Share
Classroom to Copy by Tania Yeo
Celebrating Copywriting Wins with Ex-Teachers Charlotte Ellis & Ben Henken
When my friends Ben Henken and Charlotte Ellis posted about their latest copywriting wins in the Copy Chief forum, I knew I had to get them back on Classroom to Copy to celebrate and share HOW they did it. It took a long time to schedule this across 3 different timezones -- so this episode is an accomplishment in itself. Here's what we discussed when we finally recorded the episode in Nashville, with Charlotte calling in from New Zealand:
01:26: Learn about Charlotte's past life as a preschool teacher in New Zealand, her freelancing journey, and the amazing copywriting role she just landed in Auckland...
02:07: Discover how Ben went from 12 years as a high school math teacher and assistant principal to becoming a freelance copywriter and email marketer -- PLUS the life of freedom he's pursuing with his family...
05:32: Follow Charlotte's journey from freelancing to landing her agency job (which she applied to on a whim!), including how she aced the application process, crushed group interviews, and overcame imposter syndrome along the way...
16:48: Discover how Ben landed his biggest retainer client yet and impressed them with THIS fantastic strategy for turning an Upwork assignment into a long-term project...
25:37: Do you get lonely as a freelancer? Or do you prefer having control over your schedule and who you work with? Hear our varied perspectives on the pros and cons of freelancing vs. full-time copywriting work...
29:23: Learn about Ben's month-long adventure traveling across Northeast U.S. in an RV with his wife, two kids, AND two dogs -- while ALSO freelancing and scheduling meetings around spotty WiFi!
37:25: Get Charlotte and Ben's BIGGEST tips for getting steady work as a copywriter -- whether you're freelancing or looking for full-time work -- and the #1 most overlooked way to find the best opportunities (hint: it's all about mindset).
You can connect with Ben and Charlotte here:
More episodes
View all episodes
22. From Daycare Teacher & Bartender to Financial Copywriter: Carolynn Ananian’s Journey
52:46||Season 1, Ep. 22[00:25] Introducing former daycare teacher and bartender, Carolynn Ananian, who pivoted to a successful career in financial copywriting.[01:12] Carolynn reveals why she explored numerous jobs before landing on a copywriting career.[04:26] Learn how her unique daycare teaching experience taught her some incredible skills she still uses in copywriting today – including the surprising truth about what toddlers and adults have in common![10:29] Find out why working with lawyers on Wall Street steered Carolynn away from law school and saved her a quarter million dollars![13:13] Discover how a chance interaction with a French customer while working retail at Williams Sonoma inspired Carolynn’s approach to understanding customer needs.[18:04] Carolynn shares how keeping a finger on the pulse of public sentiment helps her write better financial copy that connects deeply with her readers.[21:47] Learn how bartending (and talking to inebriated people!) gave her unique insights into human behavior that are essential for copywriting.[22:54] How she stumbled into copywriting – and the common misconception we all have about this career: “Why would I want to work with trademarks?”[28:27] How pulling an all-nighter at a bar during the Copy Chief Live conference landed Carolynn her first in-house copywriting job with Agora [32:07] Why she picked the challenging financial copywriting niche – and why becoming a financial copywriter is like getting a job on an oil rig[40:33] Get a behind-the-scenes look at Carolynn’s experience of joining Stansberry Research, one of the leading financial publishers.[50:15] Carolynn's advice for aspiring financial copywriters, including: the importance of knowing the right people – and surprising alternative roles to consider applying to.21. Former Junior College Teacher Siti Zahidah on Becoming a Public Relations Manager & Copywriter
49:45||Season 1, Ep. 21In this episode, you will discover:[0:00:42] Zahidah’s background as a former Junior College teacher who taught General Paper in Singapore for 8 years[0:01:39] Her current job as a Public Relations assistant manager for a tech startup in Singapore[0:01:51] How Zahidah overcame her imposter syndrome and feeling unqualified when she was hired for her current PR role[0:02:30] A trip down memory lane – what she enjoyed about teaching, and the challenges she faced along the way[0:05:57] Her honest, highly practical reason for becoming a teacher in the first place – something we both share in common![0:10:56] Zahidah’s fascinating past as a musician and songwriter[0:12:30] Our frank discussion on what it’s REALLY like to be a creative in Singapore[0:15:33] Zahidah’s turning point – the moment she decided to leave the teaching profession for good[0:17:09] Her thorough job search process – how many jobs she applied to on LinkedIn, and how long it took her to land her next role [0:19:53] How Zahidah leveraged BOTH her teaching and music experience to transition smoothly into public relations, marketing, and communications[0:22:35] More about her current PR role and how she works on crafting compelling stories to humanize tech products in a more relatable way[0:31:35] How Zahidah balanced her career transition with her family responsibilities and raising two children[0:37:58] Her best advice for teachers who are thinking about leaving – what to try before making the final decision, how to manage expectations, and how to prepare for the lifestyle changeYou can connect with Zahidah on LinkedIn.20. Former Pastor & VP Joshua Lee Henry on Becoming a Financial Copywriter (Instead of a College Professor)
