TCC Podcast #59: 100 headlines a day for 100 days with Justin Blackman - The Copywriter Club
TCC Podcast #59: 100 headlines a day for 100 days with Justin Blackman

For the 59th episode of The Copywriter Club Podcast, in-house copywriter and creator of The Headline Project, Justin Blackman, is in the house to share how writing 100 headlines a day for 100 days changed his writing and his business. (We recorded this one a couple of months ago and are just getting around to publishing it now—apologies Justin.) In this episode Justin shares:
•  his path from sports and field marketer to copywriter
•  what his job as an in-house copywriter involves from one day to the next
•  why he started a side gig as an outlet for his creativity
•  how Shel Silverstein helped launch his first side gig—try, fly or walk away
•  why more copywriters should consider in-house gigs instead of freelancing
•  what in-house copywriters can expect to make (yep, we asked this question)
•  what made Justin decide to write 100 headlines in 100 days
•  some of the “tricks” he used for brainstorming to stay prolific
•  how his “creativity muscle” grew as he did the work every day
•  how he found motivation from the people he said he couldn’t do it
•  how the Headline Project has helped him grow his business and list

Plus we asked Justin how in the world he balances his work along with his side projects with his family duties, and we asked his advice on what copywriters should do to move their own businesses forward. To hear his answers, click the play button below, or scroll down for a full transcript.


The people and stuff we mentioned on the show:

The Copywriter Accelerator
PT Barnum
Bill Veeck
Lianna Patch
Shel Silverstein
Hippo’s Hope
The Headline Project
Laura Belgray
Tackle Your Tagline cheatsheet
Joel Klettke
Justin’s Twitter
Kira’s website
Rob’s website
The Copywriter Club Facebook Group
Intro: Content (for now)
Outro: Gravity


Full Transcript:

justin blackman copywriterRob: What if you could hang out with seriously talented copywriters and other experts, ask them about their successes and failures, their work processes, and their habits, then steal an idea or two to inspire your own work? That’s what Kira and I do every week at The Copywriter Club Podcast.

Kira: You’re invited to join the Club for episode 59, as we talk with copywriter Justin Blackman about his journey from marketing manager for companies like Red Bull and Five Hour Energy to copywriter and content manager, what it’s like as an in-house copywriter, balancing in-house work with freelance work and a family, and what he’s learned from his 100 day headline project.

Kira: Justin, welcome!

Justin: Hi!

Kira: Thanks for being here. We’ve had a chance to get to know you better in The Copywriter Club and The Copywriter Accelerator and I think it’d be really fun to just start with your story and maybe parts of your story that we don’t know, specifically how you went from sports marketing to content creator to copywriter. So, can you share that path with us?

Justin: Yeah! It’s kinda one of these paths that seemed obvious to everyone but me. I went to U Mass for sports marketing, mostly because I wanted to work for the New York Rangers, which was pretty “high school” of me but I had a good time there and learned a lot. The biggest change was that I had one professor there that talked about P.T. Barnum and Bill Veeck, who was a baseball promoter—he owned the Chicago White Sox and the Cleveland Indians—and really, focused more on big-time promotion and making the game fun. And these guys didn’t sit in the skybox, they were down in the cheap seats with the bleacher creatures and just having fun and talking to the people.

So, I realized pretty quickly that as much as I love sports marketing, it was more the marketing side that I liked, and that branched me into field marketing. And field marketing is essentially a fancy way of saying “consumer sampling”. So, anytime you go somewhere and they’re handing out different promotional items—could be drinks, or Chapstick, or anything if you’re going to a concert or even just walking through the street and they’re handing out different items, that’s field marketing. I was super fortunate to land jobs with companies that understood field marketing for the right reasons.

