Jerrod Harlan

This week on Career Crashers, Joel is joined by Jerrod Harlan to learn about launching a career in copywriting!

Jerrod was a participant in the Praxis professional bootcamp, and decided he wanted to pursue a career as a copywriter.

“When the time came that I was having my first email back and forth with my first prospect, they asked if I had samples, and I did. Because I just put in the work to write them before anybody asked me to.”

Simply starting to write email sequences helped Jerrod, not only in building a portfolio to show prospects, but also to overcome imposter syndrome.

“Specifically, how it manifests is: ‘I’m not ready to take on a client until I read this next book, or until I take this next course or until, insert XYZ.’

And so, a lot of people want to become copywriters, and they never become one because they can’t just do it. They can’t accept that the first couple of things that they’re going to write are not good. They feel like they have to be a master before they take step 1″

With his own initiative, support from mentors, and personal projects he has been able to quickly start launching a career in copywriting.

Related: Career Crashers Podcast: Learning Skills with a Crash Mindset

Also Related: Career Crashers Podcast: Using Crash to Launch Your Career

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Show notes – Investing in Yourself and Launching a Career in Copywriting

  • Transitioning from sales to launching a career in copywriting
  • How Jerrod taught himself copywriting by simply starting to do it
  • Overcoming imposter syndrome
  • Learning better from paid work
  • Going from consuming content and not feeling ready to jumping in and getting his first four clients
  • How investing in a mentor ended up paying for itself 200-fold
  • Investing in yourself to level up
  • Becoming a six figure copywriter

Connect with Jerrod

Full Transcript: – Investing in Yourself and Launching a Career in Copywriting

Isaac
Welcome to Career Crashers, where we tell the stories of those who are not content to wait around following rules and hoping for good things to happen. Great careers aren’t found. There forged.

It’s time to crash the party.

Joel
I’m excited to be joined by Jared Harlan, who is a highly highly successful freelance copywriter. He’s also an alum of the Praxis program. And we’ve been, we’ve been talking to a few Praxis alum, and this idea of becoming your own credential, and creating a portfolio of projects in order to prove your value. That’s what we’re preaching at Crash, of course, as well.

So Jared, welcome. And I want to start with this idea of the portfolio projects and how you started doing that, in the Praxis apprenticeship, Praxis professional bootcamp portion of that program.

Jared
Yeah, absolutely. First of all, thanks for having me on. It’s great to chat with you. And just to generally chat with the Praxis sort of sphere of people. Because I’ve always been such a fan of Praxis, and I always love the people who are in it and come out of it. They’re always just such awesome passionate people.

So anyway, um, portfolio project, I would say the biggest one, you know, naturally, I went through practice a couple years ago. So a lot of it is sort of like fuzzy experience at this point. But there was really one portfolio project that changed. Really everything for me.

And so I was going through the process, and I originally started in sales. Very quickly, I had discovered out of left field, I discovered copywriting and it sounded really interesting to me that I could take my sales skill and instead, basically write it down and make money that way and start launching a career in it.

And so I needed to transition. But I didn’t really know how I started reading books, I bought courses and stuff like that. Meanwhile, I’m going through the Praxis program. And I guess there was one day where I was just like, well, writers write. You know, they just, they write things, if they’re not writing, then writers aren’t making money.

So I was like, Okay, I’m going to take everything that I’ve learned so far, and I’m going to actually write some emails, like, I’m going to write a few sequences for fake businesses, you know, businesses that I make up with promotions that I’m making up. Because I thought about it in a way of, if I do this, then I have a sample, I fulfill a portfolio project, I have a sample.

And frankly, no potential client has to know that they weren’t real businesses that I was writing for, you know, they could they for all they knew they were real promotions for real businesses. So one of them was like a New Year’s promotion for a gym. And it was like a five day sequence that they would send out from January 1 to January 5, two people who were on their list. It was either selling like an upgraded membership or like something along those lines.

And then I wrote one for a florist, in a Mother’s Day promotion. You know, three or five days, or whatever it was of a Mother’s Day promotion for, you know, flowers. And I wrote one other one, I can’t remember what it is off the top of my head. But point is, I sat down and write and wrote three email series, because that’s what I wanted to do. And it really came in handy.

