No Joke: I Pulled In Over $50k in 9 Months as a Freelancer. Here’s How.
Here’s my story…and a breakdown of my earnings.
Can you earn a living as a freelancer? Hell yes, you can, and I’m living proof. Here’s how I did it, including the path I took, a breakdown of my 2020 and 2021 earnings (thru 9/21), and some juicy details and helpful hints about how I pulled in more than $50K in 9 months as a freelancer.
If you wrestle with questions like How do I break out as a freelancer? or How can I make more money freelancing? or Can I support myself as a writer? then please know that you’re not alone. I’ve had all those struggles and questions.
And now, I’ll share my journey to becoming a five-figure freelancer-turned-coach.
Want The Full Backstory? Here Ya Go.
My freelance writing career truly began when I was a 7-year-old kid, filling my diary with entries documenting details of my life and boosting my OWN spirits. As I grew up, I just kept covering pages in ink, like this one from when I was fourteen:
Here’s the text:
January 1, 1983: Look out world! HERE’S CHRISSY! Melissa’s party was great — the best! There were a few shaky moments, but that was to be expected! We stayed up till 5:00 a.m. Ug! I just wrote Melissa a really loving letter. I told her that I really love her. She’s like a guardian angel to me (sometimes). Grandma and Grandpa are coming at 9:30 tomorrow. Dad’s coming at 10:00. GOODNIGHT. I’m gonna make this a great year.
Sigh.
Fast forward through college (Advertising major, English minor), followed by stints at advertising agencies and consulting firms, followed by earning a Master’s in Teaching and a decade of teaching children while raising three children of my own. Through it all, I journaled whenever I could and dreamed of someday becoming a full-time writer.
I got a taste of the writing life when I took on a few contract jobs writing for educational publishers—work that paid extremely well but left me feeling empty inside. Between the subject matter, all the parameters and the specific techniques required, it wasn’t the kind of writing that fulfilled me.
Then, just before I turned forty, I decided it was either now or never to write a book. Thanks, perhaps, to all those years of writing pep-talks in my journal, I managed to grow a set of balls and make the leap: I gave notice at my teaching job and told my supervisors I planned to write a memoir (my favorite genre). Naively, I told them I’d probably be back teaching in about a year.
That was in 2008, thirteen years ago. To this day, I haven’t looked back.
How I Actually Became A Full-Time Freelance Writer
The hardest part was making the actual decision to freelance. I found it harder to untangle myself from my former career than to launch a freelance career itself. I realized I had to dig deep and let go of the security of being a part of a professional community, not to mention its job security. When I told people I planned to take a year off to write a book, some (including me!) saw this as a temporary gig, something I just “needed to get out of my system.” What I didn’t realize was how much I had to learn and how long it might take to establish myself as a professional writer.
I was fortunate at the time to have a partner whose salary could support our family when I left my teaching job. Once I did, I started out by writing a ton of crap while realizing I didn’t know what the hell I was doing. I regularly compared my newbie-writer self to every writer who had a stronger social media presence or more bylines or more published works than me. I had so many doubts —and not a few tears. Plus, I constantly felt like an imposter.
I finally pulled myself out of my slump by launching a free Wordpress blog just as I started my first painful draft of a children’s novel. As I chipped away at both, I added another free blog on ChicagoNow, which ultimately lead to a paid job as a reporter for Patch.com. Though I initially earned just $10 per piece on Patch, I learned to be a journalist by actually doing it. Plus, the validation of earning money from my personal writing felt indescribable. My editor at Patch eventually gave me a weekly assignment as an opinion columnist, writing whatever struck my fancy. That column paid something like $50/week—hardly enough to live on. But by then, I was also asked to manage social media for the platform, something I’d never done before. Every day, I was learning new skills and meeting new people, and I loved it. Though I hadn’t gone to journalism school, I welcomed this unexpected education.