It wasn’t just about getting people to try out your product, it was really more about getting the chance to explain your product to people. So, I worked for Plymouth for a bit and that was geared toward running shoes. We went to long distance runners and marathons and really got a chance to spend a lot of time talking about the products with people. And I just knew that that’s what I really wanted to do. I love talking to people, I love getting the feedback, I love just finding ways and hooks to talk to people. That would end up leading to Red Bull, which is pretty much the ultimate field marketer in the entire world. Absolutely amazing brand, fantastic product, and they didn’t just hire college kids to go out and hand out cans and I know that that’s what it can look like from the outside, and they actually do a little bit more of that now, but when I was there, it was all about the right message, the right person, the right time, and really building their brand through one-on-one communication. And they didn’t care if one single interaction took 45 minutes—if that’s what it took to get a customer, that’s what you did! I had a fantastic time doing that, which is where i learned a little bit about improv training, which I know you’ve had other writers talk about that. Lianna Patch, specifically, just being able to think on your feet, and as I was managing that team, I was in Savannah, Georgia and Charleston, South Carolina, and I was running the Red Bull team there, I was noticing that essentially what a lot of the team would be doing is they would be talking about what’s written on the can.

And it would have things on the back and it would say like, “It stimulates your metabolism.” So, after lunch, we’d be going around and saying, “You’re going to want to drink this now because it’ll stimulate your metabolism!”

The average consumer had absolutely no idea what that meant, so we kind of followed it out by saying, it basically means you’re not going to get a food coma after you eat. And they’re like, OH! Great! Fantastic! I always get that. Yeah, I’ll try it.

So I created a training program that took a few months to develop—we called it Cause and Effect, where we’d always say this will cause your metabolism to stimulate so you won’t get a food coma after lunch. Looking at it now, I can clearly see that that’s benefits over features, but I didn’t know that because I wasn’t studying copywriting at the time. It was just something that I kind of developed and ended up creating a national program out of it, so I did really well there. 5 Hour Energy was pretty much the next step for people that got too old to work for Red Bull.

It’s essentially the same product, but without the branding. And a lot smaller. But, it was kind of like home, though. Everyone at 5 Hour were former Red Bull people, so it was a natural fit. Continued on with that, and after 5 Hour, I was kinda out of work for a little bit and I said you know, I understand field marketing and I get this and this is probably what I should do—I’m gonna give it a go!

So I created my own business and I must’ve spent 3 months figuring out how to build a website, and discovered Copyhackers, and just fell down the rabbit hole. I was like, this is what I want to do! But, the problem was, I spent so much time reading and learning and building out my website that I never actually marketed myself, and ran out of money real fast. So, wound up looking around and landed with IHG, and they were looking for someone in content. I went in for a few interviews and really connected with the boss, because we were just talking about writing in general and she was a former newspaper editor and magazine editor and just were talking about content and really it it off and I’ve been there ever since!

Rob: So Justin, I gotta know—did you get to drive the car with the big can of Red Bull on top of it?

Justin: Yeah, I did! It was fun, man! Mini Coopers are small, and when they have a big can on the back, they’re not very aerodynamic.

Rob: Everybody’s seen the car, that’s for sure.

Kira: I actually tried out—or auditioned? I feel like you have to audition to work with Red Bull—in college, and I got rejected! So I don’t drink Red Bull because of that. (laughs)

Justin: (laughs) I understand! That’s the kind of lasting impression we want to have!

Kira: Okay, so now that you are in your current job, what are you focused on there? What’s your day to day like now?

Justin: Well, I’m a content manager for loyalty and partnership. So, IHG Rewards Club, just the general loyalty club, the points running program about reward nights, and all the things that you can earn. I create a lot of the content for that. And that could be anything from blog posts to email to the merchandising and banners that you see on the web. We have a lot of industry jargon for it and a lot of acronyms. Essentially, I talk about points a lot.

Yeah, I put out a lot of emails. We’ve got a list of over 7 millions people that we can reach with a single email and that’s kind of intimidating but I do get to write out to them.

Kira: Wow, no pressure.

Justin: Yeah, no pressure. I’m very happy that the first time I wrote an email that went out to the full list, I didn’t know.

Kira: (laughs) So, I want to back up a bit. You mentioned that you know, after your field marketing jobs, you were out of work for a little bit and created your own business, ran out of money… What did that time really look like? Why didn’t it work? Was it just in retrospect you realized, Oh, I should’ve been marketing and when I was in it, I didn’t realize it was important? What happened and how can other copywriters try to avoid that so that they can take off with their business?

Justin: I wound up realizing pretty quickly that oh, I don’t want to do field marketing anymore, I want to do writing. I went into it thinking I was one thing, and came out thinking I was something else. Or knowing that I was something else. And, do a lot of soul searching and make sure that you’re going to make the leap for the right reasons and not be a big old dummy like I was.

