Copywriting, Depression and Travel – 2016 Year In Review

If you’ve visited my Start Copywriting blog recently, then you may have noticed that it has been over a year since I added ANY new content.

That’s right – no new videos in over a year!

So, what happened?

The truth is that 2016 was a bit of a roller coaster for me, with many changes happening in my life (good and bad). And these changes took my focus away from publishing new content on the Start Copywriting Blog.

As I look back on the crazy year that was, I decided to write this deeply personal blog post and share my journey with you. As you read the post below, you’ll learn about some of my highs and lows, which include…

  • Depression
  • Starting a TV show
  • Moving to a foreign country
  • And much more…

Now here’s the good news…

Despite my absence from posting on this blog, I really do love creating and sharing valuable content with you, my subscribers.

My goals, which I’ll share in more detail at the end of this post, include sharing a ton of new content, resources and tools to help you become a better copywriter in 2017.

So stay tuned for that!

Here is my 2016 year in review…

Web TV Show ‘Write For Business’


write for business show

In April of 2016, I was invited to host a Web TV show called ‘Write For Business,’ in a professional studio and for a global audience.

It was a BIG opportunity and I was definitely excited.

In our first meeting, the producers of the show asked me to prepare content for twelve, 45-minute episodes. As a public speaker, I know how much time and preparation goes into creating content for just one presentation. So, the idea of creating twelve episodes felt like a daunting task.

Luckily, I was able to invite my friend and experienced copywriter Kate Toon to co-host the show with me. Kate is an amazing presenter and agreed to share the responsibility of creating content for the show. Before I knew it, we were shooting our first episode!

Kate and I had a lot of fun filming and shared a lot of laughs and banter in between takes. If you want to check out a behind the scenes video from our first day of shooting, then click here to watch the video.

Loneliness and Depression


Photo source / credit Edward Honaker

I want to talk about something that many freelance copywriters never really talk about. And that’s loneliness and depression.

Anyone who knows me will tell you that I’m generally a friendly, positive and optimistic person. If you’ve watched my Youtube videos, you may have even had that impression as well.

But if I’m completely honest, for most of 2016, I wasn’t happy.

Everyone talks about the upside of being a freelance copywriter. You get to work from home, be your own boss and choose your own hours. Don’t get me wrong – these are definitely perks I’ve enjoyed for over 12 years now.

But what a lot of freelancers fail to mention is the downside of freelancing. Some of the disadvantages of being self-employed, which I’ve personally experienced, are:

  • The isolation of working alone
  • Negative clients
  • Slow months and variable income
  • Long hours and working on weekends
  • Self discipline and motivation

Being a freelance copywriter means you’re responsible for everything that happens in your business. You have to wear many hats and, at times, it can feel overwhelming.

And even though I’ve made a good living as a freelance copywriter, for over a decade, it doesn’t mean I’m immune to the downsides that come with our profession.

I was starting to feel depressed.  

I was no longer happy spending my days working from home in isolation. I began to yearn for the social interaction that comes from working in an office environment, around other people.

Even though I lived in Sydney, which is one of the most livable cities in the world, with a population of 6 million people, I still felt alone. I worked from various cafes around the city, but I still felt bored and restless.

I was ready for a new challenge and adventure.

One night, as I shared my frustrations with a friend over a glass of wine, she asked me a question that would change my life:

“But you could work from anywhere, why don’t you live and work in Thailand?”

I’d visited Thailand a few times before and
fell in love with the people, amazing food and laid-back lifestyle. I was ready for an exciting adventure, and relocating to Thailand would definitely provide that. Before I knew it, I was packing my bags and making plans to leave Sydney for the foreseeable future.

On July 28th, 2016, I flew to Chiang Mai, Thailand. It’s one of my favourite cities with its sunny weather, friendly people and beautiful countryside.

I Moved to Chiang Mai, Thailand!

Doi Inthanon in Chiang Mai Thailand

Doi Inthanon in Chiang Mai Thailand – Credit Lonely

Moving to Thailand was THE best decision I made in 2016. I went from feeling lonely and depressed living in Sydney, to feeling happier than I have felt in years!

I was so excited about moving to Chiang Mai that I recorded my first day in this video

I’ve been living in Chiang Mai for 6 months now. And while I do miss my friends and family back in Sydney, I feel much happier here. What’s so great about living in Thailand? Here are the top 4 reasons why I love living in Chiang Mai:

1. The supportive community of ‘digital nomads’

digital nomad friends

One of my biggest fears of moving to a new country was that I would continue to feel isolated. I’m excited to say the exact opposite has been true, thanks to the thriving ‘digital nomad’ community.

Chiang Mai has become the go-to destination for online business owners, entrepreneurs and freelancers from around the world. This community is known as ‘digital nomads’ and there are thousands of them living in Chiang Mai.

For the most part, the community is supportive, welcoming and friendly. There are networking events, meetups, dinners and activities happening every day in Chiang Mai. I’ve met lots of like-minded people (and quite a few copywriters!) and have made quite a few friends here.

