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Why Everyone Should Learn to Freelance

Annie Cosby
August 15, 2024 | 7 min read

Commercial producer Reese Hopper has been freelancing long enough to know all about the ups and downs of making a living off your creative skills.

As a freelance producer, he spends his days making social ads, commercials, and content for TV and streaming platforms. He also diligently records everything he learns about selling your creative skills and shares these lessons with his eager followers.

Because even though working for yourself sounds like a creative’s dream, it comes with its own risks, difficulties, and financial concerns.

So why does Reese insist that everybody should learn to freelance?

ANNIE COSBY: OK, first things first: Is it really that perfect? Why do you say everyone should learn to freelance?

REESE HOPPER: Oh, you can read many of the tough stories in my book, What Gives You the Right to Freelance? I've definitely had an up-and-down relationship with it. I think most people do. I'm never going to say it's the easiest or greatest thing ever.

But it always was an option. It was always a pathway for me to make money. And that's what's really exciting.

Initially, straight out of college, I applied for some jobs, and I didn't get them. But I needed to make money, and I had some creative skills, so I figured I could go direct to people who needed those skills.

I started freelancing as a social media manager. I would go to small businesses or small brands, even bands or whatever, and pitch them my services. That's how I first got into it.

As time has gone on, through the various ups and downs of the economy that we've seen in the past eight years or so, I've seen a lot of friends with really good, steady jobs get laid off by these big, great companies. And these friends are kind of thrust into a tailspin because they don't have the skills to go and make money for themselves. They have to get back into this — what is often a dehumanizing and grueling job application process to try to make money again.

That's when I started to realize that freelancing is such a gift, and it's a great skill set to have because it's always in your hands.

If you are a creative person or you are a person who can help a business solve a problem, it's always in your hands to be able to make at least a little bit of cash.

If you are a creative person or you are a person who can help a business solve a problem, it's always in your hands to be able to make at least a little bit of cash.

So, for me personally, as I've grown to love and appreciate it, I started to want to spread the word to as many people as possible.

That's the deeper sense of my mission. I really think everyone should be freelancing in some capacity.

AC: Even if you currently have a job?

RH: Yeah, just dip your toes in. It doesn't have to be full-time. You can keep a full-time job.

But so many of us have these skills that we can use to make a few hundred bucks here or there. And it's a powerful skill to know how to leverage that.

AC: Because the day may come when you need to leverage that. I guess it is the ultimate safety net.

RH: Definitely. But it's not only helpful in times when you're not working, it's always helpful to be able to make a few hundred bucks on the side. Like when Christmas is coming up or I want to go on that trip but maybe I can't quite afford it. What if I can log a couple of projects on the weekend and we can make it happen?

So I think it's a very empowering process. For me personally, it has increased the quality of my life in a rich, deep way. And I think it can for many other people as well.

AC: I think people, especially writers, have this kind of dreaminess about freelance work, which we tend to see as doing what you love every day, all day. Does that change when you're under pressure and your paycheck is totally dependent on your passion?

RH: There's definitely a misconception when people get into doing their creative discipline full time that it'll be really easy and wonderful. But the reality is creativity and creative endurance is a muscle that you have to build up over time.

I was always someone with big ideas, and I've always loved working on social campaigns and building strategies, but for most of my life, I had only done that for a maximum of, maybe, one to two hours a day, throughout the course of school and college.

So when I got into the working world, it was like, okay, I have to book this number of clients to pay this much to pay my bills. And I realized I didn't have the creative stamina to be working a full creative schedule. But I needed to work eight hours to be able to pay my rent and bills.

So, yeah, in those early days of freelancing, I definitely bit off more than I could chew. And there were some late nights just grinding, making it happen. But I look back fondly on that because I know now that those were the moments when I really took a leap forward.

That was a hard lesson I learned early on. And people who don't work in a creative zone are always like, "Man, you have it so good! You just get to make stuff all day."

I'm like, "No, that is hard, hard work."

The reality is creativity and creative endurance is a muscle that you have to build up over time.

AC: That endurance is definitely a thing writers struggle with. I'll say, Oh, I could finish my book if I just had eight hours a day to write! And then I get a week off from the day job and write, like, 200 words total.

RH: Yeah, and then you're so burned out and the ideas suck and you get discouraged.

It's not a you thing. It's just a creative muscle that you have to work at, just like anything.

AC: So how do you work that muscle? How do you train it?

RH: Experience. Just do it. The 15 minutes you have today, the 30 minutes you have after work or at lunch or after the kids go to bed — whatever it is. That's what you need to start with, to start building up that endurance. 