And I’ll explain how I got my first client. But when the time came that I was having an email back and forth with my first prospect. They asked if I had samples, and I did, because I just put in the work to write them before anybody asked me to write them. So that would be you know, that’s the condensed version of, you know, where a portfolio project really made a difference.

Joel
Yeah, and I love what you said about you just started writing, because that’s how you become a writer. You know, we often think, I think growing up, we’re taught to kind of prepare for the profession we’re going to enter.

But the best way to learn is to literally do that. And I’m sure it wasn’t, I’m sure you’ve continued to refine and master the craft over time and you weren’t afraid to just just start and then that allowed you to build some momentum.

Jared
Yeah. And that’s the momentum that’s incredibly necessary starting out. Because there’s this, it’s it’s a, it’s a real plague of a mindset when you want to get into launching a career in copywriting. You start thinking like, well, they call it the imposter syndrome. But specifically how it manifests is I’m not ready to take on a client until I read this next book, or until I take this next course or until insert x, y, z.

And so a lot of people want to become copywriters. And they never become one because they simply can’t just do it. They can’t accept that the first couple things that they’re going to write are not good when launching a career. They, they, they feel like they have to be a master before they take step one.

Joel
Yeah, I’m reminded of, there’s a short little YouTube video from Ira Glass, who’s the host of This American Life podcast, which has been going on for about 20 years or whatnot. And so he’s just talking about leaning into that period where you kind of suck, you just have to get your reps in, at the beginning.

You have this really high standard for maybe you see a great person at that craft. You know, what, it’s what greatness is, or you know what excellence is. And then you’re comparing that to your first repetitions, which are poor, because, or at least just not as good as what you hoped because you’re just starting out, but the he really encourages people to just just keep doing it, just keep doing it.

Then you’ll look back one day, and you’ll see that you made progress. Is that is that something that you can relate to in terms of, I mean, you’ve been writing for a few years and just just pumping out these emails and copywriting, sales letters and whatnot, have you watched yourself, just through repetition, really refine your craft when launching a career?

Jared
Yeah, it’s amazing, honestly, to go back and read some of the first things that you write. Because it’s garbage, you know? You know, it is it’s just, it’s not good. Because there’s so many things that you have to learn just by doing. And you can read all the theory in the world. But until you know how to actually apply it in the, you know, in the real world when money is on the line, it’s only worth so much.

You know, every book, you could have a wall full of copywriting books. But until you take your first paying client, and you see, you know that email, make $0 for them. And you really have to critically look at what happened. That’s when you really start learning is Adoing but then B, seeing the results from you’re doing.

Joel
Absolutely. So I’m curious how you got interested in launching a career in copywriting. I know you were sort of looking at sales. But talk us through that initial kindling of choosing the career path and launching a career. Because a lot of people who are just starting out, they might not have that clarity.

And what we kind of preach around here is don’t do stuff you hate. Just as long as you don’t hate it, and you don’t suck at it. Just go do something that is that piques your interest. So talk us through just the sort of curiosity that you had at the very beginning in terms of setting your trajectory.

Jared
Yeah. I had actually been successful in sales prior to Praxis anyway. I came from face to face sales, and I worked in car sales, and I sold personal training. And I even own my own printing franchise. This was all before Praxis, you know, I really joined Praxis, because of the community. That was my biggest motivator was joining from the community and the networking side of things. And just being around people who were successful, you know? Via the people who were at Praxis being around people who were like minded via the people in Praxis.

So that was my biggest motivator. And so naturally going into sales made sense. I just wanted to switch sort of the path that I was on. Having having been burned out of running a brick and mortar store. And I was one day I went out to lunch, and I went to Barnes and Noble. I found a book on the shelf. That was called the Ultimate Sales Letter.

And so from there, it’s like, I remember high level of certain copywriters, who I started following, but it’s so there were so many resources that I don’t exactly remember, like, what the real process was from that first moment.

