Advice for Freelancers: Learnings from My “31 Posts in 31 Days” Challenge

I started my YouTube channel, Ask the Copy Bitch, in late 2021. I often get questions from new writers and have mentored some over the years. Why not turn everything into videos and go wider?

For stretches, I’d get into it. But I also went long stretches ignoring it.

That’s not a winning strategy.

Fast forward to mid-April 2023. I wanted to “get serious” about my channel and make a go of it.

By “go of it,” I mean “make money.” 🙂

Just keeping it real, folks.

I’m happy to share free advice. But if I can monetize my channel in the process and make a few extra bucks, why not?

I think it’s smart of to have multiple revenue streams, especially those that make money in your sleep.

Do I have the right persona for YouTube? 

I’ve been working as a freelance copywriter for over 20 years. I make decent scratch. I pay the bills. I’m not one of those copywriting gurus who can teach you how to make six figures in six months. But I have my own point of view, my own stories, my own victories, and my own ongoing challenges. I’m approachable. (I think?) And I have a soft touch.

Plus, I have a plush sloth named Stewie.

There he is, working hard!

plush sloth sitting in front of a computer

I mean, how come I’m not already making bank from my YT channel, right?

Anyway, back to my mindset in April about “getting serious.”

My fiction persona has always benefited from discipline. For years, I’d write 1000 words a day. All to build muscle.

I had to take the same approach with this channel.

And so, I declared May to be “One a Day May.”

I’d publish one video and one corresponding blog post a day for the entire month.

In case you struggle with maths like I do, that’s 31 videos and 31 blogs.

Easy-peasy, right? Surely if I did this, the subscribers would flock, the watch hours would shoot up, and I could quit my day job and just make videos sharing my wisdom-pearls with the masses.

I’m not sure if this is true of all writers, but this writer can sometimes have delusions of grandeur. It’s the fiction writer in me. Yeah. We’ll go with that.

I’m happy to say I did it: I posted 31 videos and 31 blog posts in May.

But the results weren’t exactly what I had expected.

This is my post-mortem blog post on what I learned and how I can parlay these learnings into advice for freelancers—and not just copywriters. What I’m about to share below pretty much applies to any freelancer hanging out a virtual shingle.

What I Learned. And What You Can Learn from What I Learned (aka Advice for Freelancers)

I treated myself like a client.

Something I’m good at: carving out time for my own passion projects. And I’d call this a passion project for now, even though I also consider it a part of my business because of the subject. But I knew I’d have to devote many hours to this work. Hours that I wouldn’t see any immediate “returns” on. Not until the 31 days were up and the subscribers had flocked.

  • Advice for freelancers: You need to treat your copywriting business as if it’s a client. Your business is Client Zero, the Original Coke of clients. You need to devote time to marketing, blogging, writing—all the things you do for your paying clients. And it’s SO EASY to let this one fall by the wayside, especially when things get busy with paying clients or with life or both. I can’t stress this enough: FIGURE IT OUT NOW.

I wanted to quit. Several times. I didn’t.

I do think this is a normal emotion for many people. No, not everyone. And if you’re one of the lucky ones who doesn’t experience the overwhelming desire to yell SCREW IT ALL in the middle of your backyard, more power to you.

But I wanted to quit.

Starting on May 1.

As in the first day of my grand “One a Day May” plan.

May 1 was a Monday.

A rainy Monday after a rainy weekend.

I’d already scheduled a few blogs and videos, so I was on schedule, but in order to stay on schedule, I had a very demanding daily schedule of recording videos and writing blog posts, and that Monday turned into a shit show with unexpected client work. Nothing horrible, but I had little wiggle room.

Luckily, this wasn’t my first rodeo. Whenever I start something like this—writing a novel, going back to school, working with a new client—I get an overwhelming desire to quit before I even start. Part of it is fear of failure. Part of it is fear of success. Part of it is just plain laziness since I know how much work I need to do.

I was able to talk myself off that cliff pretty quickly since I had anticipated it.

  • Advice for freelancers: At times, you will want to quit. Don’t. Push through. I know this is easier said than done. But seriously, don’t quit.

Perfection is the enemy of the good.

Who said that? Voltaire? Whoever it was, they were right. I’ve long since abandoned perfection so this wasn’t a huge issue for me this time around, but I know perfection can be an issue for creative types, especially those just starting out.

