Lessons From 3 Months as a Full-Time Freelance Writer

Since mid-December 2022, I’ve been freelance writing full-time (FT). Freelancing full-time has been a personal and professional goal of mine for many years. 

On the personal side, I’ve wanted to travel the world since I was 16. Now that I’m 31 and engaged, I know time is running out to travel without being tethered to adult responsibilities like a mortgage and children. A fulfilling FT job is great, but even in the age of remote work, working FT while traveling the world felt unrealistic to me if I was actually interested in succeeding in my role. Additionally, a full-time job makes it harder to dedicate time to personal writing projects, like my satire newsletter.

On the professional side, I’ve always wanted to try working for myself. Freelance writers are essentially one-person content agencies. If things work out, maybe I scale freelancing into a proper business and farm out work to other writers. If it doesn’t… well, I can always go get another FT job. In the meantime, I’m learning a lot about how to run a business, market myself, and manage stakeholders and budgets, while also getting to peek inside / learn from the content operations of other businesses. I’ve always put a lot of stock in what jobs can teach you, and I believe what I’m learning as a freelancer today will help me in whatever the next phase of my career looks like.

From both a personal and professional perspective, I know I would have regretted not trying to freelance, and sticking with the “safe” route of a FT job with healthcare, benefits, etc. Like I said, I can always find another FT job, but I don’t always think this freelance route will be open to me.

So here I am, in a house in the Brazilian countryside as I write this blog post. My goal here isn’t to make some glamorous portrayal of what it’s like to be a freelance writer. Instead, I simply want to share some things I’ve learned over the past 3+ months. I always think the best people to take advice from are the ones who are just a little bit further along than you are, so I want this to be the guide I wish I could have read 3 months ago. If you’re thinking about traveling while freelance writing, I hope this gives you a better understanding of what you’re walking into.

Money

My income goal for freelancing is to earn enough money to support traveling with my fiancee in relative comfort (e.g., Airbnbs in decent locations, dinner out 1-2 nights per week)—and without having to burn through our savings (I’m overly cautious, so I built up a savings cushion that could support me for 6 months if I went without work). As such, I pegged the amount I needed to make per month at $10k, which is a respectable salary for a writer (albeit a comedown from my FT salary at my last job, and w/o insurance or benefits).

Every month so far, I’m proud to say I’ve exceeded my income goal with relative ease. In fact, I’m now wondering if I was being too modest. I don’t say this to brag—just to give others an idea of what’s possible.

Regarding my rates, I’m currently charging $125 per hour (for content consulting, SEO work, copywriting, email marketing, etc.) or $1k per project (for singular articles). Note that I work primarily with startups and VCs, and I have 7+ years experience in the technology sector. Your rates may differ based on your experience, expertise, and niche. But I do believe a six-figure income is possible if you have the demand (which I’ll discuss more in the next section).

In terms of taxes, I hired a tax firm that specializes in working with freelance creatives to help me. They advised I file quarterly taxes (because taxes aren’t taken out when you’re paid as a freelancer), set up an S-corp if I expect to earn over $100k in 2023 (because you’ll see real tax savings), track business-related expenses (incl. any meals out with friends in which you discuss your work) , and create a separate bank account that I can pay myself out of. I haven’t done any of those things yet—but I plan on. 

When I do get around to it, here are the tools that’ve been recommended to me for setting up my freelance business:

• Stripe Atlas or LegalZoom for S-Corp or LLC formation
• Mercury Bank for business banking
• Gusto for paying myself from my business income
• QuickBooks for managing taxes

Getting clients

I think I’ve been able to exceed my income goal because I’ve been fortunate to have a lot of demand for my services. Having demand allows me to name my price and turn down lower-paying work. 

Most of my demand has come from warm introductions via people in my network. I’m fortunate to have worked with a lot of founders, operators, and VCs who know a lot of other founders, operators, and VCs. So when I put the word out a few months before I left my FT role that I was taking on freelance work, I received more introductions than I could handle.

It also helps that I maintain an active social media presence (where I tweet about things going on in my industry) and up-to-date website with work samples. Both can be valuable forms of social proof when a referral is performing their due diligence on me.