I’ll mention here that, while I was writing for free on my blogs, I never thought of the work as a transactional thing (ie., “If I write for free now, someone will eventually see it and pay me for my work.”). I wrote for free because I didn’t have an option, and because I needed to put my words into the world, and because NOT writing felt like not breathing. If you’re a writer, you get this (and if you don’t get it, just scroll down to the earnings section). I firmly believe that writing from a place of pure passion was the secret ingredient to making some of my columns go viral.
After 3 years of writing full-time, I finished my children’s novel and landed a literary agent who helped me shop the manuscript around to publishers. Around that time, I was tapped to write a weekly opinion column for the Pioneer Press, a local paper distributed by The Chicago Sun-Times. Not long after that, the Chicago Tribune Media Group bought Pioneer Press from The Chicago Sun-Times, and I found myself with a new byline. At this point, I was making about $100/column, once a week. Though it wasn’t enough to support myself financially, this was definitely progress.
Around this time, I decided to launch a workspace for writers, one that might help to supplement my writing income and keep me connected to other writers. I imagined a comfortable gathering space —the kind in which I’d like to spend time—and a community of writers of all levels. I created the space within my own home and called it Writers’ Haven Michigan. Almost immediately, the business model took off. I felt like I was hitting my stride.
And then, some major life events occurred, and my writing completely stopped. I had to take care of my family and myself.
When I came back to writing, about a year later, I was back at square one. I started writing again for free, focused almost exclusively on my very real and raw vulnerability. This wasn’t a strategic or even conscious plea for attention or pity. It’s that writing about grief and trauma and depression was literally all I had to give.
Around this same time, someone asked if I’d be interested in co-authoring a biography. I’d never done anything like that, but I love biographies almost as much as I love memoir. By now, I’d learned to say yes to every opportunity. I signed my first book deal, thrilled to learn I’d be paid for my efforts.
Hard at work on the biography, I kept writing my own pieces here and there. I was published in magazines and on platforms like this one. Up until this point in my career, every assignment, every discovery, every byline, and every lesson learned felt like a very small yet very significant step. And when one of my essays received an honorable mention by the National Society of Newspaper Columnists, I couldn’t believe it.
In 2019, I decided to bring Writers’ Haven back, this time in my Chicago-area home. While continuing to work on the biography, I spent nearly a year doing all “the things” to prepare to relaunch my cooperative writing space. I created an LLC, prepared the rooms, overhauled my website and spread the word about Writers’ Haven. Still, I was scared. I was no longer sure about how much to charge, let alone whether clients would even want to book space here.
And then, in January 2020, just as I began welcoming clients to the space and realizing the business was, in fact, a very good idea, I developed an infection that required major surgery in February. I could hardly believe this was happening. I had to close the doors to my one-woman business. Once again, I was back to square one.
I tried boosting my own spirits. Don’t worry, I told myself. You’ll heal and regain your strength, then reopen the business in March.
And then, the global pandemic hit.
No longer able to welcome clients into my physical space, I seriously questioned everything. Am I even a real freelancer? After all, I’m counting on income from Writers’ Haven, not from my writing. Who am I kidding? Emotionally crushed and quietly panicked, I immediately applied for Pandemic Unemployment Assistance (PUA).
As I isolated while the pandemic dragged on, I continued to work on the biography and took some temporary jobs, first as a Census Enumerator in July, then as a Contact Tracer in November, following the COVID-19 Thanksgiving surge. I’d hoped to make some money while hemming and hawing over what to do with Writers’ Haven. Unclear about where the pandemic would take us as a society, I’d fall asleep wondering how I’d moved so far away from my focus on freelance writing. Was my dream fading? Was I a complete failure?
Since I’d spent much of December of 2020 investing in new writing equipment and updating my website content (including more details about my coaching style and more examples of my writing), I didn’t want to give up on Writers’ Haven. But on a lark, I decided to add some detail to the CONTACT ME page on my website. I added checkboxes that described every kind of writing I’d ever done (including articles, content writing and press releases), as well as other types of writing I’d only dreamed of doing (like memoir coaching). And then, the most amazing thing happened.
