How this freelancer made $27,000 in 1 month

You read that right!

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If there’s one thing I love to celebrate, it’s freelancers getting fucking paid — and goodness do we have someone to celebrate today.

Last week a freelancer reached out to me about an unrelated topic, and after we started talking, they dropped a bomb on me: This month they’ve made $27,000.

My first reaction:

I’m sorry, what?! As in, twenty-seven thousand U.S. American greenback dollars?!

Yes, dear reader, that is correct. On top of that, this person regularly has $15,000 months. Lmao whaaaaaat.

So, of course, my first instinct was: Please let me interview you so you can teach us how to be like you. They requested anonymity, which I have granted, and below is a transcript of an interview conducted over Gchat last week. Go forth, freelance friends, get fucking paid.

***

Tim Herrera: Hello! So before we get to the goods, can you tell me a little about the type of freelancing you mostly do? And how long have you been doing it?

Anonymous: I've been freelancing for about 10 years. I started out contributing to small blogs that paid basically nothing, but over time, I've grown my workload to several different higher-paying clients. I mostly do journalism (stories I pitch or I'm assigned) and content writing for startups of various types. I've written for schools, universities, healthcare organizations, software companies, and everything in between.

TH: How do you find work, particularly things that aren't with editors you already work with?

Anonymous: I subscribe to a lot of newsletters with writing opportunities, and I keep my resume and clips at the ready so I can email editors looking for new writers as soon as they put out a call. In those emails, I explain my background, why I'm a good fit, and clips I've published at similar publications. Finding non-journalism work can be trickier. In the past, I've cold emailed the content managers at companies I admire (apps I use on a regular basis, for example). Once I establish relationships with editors I'm writing for, I ask if they have any colleagues looking for writers or continue freelancing for them wherever they are. That's a great way to get plugged in at a new pub!

TH: Which newsletters do you like?

Anonymous: I subscribe to Sonia Weiser's Opportunities of the Week and Write Jobs PLUS+!

TH: Okay so, now the question we're all wondering: Literally how the fuck did you make $27,000 in a single month?!

Anonymous: Over the past few years, I've started getting regular work for $1/word or higher clients. I try to prioritize those, of course, but I also do lots of work for lower-paying clients. So a combination of a few high-paying things a month and LOTS of lower-paying assignments a month (and some in between) is how I usually hit $10-15k a month. I took a month off over the summer to, you know, not be burned out, and by the end of the summer I was feeling kind of frantic about finding new work to make up for the lost income. So I aggressively started introducing myself to new editors and stacked that work on top of my existing workload! September is usually a busy month for me, but this is my biggest month yet.

TH: That is insane! Okay so I have many follow-ups. First, how do you manage so much work? What does an average day look like when you have so many assignments, and how many hours per week do you end up working?

Anonymous: I probably work about 50 hours a week. [Update from Tim on 9/21: This person said they produced around 60-ish individual pieces over the Big Month.] I try not to work nights so I can get sleep and spend time with friends, but I end up working some Sunday afternoons (which I actually kinda like — prepping for the week is a good way to get rid of the Sunday Scaries). Usually, I work on emails and simple, shorter articles in the morning, do calls and reporting for new stories late morning, and dig into bigger pieces in the afternoon. I use Evernote and an Excel spreadsheet to track my work, and that's worked pretty well for me! That said, I don't follow a strict routine for any of it. I sort of fly by the seat of my pants in most of my life, but I'm also a pretty efficient person and I thrive with a bit of stress.

Breakdown of a $27,000 month:

TH: Can you be a little more specific about how you find high-paying clients? I feel like one of the most common questions I get on panels is: Where are all the big payers?

Anonymous: Trade journals usually pay more than, say, huge media conglomerates. I also do a lot more print work these days, which always pays more than online stuff. That didn't happen right away — I started out writing for sites, and over time, editors started asking me to contribute to the print editions, too. I also use Crunchbase to find startups that might need content. I check out their blog to see if they're publishing already, then I reach out to them. Once I hook them, we talk about rate. If they have tons of seed funding, I don't feel bad asking for more money. (Actually, a good reminder: No journalist should ever feel bad asking for more money.) Also, if I've been working with a pub for a while at the same rate, I ask for an increase after several months of working together. Most editors are respectful enough to consider it, and if they don't or can't, I'll focus on work that pays more.

I'm also at a point in my career where I've come to terms with the reality that, for me, money is more important than prestige. I care more about paying off my loans and building savings than, say, writing for prestigious or "cool" publications that may pay less. (It also helps that I literally never want to write a book, so I don't have to think about bylines or building a platform.) I also care more about building relationships with editors than simply accumulating more work with editors who make me feel horrible. Focusing on these things has helped me earn more and be happier while I do it!


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TH: So, on money: Can you talk about what you charge? Since you've been doing this for 10 years I would imagine the overall average per story you make has increased, but now, what is a "good" rate? And how much does that vary depending on the place you're negotiating with?

Anonymous: I think more about the value of my time than anything else. I don't charge by the hour — I only do flat fees these days — but every rate involves a certain amount of work (and headaches). I do $200 articles, but they're usually really simple and don't need much heavy lifting other than the actual writing. I also do $2,000 articles (usually with $1/word clients) that require a lot more reporting and revision. I don't have a formula, but in general I try to focus on work that pays me for the actual time and energy I'm putting into it. I generally don't do work for under 50 cents a word unless I really like the editor, it's relatively easy, or I'm super interested in the topic. One dollar per word or above is ideal, but those are much harder to find!