Rob: That’s cool. So let’s talk a little bit about what you’re doing in-house, like you mentioned some of the things that you’re writing, but what is being an in-house writer look like? Obviously you’re not writing every single day, eight hours a day, there are meetings, there’s strategy… Tell us what that all involves.

Justin: IHG is a big, big behemoth of a company. We’ve got a 30-story office building and I’m just a cog in the machine there. The thing that I love about IHG and just being surrounded by all of these people and this whole corporate machine, is: I have access to so many people. I’ve got meetings with our content operations team, who make the websites go live and can understand the coding and why certain things will work and why they don’t work. We’ve got data analysts that will tell you everything about how our websites are performing and realize how to optimize it and will learn from all of the different programs and all of the other hotels because we have 12 brands, so we know if something has worked for one it’ll probably work for another but there might be a reason why it doesn’t.

We have all the different brand voices, so I have to translate it into something that will fit into continental hotels, which is more higher end as opposed to something like Staybridge, which is more your mid-to-lower scale. So, I get the chance to work with all these different brands. We’ve got stakeholders because we are a public corporation. There’s definitely revenue attached to everything.

We have to always make money, which is the ultimate goal, but we’re still trying to find a balance. And I feel like we’re all on the same page, but there are times that I need to say hey, I feel like we might be going a little too far in one direction, maybe we should pull it back and remember that the consumers come first. Usually, people agree with that. We all have goals—there’s definitely some pressure to hit them. There’s definitely a lot of meetings and it’s just nice to have all of these resources and just so much more than I ever could’ve imagined and never would have had a chance to do on my own.

Rob: So, one of the things when I worked in-house that I really liked is that I didn’t have to deal with a whole bunch of clients, you know, tracking down the work and that sort of thing. But in some ways, that’s not really true. You have a lot of different clients—they’re just internal. They all have the same company name, right? So how does that work for you? In providing for different areas of the company, the kinds of projects that you work on, etc? How do you balance all of that?

Justin: It’s tough! As much as I always say that I’m writing for the end consumer, it does have to go through several rounds of reviews internally, so there are times that I need to sort of gear a little bit more towards the stakeholder, and you have to write for approval. So, yeah, sometimes some of your messaging gets lost and you have to cut out the personality to it just to make it a little bit more universal.

We also have to do translations, because we write world-wide, so we have to take out some of the colloquialisms that we might use. I remember getting slapped on the wrist because I put the word “awesome” in something once. It was geared toward millennials, so it made sense, but they were like “we can’t translate awesome!”

Kira: Man! That’s a bummer!

Rob: If I couldn’t use the word awesome, I don’t think I’d be able to write anything! (laughs)

Justin: It’s tough, man, it’s tough!

Rob: It’s an awesome word!

Justin: I agree, and I like to use it! I think we overuse it a little bit, but…

Rob: Of course.

Justin: I guess at IHG, I don’t have the chance to overuse it.

Kira: So how do you stay creative? I think anyone who’s visited your website or worked with you—I’ve worked with you—knows you are one of the most creative copywriters. How do you really stay creative when there are constraints and you’re writing for a global market and you have different stakeholders? How do you do it personally so that you can make sure that not only are you selling and making money but you’re also personally satisfied and in touch with building the brand and connecting with that consumer?

Justin: First off, thank you! Secondly, it’s a balancing act. You kinda give up some of the creative freedom for a steady paycheck and things like that. I try to put it in where I can. After two—going on three—years I realize that it’s not always going to be as creative as I want it to be which is sort of why I do my own thing on the side.

That’s where Pretty Fly came from. And, the way that that started was as I mentioned, I write for 7 million people, but i don’t write for myself there. I’ve always loved children’s stories and I kind of in my heart always want to go back and one day write a children’s story, and I actually started to do one with my daughter. I was like you know what? I’m gonna write for me! And she was 6 at the time.

We were having a fantastic time doing this and we had an outline of the story and I’m writing for her and I’m loving it and she’s being really creative and just kind of getting me going and it’s right in my wheelhouse… and then, we have a really pivotal point in the story and my daughter wants to introduce some new characters and some new animals and take control of the story, and I’m just like what are you doing kid?! I love you, but you’re a terrible editor!