52:35||Season 1, Ep. 20[00:00] Introducing one of my biggest mentors, Joshua Lee Henry, and how he’s been instrumental to my copywriting journey…[02:37] Joshua shares how he always wanted to be a teacher, including how he became a mega-church pastor and his original plans to become a professor…[12:28] The powerful story of Joshua promoting his services as a copywriter, door-to-door, after falling on hard times (this is one of the stories that kept me going when I thought I was gonna give up on copywriting)...[17:47] His first few copywriting jobs, how he got started prospecting clients, PLUS what gave him the conviction to choose freelance copywriting over another full-time job…[22:35] Joshua’s SECRET to accelerating his copywriting career faster than anything – and replacing his income from his full-time job…[25:16] Why you can’t get good – or far – in copywriting just by reading books or watching YouTube videos…[31:02] The surprising skill overlaps between being a pastor, teaching, and copywriting… and why a planning sermon is like writing a 45-minute VSL…[39:02] “The biggest HOAX of my life”: Joshua’s honest (and controversial?) opinion on going to college, and the more VALUABLE skill he thinks we should be mastering instead…[43:52] A day in Joshua’s life: his experience as a financial copywriter and copy chief at Banyan Hill, other projects he's working on, and the difference between being a copy chief and a copywriter…[51:04] Joshua’s words of encouragement for those sitting on the fence and considering a career in copywriting.You can connect with Joshua here:LinkedInWebsite19. Kristy Chadwick on Overcoming Burnout & Finding Community through Copywriting
35:13||Season 1, Ep. 19In this episode, you will discover:[00:48] Kristy Chadwick’s journey from working in a bank… a law office… a theme park… to stumbling into teaching - PLUS why she thanked her boss for making the surprising decision to fire her from her teaching job last Thanksgiving…[08:57] How she discovered copywriting after teaching, and why her entire life began to change after joining the Copy Chief community and Kevin Rogers’ Escape Velocity program…[13:01] “These people believed in me, so how dare I doubt myself?”[13:27] How the Copy Chief community helped both of us create better personal and professional boundaries as former teachers who struggled with setting boundaries…[16:42] The top 5 teaching skills that Kristy says will translate seamlessly into copywriting (PLUS: she shares a great document that shows you how your teacher skills translate to real-world skills!)…[23:55] The #1 thing Kristy wants you to know - and a powerful message for teachers who currently get the “Sunday Scaries”, take work home every night and weekend, and can’t see themselves still doing this in 10 years…[26:39] "It's never too late to become what you might have been" - Kristy reveals the No. 1 secret ingredient we both used to make the leap to a completely different career…[28:40] Kristy’s advice for former teachers who’re considering copywriting - and her GREAT strategy for building your copywriting skills regardless of your budget…[33:19] How to approach imposter syndrome (hint: it’s not about making it go away completely!) Kristy Chadwick was a teacher for over a dozen years and is now building her new dream in writing, coaching, consulting, and community building. She is known as a “powerhouse” and a “conduit of community” in the Copy Chief universe. Kristy loves sharing stories, building people up, true crime documentaries, live theater, foreign films, satire, dark comedy, and her 7-year-old daughter’s pretend YouTube videos. Any of the above are even better by the ocean. You can find her online here on LinkedIn, Medium, and her website. Recommended Resource: Teacher Skills Translated18. Melanie Warren - From Teaching 9th-Grade Algebra to Becoming Tony Robbins' Copy Chief
