I Just Finished My Second Year as a Freelance Writer. Here’s What Happened.
The good, the bad, and the ugly.
Hi, hey, hello!
October is almost over, which means it’s now been two years since I became a freelance writer. 🤯 I started this career without a lick of professional experience. I’d never gone to journalism school, had connections, or a portfolio. But, I was hell-bent on somehow getting paid for my writing.
I’m proud to say I pulled it off. But man, it’s been a journey.
In this post, I want to tell you the details of being a second-year freelance writer — the good, the bad, and the ugly. I’ll share the embarrassing and the accomplishments in hopes that you, too, can be inspired to make the leap.
So without further ado, let’s take a stroll down memory lane.
The second year started off strong. 💪
I booked a one-way ticket to Costa Rica to give this “digital nomad” thing a real go. Once I landed at SJO airport, I hit 10,000 Twitter followers. This was a *major* accomplishment since it took 17 months (517 days) of consistent Tweeting to get there.
I spent November in Cahuita, sharing a home with another solopreneur friend, Reena. Cahuita is a lovely town, dotted with palm trees and black sand beaches. Reena and I spent most of our days working but would take slices of time here and there to go surfing, hiking, or swimming.
November was kind to me, client and money-wise.
I made $350 from affiliate income thanks to Ship 30 for 30. I wrote some case studies for On Deck and continued writing Snail Mail, Slow Growth’s newsletter. But I was most excited about this new client who’d hired me for ghostwriting.
I’d negotiated my highest rates yet — but I couldn’t have predicted what happened next.
This client, albeit very kind, was…distracted. It was clear their priority wasn’t creating content — it was to launch their startup into the stratosphere. As a result, they weren’t answering any of my emails or follow-ups. Luckily, they’d paid an initial deposit (so I wasn’t totally screwed).
They finally got back to me a few weeks later and apologized for their absence. They then proceeded to pay the second half of the retainer (mind you, we’d published zilch) and asked if we could renew it.
I was flabbergasted. I’d been paid $4,000 for…nothing.
It wasn’t necessarily a good feeling. If someone is hiring me, I’m there to help them! But, I suppose it’s better than the alternative — the client never pays you. Anywho, the guy disappeared right after and I never heard from them again.
The good times kept rollin’. I opened a business checking account with Novo. This was a big win because I finally said sayonara to PayPal and Wave’s pesky invoice fees. This move saved me hundreds of dollars.
I migrated from Cahuita to Santa Teresa to spend Christmas alone. As the holidays approached, work dwindled. I failed to really care, surrounded by palm trees, surfboards, and jungle parties. I’d pay the price for this nonchalance eventually.
I flew home to NYC and got Covid, because of course.
It was brutal. I battled brain fog, nausea, and bone-deep aches. This absence of energy, paired with my failure to prepare for the next quarter, resulted in my lowest month to date: $2,500.
As fellow freelancers posted their 💰 gains on Twitter, I slipped into a woe-is-me mindset. I felt pretty shitty and like I was falling behind the invisible finish line of career growth. I messaged old clients to see if they needed help, and with a stroke of luck, got connected to The Leap.
I picked up as much work as I could, rolled up my sleeves, and got to writing. ✍️
A fellow agency owner reached out and asked if they could sponsor my newsletter, Internetly. He offered $250, which was solid considering Internetly’s small (but mighty) audience of 1,000-ish subscribers.
I managed to scrape up extra cash but closed out February just shy of $4,000. Not my worst, but certainly not my best. To distract myself, I brainstormed my next digital nomad destination and decided to get a one-way ticket to Medellin, Colombia. 🇨🇴
Here’s where *crack knuckles* things got interesting.
Things were back on track! I cracked my minimum of $5,000 a month, and this time, I could spend my free time exploring Colombia.
But, here’s the thing about digital nomading. I like to operate on a 9-to-5 schedule, Monday through Friday. Once you’re traveling, you chuck that out the window because you become an opportunist.