Getting enough project work will force you to do it, too. Then you have to produce, and you have a deadline. With each project, there are a lot of learnings and gains.

AC: OK, so say I've decided to freelance. What is the hardest part — what should I focus on first?

RH: For many people, the hardest hump to get over is learning how to pitch. The only difference between a professional and a hobbyist is that the professional is the one who decides to pitch.

The hobbyist could be exponentially more talented or artistic, but the professional gets out there and says, hey, I have an offering. You can buy it. Let me help you.

And it's really difficult for a lot of people, especially in Western culture, I think, because it's not something that we do all the time. We don't negotiate often. We don't barter. In many ways, our culture and society has been designed to have us do that as little as possible.

But in this creative world, there's a ton of pitching and negotiating. And that's just a skill that a lot of people haven't learned.

And it is nerve-wracking to get over at first. I mean, public speaking is still like one of the top fears. So I get it.

AC: That would definitely be one of my weaknesses.

RH: And, you know, freelancing is really challenging in so many ways because it exposes you. It exposes the things that you are bad at — which is different for everybody.

Some people might be really good at budgeting, some are really bad at it. Freelancing will expose that.

Some people might be really good talking to strangers, some are bad at it. Freelancing will expose that.

Freelancing is really challenging in so many ways because it exposes you. It exposes the things that you are bad at — which is different for everybody.

AC: That's true. It's so much less structured than a regular job.

RH: Yeah, the traditional path has a lot of padding on the walls. A traditional 9-5 job has a lot of aspects figured out for you: your income is set; your taxes are pulled out of your paycheck; you have sick days, paid time off. Depending on the job, of course. But these are all padding designed to make the working world easier.

And I'm not bashing these at all. These are awesome, amazing things that haven't always been part of American life. These are great things that protect everyday people all the time. Right?

With freelancing, there are so few of those pads. If you get sick and you have a deliverable due, you have to figure out what to do. If you want to take a vacation, you're not going to be getting paid for that. There are all these different things that you have to figure out, and it challenges you in so many ways.

You'll bump into those walls. You'll get some bruises. And you'll learn some lessons the hard way. 

But the beautiful thing is it will force you to grow in so many ways and so many spaces that you might not have otherwise.

The beautiful thing [about freelancing] is it will force you to grow in so many ways and so many spaces that you might not have otherwise.

AC: What's your #1 piece of advice for somebody thinking about freelancing?

RH: Ask yourself, What would you do if you couldn't succeed? This is the first chapter of my book.

Everyone asks, What would you do if you couldn't fail? The trouble for creative people is we're too creative. We want to do a million things, and we can't pick one.

Instead, ask yourself: What would you do if you couldn't succeed? What would you do if the best you could hope for is to be average? To make a medium salary for a medium amount of notoriety? What is that thing you would still be doing? What's the thing you'd be doing for free anyway?

That's the thing you should hone in on as your freelance offering or as your creative discipline, because that's the thing that you're going to be motivated to work on, even through those early dips, when nothing makes sense and no one's picking up the phone.

AC: So people can find more of this advice in your book?

RH: Yes, What Gives You the Right to Freelance? helps people overcome their mental blocks and find work-life balance in freelancing so they can achieve the career of their dreams.

It's broken up into five main sections: getting started, pitching, doing the work, client care, and work-life balance. It has a lot of stories from my journey so far, and helpful lessons that I've learned, the easy way or the hard way.

Find What Gives You the Right to Freelance? by Reese Hopper on Amazon or therighttofreelance.com.

Follow Reese on Instagram or visit his website for more info.

December 30, 2025 3 min read

It’s Freewrite’s favorite time of year. When dictionaries around the world examine language use of the previous year and select a “Word of the Year.”

Of course, there are many different dictionaries in use in the English language, and they all have different ideas about what word was the most influential or saw the most growth in the previous year. They individually review new slang and culturally relevant vocabulary, examine spikes or dips in usage, and pour over internet trend data.

Let’s see what some of the biggest dictionaries decided for 2025. And read to the end for a chance to submit your own Word of the Year — and win a Freewrite gift card.

[SUBMIT YOUR WORD OF THE YEAR]


Merriam-Webster: "slop"

Merriam-Webster chose "slop" as its Word of the Year for 2025 to describe "all that stuff dumped on our screens, captured in just four letters."

The dictionary lists "absurd videos, off-kilter advertising images, cheesy propaganda, fake news that looks pretty real, junky AI-written books, 'workslop' reports that waste coworkers’ time … and lots of talking cats" as examples of slop.