In early 2021, my website contact page started filling up with requests from writers (established and new) in search of coaching help with their memoirs. These people all told me they hoped to find a coach who knew what it meant to struggle, someone who had the language to describe hardship and trauma… someone familiar with resilience. And you know what? When these requests kept coming in, one after the other, all my self-doubt and uncertainty completely disappeared.
Well…not all of it, but most.
I didn’t yet know the first thing about how much to charge clients for this work, or how to create a process by which to manage all their projects —but I taught myself quickly. The best part was, I knew I could do all of this ONLINE. What I knew for sure was that my innate skills were needed, and that none of this felt like work. It felt interesting, challenging, and like an honor to help people bring their personal stories to the page. I knew I was meant to do this work. I knew these clients had found me for a reason. I knew that all these years of writing for free and fretting and toiling had lead to something meaningful.
By March of 2021, I was still a Contact Tracer by day and a writing coach by night, trying to make both work. One night, feeling exhausted, I let myself do the math and stopped to take a very, very deep breath. I was making about $30/hour as a Contact Tracer and charging $150/hour as a writing coach. Plus, I had a waiting list of clients. And though I felt torn over the idea of leaving my job as a Contact Tracer (since it was meaningful and gave me a sense of purpose), I knew that my coaching work was ALSO meaningful and purposeful work…and it came far more naturally…and it would allow me to support myself.
And so, in March of 2021, I quit my job as a Contact Tracer and turned full-time to memoir coaching. What follows is a breakdown of my income.
How I Pulled In $50k in 9 Months as a Freelance Writer-Turned-Memoir Coach
As I’ve explained above, my path hasn’t been easy or circuitous, but I’ve finally found my sweet spot as a freelancer: Memoir Coaching. Once I committed to doing this work full-time, the results have been astounding.
It’s still hard for me to wrap my head around this, but since I relaunched Writers’ Haven in 2020, I’ve signed 26 clients, and that’s without any marketing or prospecting. And, they’ve all come to me, either through my website or word of mouth. The investments I made in my website —both in its initial development and the content within—have been worthwhile efforts. When clients can find you, it’s an amazing thing.
On a more detailed level, here’s how my 2021 income breaks down thru Sept 21st:
As these charts illustrate, my 2021 earnings to date are:
$42,824 (78.7%) from Memoir Coaching
$6,417 (11.8%) from Freelance Writing
$5,166 (9.5%) from Contact Tracing
$54,407 Total (thru 9/21/21)
To me, the most fascinating part is how my 2021 numbers compare to the prior year. In 2020, just as I’d relaunched Writers’ Haven at the start of the pandemic, my income was scattered, at best. But in early 2021, when I started believing in myself, I eliminated non-writing jobs and turned my focus primarily to coaching—and that’s when things really took off. My coaching income skyrocketed, but my freelance writing income also increased. I guess it’s true what they say: A rising tide really does lift all boats.
This year alone, I’ve made $42,824 from coaching, another $6,417 from freelance writing, and $5,166 from contact tracing, for a total of $54,407. And if you break the coaching numbers down even further, you’ll see how my earnings built over time:
As illustrated in the bar graph above, since I began coaching in 2020, I’ve contracted with 26 clients. Eight clients signed in 2020; another eighteen have signed so far in 2021.
In 2020, six of my eight clients paid me; the other 2 were pro-bono.
In 2021, I’ve been paid by twelve clients. Specifically, nine of the eighteen new clients have requested work and paid me so far—including one A-lister whose job astounded me in its size and scope, accounting for 46% of my 2021 income; additionally, three of last year’s clients requested more work this year. And, there’s still more work to come in 2021, as well as many more invoices to send out and collect, but that’s just a current snapshot.