Joel
Yeah, it sounds that you, it sounds like you followed that rabbit hole. Or you did and you weren’t afraid to do that was also I think, a factor when people are first starting out that they don’t want to get caught into one tear one job type out of fear that that won’t be their number one passion for the rest of their life. The fear that they’re gonna get stuck when launching a career, and end up not liking it, maybe down the line.

And what you just did is, you were interested. You kind of caught this motivation, and momentum. And he just kept on going and kept on going. And for you, it’s really worked out. So tell us about how it proceeded from there. And how you went about finding that first client when first launching a career?

Jared
Yeah. Um, so it got to a point where we actually found out my wife was pregnant. And this was mid 2018, I think I want to say, yeah, mid 2018, like, May. And found out she was pregnant. It was like this moment where I took over. I took over a failing print shop, and I built it to where it was profitable.

But there are so many hard costs on a brick and mortar store that you have to make so much every month just to take any money home. So I was making very little even though I was like a business owner.

And it got to this point where I found out she was pregnant. I just thought, I got to make shit happen, like now. You know, I have eight months to get my stuff together. Or I’m gonna have to go back to like selling cars or anything. Because that was really the last thing that I was making any decent money at. I’m gonna have to do something, you know, at this point I was it was cemented that I wanted to do copywriting.

But I also wasn’t going to be the person that if my first child was born was going to be like, Oh, I have to follow my dreams. No, I needed to support my kid. And that was like, first and foremost. But it was really that fire. That forced me to critically look at what I was doing. And the actions I were taking in launching a career. I was I was taking. And what I was doing at that point up until that point was just buying a lot of stuff was just buying a lot of courses and books because I was in that frame of mind.

Like, I’m just not ready. I’m not ready. You know, I had samples and stuff. And I wrote but it’s still really scary to just try and get that first client. So I ended up I was on a guy’s email list. His name is Chris Orr is a koski.

And so he sent me back that Yes, he is. It’s not like his full time thing he rarely does. It’s just on the side because he wants to you know, he wanted to be a working copywriter. He didn’t want to be a mentor for a living. And so he sent me the price and you know, I was like, oh, okay, I mean, I can’t really justify this purchase.

But if I don’t have someone’s help, I’m going to keep toiling away in this purgatory that I’m in. So I hired him. And the benefit of hiring him as a mentor was that like I said, he was in the trenches. He was working, he had tons of clients, his schedule was booked, but he still had clients coming to him. He What’s he going to do in that situation? Somebody comes to him and they want copywriting work. Is he going to tell them? No, I’m too busy go away?

No, he’s gonna say, Well, I can’t do it for you right now. But I have a mentee who I can introduce you to who, you know, I look over all their writing. And I make sure it’s good before it gets sent to the client. You know, whatever, would you like me to introduce you? So that’s how I got my first four clients actually was through introductions from Chris.

And he didn’t close them for me or anything like that. He was just an introduction. And I had to close on my own, which was fine, because, again, I came from sales. So talking to the prospect was fine. And, you know, feeling confident enough now that I had Chris, who was I was standing on the shoulders of Chris, really. I knew that no matter what, even though I didn’t really know what I was doing in a, in a money up for grabs situation, Chris would guide me in the right way. And he would edit and he would critique my writing, and that wouldn’t make it good.

Because of that, you know, all four projects were successful. They did really well. You know, the first project that I did what they hired me for, I earned them back over 10 times what they paid to me. And that’s the beauty of direct response, by the way. Is that you can see the results, your clients can see the results. So you as a copywriter don’t become an expense, you’re an investment when you know what you’re doing.

And so that was that gave me like this first inklings of confidence, like, okay, I can do this, I know what I’m doing. Yes, I need somebody to critique me and, you know, shred my writing and stuff. But at the end of the day, who cares? Like if it hurts my feelings that they’re shredding my writing, it just means that my clients are going to be successful, and I’m going to make more money in the future.

Joel
Yeah, you got your first client there. And I love that. You were in a situation where your wife was pregnant, and you were trying to just, number one, support your kid, right? And so financially, that was like that was serving urgency yet, you felt so you felt a little bit hesitant about investing in this mentor. But you knew that that was really what you needed. And you were willing to put in that money in at the beginning, upfront, and the ROI, probably at this point is you can’t even calculate, you know?