I was just kind of realizing, alright, now I’m writing for seven million and one people but I’m still not ready for myself. So, that’s when I created Pretty Fly Copy. And that was like, I’m going to do this for me! It actually started out as a blog, just sort of writing for myself and it evolved into actual copywriting. But that’s where I get to be me, and I love my site. I love the voice on it. I actually went a few months without looking at it and I went back and I looked at it and I was like, I still love this! This is me! This has got my fingerprints on it. That’s where I find the creativity. And I really only work with clients that shit my style and pimp my brand and I guess I’m fortunate to be in a position, I guess monetarily, that I can say no to clients and if it’s not something that I think will be my style and if it’s not going to allow me to express myself, I probably won’t take the client.

Rob: I dig your website. I like the voice there as well, and I love the fact that it’s sort of an iteration from Shel Silverstein and some of the influences you’ve had, like when you talked about your children’s story. You started Time to Fly, and then you say that you failed or that you fell—tell us a little bit about that failure and how you sort of picked yourself up from there.

Justin: Sure! Time to Fly was after 5 Hour Energy when I thought that I wanted to get into field marketing. I loved the logo that I had on that site—I still have it somewhere—it’s a flying hippo, which is based off of a Shel Silverstein poem, called the Hippo’s Hope, it’s tattooed on my shoulder, and so that was when I went into field marketing but I spent so long on Copyhackers that I never actually launched, but learned everything it taught me for Pretty Fly.

But the idea was, in Hippo’s Hope, there’s the story about a hippo who builds a set of wooden wings and he walks up to the top of a hill, and it goes to like a choose your own adventure style, and in one, he jumps and he falls and he breaks all his bones. In one ending he jumps and he flies away, and in the other ending, he turns around and goes home and has cookies and tea. And I sort of took the idea of that—either try, fly, or walk away, and that’s kind of been my motto ever since. Everything that I’ve been doing has a fly theme into it.

I went from Time To Fly to Pretty Fly, and I knew all the reasons why Time To Fly failed, and it’s because I just didn’t have the hustle and didn’t really know how to put myself out there. I think I was afraid. Working in-house gave me a safety net and I can go out and if I don’t get a client, that’s okay, because I still have my day job and it still gives me all the time and all the finances and I’m covered and I’m good and I get to write and I work with amazing people. Pretty Fly’s where I go when I need a little bit more creative outlet and it just lets me be me.

Rob: So, your favorite Shel Silverstein poem is…?

Justin: It’s gotta be Hippo’s Hope. I love it. I mean, I do love Where The Sidewalk Ends—definitely one of my favorites… but I mean, Hippo’s Hope is tattooed on me. I actually have got four Shel Silverstein poems tattooed on me, but Hippo’s Hope is number one.

Kira: Whoa!

Rob: Super fan.

Kira: Awesome. Should more copywriters look for their in-house gigs, similar to your own, are we potentially not thinking about it when it could really benefit our long-term career?

Justin: I definitely would not knock it. If you are starting out or are mid-level and are struggling a little bit, yeah! I recommend it. I love my job. Again, I don’t have to worry about money too much. You definitely sacrifice creative freedom, but you get so much out of it. I learned about writing for mobile and web and even a little bit of direct response and I get so much experience that I would have never had just focusing on other blog content, which is what I originally wanted to do, or email, and just getting the chance to write to seven million people and seeing how my work can perform and testing against the agency controls that we have on Pages, yeah. It’s such a great experience and you learn so much.

And you know, even just working with designers, which I never got a chance to do and seeing how my copy’s going to work into the layout and seeing how certain text wouldn’t work based on the layout of a page. I recommend it. It’s good money and it gives you such amazing experience.

Kira: And speaking of money… of course we have to ask, because we’re nosy: Without sharing your exact salary, would you mind just sharing some rough numbers as far as what an in-house copywriter may make at different levels?

Justin: Sure! Now, there’s obviously different areas and different levels and we have a lot of contractors—anything from fulltime to part time contractors—that work two or three days a week depending on where they are, and I’d say that in-house, you’re probably looking anywhere from $50,000 to over six figures. It really just depends on your market and what company it is.

Kira: Cool!