To recap:
2020: Earned $4,883 from Coaching
8 New Clients Signed On
6 Clients Paid $4,883
2021: Earned $42,824 from Coaching
17 New Clients Signed On
9 New Clients Paid $37,435
3 Existing Clients Paid $5,388
And, if you’re wondering what I DO to earn all that money coaching, please stay tuned, because I plan to write another post about my whole process. Believe me, I think you’ll find it’s a fascinating story in itself, and I can’t wait to share that piece soon.
An Important Note About Probability, Privilege, and Presumptions
To be sure, my path has hardly been “the norm”, and I’m deeply aware that my chances of earning 5-figures from a freelancing career significantly increased because 1) I am a white woman and 2) I had the financial support of a partner when I launched my career. And while my journey has presented its share of “challenges”, I’m mindful of how fortunate I’ve been, and I do not take these numerous opportunities for granted.
Soon after posting this article, I shared it with one of my writers’ networks. Some of the feedback was positive, though much of it was not. I took in all those comments with appreciation, curiosity, and not a little overwhelm. The primary critiques were that 1) I hadn’t sufficiently acknowledged my privilege, that 2) writing for free is deeply discouraged, and that 3) disclosing my earnings was highly inappropriate.
Without defensiveness, I’d like to respond collectively to those comments:
Thank you for taking the time to write. I’m grateful, as always, for feedback.
As for the privilege I experienced early in my career, it’s 100% true that my financial security gave me a huge jump start that many do not and may never have. As mentioned earlier, I realize I was fortunate, but there’s so much more to the story. What’s most infuriating is that someone like me— white and financially secure—can decide, mid-career, to take a huge leap and change course, whereas few individuals from marginalized backgrounds/circumstances know the freedom/choice of following one’s dreams. And why is this still an issue in 2021? What can we do to address this injustice? What steps can be taken to ameliorate the disparity? What barriers and roadblocks can we remove to allow every individual to follow their most authentic path?
Though I sometimes shared my work for free, I started my career needing nothing more than desire and intention — which are often the only tools needed by those of us who know privilege. The unfortunate reality is that, for too long, desire and intention have regularly been the only keys needed to open doors to exclusive opportunities — and, my God, that’s just so fucked up.
I’ve been a single mom for quite some time now, working full time and trying my best to encourage myself and support myself as a freelancer. Along my way, I’ve always tried to remind myself that I’m far more valuable than that initial $10/column pittance I was so grateful to receive. And because of my privilege, I pretty much knew it to be true. I kept pushing ahead because I could, because I had options, because I had a safety net, and because I maintained access to and a foothold in a world that tends to navigate around the margins.
Early on in my career, was I exploited by the publishing industry? That’s a complicated question. The short answer is yes. Did I also collect a ton of valuable experience (and multiple bylines) early on? Also yes. And did those early days when I barely earned anything help me to build my voice, my confidence, and my connections? Absolutely. The challenge was, I didn’t know how to embrace my worth early on at all. And so, my advice to all freelancers is to ask for more compensation than you believe you’re worth. The worst they can say isn’t, “No.” It’s more like, “Not yet.”
I’ve learned that if there’s anything this journey requires, it’s the ability to keep moving forward, particularly when feedback is negative. We all come from unique circumstances, and we do with them what we will. I’ve worked very hard as a freelancer, and I have no intention of stopping. I hope my story inspires others to consider taking steps to launch their own freelance careers. It’s not easy. And, many actually do it without a partner and end up making far more money than me. My path and its results may not be typical, but it’s just one of many freelance experiences. If you told me 8 years ago that I’d have a paid, weekly newspaper column, a book deal, interviews with Barack Obama and Donald Rumsfeld, and more coaching clients than I can manage, I’d have laughed you out of the room. I know my story isn’t typical. Is anyone’s, really? At the risk of pissing some people off, I’ve been honored to share my story…and to learn about others and myself along the way.
I must add here that even when I did have a partner’s financial support, every word I wrote, every idea I had, every promotion I earned, and every award I won was my own doing—as was every single mistake. In fact, I made several, massive mistakes when writing this very piece.
