0 to $5K: How I Reached $5,000/Month in Four Months of Freelancing

I laughed when I realized I would be able to write that headline.

For one, I hadn’t quite put my finances together. I didn’t know I had reached this milestone until well over a month after it was achieved.

But the headline really tickled me because I read so many articles of this nature when I went freelance. Like, ardently. I would click on every single one I came across as if the answer to the question how DO you make money writing? and then voilà, I would start making money within a week. Right.

I wanted to believe these articles would contain the holy grail answer that would get me jobs and make me money and sure, a lot of them have decent advice, but, having arrived at this place (I’d love to think I have ~arrived~ but sometimes I wake up and think all my clients will vanish and I’ll be back at zero), I can say I kind of…didn’t work that hard for this?

I’m trying to balance giving myself credit while also being realistic. So let me break it down and you can see if you agree that it wasn’t, like, that hard.

How I Started Freelance Copywriting

My income is 90% from my company, Picante Collective, a small digital marketing and creative agency that I founded alongside four other people. I have three anchor clients and a few other smaller clients which get just a few hours of my time each month. Most of my work is copywriting with some project management and strategy sprinkled in. The other 10% of my income is from virtual assistant work which pays significantly less but is sometimes more fun.

While I technically went freelance in March 2021 after working in marketing for five years, I’m starting this timeline from August because that’s when I feel like I started actually trying to get clients. (LOL, sigh @ past maeve). I don’t entirely know what I did from March to June; I know I did some work, but it was very sporadic. I spent a lot of time on my own creative writing and fretting about how to make money, reading the aforementioned articles–you can see how productive that was. I mean, I did write 30K words of a novel that I only refer to as a “story” to protect my own ambitions, but I digress. I was fortunate to have low living expenses at the time (and some savings) and spent most of my time doing an immense amount of inner work to recalibrate my relationship to time and money (more on that in another article).

How I Landed My Clients

August — Client 1 was a relatively easy sell because we had already worked with them and a former colleague of ours is on staff there. And, to be clear, I didn’t do the selling. I was away for my brother’s wedding while my teammate did the heavy lifting on the sale. Regardless, we were able to sell a moderate-size email retainer to them, which splits between me and said teammate.

September — Client 2 messaged me on LinkedIn for a social media job. I went into a 30-minute Zoom with them thinking it was a conversation when in fact it was an interview (how do you answer “Why do you want this job?” when you only fully learned what it was 10 minutes prior?), did a small piece of test content (pay writers for these tests, people!), and was hired. The kicker about this particular client is I was able to double the monthly fee after month one because, well, it was necessary. In month two, I also expanded the retainer to take on another account. This is my largest client.

October — Client 3 reached out after I had applied to a contractor job on their site all the way back in August (through a newsletter–shoutout to Content Writing Jobs!) and said they were restarting their search. Great! Two interviews, two references, and two months later, I finally closed them. Lengthy, but worth it.

My first $5K+ month was November. I had about three different one-off projects in the air between October and December; most of them paid in November, finally putting me over the line. These projects were all referrals or from friends.

And that’s…kind of it. The rest of the cracks get filled in by smaller retainer clients which I share with the rest of the team, plus the aforementioned VA work. The smaller clients have all come from my teammates’ gyms, interestingly enough, and are very small businesses. The VA work came from a friend passing on another friend’s call for a VA who then referred me to another organization to do similar work for them.

My Thoughts on Finding Freelance Marketing Work

I have gotten a lot of outreach from LinkedIn, and I really believe optimizing your profile and spending time on there can pay off, but other than Client 2, I haven’t closed any jobs there. Then again, when I actually apply for jobs on LinkedIn, I rarely submit a cover letter, because a cover letter for a contract job just feels a little offensive. So perhaps I am not doing myself any favors.

I have also had several almost-clients through Facebook Groups, of all places. That site is a dumpster in every way except their Groups, which are really the only one of their kind. One of the groups I’m in is so active that if someone posts a job opportunity, the post gets 50+ comments in one day. I never bother applying if that’s the case because you would not believe the specificity of some of these people’s niches…!

So in reality, my advice is: keep your eyes and ears open. Really, that’s it. I got one website project because my sister-in-law’s family friend was talking about her business and I jokingly asked if she needed a website. Word of mouth will always be the backbone of marketing and creative work because it relies so heavily on trust. Everyone thinks that they hate marketing and marketers when in reality, it’s simply an overwhelming task for someone who doesn’t understand why they need marketing. So, someone you know asks their friend whose company just redid their website who did it and if they liked them and then boom, another job.

I think it’s normal and logical and possibly even fun that your first few clients are people you already know or who are in some of your outer circles. Our favorite clients are in fact our friends or at least feel very friendly. It is so much more invigorating to get off a meeting where you feel like you were a human with emotions and real conversation rather than just a task-reporter delivering information.

How I Did It

Ok, here comes the part where I give myself credit. In order to have accomplished any of this, I have to be good at what I do. You don’t just get a referral because you have a good relationship–you have a good relationship because you do good work.

Closing a job is hard. Selling is exhausting. Negotiating price is exhausting. And, for what it’s worth, keeping a client is almost just as hard. Building these relationships is a delicate art.

But when I sit back and look at what I’ve built so far, when I get off a call more excited than I got on it, when I read back a piece of really good copy, I feel a distinct sense of deep satisfaction that comes from knowing I did it all for myself.

NB: I wrote this in December 2021. I am heading into March 2022 with five clients and completely full books, staring down my first five-figure month.