Joel
So it really just speaks to like, oftentimes we get in the scarcity mindset when launching a career, we’re like, well, I don’t have enough money to get started. So I can’t get started, or I can’t afford to do that. But when you start looking at the bigger picture, and how, over the over time, you have some delayed gratification, that it’s actually smarter to spend money upfront, you know?

Jared
That investment, I can tell you pretty, pretty close, with a pretty accurate range that that investment multiplied itself by around 200 times.

Joel
And so you had a similar story to as well getting a more recent client going to a conference, am I right, that conference was fairly expensive, but it also paid off?

Jared
Yeah, I mean, really, like, I don’t talk about my backstory a whole lot, because it’s very like, and I’m using heavy air quotes here, like, Guru story, you know, the I was broke and now I’m rich, whatever. That’s that’s used in so much marketing. But in all honesty, like that’s sort of been my that’s been my, my journey was like that guru story of, I didn’t have money.

So I got my first client in May. And then the following, the following March. Yeah, so almost a year later, I was in a place where I was making good money. I was making right around like 50,000 a year being a copywriter. I’d gotten a solid gig where I was a W-2 and I was doing some outside work.

So things were good. Now I used a lot you know, I use that money to pay off debt that I had that I had accrued by buying copywriting stuff. just paying off things paying off student loan debt, you know, whatever. From the one year that I went to college, which still racked up quite a bit.

And so I was in a place now where I was on this a list copywriters email list. She was holding an event in Washington DC, which is only, you know, six hour drive from me. And the ticket was like, $2500.

But again, at this point, that was a, you know, I can spend it without putting it on the credit card. But isn’t the smartest decision, you know, I had a new kid, because now my kid had been born, my daughter had been born. I’m trying to support us.

And it was really, it was really my wife, who pushed me into doing it. Because I was talking about for like, two days, three days in a row, I was talking about how I really wanted to go to this, but I couldn’t justify the cost. And she was like, quit being an idiot, like, just do it and start launching a career in copywriting. They just just go, you know, that you’re going to meet good people, you know that you’re going to get something out of it, like, just spend the money and go.

So I did, cuz she pushed me into it. And when I was at that event, I happen to start talking at the lunch table to another attendee who happened to be the copy Chief, from a big health company from like, a $15 million a year health company. We just got alone.

And this was, you know, A, this wouldn’t have happened if I went to the if I didn’t go to the event. But B, it was so serendipitous. I was just standing at the table getting lunch, and I started talking to the one or the other, like, it was a very small event, I think there were 12 attendees, one of the other 12 attendees, and she happens to be this really high position in this big company.

And so I, we were chatting and she liked what I had to say. She liked my passion and enthusiasm around copywriting. And we were sitting down at the bar later after the event was over. And she asked me if I would like send her samples or something because she wanted to see, she was she was intrigued that I had that I had under a year of experience at this point. But I was so knowledgeable about it, because again, I went down that rabbit hole and I you know really like to deep dive into things when I learned them.

So I showed her literally pulled up Google Docs on my phone and showed her a sample of a long form sales letter that I had written. And she was like, we need to talk about you writing for us, for Natural Health Sherpa.

So that was the start. I kept up with her over the next few months. But like two or three months later, she reached out saying that they were ready to hire a couple of writers on a what’s that called probational period basically are like a little intern period where they want to just see if you have the chops.

So they hired me and three other writers on a just to contract like 10 hours a week contract. And I ended up getting hired full time, two months later. And that was you know, that job pushed me into being a six figure copywriter within a year and a half.

Joel
So with your story, we can see that it’s about actually doing the work, creating the copywriting samples and just writing and learning, finding people to coach you, and then investing in yourself. And also this sort of networking. But it sounds like this interaction was really organic where, yeah, it was serendipitous. But it sounds like you were at this lunch table or at this bar table.

And you probably just kind of just started talking to her in an because you’re interested in people and then that led to an unfolding of that conversation and an opportunity. So you see how all these elements are at play. And at no point were you pressing apply on Indeed or right?

