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. Iâll never forget that day â I was at a Halloween party, dressed as the Wish.com version of Ariana Grande (donât ask how I pulled this off).
Amidst blood-red fruit punch, plastic skeletons, and cobwebs, Paypalâs email read: â$551.50 has been deposited into your account.â The freedom Iâd always dreamt of was now becoming reality.
But fast-forward to today and thereâs no denying it: This year was intense.
With the fear of AI, layoffs, and a recession, the freelancing landscape has beenâŚtumultuous, to put it lightly. So, I want to give you an honest look into what happened during my third year as a freelancer. Letâs dive in. đââď¸
The 3 Big Wins
Found a âTeamâ
My biggest client is Smooth Media (I write three weekly newsletters for them!). Over the past year, Iâve gotten to know the team, and spoiler â theyâre absolutely wonderful. A good portion of them are based in NYC, so Iâve 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 Iâm grateful to know these amazing people. đŤś

<3
Income Steadily Rising
Letâs 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 doesnât factor in all business costs. I can share those details (as well as how I manage my money) in a separate newsletter if youâre interested.
For additional transparency:
I stash away 30% of every invoice for quarterly taxes.
I pay $400 a month for health insurance (which doesnât include dental or visionâŚthanks, 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! Itâs also important to note my hours: While I did work many weekends, work felt manageable. On average, Iâm 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)
Started to Write Faster
I used to have the belief: âIf I didnât struggle and spend lots of time writing this, itâs not good.â That meant long working hours, grueling assignments, and wanting to bang my head against the keyboard 24/7.
This year Iâve been unlearning this and realizing writing can be âeasy.â
Iâve 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 Iâve spent a total of 144 hours (thatâs 6 days straight) writing their newsletter. Iâm telling myself that itâs normal for my brain to now know exactly what to do to get it done fast (without compromising on quality).
Picasso's Napkin and the Myth of the Overnight Success
fee.org/articles/picasâŚ
— Barry Ritholtz (@Ritholtz)
Jun 8, 2017
The 3 Big Losses
Lots of Missed Opportunities
Iâve lost count of the number of times a call went great only to never hear from that person again. Iâve had clients ghost when they saw my rates, when I double-emailed them, or when I reached out to them six months laterâŚthe list goes on.
I also decided to break my âno unpaid trial assignmentsâ rule for one startup. I âpassedâ 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 â if youâre going to an unpaid assignment, know their rates beforehand.
Terrible Timing on Gumroad Product
Earlier this year, I launched âThe Freelance Writers Guide to Twitter.â 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, Twitterâs interface changed dramatically (thanks, Elon). Anyone who was on Twitter in 2020â2022 can tell you that the differences are vast. As a result, my guide lost relevancy, and I donât feel comfortable promoting it today. So much for âpassive incomeâ (kidding, kidding).
Many Stories Never Saw the Light of Day
This year wasnât 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.
Anyway.
Next, I worked with Lens (a by-product of Stir) on a handful of personal essays. Unfortunately, the publication shut down and doesnât seem as though itâll 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, âWho would want to read your self-absorbed stories?â
Not a single pitch got a response.
Not surprising, considering my work ethic paired with the fact that publications arenât exactly freely handing out assignments at the moment.
There are a lot more details about my third year that I couldnât 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, âI would never say this.â (Hey, it happens).
This career isnât easy, conventional, or guaranteed â but Iâm so unbelievably thankful for the freedom and creativity itâs bestowed into my life. I canât 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 â$10K monthsâ and â$300K in one product launch.â
This is your reminder that ultimately, freelance writing is still a job. To get in a place to earn that kind of money, youâre often working for years at a regular salary, slowly building yourself up. Iâm right there alongside you.
If thereâs anything else I can do to help, please let me know by voting below! đ
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âď¸ Quick Writing Tip
For copywriters: Instead of your call to action sayingâŚ
Buy now.
Sign up now.
Register now.
âŚswap the ânowâ for a specific date and time.
âNowâ is an intangible moment. After reading your CTA, the ânowâ has passed.
A specific timeline makes it feel more real, boosting your chances of a prospect taking action.
Example:
Buy today.
Sign up by Tuesday at 11 AM ET.
Register by the end of this October.
Inspired by this Tweet!

đĽ Content Diet
đ Killers of the Flower Moon by David Grann â Did I pick up this book because itâs being turned into a movie with Leonardo DiCaprio? Yes. Does it happen to be a masterful work of literary journalism thatâs the pinnacle of storytelling? Also yes.
đ Make Classics, Not Content by Lawrence Yeo â If the content creation hamster wheel has you feeling burnt out, Lawrenceâs article will help shift your perspective to a more sustainable way of writing.
âď¸Content Brief by Brooklin Nash â Brooklin generously shared his (incredibly detailed) content brief template so youâll nail your clientâs article on the first go â and become their favorite freelancer.

Thanks for reading!
Have a beautiful week, wherever you are.
Stay Creative,
Alice