Here are some of my answers to the most frequently asked questions I get about transitioning from teaching to copywriting. It’s a work-in-progress and I’ll add to it as I get more!

Note: this post may contain affiliate links. I may earn a small commission when you click, at no cost to you!

Q: What is direct response copywriting?

A: Direct response copywriting is the art of selling with words.

The goal of your writing is to grab your audience’s attention, keep them engaged, and eventually convince them to take immediate action… like buying a product or signing up for a service… hence the term ‘direct response’.

Are you starting to see the similarities with teaching?

Teachers sell students on ideas, topics, heck – even homework – every single day!

Plus, we rely heavily on DATA to track and measure the performance of our copy. 

Metrics like click-through rates, conversion rates, and sales data tell us whether or not the copy resonates with our target audience – enough for them to take action…

…Much like how teachers are masters of analyzing data to develop relevant, engaging, and EFFECTIVE materials for our students.

Q: How is direct response copywriting different from content writing?

Direct response copywriting and content writing can look very similar.

Both can be informative, valuable, educational, entertaining, and engaging for the reader.

Both aim to build trust, establish authority, and provide value to the reader.

But the answer lies in the phrase “direct response”.

Like I mentioned earlier, direct response copywriting is about persuading the reader to take immediate action…

…Whereas content writing builds awareness and a relationship with the target audience over time, and you might not see an immediate response.

Examples of content writing include blog posts, articles, guides, and tutorials…

…While examples of direct response copywriting include an advertisement for a weight loss product, a sales letter for a skincare product, an email marketing campaign for a travel agency, or a landing page for a webinar.

In other words, content writing aims to inform and entertain, while direct response copywriting aims to persuade and prompt an immediate response.

One isn’t better than the other, by the way.

Both are ESSENTIAL to any marketing strategy — it all depends on YOUR preference as a writer.

Q: What were your teaching background and subjects before you got into copywriting?

A: I was a high school teacher who taught art and English literature in Singapore for 6 years.

Q: What type of copywriting do you specialize in?

A: I specialize in financial copywriting. Currently, I work for a company that sells courses, workshops, and live events related to real estate investing.

Q: How did you transition from teaching to copywriting?

A: I initially planned to start an online tutoring business to help pay for my travels around the world… only to get cut off from my biggest market, China, due to a ‘ban’ on foreign tutors.

Plus, I found out I would be making LESS money than I was making as an in-person teacher anyway.

Naturally, I panicked. 

In fact, copywriting was my backup plan! 

I couldn’t believe there was an industry that would pay me well to write… So I did my research, was convinced, and went all in. 

I started by studying and practicing copywriting every day. My experience teaching Literature actually helped me analyze and break down copy texts quickly… so I could understand exactly how copywriting worked and reverse-engineer good copy from there. 

I also had fantastic connections through my Copy Chief community — where I had access to unlimited copy critiques, great copywriting training, a fantastic and supportive community of copywriters, a high-quality job board where I constantly applied for work, and supportive mentors like Kevin Rogers who connected me with amazing job opportunities.

Q: Were you overwhelmed during your transition into copywriting?

A: I was definitely overwhelmed! There are so many resources out there and it’s easy to go down a rabbit hole, get analysis paralysis, and never take action.

I dealt with this by talking to more experienced copywriters and getting their advice on what they wished they’d done while starting out – which was getting hands-on experience like actually reading and writing copy every day.

Joining Copy Chief also saved me a lot of time and overwhelm. 

First off, the community also comes with its own training dashboard where I had access to any and every type of training I could dream of – all at my fingertips. Instead of blowing my money on several different courses, I paid one fee and had everything I needed in one place.

Also, thanks to their unlimited copy critiques and high-quality feedback, I improved my copywriting very quickly, gained a strong sense of focus and confidence, and eventually… knew when I was ready to apply for jobs.

And when that time came, the forum already had its own job board with vetted job listings. There was no shortage of opportunities to apply for there!

Q: Did you create a portfolio and how did you do it?

A: Yes, definitely. Creating a portfolio as a brand-new copywriter is MORE important than your paper qualifications and how many years of copywriting experience you might have under your belt.

Here’s my process: I looked up my dream clients online, researched their products/services, and practiced writing copy samples based on those products.

I got tons of feedback off the Copy Chief forum, improved my samples, and picked the top 5 to include in my portfolio.

The actual samples I would send to each potential client would depend on their business and what they’re selling.

Q: What was your timeline like from leaving your teaching job to becoming a copywriter?

A: I left my teaching job in July 2021, and I landed my first real client in July 2022. 

That said, I didn’t start studying copywriting until February 2022, so technically, I broke into the industry within 6 months. 

It may seem fast, but I know many teachers who transitioned into copywriting who have similar timelines. 


By leveraging our existing teacher skills and adaptability as educators!

Q: Did you struggle with your decision to leave your teaching career and how did you cope with it?

A: Of course! I knew I was going to leave when my contract ended… but I still struggled to leave behind my students and colleagues I’d grown close to. 

That said, I also knew I wasn’t doing my students any favors when my heart was no longer in the right place and I was burnt out. To my surprise, my students and colleagues were very supportive and encouraging when I told them about my plans to travel the world!

Despite having savings, I also felt the pressure of needing to figure it all out ASAP… and I was definitely plagued by fears of going broke if I didn’t have it all figured out in time.

Plus, I needed time to grieve what I was leaving behind… and to recover from years of burnout.

So I threw myself into my art – without expecting to turn it into a career. 

When I felt up to it, I explored various online career options that would suit my digital nomad lifestyle. Teaching ESL online seemed to be the most obvious option to me. 

The exploration process is also how copywriting got on my radar!

To feel financially secure enough to study copywriting, I did 2 things. I reduced my expenses (which was easy in Tbilisi, where I’m currently based), and I took on a few 1-1 online tutoring jobs where I could still get paid decently to make my monthly bills.

I think it’s all about giving yourself time, space, AND the financial security to recover and reassess. This will look different for everyone, of course – which is why I love interviewing other teachers-turned-copywriters and discovering their unique journeys into this exciting and fulfilling profession.

Q: Do you ever miss teaching?

A: I miss my students – they were the best part of the job. But I don’t miss the broken education system. 

That said, I find myself slipping back into my teacher role ALL the time. I love training new copywriters at the company I work at. 

When I find exciting new ways to get the job done, I’m always sharing resources and videos with my Copy Chief community. 

I think we have so many leverageable teacher skills that never truly go away when we transition into a new role… so I don’t miss something that hasn’t actually gone away, lol.


Ready to join me and a super-friendly, supportive community of teachers-turned-copywriters? Go HERE to join us in the Copy Chief community. Note: as a Copy Chief affiliate I may earn a small commission when you join, at no cost to you.