In terms of process, I’m usually connected on an email thread with the client. We set up a call where I explain what I can do for them. I never try too hard to sell myself on the call. Instead, I go over my background and experience, ask what they’re looking for, and explain how I think I can help them (if indeed, I can). If they like what they hear, I draft a statement of work, and we get cracking. Since I’m still early in my freelancing journey, I generally try and say “yes” to as much inbound as possible—as long as they’re willing to meet my quote.

Not all the clients I’ve been referred to have worked out. For the 10+ clients I’ve worked with to date, there’s been another 10 or so who’ve taken a meeting and not followed up, ghosted me over email, or never assigned me a second project after I completed the first (even though they said they liked the work). I think this comes with the territory as a freelancer, and I try not to be bitter about it. However, I do think freelancers need to guard their time vigilantly. Disorganized clients who don’t have a vision for content or a dedicated individual managing you will be a drain on your time (time that could be spent working with more organized, better-paying clients). In those instances, it’s important to be able to walk away if you can afford to. 

While I’m taking on a lot of work to start, my goal is to whittle down my client roster to a handful of businesses that assign me consistent work month-to-month and pay their bills on time (I currently have 2 such “anchor” clients). This tends to be less work than doing one-off projects for a bunch of different clients, which is better for the work/life balance I’m seeking while traveling. 

For the time being, the network referrals have been a huge boost. I also think the macro environment in tech right now, with widespread layoffs, has made flexible contract workers like myself more appealing. In the future, I imagine I’ll have to hustle a bit harder for clients. 

A quick note: when your livelihood relies on having people you know connect with you with work, it’s advisable to return the favor and try your best to connect others in your network. Most people won’t forget the favor. 

Routine

As I said before, I take on a mix of hourly and project-based work. The hourly work is things that are easy to budget time around (i.e., preparing a content calendar, writing a strategy doc). The project-based work are writing projects where it’s difficult to determine how long it’ll take to complete (as most writers know, some blogs can take you 3 hours, and other blogs take 8 hours). In the latter instance, it’s fairer to the client in my opinion to quote one static price. 

In terms of process, I try to get a clear idea of workload at the beginning of the month, then map out all the work in a tracker I created in Google Sheets. For example, Client X wants 2 articles this month, while Client Y expects 40 hours of availability across a handful of projects. Once I have mapped out all the work expected of me for the month, I can figure out how and when I want to complete it (one of the best perks of freelancing, in my opinion). Of course, new work will always pop up in the middle of the month, because life isn’t simple. I try and take on as much as I can as long as it doesn’t interfere with travel or missing a deadline for another client. I also generally err on the side of underpromising and overdelivering, whenever I can.

Day-to-day, I do what I’ve always done in any job I’ve had: Pick the 3-5 most urgent items and focus on executing them. If nothing is super urgent, I pick the most challenging items (typically the writing heavy assignments). I don’t have many meetings each week (maybe 3-4 tops), but I try to stack them on a single day (usually Monday), so I can maximize uninterrupted deep work time.

Work / life balance

As I mentioned in the intro, one of the main reasons I chose to freelance while traveling was work/life balance. I found that, in a FT role, I often ended up working hours where I didn’t feel productive simply because that’s when I was expected to be working. As a freelancer, I generally can work when I want, which is usually from 9AM – 1PM, 4-7PM, and then maybe another hour or two late night if I feel I didn’t get enough accomplished that day.

I’ve found I get more done in less time because I’m not trying to force the work—I’m just doing it when my brain wants to. Setting my own schedule also provides the flexibility to blow off work on a random Tuesday if I’m not feeling engaged or want to go exploring.

In general, I’d say I definitely work less hours per week as a freelancer than I did as a FT worker. While I also earn less money, I do think if I dedicated myself to working 50+ hour weeks as a freelancer, I could match—if not exceed—my old FT income. Another benefit of freelancing: the only cap to your income is the amount you want to work. 

When I’m not working, I’ve also found it easier to unplug from work. I’ve been able to dedicate more time to my personal writing, and I’m not as anxious about late-night Slacks or emails. I don’t concern myself with office politics or my next performance review. I can focus on doing great work while I’m working, and ignore it when I’m not.