Jared
Yeah, yeah. I got one client from an actual email that I sent and it wasn’t even a cold email. It was an email where I was on a copywriting job board. I saw somebody that posted that they were looking for copywriters. I was clearly not qualified for what they were looking for. But I sent them like 1000 word email just being real and showing my hunger for being better and enthusiasm.

And you know the few samples that I had at that point because you know what, what would I have to lose him saying no, right? That’s it. But he ended up hiring me and I ended up writing seven sales letters over the course of the next year for the guy. And I’m even doing some work now for him. So all because I just sent that email. But that’s the only time I’ve ever had a client that wasn’t from a referral or meeting them in person at an event.

Joel
Awesome stuff. Hey, so to close it out, just speak to anybody who might be sort of curious about launching a career in copywriting. And obviously, we’ve just, we’ve just outlined some great steps to get going. But any overall advice as well as what’s something that’s maybe a myth about copywriting, I think people hear it. And it’s kind of a sexy profession from the outside maybe, where you just kind of get to put up your feet and write, write some emails, and make a lot of money.

But like, What’s something that’s maybe a misconception about launching a career in copywriting in any overall advice you have?

Jared
There’s the they call it the writer’s life, right, where you’re sitting on a beach sipping on a margarita with your computer on your lap. When you’re really in the trenches, copywriter, that’s not most people. That’s probably not you’re going to be your experience when launching a career. And it’s especially not going to be your experience when you’re starting out.

Because no matter what, no matter what a course sales page says, no matter what they say about Oh, how much money you can make by writing, you know, one email a day or whatever you can, don’t get me wrong, you can make a lot of money writing one email a day. But you have to work to that point, you have to bust your ass to get to that point where you are sitting in front of a computer for, you know, sometimes eight to 12 hours a day.

Like I remember back in the day, or I say early days as if I’ve been doing this for a decade. But like early days where I was first working on long form sales letters, they’re brutal man. They are brutal to write because they can come out to be 25, 30 pages, and up to 10,000 words, and it’s hard.

And there were days where, you know, I had a deadline. It was the day before and I was like, I only have like half of this done and you just sit your butt in a chair. And you have to, like you can’t do anything, you just have to finish on the deadline or else you’re gonna lose credibility to the client.

So as you start getting those results, you can start to relax a little more, charge a little more and have a little more time. But it’s just like anything else you need to go in and be prepared to do the work. And the biggest advice that I can give to somebody who wants to break into copywriting is get accustomed to hearing No. People, you know, saying no to hiring you. But not only that get accustomed to your copywriting failing.

And I don’t mean failing as in like, I mean, failing is embalming, where it doesn’t produce any results for the client. Because again, it comes back to that whole thing that we talked about in the beginning of your first five sales letters, your first 50 emails, whatever it is, they’re gonna suck. They’re going to suck compared to what you can be in a year from now or in two years from now, when you look back. And you have to keep pushing past that point where you hear from your client, oh, this made $2. This made $100 and I paid you $300.

Like you know, much of the time when you’re a beginner, you’re not going to get rehired by people that lose money from your writing. So you have to keep creating new connections so that you keep getting new clients. As you get better you work with bigger clients who understand that the majority of the time copywriting fails. And in fact, it’s about finding the one out of 10 times that it crushes it, that to pay for all of those other failures.

But lower level clients don’t always understand that, because they’re in this thing where they have to make money and so that every investment that they make has to be profitable, which is understandable. So that’s like the detour route of saying of my advice is just be used it just get used to the idea of your writing bombing and accept it and learn from it moving forward.

Joel
It’s good stuff. Good advice. Hey, Jared Harlan, Thanks so much for sharing your time and wisdom. Everybody can reach out to Jared on LinkedIn if you’d like and thanks again for making it happen.

Jared
Thanks, Joel.

Isaac
Like what you hear? Go to crash.co and join the career revolution. Do you want to share your own career crash story? Send it directly to me at isaac@crash.co.

If you’ve got a story you’d like to share, don’t hesitate! Email Joel at Joel [at] Crash [dot] co.


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