26:03||Season 1, Ep. 18In this episode, you’ll discover:1:03: Melanie’s background as a former 9th-grade algebra teacher with a huge caseload of IEP students… and all the cool strategies she used to get their attention4:51: “My whole life has been about children… but [now] they're a little bigger, and I can get out of the house. What am I going to do?”7:46: How teaching forces you to fight imposter syndrome - and why you should do the same with copywriting9:12: “When you're on a steep learning curve like that, everything feels like the biggest deal ever. [But] it's mostly not. It's just that you're becoming a person who was always living on their edges.”10:19: Why being a former teacher helped Melanie snag a place on Kevin Rogers’s Copy Chief team… as well as her first paying retainer client12:32: How she became one of Kevin’s first copy coaches for his Real Free Life program… and how the attendees inspire her as a coach14:46: Melanie’s #1 secret for going from a sudden layoff to an interview with Tony Robbin’s team… just a few days later!17:21: How she survived the emotional hiring process by brilliantly using the top 2 strategies every great copywriter uses in their copy19:40: The surprising number of skills Melanie transferred over from teaching to copywriting - including the ones we take for granted21:30: How Melanie juggled five kids with copywriting and freelancing… and how she’s using the same skills she used as a super-Mom as a copy chief today24:22: Her advice for anyone who’s on the fence about leaving teaching for copywriting… and why she can’t think of a teacher who wouldn’t excel at copywritingYou can connect with Melanie here:https://www.linkedin.com/in/melanielwarren/https://9buyersystem.com/16. Sean MacIntyre on Why Copywriting Is More Than Just Paying Off Your Student Loans & House with a Single Check
32:44||Season 1, Ep. 16here’s Part 2 of the priceless interview I did with Sean — the first teacher-turned-copywriter AND financial copywriter I ever met:[00:23] Why Sean is of two minds about niching down as a copywriter… and why having a niche could make you struggle MORE in the beginning…[02:40] What makes financial copy “a WEIRD freaking world” that’s different from any other type of copy… and what you need to be prepared for if you want to break into this industry…[03:19] Why a few of us IGNORED Sean’s advice about niching down and went for it anyway [03:39] Sean: “Approach it with a monomaniacal singularity of purpose. Just go after it. But most people are not like that… Most of those people don’t make it.”[04:00] His secrets for succeeding at a generalist copywriting career… getting really good at copy… and becoming known for your quality of work, NOT your niche (be warned, there’s a lot of talk about candles here)…[06:29] Sean: “If you’re not passionate about something, if there’s not a particular niche or topic that you’re just like, ‘Oh my God, I want to live, breathe, eat, shit, consume financial copy every single day of my life for the next 18 years…’ If you’re not that person, man, just let yourself become the candle guy.”[08:00] His 3 steps to a BETTER, less stressful, faster-to-monetize copywriting path…[08:06] Sean TURNS the tables on me and asks: “As you were learning copy, were you trying to go the broad route or were you trying to hyper-specialize at first?”[11:16] What you could miss out on if you ONLY hyper-focus on the most financially profitable niche…[13:55] Sean’s journey from having a strong distaste of the financial industry DESPITE growing up around stockbrokers and Bloomberg terminals… to finding REAL meaning in financial copywriting…[16:23] How it’s possible to write ethical, evocative, emotionally compelling copy that STILL makes sales…[19:14] Why being a copywriter is like being in the MAFIA… and how it can get surprisingly lonely…[21:13] Sean: “You know, my job is to show up and teach people and get paid… Switching from that mindset to being like, ‘Oh my God, my pay is directly connected to how much work I do and the quality of the work that I do.’ Most people never experience that.”[23:33] What he would say to himself if he could go BACK in time… and how he would approach his career and mindset differently…[25:43] Sean: “I was able to pay off all my student loans with a single check. I was able to buy a house with a single check.”[29:11] Sean: “Teachers are horrifically mistreated and underpaid. But, unfortunately, you know, we don’t get to live in the world we want. We have to live in the world that we’re in.”[31:42] His advice for anyone transitioning from teaching to copywriting, why you DON’T have to quit your job, and how this could be a FAR more fulfilling career for you.If you want to check out more of Sean’s work… He’s the chief editor and analyst at diywealth.com (which I used to write for back in the day), which also has a very entertaining YouTube channel. Also, check out his copy YouTube channel, Copy That! You’ll find lots of fantastic free tutorials to get you started in copywriting there.15. Sean MacIntyre’s Journey From Grading Papers & Waiting Tables to Becoming a Top Agora Financial Copywriter
