personal essays to publications. I gave this a half-assed attempt, partially out of the fear of, “Who would want to read your self-absorbed stories?”

Not a single pitch got a response.

Not surprising, considering my work ethic paired with the fact that publications aren’t exactly freely handing out assignments at the moment.

There are a lot more details about my third year that I couldn’t boil down to three wins and losses.

I hired a VA who saves me ~12 hours a month.

My Twitter growth was nonexistent (100 new followers in 12 months).

I tried ghostwriting for someone and one of their first comments in the Google Doc was, “I would never say this.” (Hey, it happens).

This career isn’t easy, conventional, or guaranteed — but I’m so unbelievably thankful for the freedom and creativity it’s bestowed into my life. I can’t wait to see what next year brings.

I hope this annual review gave you clarity. So often, the online writing world is flush with cash and grandiose statements about “$10K months” and “$300K in one product launch.”

This is your reminder that ultimately, freelance writing is still a job. To get in a place to earn that kind of money, you’re often working for years at a regular salary, slowly building yourself up. I’m right there alongside you.

If there’s anything else I can do to help, please let me know by voting below! 😊

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Thanks for reading!

Have a beautiful week, wherever you are.

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