What I Learned After a Year of Freelance Writing Full Time

Here are my takeaways, insights, and tips from my first year of freelance writing full time. Hopefully, this helps you in your journey!

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The other day, I got off a call with a prospective client and realized something. I had zoned out halfway through the call. Pure autopilot. I think my eyes widened unblinking like that one horrified cat meme. Client nonplussed. It was pretty bad.

So what the hell happened?

A stunned cat with the thousand-mile stare, the same look I had when I first considered freelance writing full time.

When it comes full circle, you realize a few things

As it turns out, that client call fell on the one-year anniversary of my leap into freelance writing full time in September 2020. And it hit me square in the eyes:

It’s all up to me now. Which calls to accept and what to say. How to negotiate timeline, budget, and scope. When and where to drift off into some kind of frontier existential reverie.

In that moment, I realized a few things about my future in freelance writing:

1. It can be what you wanted all along

It really can, only I’m not sure I knew exactly what that meant when I “took the leap” in the first place. The work is there. The flexibility is real, as is the income (I’ve replaced my corporate salary ten months into my first year). I’m getting better each day, I think. I’m finding the contours of my particular writing business and service offering(s).

2. Most people still ask what “content writer” means

I can’t explain it. Literally, I don’t know how to explain what I do to my friends, family members, or even business contacts. Ironic, right? Especially coming from someone that helps other people and businesses articulate themselves.

Maybe I should take Diane’s advice:

A LinkedIn comment from Diane Burley advising me to "call yourself a B2B storyteller."

3. Your content specialization will reveal itself to you

At first, I didn’t know what I wanted to write. So I took on a lot of different assignments, some of them good fits, others not so much. Over time, I’ve worked on three particular content types more than any other—my specializations now, even if I took a circuitous route to find them: 

To see some real-world examples of my work, read my blog posts for Coveo.

4. A non-linear working style ain’t all that bad

I might sit down and knock out a 1500-word blog post before lunch. I might write one sentence of web copy in a half hour (headlines, grr). Overall, I have a general idea of how much time I’ll need for each assignment (breaks and walk-aways included). 

In the end, the chaos works remarkably well for me. The only time I move deadlines is when my toddler-creature gets the sniffles.

Graphic with text "Through chaos, order."

5. It helps to know where your clients come from

If I know that I get most of my clients from a particular source, I’m going to devote a little more time toward cultivating that source, right? That’s why it was so helpful to finally sit down after a twelve months to see just where my freelance writing clients came from. Here’s how it breaks down for me this first year of freelance writing full time: 

  • 70% from Upwork, 52% of which are long-term
  • 20% from long-term “organic” clients (website and LinkedIn)
  • 10% from “net-new” clients from both sources, including referrals

Coincidentally, my monthly revenue breaks down almost exactly the same way.

A pie chart depicting how many clients come from Upwork (70%), Organic (20%), and Net-New & Referral (10%).
A breakdown of where my freelance writing clients come from

6. A bookkeeper can be a big help

Estimated taxes didn’t surprise me—I knew I had to pay quarterly estimated taxes as a freelancer. The thing is, I overpaid on my estimated taxes last year and ended up waiting months for a sizable check from the IRS. 

Like most freelancers, I don’t like waiting for big checks. While I do have an accountant, I plan to hire a bookkeeper to help me make more precise estimated payments. 

UPDATE: I totally did it! With the help of Collective, I turned my business into an LLC taxed as an S-Corp. The fine people at Collective are handling everything (and I’m learning a lot). If you’re a solo proprietorship making more than $100K a year, this solution might make a lot of sense (and save you thousands). Check it out and use my promo to get a free month of Collective should you choose to sign up (yes, that’s an affiliate link, FYI).

Sorry, Not Sorry

About that call I referenced at the beginning. I don’t recommend zoning out in the middle of client calls. (As you might have guessed, it didn’t work out.) Still, it was incredibly rewarding to get through that first year freelance writing full time. If nothing else, I got the opportunity to look back, take stock of things, and see how it all shook out. This information will be handy as I plod through year two.

Oh, and I almost forgot one thing: I don’t miss my corporate jobs at all.

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