Rob: So I want to shift gears a little bit and talk about the project you’ve been working on for the past… well, by the time we go live with this, you’ll just about be wrapped up, or have just wrapped up the Headline Project. Tell us about that, what got you started on it, why you’re doing it, and how it’s going!

Justin: It’s your fault!


Justin: It’s The Copywriter Accelerator! It made me and broke me in the same day. (laughs) We were on a call just sort of talking about niches and where we wanted to go—I always feel so pompous when I say niche.

Kira: I feel the same way, but I refuse to say niche. I like niche better but I always feel like a jerk.

Justin: Yeah, it’s like “jif” as opposed to GIF. I know it’s “jif”, but everybody says GIF, and I’m going to say GIF. It’s just one of those words. But anyway, so, The Copywriter Club Accelerator—I was really trying to figure out what my niche would be and I thought I wanted to work for good-hearted companies, like the B-Corps that were giving back to their community because I’d worked with one and I really enjoyed it. And then, I’m working on another client, totally different, and it’s like I don’t know what I want to write about. Maybe I’ll just sort of try different things and I knew what I didn’t want to do and that was click bait. I despise things like BuzzFeed and… they’ve got good articles and good content but I hate the click bait words and click bait headlines.

So, we’re just sort of talking and said maybe I should just start working on some headlines for people, and I think it was Bayardo in the group said, “Yeah! Why don’t you just write 100 for 100 days?” And being dumb I was like, “Yeah, okay!” So I think it was the next day I started writing 100 lines and I’m what, 76 days in right now, I think? And I’m too dumb to stop. (laughs)

But, I’m nearing the end, I’m very happy about it. It’s been a heck of a challenge. I’m really glad I’m doing it but I’m going to be so happy when it’s over.

Rob: So let’s talk about how it’s been going! What have you learned from it? What’s hard about it? What’s gotten easier?

Justin: Sure! As far as learnings… I’ve learned what I’m not good at, which is really important to do, so I’ve learned that writing for any formal type product—anything like self-empowerment or woo-woo—that’s not me. I struggle with tech.

Kira: You don’t do the woo? (laughs)

Justin: I don’t do the woo. I don’t. I tried! I failed. (laughs) Those lines are not good. And anything that’s a little bit more female-oriented. The post that always comes to mind—there’s one for family photography and new mom photography that I tried—and I just hated that one. I can’t get this. I can’t picture it. I don’t know why anyone would really want to hire me for that, but if they ever did, I would say no. No. Definitely not.

Kira: (laughs)

Justin: And I learned that my niche is nowhere near what I thought it was. As I said, I thought it was going to be like B-Corp and good companies, but it’s really more about the style of the business than the category of the business. I like some of the more out-there fun type of brands, but I also learned that I’m not as wild as some of the brands that are currently out there.

Kira: What?!

Justin: See, there are a few that I immediately looked at and said, you know what? I want to write for 100 headlines for Freakers, which is a sock company and they also make beer coozies. They have some of the best branding in the entire world—I absolutely love them—and I looked at their site and I was like you know what? They don’t need 100 lines from me. They’re fantastic and I don’t even know that I could write like this! It’s great!

So, I needed to find brands that are sort of going for personality but haven’t gotten there yet but I just realized that it’s really more of a social, the way that people’s voices have taken off and they’ve been able to be wild. I’m not big on social—I don’t do a whole lot with it and I don’t have that style that I see a lot of really funny people on social have. So, I learned that I can’t do that.

And I know that a few of the ways that I’ve been able to get my favorite lines are by pulling from outside sources. So, songs, memes—that was a huge one for me.

The day that I was searching and I clicked on Google images and I was hit with a bunch of memes for a category—it was for owl rescue, I was doing something on how you can adopt them now—and when I clicked on images and I was hit with stuff with Harry Potter and different puns that people had posted memes with, the lines wrote themselves after that! I highly recommend that. That was a great stumble-upon that I had.

Even Reddit—something i had never really been on and spent time on—but you can do some searches there and find some really interesting inspirations. Terrible, terrible people on Reddit, but also some really funny ones. I’ve also been surprised at how many posts I can swipe from that are completely unrelated to what I’m working on at the time. There was one that I did for improv comics and it was actually improv corporate training called Do More Improv and it’s in the first 10 days—I wanna say it was like day eight—that post has come about time and time again and the lines that I’ve written for that are so usable in different blogs and you know, once I have the lines and they’re written in my brain, just sort of ways to pull from it—I kind of created the ultimate swipe file accidentally.