The original sense of the word "slop" from the 1700s was “soft mud” and eventually evolved to mean "food waste" and "rubbish." 2025 linked the term to AI, and the rest is history.

Honorable mentions: conclave, gerrymander, touch grass, performative, tariff, 67.

Dictionary.com: "67"

The team at Dictionary.com likes to pick a word that serves as “a linguistic time capsule, reflecting social trends and global events that defined the year.”

For 2025, they decided that “word” was actually a number. Or two numbers, to be exact.

If you’re an old, like me, and don’t know many school-age children, you may not have heard “67” in use. (Note that this is not “sixty-seven,” but “six, seven.”)

Dictionary.com claims the origin of “67” is a song called “Doot Doot (6 7)” by Skrilla, quickly made infamous by viral TikTok videos, most notably featuring a child who will for the rest of his life be known as the “6-7 Kid.” But according to my nine-year-old cousin, the origins of something so mystical can’t ever truly be known.

(My third grade expert also demonstrated the accompanying signature hand gesture, where you place both hands palms up and alternately move up and down.)

And if you happen to find yourself in a fourth-grade classroom, watch your mouth, because there’s a good chance this term has been banned for the teacher’s sanity.

Annoyed yet? Don’t be. As Dictionary.com points out, 6-7 is a rather delightful example at how fast language can develop as a new generation joins the conversation.

Dictionary.com honorable mentions: agentic, aura farming, broligarchy, clanker, Gen Z stare, kiss cam, overtourism, tariff, tradwife.

Oxford Dictionary: "rage bait"

With input from more than 30,000 users and expert analysis, Oxford Dictionary chose "rage bait" for their word of the year.

Specifically, the dictionary pointed to 2025’s news cycle, online manipulation tactics, and growing awareness of where we spend our time and attention online.

While closely paralleling its etymological cousin "clickbait," rage bait more specifically denotes content that evokes anger, discord, or polarization.

Oxford's experts report that use of the term has tripled in the last 12 months.

Oxford Dictionary's honorable mentions:aura farming, biohack.

Cambridge Dictionary: "parasocial"

The Cambridge Dictionary examined a sustained trend of increased searches to choose "parasocial" as its Word of the Year.

Believe it or not, this term was coined by sociologists in 1956, combining “social” with the Greek-derived prefix para-, which in this case means “similar to or parallel to, but separate from.”

But interest in and use of the term exploded this year, finally moving from a mainly academic context to the mainstream.

Cambridge Dictionary's honorable mentions: slop, delulu, skibidi, tradwife

Freewrite: TBD

This year, the Freewrite Fam is picking our own Word of the Year.

Click below to submit what you think the Word of 2025 should be, and we'll pick one submission to receive a Freewrite gift card.

[SUBMIT HERE] 

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Sources

December 18, 2025 7 min read

What can Jane Austen's personal letters teach writers of today?

December 10, 2025 6 min read

Singer-songwriter Abner James finds his creativity in the quiet freedom of analog tools. Learn how his creative process transcends different media.

Abner James went to school for film directing. But the success of the band he and his brother formed together, Eighty Ninety, knocked him onto a different trajectory.

The band has accrued more than 40 million streams since the release of their debut EP “Elizabeth," and their work was even co-signed by Taylor Swift when the singer added Eighty Ninety to her playlist "Songs Taylor Loves.”

Now, Abner is returning to long-form writing in addition to songwriting, and with a change in media comes an examination of the creative process. We sat down to chat about what's the same — and what's different. 

ANNIE COSBY: Tell us about your songwriting process.

ABNER JAMES: The way I tend to write my songs is hunched over a guitar and just seeing what comes. Sounds become words become shapes. It's a very physical process that is really about turning my brain off.

And one of the things that occurred to me when I was traveling, actually, was that I would love to be able to do that but from a writing perspective. What would happen if I sat down and approached writing in the same way that I approached music? In a more intuitive and free-form kind of way? What would that dig up?

AC: That's basically the ethos of Freewrite.

AJ: Yes. We had just put out a record, and I was thinking about how to get into writing for the next one. It occurred to me that regardless of how I started, I always finished on a screen. And I wondered: what's the acoustic guitar version of writing?

Where there's not blue light hitting me in the face. Even if I'm using my Notes app, it's the same thing. It really gets me into a different mindset.

 "I wondered: what's the acoustic guitar version of writing?"

I grew up playing piano. That was my first instrument. And I found an old typewriter at a thrift store, and I love it. It actually reminded me a lot of playing piano, the kind of physical, the feeling of it. And it was really fun, but pretty impractical, especially because I travel a fair amount.