That’s not to say there isn’t broader anxiety around freelancing. As a freelancer, you’re usually the first one to go if a business needs to cut budget. A client can dump you tomorrow for any number of reasons and you’d have to just take it on the chin. I try to keep that in mind to keep me humble. For better or worse, I think of every assignment as an audition to keep my job. 

Working relationships

One of the things I missed most as a remote worker is the bond / community that forms when you work in an office with colleagues. I’d say that feeling is amplified to an extent as a remote freelancer. You’re generally at the bottom of the organizational totem pole, and can go days if not weeks without a response to your email or Slack. That’s not to say I haven’t met some great folks in my short tenure as a freelancer (including some who have referred me to other clients). 

I usually have one person who I communicate with at my client companies, and that person is generally a content or marketing person. My largest client asks for a weekly standing meeting, but I communicate with all my other clients asynchronously either via Slack, email, or text. We set one-off meetings as needed.

I think there’s a ceiling to how enmeshed you can get in an organization as a freelancer, for all the reasons I mentioned previously. I just think freelancers are kept at a certain distance, but maybe that’s just been my experience.

Concerns

Aside from the ever-present fear that all my clients will drop me tomorrow and I’ll be left penniless, the other thing I’ve spent a lot of time thinking about are AI tools, and how they affect the writing profession in general.

I chose to become a FT freelance writer about 4 weeks after Open AI rolled out ChatGPT. The main thing ChatGPT did, in my opinion, was make it possible for every business to produce at least halfway decent copy at zero cost.

ChatGPT and other AI writing tools are a threat to writers who don’t bring anything else to the table besides writing chops. That’s why I try to position myself as a “full-stack” content creator in exploratory calls with clients (i.e., not just writing, but also SEO, website copy, social media, PR, emails, etc.). I’ve been asked about AI from a handful of clients—although not as many as I expected (I suspect the clients who ghosted me outsourced my role to AI). When prompted with the AI question, and how it impacts my work, I offer some version of the following:

To stay relevant and increase productivity, I think all writers should learn how to leverage AI tools. I leverage ChatGPT myself to help me outline blog posts, think of headlines and taglines, and do research. At the same time, I’m not worried yet about ChatGPT replacing the need for writers, because there’s a human element to content creation grounded in lived experiences and net new knowledge that ChatGPT cannot yet replicate. In a world where every brand uses AI, the brand that pairs AI with a great writer wins.

My take may be misguided, and my livelihood may be under greater threat than I realize. But given what I’ve seen of AI tools so far, if every brand fired their writers and relied solely on AI copy tomorrow, it’d be like turning every restaurant into a Cheesecake Factory: the food might be decent, but there’s nothing unique or interesting about it. Maybe that works for some brands, but it won’t differentiate you from your competitors. As such, I think there’s still a place for creative writers within an organization that know how to market a brand compellingly. 

To date, I’ve yet to rewrite an AI-generated article and file that to a client, because I believe handing over that much of the content creation process to the AI is as good as signing my own death warrant. I’d much rather use the AI as an assistant that helps me figure out how to say things or present new information, than turn into a copyeditor for ChatGPT.

So far, so good

To recap:

• I’ve been able to exceed my monthly income goal as a freelancer every month so far.
• I benefitted from strong demand facilitated by my professional network.
• My work routine is largely the same as it was as a FT worker: focus on the 3-5 most urgent / challenging assignments on any given day.
• I generally work less hours as a freelancer than I did as a FT worker, and feel less stressed about work.
• It’s hard to form strong working relationships with clients as a remote freelancer.
• I have a general anxiety / fear around losing clients (common amongst freelancers, so I hear).
• AI tools present a new challenge and opportunity for freelance writers (the challenge is selling clients on hiring a writer when ChatGPT exists, the opportunity is an exponential increase in productivity).

Overall, I’d say things are going better than I expected as a freelancer. I realize I’m very fortunate, and there will probably be more adversity in the future (especially as my expenses increase… I do have a wedding to plan!). I hope this has been helpful for anyone who read. If you have additional questions about my experience, feel free to shoot me at spyzguyz@gmail.com.