  • Advice for freelancers: If you spend all your time trying to get something perfect (a blog post, a video, a business plan), you’ll never get anything done.

Nothing good comes from comparing yourself to others. But your doubt monkeys will love smoking that crack.

Oh, man. I purposely avoided looking at the competition on YouTube, even though that’s usually considered a best practice when developing video content: Look at what the competitors in your niche are doing and either do it better or find the topics they haven’t covered that still receive searches.

I was SO naïve when I started my copywriting channel, figuring I was the first brilliant copywriter to even THINK of doing such a thing.

LOL, nope.

There are SO many copywriters on YouTube who are crushing it that I’ve often wondered if there’s a place for me considering it really is a niche topic.

Honestly, the jury is still out, and I’m still figuring out what the best content is for me to focus on.

I suspect it’s going to be honest, vulnerable, messy posts like this. Because if someone needs a tutorial on “how to write a headline,” for example, there are better places to get that info.

That said, toward the end of the month, I did start looking at my competitors more and not just on YT but also on LinkedIn. Again, there are people CRUSHING it.

We all know comparing ourselves to others—especially the “others” we encounter online—isn’t healthy. But my doubt monkeys love smoking that crack. My doubt monkeys also get really nasty when they’re high on that shit. I have to limit my exposure, walk away, remind myself I am worthy, blah, blah, blah. It’s hard. Sometimes I allow myself to wallow, too. The key is getting out of the funk. That’s not always easy.

  • Advice for freelancers: I know you’re going to do it. I know you’re going to look. Because comparing ourselves to others is another wholly human flaw. My advice: limit your exposure. Wallow if you must, but only to a point. Get your ass off social media and do something to distract yourself.

Checking stats repeatedly isn’t healthy. (I’ve been down this road before.)

I self-published a couple of novels over a decade ago, and I became obsessed with checking sales and reviews. FOR YEARS.

My YouTube channel and Google Ads Sense account replaced this obsession.

I’m now limiting how often I check.

Checking too often is a waste of time. Maybe someday my channel will be at a point where checking it three times an hour makes sense due to all the activity, but I’m SO not there yet.

Also, it’s not healthy for my psyche.

  • Advice for freelancers: Freakin’ results. I know you want to see them, too. More clients. More sales. More revenue. Yes, you need to be aware of your numbers. But that little tart named Awareness likes to flirt with that cad called Obsession. Be careful if they hook up.

Cliché time! It’s a marathon, not a sprint.

Can I come up with something better?

  • It’s risotto, not instant rice.
  • It’s a novel, not flash fiction.
  • It’s waiting in line at the DMV, not breezing through the self-checkout.

I’ll stop now.

You likely get my point.

Inherently, most of us know when we’re building something—a business, a YouTube channel, a house—it doesn’t happen overnight.


I was hoping 31 days wouldn’t be the same as “overnight” in the universe’s eyes. I mean, c’mon. Waiting a whole month for glory feels fair, right?

  • Advice for freelancers: If you’re a new freelance copywriter, don’t expect overnight success, despite what some of the online copywriting gurus tell you. I’m not saying they’re lying. (They’re not.) But not everyone is going to follow that trajectory. I reckon there a more people like me out there than not. Slow and steady can win the race, too. Eventually.

I hit a wall. But not when I expected.

I worked two weekends during May full time on this crazy little venture. I’m talking 8-hour days on Saturday and Sunday. See “treating yourself like a client” above.

I was determined not to work Memorial Day weekend. And I didn’t. I had everything recorded, written, produced, polished, and scheduled by the end of the day on Friday, May 26. Stewie and I could take the weekend off from video-making. I was caught up on work, too. So it would be a work-free weekend.

I expected to be exhausted over the weekend. But I was still wired. I did fun stuff over the weekend, but I also did some work—I did my editorial calendar for June and July and settled on a Wednesday and Friday publishing cadence. I worked on my humor writing. I did some bookkeeping. Etc.

Not because I had to, but because I had some pockets of time here and there and was still buzzing on adrenaline.

But I hit a wall on Tuesday, May 30. As in when everyone went back to work, including me. It was also a bit of a depressing whiny wall. Why did I bother with any of this, what a waste of time, there are so many other channels and copywriters who are doing it better, when can I retire, I just want to draw and watch birds.