And so I wondered, is there such a thing as a digital typewriter? And I googled it, and I found Freewrite.

AC: What about Freewrite helps you write?

AJ:I think, pragmatically, just the E Ink screen is a huge deal, because it doesn't exhaust me in the same way. And the idea of having a tool specifically set aside for the process is appealing in an aesthetic way but also a mental-emotional way. When it comes out, it's kind of like ... It's like having an office you work out of. It's just for that.

"The way I tend to write my songs is hunched over a guitar and just seeing what comes. Sounds become words become shapes. It's a very physical process that is really about turning my brain off."

And all of the pragmatic limitations — like you're not getting texts on it, and you're not doing all that stuff on the internet — that's really helpful, too. But just having the mindset....

When I pick up a guitar, or I sit down at the piano, it very much puts me into that space. Having a tool just for words does the same thing. I find that to be really cool and inspiring.

"When I pick up a guitar, or I sit down at the piano, it very much puts me into that space. Having a tool just for words does the same thing."

AC: So mentally it gets you ready for writing.

AJ: Yeah, and also, when you write a Microsoft Word, it looks so finished that it's hard to keep going. If every time I strummed a chord, I was hearing it back, mixed and mastered and produced...?

It's hard to stay in that space when I'm seeing it fully written out and formatted in, like, Times New Roman, looking all seriously back at me.

AC: I get that. I have terrible instincts to edit stuff over and over again and never finish a story.

AJ:  Also, the way you just open it and it's ready to go. So you don't have the stages of the computer turning on, that kind of puts this pressure, this tension on.

It's working at the edges in all these different ways that on their own could feel a little bit like it's not really necessary. All these amorphous things where you could look at it and be like, well, I don't really need any of those. But they add up to a critical mass that actually is significant.

And sometimes, if I want to bring it on a plane, I've found it's replaced reading for me. Rather than pick up a book or bring a book on the plane, I bring Traveler and just kind of hang out in that space and see if anything comes up.

I've found that it's kind of like writing songs on a different instrument, you get different styles of music that you wouldn't have otherwise. I've found that writing from words towards music, I get different kinds of songs than I have in the past, which has been interesting.

In that way, like sitting at a piano, you just write differently than you do on a guitar, or even a bass, because of the things those instruments tend to encourage or that they can do.

It feels almost like a little synthesizer, a different kind of instrument that has unlocked a different kind of approach for me.

"I've found that it's kind of like writing songs on a different instrument, you get different styles of music that you wouldn't have otherwise... [Traveler] feels almost like a little synthesizer, a different kind of instrument that has unlocked a different kind of approach for me."

AC: As someone who doesn't know the first thing about writing music, that's fascinating. It's all magic to me.

AJ: Yeah.

AC: What else are you interested in writing?

AJ: I went to school for film directing. That was kind of what I thought I was going to do. And then my brother and I started the band and that kind of happened first and knocked me onto a different track for a little while after college.

Growing up, though, writing was my way into everything. In directing, I wanted to be in control of the thing that I wrote. And in music, it was the same — the songwriting really feels like it came from that same place. And then the idea of writing longer form, like fiction, almost feels just like the next step from song to EP to album to novel.

For whatever reason, that started feeling like a challenge that would be deeply related to the kinds of work that we do in the studio.

AC: Do you have any advice for aspiring songwriters?

AJ: This sounds like a cliche, but it's totally true: whatever success that I've had as a songwriter — judge that for yourself — but whatever success I have had, has been directly proportional to just writing the song that I wanted to hear.

What I mean by that is, even if you're being coldly, cynically, late-stage capitalist about it, it's by far the most success I've had. The good news is that you don't have to choose. And in fact, when you start making those little compromises, or even begin to inch in that direction, it just doesn't work. So you can forget about it.

Just make music you want to hear. And that will be the music that resonates with most people.

I think there's a temptation to have an imaginary focus group in your head of like 500 people. But the problem is all those people are fake. They're not real. None of those people are actually real people. You're a focus group of one, you're one real person. There are more real people in that focus group than in the imaginary one.

And I just don't think that we're that different, in the end. So that would be my advice.

AC: That seems like generally great creative advice. Because fiction writers talk about that too, right? Do you write to market or do you write the book you want to read. Same thing. And that imaginary focus group has been debilitating for me. I have to silence that focus group before I can write.

AJ: Absolutely.

"I think there's a temptation to have an imaginary focus group in your head of like 500 people. But the problem is all those people are fake... You're a focus group of one, you're one real person. There are more real people in that focus group than in the imaginary one."

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Learn more about Abner James, his brother, and their band, Eighty Ninety, on Instagram.