44:48||Season 1, Ep. 15As promised, meet Sean MacIntyre – the first teacher-turned-copywriter I ever met. He’s one of my biggest inspirations in this crazy copy journey I’m on, and I’m so glad I finally got to interview him.This was such a fun conversation that we ended up chatting for more than an hour… So I’ve decided to break the episode into 2 parts.Here’s part 1:[00:00] Why meeting Sean was the first time I realized there’s a lot more I can do with my teaching and creative background…[01:25] How I first learned copywriting in 6 hours from a friend of Sean’s (Hi Alex Myers!)…[02:00] Follow Sean’s journey from teaching English to college students… to becoming one of Agora’s top financial copywriters… and running his MANY other businesses and YouTube projects…[07:00] Why the most painful aspects of teaching made it an “unsustainable lifestyle” for him even though he loves teaching…[10:26] Quote: “I don’t want to do that. That sounds silly and dishonest and I have a horrible chronic disease called integrity.” – Sean[12:15] Check out the crazy route he carved from doing odd jobs and freelance writing… to becoming a proofreader, copywriter, and then publisher* at Agora – within 13 months!(*Which is kind of like the CEO in this universe)[15:06] Can you guess the copywriting/business/entrepreneurship pioneer who first mentored Sean as a copywriter?[17:45] Quote: “The first copy that I ever sent to him in 2016 – he responded, and I quote, ‘This copy sounds like copy. Fucking stop it. Rewrite this so that your copy doesn’t sound like copy.’” – Sean[18:52] The #1 misconception people have about copywriting mentors – and how to tell when you ACTUALLY need one during your copywriting journey…[25:00] The top mentee qualities that mentors and experienced people respond well to (plus a mini-rant from yours truly about online communication)[27:13] Sean reveals all the best secrets he shared in our copywriting community about getting good at copy… Plus: why you need to STOP browsing the internet with AdBlock on…[31:44] At this point, we start nerding out about financial copy and what on EARTH a Big Idea really is…[34:56] How often do you REALLY find a Big Idea? And how important are they, really? [38:00] The surprising thing Sean believes sells even BETTER than Big Idea copy…[38:50] How the pioneer of Big Idea copy “co-opted” the term from David Ogilvy… and why most people misuse the term…[41:02] The BIGGEST skill Sean transferred from his teaching career that best prepared him to think deeply about copy…[42:42] Quote: “Really good copywriting is… almost conversational in nature. It’s very friendly, it’s very supportive, and learning how to speak in that register and how to write words and sentences that cut out the fluff and very succinctly deliver messages in that register… requires a lot of deep reading, a lot of thinking, a lot of practice.” – Sean…This episode is to be continued.If you want to check out more of Sean’s work… He’s the chief editor and analyst at diywealth.com (which I used to write for back in the day), which also has a very entertaining YouTube channel. Also, check out his copy YouTube channel, Copy That! You’ll find lots of fantastic free tutorials to get you started in copywriting there.14. From Teaching in China to Writing Financial Copy with Alex Perry
41:06||Season 1, Ep. 14Introducing Alex Perry, my fellow financial copywriter.0:02Alex’s unique teaching background and teaching background.Her journey of becoming an English major.Her journey into direct response.Teaching in Wuhan, China.3:25Learning mandarin for the job in hong Kong.Leaving America for China.Deciding to leave China during Covid-19.Why did you decide to pursue copywriting? 9:05Going back into journalism after a lacklustre experience.The freedom that copywriting gave her in her 30s.What she loves about the craft.The perfect marriage of creative writing and copywriting. 14:17The best kept secret for English majors.How financial copywriting differs from other forms of writing.Teaching experiences that transfer over to copywriting.Why copywriting is more lucrative than writing? 19:24Why copywriting is a great way to hone skills.The key to being a good writer.How copywriting can help pay the bills.Why copywriting can be a grind.Why royalties are dependent on the list.The financial freedom of copywriting.25:35The financial freedom that comes with copywriting.The first taste of financial stability.The learning curve.How the financial publishing industry is changing.29:58The financial copy market aligns closely with the stock market.Measuring success by getting words on paper every day.The one thing that keeps her going.How to break into the copywriting industry.35:33How to get started with copywriting.The 3 things that build the best copywriters.Using LinkedInAbout Alex Perry: Alex is a copywriter with 6+ years of experience in direct response. She’s generated over $5 million in sales in the Fin Pub industry and have helped raise over $10 million for companies going through Regulation A+ offerings. She’s also written multiple top-performing lead gen and YouTube campaigns. She’s a marathoner, avid book reader, and writer of fantasy and science fiction short stories. She also has a dog. Alex says, “If you know me, you already know this because I have likely made you look at photos of that dog.” You can connect with her on LinkedIn here.