If you meet a group of folks and they offer you to tag along to a waterfall tomorrow, you say yes. If a surf instructor asks if you want to go surfing like…right now, you say yes. Traveling solo is all about capitalizing on the moment.
As a result, you work at oddball times. I wrote every single day for at least a few hours, either early in the morning or late into the night. I pulled it off, but it wasn’t sustainable. I’d end the days exhausted.
I missed my boyfriend terribly. I was sick of constantly feeling sluggish after eating a mixture of oil, fats, and salts. I resented having the same conversations with nomads (“Where are you from? Where are you headed next?”) on repeat.
In short: it was time to go home. 🏡
Once I arrived in NYC, I stumbled into two new client opportunities — first, with Zapier (I pitched them) and then OutVoice (they found me). My article with Zapier got syndicated in Fast Company, which was really cool to see!
At the same time, I was working on a one-off piece with another new client. The goal was to turn a Huberman Lab podcast episode into an article.
The whole process did not go the way I anticipated.
If you’ve listened to an episode of Huberman Lab before, you know just how information-dense his episodes are. It’s riddled with terms such as “transcranial magnetic stimulation”, “negative neuronal information”, and “brain-derived neurotrophic factor”.
Paraphrasing Dr. Huberman’s ideas were more labor-intensive than I could’ve predicted. The hours I spent re-listening to the podcast, doing additional research, and editing were quickly compiling — and it far exceeded the cost the client and I had originally agreed on.
Ugh. This put me in the unfortunate position of having to message the client and ask if we could increase the rate (which I’d already negotiated at the beginning of our agreement).
Luckily, they were pretty understanding about it. After a grand total of almost 26 hours spent on this article, I’m glad to report it was published…nowhere.
Jokes aside, I’m not too sure why it was never published. I didn’t send a follow-up email inquiring about it. Deep down, I know it stems from fear and insecurity — a pervasive doubt that my writing wasn’t good enough to go up on their site and they just didn’t have the heart to tell me.
As New York City started to defrost, I was chasing a late invoice.
It was only $650, but it took months to funnel through. I failed to realize just how much this type of tomfoolery can negatively impact your headspace. I’d try to start my days and then get so bothered I couldn’t even focus on client work.
I had. In fact, I’d binged a bunch of her podcasts earlier that year. Kat Norton was a goddamn rock star, creating a multi-million business empire off of Microsoft Suite courses and TikTok — alone. She inspired the hell out of me.
It turns out she needed a writer. We all connected and I landed the gig. 🎉
I still feel giddy about this opportunity. I know that if this job had been posted on LinkedIn, it would’ve been inundated with resumes (Smooth Media’s latest job posting garnered 200 + applications).
But because I'd spent the past 1.5 years building an audience on Twitter, networking, and sharing my writing online, I’d bypassed the entire competition. Back in 2020, I couldn’t even get a single reply to my cover letters. Today, I soared past hundreds of applicants.
And it’s not because I’m “smarter” or “more talented.” It’s because I used the internet to teach myself everything and share my ideas. You can do the same.
As I integrated myself into the Smooth Ops team, I decided to visit Mexico. 🇲🇽
The work with Miss Excel came in the nick of time as another long-standing retainer client decreased our scope of work, slashing compensation by 65%. Good lord. But because I had Miss Excel, I made the same amount (even a bit more) than previous months.
Otherwise, June was a chill month, except that I caught a gnarly case of food poisoning while in Puerto Escondido. It was brutal, and I couldn’t work for about three days which put me pretty behind.
After vomiting my guts out (classy) I flew to Mexico City and spent my remaining days eating tacos, sipping mezcal, and dancing to reggaeton. Overall, not a bad way to end our time in Mexico. :)
July was another solid month.
With three retainer clients, I could count on consistent income. I was even able to say no to some pretty good projects, even though it hurt my heart (and wallet) to decline. But, I wanted to prioritize my free time – and not burn out as I had January 2021.