I said it was whiny, right?

Again, not my first rodeo. Been there, done that many times over the years in relation to my copywriting business but also my fiction writing endeavors.

What do I do when I’m like this?

I’m gentle with myself.

I allow myself to lean into the feelings—to a point.

I warn people, like Mr. Word Nerd, that I’m feeling this way so that if I’m grumpy or snappy around him, he knows it’s not him.

I sat in the sun on my porch in the middle of a Wednesday afternoon.

I drew a picture of George Clooney.

I watched birds.

I allowed myself to think that I’d take a break from the blog and videos, even though I’d planned on putting this blog post out on Friday, June 2. In addition to a corresponding video.

And doing all of the above was enough to get my butt back in my chair and writing this here blog post.

  • Advice for freelancers: You’ll hit walls, too. Often when you least expect it. My best advice is to think about it now—what’s worked in the past to help you get back up and dust yourself off? What do you think might help that you haven’t tried before? Fill your back pocket with these nuggets and pull ’em out when you hit the wall. AND THROW THOSE NUGGETS AT THE WALL INTO YOU MAKE A HOLE THAT YOU CAN CRAWL THROUGH. As that annoying saying goes—annoying because it’s true—this too shall pass.

I made new goals.

It’s funny. I’m not usually a goal person in the traditional sense. I might have a hazy goal in my head for fiction writing (like 1000 words a day). But I rarely set goals on January 1, for example.

I don’t know if it has something to do with turning 50 or what, but I’ve been extremely goal-oriented this year, with both my copywriting business and my creative writing endeavors.

You already know about my “One a Day May” goal.

But I also had some personal goals during this time, including doing a daily morning yoga session in May, which I also achieved. I’m a very basic yoga bitch. I do the same 25-minute morning session every day, which is full of stretches and gentle ab exercises. I also got back into my walking game. I have a route around my new house that works for me. It’s about 30 minutes. Normally, I’d focus on doing at least 45 minutes, but I was OK with hitting 30 + yoga.

At the beginning of the year, I decided to take a break from long-form fiction. My goal was to submit a short story (or some piece of creative writing) monthly.

I’ve exceeded this goal because I reconnected with my love of humor writing. And I’ve had success! Allow me to indulge by sharing links to the pieces that got published in the last few months.

As for my new goals . . .

  • I’m continuing with yoga and walking.
  • I’m still submitting pieces monthly, at least. (Landing something in McSweeney’s is my ultimate goal.)
  • My big hairy scary goal for the YT channel is 1000 subscribers and 4000 watch hours by the end of the year. Honestly, this feels like a tall order right now, given where I’m at. But I also know growth can happen exponentially ON yt. One good video that somehow takes off can boost watch hours quickly.

My short-term goal is to simply get to 100 subscribers, lol.

Oh, in terms of videos . . . the goal is to stick with a twice-a-week cadence and to have 100 videos total by December 31. Totally doable if I mostly stick to the schedule.

  • Advice for freelancers: I think it’s good to have a mix of short-term achievable goals so that you don’t always feel like throwing yourself off a cliff when your big, hairy, scary goals (which I think you should also have) don’t always work out exactly how you imagined.

Nothing ever goes exactly how I imagined. (And it probably won’t for you, either.)

Actually, probably not totally fair. I sometimes stop and consider my surroundings—like the house Mr. Word Nerd and I bought together last Halloween—and I can recognize that it very much aligns with the picture I had in mind for years.

So there might be some truth to the law of attraction etc.

But in the immediate moments, like coming off my “One a Day May”—no. This doesn’t look like what I had hoped or imagined. Things rarely do, for me. But maybe a year from now, things will be closer?

  • Advice for freelancers: Things probably aren’t going to go exactly how you plan things, either. Life happens. Clients throw curveballs. You might throw yourself a curveball. Sometimes you have to, dog help me, PIVOT. It’s OK. It happens.

Beyond that, all I can say is keep trying, keep doing.

Of course, I did a video on my video project. 

I share a few nuggets in the video that I don’t share here.

Got a Question for the Copy Bitch?

That’s me! I’m the Copy Bitch. Contact me or visit my YouTube channel and leave a comment on one of my videos. I might make a blog post or video with the answer.