Once you do the work and it’s yours and you can reference it for yourself, it just becomes such a great thing to pull from. So I’m happy that I’m doing it.

Kira: I’ve used your website and this project and my own swipe file as I’ve been working on projects and brainstorming and coming up with different headlines as well. I’d love to hear more about your actual process! So, once you’re sitting down and you’re like, alright, I’ve got to write 100 today, what does that look like, step by step, behind the scenes? What aren’t we seeing that’s actually happening?

Justin: Oh, there’s a lot of rum. A lot of rum and a lot of beer. (laughs) It’s changed a little bit over time—it’s evolved—and I’m actually changing it up again right now. I had a list that—it was probably about 370 headlines and different formulas  that I had gathered from different websites—and I started with that and I used, I’d say the one that became the go-to for me, at least for a while to get me started, was Laura Belgray’s Tackle Your Tagline cheatsheet.

Go download that right now. I’ll wait. Hit pause. Go get that one.

When you come back… I essentially took the blank for blank, and six ways to blank, and I took that and I started going and over the first 10 days, I probably whittled it down to about 100 lines that I liked, and I just set them there for reference. The goal was to start writing out my own, and I’d say the first days I was able to write 15-20, and the I’d reference a few of the templates, I’d see like 3 lines, and then write another 15-20, and go back… It got to the point where I can write between 60 and 80 without looking at the template. Just from the repetition.

Just from knowing what the styles are, pulling messaging in, and being able to put myself in the scenario and feeling all the feels that I want the reader to feel and just getting a little bit more sensory with it. I try to write 50 at a time over the course of two sessions. It doesn’t always happen, but a lot of the time it’s 100 at once, usually. But I don’t have a chance to do it during the day and I have to do it late at night. So, there’s a lot of that. Then, I have to randomize the order when I go back to look at it, and that’s not to cheat so that it makes a more interesting post, which, I kind of feel like it is sometimes, but the reason is, I hate every single line of text that I write when I’m done.

I need about 3 or 4 days away from it to look at it and say hey, these are pretty good! But when they’re in order, I see my train of thought being written out. I see how one line of thought leads to the next, to the next, to the next. So I need to scramble that up so I lose that train so I can see each line individually. From there, I wait about 3 or 4 days to go and find those lines and then, when it comes time to post them, which I’m a couple of days ahead of what you guys are seeing—I’m five days ahead right now—I run down the list, highlight my favorites, and you know, describe the learnings of each lesson.

Rob: One of the things that has been interesting to me as you’ve written about the process and how things have gotten easier for you, is that creativity is really a muscle and the more you exercise it, the better you get at it, the easier it comes, and I think I’ve seen that as you’ve written and the lines have gotten better, I think, for the most part. If you take the set of lines from day 75 they’re significantly better than the set of lines from day 2.

Justin: Oh, agreed. I think, early on, I was definitely relying on the formulas too much. The first post was almost 100% formulas and totally different from what I was going for. Yeah, it’s just sort of getting into that flow. As I said I could write 60 to 80 without taking a break and without even looking at a template.

Yeah, I’ve learned to—I kind of said it before—put myself in this situation and think about… and this is where I’ve actually pulled from my field marketing days a little bit more… from having spoken to so many people on different scenarios about giving out Red Bull and Five Hour, that I think about specific situations that I was in that I was talking to people in and I’ll put myself in that spot as I’m writing the lines and just being able to pull from that marketing background… and just building that arsenal of scenarios. It’s helped me be more empathetic with my writing.

It’s something I think I’ve always been able to do but I can do it even better now and yeah. By far, being creative and pulling from different scenarios and lists and pop culture. It works.

Never gets easy, but it gets easier.

Kira: So, what kind of motivates you at this point? I mean, this is a big challenge. I imagine it’s painful some days, maybe not, but what keeps you going and what advice would you give to someone who is considering taking on a big challenge? Maybe not this exact challenge, but something that feels daunting?