TH: I love that you mention working with specific editors — I think finding editors you like to work with is almost more important than finding the work in the first place. How do you build a long-term working relationship with an editor? And, as has happened to many people in the pandemic, what do you do when an editor you've worked with a ton leaves that position?

Anonymous: Many times, maintaining good relationships with editors is as easy as filing clean copy on time and following through on what you said you'd do. But I think I also have a pretty good nose for good people. If an editor makes me feel bad about myself or doesn't understand I'm a human who makes mistakes, I usually don't work with them again. That makes it easier to maintain a long-term relationship, because we respect each other!

I've definitely had editors leave publications I've loved working for. If the pub still pays freelancers, I'll usually email an intro to another editor at the publication and let them know I'd like to continue working with them. When editors go to other publications, I sometimes continue working with them there. Other times, like if an editor gets laid off or goes freelance and there's not an opportunity in the same pub, I'll say goodbye and seek new work. It's always tough to move on, but I'm grateful to have work to fall back on.

TH: As a matter of personal philosophy, I think we should all ask for more on (almost) every assignment. When do you think is the right time to revisit a rate at somewhere you regularly write for? And, just because this comes up all the time — has an editor ever reacted badly to your asking?

Anonymous: If I've been doing solid, ongoing work at the same rate for an editor for six months or so, I'll usually ask for a rate boost. It doesn't have to be a lot; for example, I could bump a $500 flat fee up to $600. Sometimes, they can't swing the $100 increase, but they'll offer $550. If the relationship is worth it, I almost always say yes (then ask for another increase later!). I've never had any editor react poorly, but I've had people say they just can't swing it. The folks I choose to work with are usually respectful and understanding, and I really think they'd pay me more if they could.

TH: This is a complicated question because it really varies, but generally speaking, how often are you pitching in a given week? And how much of your work comes from editors assigning you rather than you pitching? 

Anonymous: I'd say 70% of my work is assignments and 30% is pitched. I don't have a pitching routine, but I do keep a document of story ideas with potential sources for when editors put out a call for pitches. That way, I can beat the crowds a bit. I probably pitch once a week, or whenever I see an interesting call for pitches that pays well.

The assigned work is key because it not only keeps coming but it cuts down on the mental labor of coming up with story ideas and going back and forth with an editor about something that might not get picked up.

TH: What are your top three pieces of advice you'd give to someone just starting out?

Anonymous:

  • Only write for pubs you actually care about or read. When I first started out, I wasted so much time pitching "cool" or "respected" publications I didn't keep up with because I wanted amazing bylines. Editors can tell when you don't read their pub, and you'll do better work when you actually care about the place you're writing for.

  • Master the art of a solid pitch email. I use the same formula every time: a subject line with PITCH and my idea, a brief elevator pitch of the story, why it fits at such and such pub, and relevant clips. I also include potential sources when I can to show the editor I've already done some homework on the topic.

  • A "no" isn't always personal. [Note from Tim: Extremely true!] Often great ideas just don't fit the editor's calendar or budget, or the pub has already done something similar. Or, maybe it just doesn't fit the vibe of the publication (you'd know that if you read the pub!). If you care enough about the story, pitch it around until it lands somewhere.

TH: I love this! And now a quick lightning around: 

  1. Did you hold a staff editor or writer job somewhere before going freelance? 

  2. Did you attend a private or Ivy league school? 

  3. Is any of your income passive? 

  4. How do you balance working with a home life?

Anonymous:

  1. No! I’m self-made!

  2. I went to a private school, but not even close to Ivy league. I didn’t have any help from my family, so I paid my way with student loans I’m still paying off today.

  3. No, it’s all from writing.

  4. I’m not perfect at it. I try not to work at night or on weekends, and I try to get as much sleep as I can so I can function in work and in life. Also, I go to therapy weekly to stay on top of my mental health!

TH: Wonderful! Thank you so much for chatting. Any last words you'd like to share about making those big bucks as a freelancer?

Anonymous: Making money is obviously important, but don't say "yes" to anything that will harm your mental health. Protect your own well-being at all costs, even if it means taking less work or saying no to a great opportunity. Your future work will be better for it.

Oh, a few other things …

• [Update 9/21: This has been claimed] Student journalists! DAME Magazine is sponsoring two yearlong subscriptions to FWT here on Substack. Email me at freelancingwithtim@gmail.com to claim one. (First responses get them, so act quick!)

• [Update 9/21: This has also been claimed.] Additionally, a very kind and generous journalist who wishes to remain anonymous has offered to sponsor yet another yearlong subscription for a student — email me to claim it!

• Our pal Jessica Huseman has launched a fantastically helpful series of trainings on digital skills, including lessons on records requests, interview techniques, project management, and more. Check them out here!

For paid subscribers: The only pitch template you’ll ever need. Not sure how to write out your pitch? This post details my favorite structure for pitches. Also for paid subscribers: The full archive of recorded Zoom panels and workshops, and The dos and don'ts of writing the perfect pitch.

• I am now offering one-on-one coaching! This can include anything you need help with: pitch feedback, writing and/or editing coaching, story development, story editing, social strategy, and anything else. Book a timeslot here.

Okay bye ily!

-Tim ❤️