I started to experiment with subcontractors and hired two as a trial experiment.
The first one had really solid ideas, and I could use them as building blocks for my own — which accelerated the writing process.
However, by the third or fourth assignment, they started to hand in writing riddled with errors. We’re talking incorrect usage between “then” versus “than”, “their” versus “there”, and some sections were completely missing punctuation. 🤦🏼♀️
Listen, it’s normal to make some errors here and there – I do it, too! But this felt careless, especially since Google Docs will underline your errors in red.
I hired another subcontractor to help with an outline for a case study. When I asked for their rate, it seemed…low. I was asking for a good amount of labor — listen to an hour-long transcript, do additional research, come up with headers, flesh out paragraphs, and organize everything. For me, this process takes at least four hours.
So, I offered to pay them more.
Does this make me a “sympathetic” person? Perhaps. Does it make me a good negotiator or businessperson? Absolutely not.
In the end, the outline was just…okay. But the onus was also on me — perhaps I didn’t explain the task well enough. That’s the thing about subcontractors. You hire them to help get your time back, but the process of hiring, onboarding, sending documents, and training them takes so much time.
If you’re still reading this annual review, thanks for sticking around. We’re almost done, promise.
In August, I decided to take a week off to surf in Portugal. 🏄🏼♀️ Sure, those five days weren’t PTO (jealous of the 9-to-5ers) but it’s a small price to pay to be able to take off without having to “put in a request.”
I turned 26 years old. This meant having to find health insurance (womp-womp). I nearly had a breakdown trying to navigate the archaic healthcare websites and getting quoted about $700 a month.
With some sleuthing, I was able to score a plan for a couple hundred less. It goes out of my business account, so I’m *crossing fingers* that I can dock it as a tax write-off.
Otherwise, in September a thread of mine went bonkers and garnered over one million impressions – leading to 20K followers.
The spotlight came with scrutiny. The thread was littered with comments from people making fun of my lifestyle or not believing a word I’d said. Some dude straight-up asked me to submit tax documents to prove my income.
It’s to be expected! If that thread can help even one person (which it seems it did) then that’s what counts. 💫
The last month!
October’s been an interesting one. I was chatting with another big client about potentially helping them with their newsletter. We’d discussed rates and gone over concepts all over the phone.
So when I sent over the contract and never heard from them again, I was perplexed.
I might never know why this client ghosted. Perhaps my rates were too high for their liking, which is a good thing. If no one is deterred by your price, that means you’re aiming too low.
However, my insecurities seem to disagree. I started to lament over the possibility that I wasn’t a good negotiator, or cunning enough to close the deal. I didn’t sell myself well enough, I thought.
As a freelancer, because you’re doing everything yourself — marketing, accounting, writing, networking — these types of self-deprecating thoughts quickly multiply if you do a less-than-perfect job.
It’s a daily battle to swat them away. Right now, I’m fixated not on what I’m doing, but on what I could, should be doing.
“I should have a course by now or some kind of digital product.”
“I should’ve had my first $10,000 month by now.”
“I should’ve closed that client, and the fact I didn’t is a sign failure is imminent.”
But if there’s one thing I’ve learned while freelancing, it’s that it’s a process of going, “Okay, this is hard. But let’s push through and see what happens.” I’m not kidding when I say this thought process is why I am where I am today.
Despite the crippling imposter syndrome or comparison, I can say I’ve made it far. I’m projected to have earned $100,000 from this career by January 2023. Mind you, that’s over 2 years and some change — but still. The first time Medium paid me .67 cents for my article I nearly shed a tear from joy. It’s crazy to see how far I’ve come.
Whoever you are, whatever you do, I promise you can also get to where you want to go. It takes grit, perseverance, and ridiculously boring consistency, but that’s a small price to pay to be able to live life on your own terms.
I hope this annual review helped or inspired you — and if you’d like to keep following the journey, you can subscribe to my newsletter here.