Justin: If it feels daunting, do it. It probably means you’re heading in the right direction. As far as motivation, to this day, the wallpaper on my computer is still from Joel Kletke saying “I give this exactly three days lol”—and that was the day that I announced it. It was written seven minutes after I posted that I was going to do 100 headlines for 100 days. And now, it crushed my spirits for a few minutes and Joel is a great guy, I will say this: He and I have spoken since then and he’s patted me on the back and he’s cheering me on, but that was my motivation.

Once I put it out there, I was like, alright, well, I have to do it now. So, I would say once you decide that you should do it, tell someone, and that will hold you accountable. I could’ve done this by myself and I was like, yeah, no one’s watching, and I could’ve given up, but the fact is, there are people watching and I’ve had writers reach out to me that I respect and really accomplished people reach out to me and are cheering me on… yeah, people are watching, so say you’re going to do something and then do it. That’s the biggy. There’s nothing special about me, I don’t have any characteristic or trait that makes this any easier for me than it would be for you—just do it. Nike up!

Kira: I’d love to hear—I know you’re not finished yet—but what has the impact been as far as your business, positioning, recognition, and how are you using it to grow your business, too?

Justin: Some of the most motivating feedback that I’ve gotten are just from copywriters starting out that have reached out to me and said hey you just encouraged me to try a 30 day blog challenge! Or, I love watching what you’re doing, and I want to do something like this but I don’t know what yet.

To me, I still kind of feel like I’m that beginning copywriter that was just reaching out to people to get my name out there and to say hi and to tell people that I like them, so to get that feedback from others right now is insanely rewarding. That means so much to me, and I have every email that people have sent to me cheering me on, and it’s been fun. My email list before the headline project was 2, and they were both me, from different addresses, and now I’ve got about 100 people, which is 98 more than I had before! Or 99 I guess.

Not a ton, but that’s enough to keep me going and I get people writing back when I send out and it lets me know that I’m not in a void. And I think that the part that I need to remember is that I’m kind of doing this for me more than I’m doing it for other people, so as far as the growth of my business, it’ll come.

I’ve already written some lines for a few people who have said, hey, I like what you’re doing, and I’ve got something and I’m thinking of you. I’ve had some people reach out to me—some other writers that I respect—asking if I’ve got time to take some referral work. I love that! That wasn’t the goal of the project, but it’s amazing and I just, I love being a resource and a little source of motivation for people. To me, that’s worth more than any amount of money I could ever make from it.

Rob: And where do you go from here? What does Day 101 look like?

Justin: More rum, but this time, happy rum. (laughs) Not to take away the pain. I’m going to take a little bit of time and take my wife somewhere, and we’re going to go out for a good dinner—just me and her—because I owe her the world for supporting me while I was doing this. I’m probably going to step away from the computer for a week and probably shut down and just not write.

I need a break, and I think I need time to process what I’ve done. It’s just starting to click in what this achievement actually is. I think I’m in a little bit too deep right now but I need time to process it. It’s going to feel good. I’m going to enjoy getting my lunch hour back at work—that’s probably a biggy. I’m gonna enjoy more family time, spend more time with my kids. Once I catch up on that, pay them all back for allowing me to do this, then it’s time to take what I’ve learned and put it into practice.

Kira: So yeah, I was going to ask you next: How have you balanced this? Or, you know, just the business and the job and the headline project and the family? What has that looked like for you, especially since you’re in the hard stage now and many of us can relate so, even though it’s not ideal right now and you’re going to make it up to everyone later, how do you make it work now so that you’re not, you know, sleepless and your family doesn’t hate you right now?

Justin: I don’t, and they do. (laughs) There’s even a few posts in the recap that I’ve sort of just dialed this one in because I need to go and spend some time with my family. There was—somewhere between 40 and 50—somewhere after that recap, you can read it and see that I’m getting burnt out at that time and things at home weren’t great because of this. I wasn’t active because I was spending so much time on the project. I reprioritized after that—I tried to get everything done on the lunch hour—as opposed to dividing it up and bringing stuff back home. When I started, the first post, I was 8 days ahead. So, I was writing day 9 when I was posting day 1.

