Tired of Rejections? Here’s How Become a Highly Sought-After Copywriter with Your Unique Teacher Qualities

If you’re a transitioning teacher who’s considering copywriting as a career switch…

Or you’re tired of getting yet ANOTHER rejection for a resume you spent hours perfecting, this post is for you.

You see, six months after I’d left teaching, I was in FULL-BLOWN panic mode.

I’d just discovered many of the online tutoring companies I wanted to work at were shutting down.


The biggest market for these companies at the time was China…

Which decided in 2022 to ‘ban’ online foreign tutors…

Claiming they gave wealthy kids an unfair advantage over their peers.

I started wondering if I’d made a HUGE mistake…

All because when I left teaching, I assumed no one would hire me…

Unless I added a spanking new set of paper qualifications to my resume.

(Sound familiar?)

Even after a scholarship from the Ministry of Education in Singapore… four years at one of the top art schools in America… and 6 years of teaching experience…

I thought the only job I could do as a digital nomad was to teach English online.

(There’s nothing wrong with that — but I wish I’d discovered other options!)

So I invested some cash and almost two months getting my TEFL certificate… and never got to use it.

That’s a good thing by the way.

This passage from my weekly reading at work explains it all (yes, I’m getting paid to read amazing books, among other things, and I’m in heaven):

“No matter what your job title is, no matter what you did before coming to Agora, we want you to feel like there’s no limit to your potential here. Because it’s true. From the very beginning, Agora never had job requirements. Job requirements come from a bureaucratic approach to business. At Agora, you never needed a certain kind of education or a certain number of years of experience. The only questions were ‘Who wants to make this happen?’ and ‘Who wants to do the job?’”

(Agora is a major online publisher of health, finance, and investing newsletters. I currently do contract work for its offshoot, now a public company of its own, Marketwise.)

Here’s the thing:

This quote doesn’t only reflect the culture at Agora or Marketwise.

At every step of my journey — from Upwork… to freelancing… to working inhouse…

I’ve noticed there’s 3 important qualities clients care about MORE than a copywriter’s years of experience, qualifications, or resume.

These are 3 qualities that you, as a teacher, are uniquely positioned to offer.

Most transitioning teachers don’t seem to be aware of these qualities…

But they make all the difference when it comes to dealing with imposter syndrome…

Finding dream clients…

And replacing your teaching income with a lucrative copywriting career.

Every teacher-turned-copywriter I know uses these 3 qualities to find success in their journeys.

Here’s what they are:

Your dream client is looking for a copywriter who:

1 – Cares about their business

2 – Wants to help solve their problems

3- Has great ideas

Yes, they sound simple… But they’re not as easy as they sound.

Let’s break each one down.

1 – Your dream client wants YOU to care about their business.

Say you see a great gig online on the Copy Chief job board.

Do you just shoot off an email in 15 minutes with a generic portfolio?

You’re probably never going to hear back from them.

So how do you show them you care about their business?

Think about it.

Do you start the first day of the school year dumping lesson material on your students?

What’s the first thing you do when you get a new batch of students?

This is a process I’ve used over and over to get a response from every job listing I’ve applied for.

And you can find out how to master this process in just a moment.

But first, let’s move on to #2.

2 – Your dream client wants YOU to help solve their problems.

Let’s say you’ve scored a prospecting call with this dream client.

You have 20-30 minutes on the phone or Zoom with them.

What do you talk about?

Do you ask about the pay? The hours? The number of assignments?

That’s a big mistake…

A surprisingly common one among copywriters…

Where your number 1 job is to sell your prospect a solution to their problem!

And as a former assistant copy chief…

You’d be surprised at the number of messages I’ve gotten where the copywriter only talks about himself/herself.

(I ignore those entirely.)

After all…

Once you’ve gotten your students’ attention… would you just start talking about yourself in the classroom?

Or extolling the virtues of your subject?

No, you find a way to make your lesson relevant to your students’ lives.

Similarly, you want to position YOURSELF as a relevant solution to your client’s problem.

There’s a simple question you can ask your client — whether it’s on a call or via email — to achieve that.

You’ll find out what it is in a moment.

Let’s talk about #3 first.

3 – Your dream client wants YOU to have great ideas.