For example, I mistakenly typed “6-figure income” instead of “5-figure income” in the original text—not once, but twice. What the hell?!? Was my error caused by aspirational/wishful thinking? Was it my dyslexia? Perhaps a bit of both? I’m grateful someone pointed out my error, and that I could correct it.
Lesson #1: Always use an editor (which, for this piece, I clearly have not)
Moreover, after I shared this article in an online forum and received mixed feedback, I edited the piece to include some of those comments (without mentioning any names). My intention was to be transparent and offer readers a perspective on how my piece was being received. In doing so, though, I made an egregious error. Even though I didn’t use their names, I had not explicitly gained permission from the individuals who shared their comments. Therefore, I was:
1) in violation of the online writers’ group’s posting rules and
2) demonstrating nothing short of sloppy journalism.
Shame on me. I immediately took down the comments and apologized to the individuals who wrote them.
Lesson #2: Always ask for permission to share someone’s comments, even if you’re sharing them anonymously.
Like most missteps, these errors were humbling and embarrassing. And yet, this is exactly how lasting learning happens.
Still, if you’re considering carving out a freelancing career but you’re not sure how to do it … or you’re on your own … or you’re working full-time, know that you, too, can still do it. Any significant career headway I’ve made happened well after I was completely on my own. Until then, my first steps into freelancing were one big exercise in trial and error, steep learning curves, regular screw-ups, immense tests of patience and constant efforts to maintain belief in myself—especially when others referred to what I was doing as just “a hobby”.
Epic Lessons From 13 Years As a Full-Time Freelancer
- The freelance community must broaden its recognition of professionals in marginalized communities living below the poverty line while trying to “break in”. We must acknowledge, support, and encourage their efforts, and the first step for many of us is naming and addressing our privilege.
- We don’t go into freelancing on a whim. We go into this for the long haul.
- We may end up having to write a ton of crap for FREE before finding our sweet spots. For some of us, that’s a dealbreaker. For others, it’s worth it.
- Just because you don’t get paid doesn’t mean your effort lacks value or purpose. Think of everything you do as an investment in your future. That’s not to say you should give ALL your work away for free, but think about this: Do you get paid to write your resume or a cover letter? No. Do you get paid to pitch and submit? No. Sometimes, sharing unpaid work early in your career will yield invaluable returns later. Had I not written a free blog, I may not have been discovered by an editor. That being said, I wish I’d raised my rate earlier.
- It’s not uncommon to question yourself, your skills, your intentions, your path, your ideas, and your sanity along the way. Buckle up for this, and keep moving forward.
- Find a community of like-minded souls.
- Vulnerability is a strength, so flex that muscle often. Express your limitations and ask for help. You don’t have to be a hero. Letting people know about your blind spots and what your weak areas does not make you weak — it makes you more human.
- Mistakes and missteps are just as valuable as bylines and awards. For instance, a magazine publisher once offered to pay me a handsome sum if I’d turn a piece around quickly. I scrambled to get the work done (and even worked on it at the hospital bedside of someone I loved), and turned it in on time. And then, I was never paid. Unfortunately, even though I’d done work for this magazine in the past, I was never offered a contract. I was more focused on the bylines than on protecting myself and my work. After trying for more than a year to collect the payment I was promised, I realized how critically important contracts are…and I never made that same mistake again…nor will I ever.
- Let go of feeling like you’ll never catch up to those who’ve been doing this longer than you. Every single freelancer (even the most seasoned, experienced professional) begins at square one on each new project. Plus, fresh, inexperienced eyes can often bring tremendous value, energy and perspective.
- Keep your eyes wide open. Keep an open mind. Stay open to learning. Be willing to adapt. Recognize there will be challenges and feedback.
Wishing you the best of luck with your writing, and feel free to reach out with stories of your own freelancing journey. I’d sincerely love to hear how it’s going.
Christine Wolf is a writer and coach in Chicago. Read more of her work (or better yet, get in touch!) at www.christinewolf.com.