It wasn’t until I think I hit about the 50 day mark that I actually cashed in one of those days—I’ve since cashed in 3—I went camping with my kids and that was great. I realized that family always needs to come first. That’s big. And this list will wait. And I even had people write to me—and they were like, man, we don’t care if you take 107 days to do this—it’s fine! We just like you watching you and once I sort of got that validation from people that it’s okay and they understand that I’m human, it let me put my guard down for a minute and be a dad first and foremost.

So I’m in a good spot now, again, I’m happy that it’s over and my wife is happy that—well, it’s not over yet, but my wife is happy that it’s nearing the end. I’m going to be glad that I did it. We even spoke before I started so she had a heads up that I was going to be working my butt off for a while, but I didn’t balance it well at the beginning and that was a mistake on my part. I’d say that was one of the bigger learnings was how amazing my family is and I need to spend more time with them.

Rob: Very cool. So, you mentioned that the headline project came out of the Accelerator. This may sound like a self-serving or a selfish question, but having gone through the Accelerator, what else did you get from the focus on establishing a foundation for your business that that program gives?

Justin: The networking was phenomenal and I think I was always a little hesitant to invest in myself—you know, I’d look at some of the courses and be like, wow, that’s—I need to work to get all that money back! But, every time I have invested in myself, it has paid for itself.

So, do that first and foremost.

Get the training that you need.

And Rob, I think you were actually talking about that in the 50th [episode] that you guys just did. So, invest in yourself, it’s worth it. Build a network, even a Slack group, just so you can get some feedback. You know, just being able to bounce your ideas off other writers. You know, hey, how’s this? And, is this fine work? That’s been great.

And as far as just sort of the foundational… I guess I didn’t know what I didn’t know. And that was big. I knew that there was some stuff that I needed to get in place to build my business, but I didn’t know what it was and I didn’t know where to even begin searching for those resources because that just leads you down a different rabbit hole of other things that you don’t know.

So, being able to network with other people that have successfully done it and made the mistakes… and again, I’ve started a business and failed it, I didn’t know all the reasons it failed, but now I feel like I do. And you guys really just fast-tracked me with all of that. It would’ve taken me months upon months of doing things wrong to ever even realize how far down I had gone without it.

Kira: Awesome. I am really curious because you were in the Accelerator and you have slightly different background, you’ve been in this big challenge, you’ve observed copywriters in all of these groups… what do you notice as far as a missed opportunity for copywriters today? As far as, maybe we can up our game or there’s an opportunity that we’re missing?

Justin: I’d say that there are a few different thing. One is embracing the constraints that are put on you. I’ve been listening to Jay Cuzno a lot and he’s been talking a lot about writing in a box and that you’re always writing in a box, you just might be in a box that you’re not comfortable in, but you’re always in a box whether it’s the resources you’ve got, or your deadline, or your clients, things that you have to say, things that you can’t say… don’t get too upset with that and just accept the fact that okay, this is what it is.

Don’t complain about it and just go forward and you’ll find a creative way to do it. That’s an important one. You just hear a lot of people trying to change a situation that they don’t like to fit their style a little bit more and while I admit that you do need to find clients that are the right fit for you, sometimes accepting a new challenge that’s uncomfortable is probably a good idea. I’d say, reaching out and just talking to people. Building your network. I mean, The Copywriter Club has what, 4,000 people now? And you hear the same people over and over. Chime in! Speak up! Be heard. Develop a voice for yourself. You know, it’s not like there’s anything truly special about me. I just did it and it’s been awesome for my career and awesome for my development and my confidence. Just talk. And reach out and talk to people.

Rob: Awesome. I love what you’ve done and I love the headline project. We should probably say that we’ve stolen one of your lines that we’re going to be using for our own tagline when we do our rebrand that we love. We’re excited to see that actually in print some day! If people are looking to find you online, Justin, where do they go and how do they get the wrap on the headline project and what you’re up to next?

Justin: Well, I’m at; I’m on the Twitter @prettyflycopy, and you can actually find the headline project at, which is just the redirect to Pretty Fly Copy, and I’m always in The Copywriter Club on Facebook!

Kira: Thanks for hanging out with us Justin! We’re excited to see you wrap up and celebrate with you, as well, in Florida, next month!

Justin: Looking forward to that!

Rob: Thanks Justin!

Kira: Thanks Justin!

Justin: Alright, thank you!


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