Oftentimes, clients are coming to you in a moment of desperation.

They don’t want order-takers.

They want someone who has done 1 and 2, and is ready to take charge and propose great ideas for their business.

Because chances are, they’re all out of ideas.

And teachers are naturally creative and adaptive, especially in response to HUMAN BEINGS.

You just have to pay attention.

So how do you show your dream client that you have these great ideas?

Think about the portfolio you’re sending them.

Does it show you’re paying attention?

Are you just sending them everything you’ve ever written?

And what do you do if none of your samples are relevant to their business?

There’s a lot more I can’t cover today…

So here’s my proposition for you:

If you’d like my help leveraging the top 3 qualities you ALREADY have as a teacher to break into copywriting…

Here’s what I’d like to offer you: my Classroom to Copy Coaching Program.

I’m looking for TWO transitioning teachers to work with, 1-on-1, over the course of the next 3 months.

You’ll get my full support to:

>> Transition smoothly out of teaching… and leave behind the stress and burnout…

>> Gain confidence in the qualities you already have as a teacher to become a great copywriter…

>> Leverage those qualities to grow your portfolio and find your first clients.

You’ll get all my secrets to:

>> Generating new client leads on LinkedIn without sending a single DM to a stranger

>> Getting consistent responses from the Copy Chief job board, Upwork, and whichever platform you’re using

>> Successful calls and email interactions with your dream clients

>> Creating a high-quality portfolio that sets you apart from other copywriters

>> Joining and participating in online copywriting communities to find more clients and work

Within 6 months of leaving teaching, I’ve used all of the above strategies to get a steady stream of qualified leads on LinkedIn… a response from every job I’ve applied for on Copy Chief and Upwork… projects with dream clients like Banyan Hill and Mirasee… a meaty in-house role at Cardone… and my current role with my dream client.

This is what the coaching program looks like:

>> You get one 30-minute coaching call every week for 3 months

>> You get 3.5 hours of coaching homework to complete every week

>> You can ask me anything via Voxer text messages/email during business hours. I’ll reply once a day.

>> You’ll get my support and coaching to work on:

>> Overcoming imposter syndrome and any mental blocks
>> Your copywriting portfolio
>> Getting clients and work
>> Talking to clients
>> Your networking skills

This is for you if:

You’re a transitioning teacher.

You want a career that lets you have more control over your schedule.

You’re looking for a job that allows you to spend more quality time with your loved ones.

You’re eager to explore a career with more room for growth and advancement.

Sounds cool? We’ll also work well together if:

You already know what direct response copywriting is

OR You’ve taken this free 5-hour course (the same one that gave me a solid foundation to kickstart my copywriting career)

You know that copywriting is for you. Read this FAQ if you want to find out more.

Plus, to make this program work, I need to know if:

You can commit to 30 minutes of coaching a week.

You can commit to 3.5 hours of implementing our coaching homework every week.

You’re committed to leaving teaching in the next 12 months

You recognize this coaching relationship is only going to work if YOU put in the work too

Finally, you need these qualities — not just with me, but with copywriting in general:

You can meet deadlines.

You are open to feedback and actively seek opportunities to keep improving.

You have strong writing skills.

You’re curious and love research.

You show attention to detail.

You’re adaptable.

You’re self-motivated and take initiative

You’re disciplined in taking steps to becoming a copywriter.

This is NOT for you if:

You’re not a teacher.

You need to work on your English.

You’re not sure what direct response copywriting is.

You’re not sure yet if you’re going to leave teaching.

You’re not sure what to do AFTER leaving teaching.

You’re not keen on freelancing.

You think copywriting is easy or you think you know all there is to know about copywriting.

You can’t handle feedback.

You miss deadlines often.

You can’t commit to 4 hours a week to this program for the next 3 months.

You do not take ownership of your journey.

You think I’ll be finding work for you.


I’ll be providing more information soon… but in the meantime, if you’re interested, feel free to contact me using the form below.

It’ll only take you a couple of minutes to fill it out, and soon we’ll be discussing your next steps toward copywriting and leaving teaching.

Remember, I only have room in my schedule to take on 2 new clients right now… and if you’re serious about leaving the classroom behind in the next 12 months, I’m here for you.

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