2. Friendly Thai People

smiling thai people

Thailand is known as ‘The Land of Smiles’ because of the warm and friendly Thai people. It’s not uncommon for total strangers to smile at you on the street. I’m not sure if it’s the sunny weather, laid back lifestyle, culture or their Buddhist religion, but Thai people are incredibly friendly and welcoming people. It’s an absolute honour to be living amongst such positive people.

3. Delicious Thai Food

pad thai noodles

Thai food is internationally famous. Whether you enjoy spicy, sweet, sour or salty, there is a flavoursome dish on the menu for everyone. My favourite dishes are Pad Thai noodles, Khao Soi, and Massaman Curry.

If you get bored of eating Thai food, there are literally hundreds of restaurants serving western food as well. And the best part is, the cost of eating out is so ridiculously cheap, it doesn’t make sense to stay at home and cook.

For example, the average cost of dinner for two at a decent restaurant is usually between $5 and $8! Of course, you can always eat at fancy restaurants and spend much more.

4. High standard and affordable cost of living

chiang mai apartment

The cost of renting an apartment back home in Sydney, Australia is expensive. For example, if you wanted to rent your own 1-bedroom apartment in a nice neighbourhood, you’d be looking at spending between $650 and $1,000 AUD per week.

However, the cost of renting a 1-bedroom apartment in the popular and trendy Nimman area of Chiang Mai is surprisingly inexpensive, in comparison. You can rent an apartment from as little as $150 AUD per month!

In the video above I give you a tour of the apartment I rented for 5 months. It’s a 1-bedroom, fully furnished apartment with modern amenities (air con, flat screen TV, washing machine, kitchen, etc). It’s located within a five minute walk from the Nimman area and it cost me just $550 AUD per month!

My Goals For 2017

I’ve got big plans for 2017.

My goals include sharing a ton of new content, resources and tools to help you become a better and more successful copywriter in 2017.

New Start Copywriting Website (and fresh content)

Start Copywriting feels a bit outdated and is in need of an update. I’m currently working with a web designer to give the whole site a fresh new look. I’m also editing lots of videos from various presentations I’ve given on copywriting, which I will be uploading to the blog soon. So keep an eye out for new videos and posts!

60-Minute Copywriting Software

For the last 6 months, a team of software engineers and I have been working on a brand new copywriting software program. This is something I’m truly excited about.

The software allows anyone, even people with NO copywriting experience, to create professional, engaging and unique website copy in 60 minutes or less…

I can’t say too much about it yet. But I plan on releasing the copywriting software within the next few weeks to a handful of beta testers. As a subscriber to my newsletter, you’ll be the first to know about it!

Copywriting Community

Another project I’m excited about is building a private copywriting community. It’s going to be a supportive and welcoming place where you can connect with top copywriters, business owners and online marketers. You’ll be able to share your copy and get immediate feedback and advice on how to dramatically improve it.
I’ll also be uploading new courses and training inside the member’s area, too.

What about you? What are YOUR goals or plans for 2017? Let me know in the comments below. I’d love to hear from you and I read all comments posted here.


  • I’m a friend of the lovely Kate Toon too. What a great post and I’m so happy to read that you’re feeling much happier now with where you’re living. As someone who was treated for clinical depression for 12 years, before being re-diagnosed with bipolar disorder in 2014, I completely get how challenging it is to run a business when you can barely get out of bed.

    But it sounds like you’re feeling much better and I wish you every success with your big plans for this year. x

    • Hi Sharon! Thank you for your kind words and support, I truly appreciate it. It’s amazing what a change of scenery can do to elevate happiness. It was a challenging post for me to write, but I’m glad you can relate. Thanks again.

  • Nadia Barlow

    Hi Jesse, I met you at a copywriting meet-up with Kate Toon in 2016 – I guess 2016 wasn’t all bad hey 😉
    I reckon there are more than we realise who feel isolated and like they lack community, despite being surrounded by millions of people. That’s why I prioritise my social life so much – having friends is really important!
    Sounds like lots of exciting stuff coming up this year, I look forward to hearing about the new software. Nadia.

    • Great to hear from you Nadia! Judging by the amount of comments, emails, phone calls and private messages I received from fellow freelancers, I can see that feelings of loneliness and depression are more common amongst freelancers than I imagined. Thanks for the comment and here’s to a bigger and better 2017!

      • Nadia Barlow

        Most definitely. Although some days I’m really grateful to be able to at home and just be in my own little world 😜

  • Carl Weitzel

    Hello Jesse, I actually just came across one of your Youtube videos and found it very helpful, then I noticed you have not put out any new content for a while. This lead me to check out your site and FB page, and read this article. I really enjoyed it, it is helpful in that it shares insight from your life that is useful to where I am in my own. Thank you, and I hope to see more content from you in the future.

    • Hi Carl, thanks for the kind words! As I said in the article, I plan on creating a lot of fresh new content this year. I appreciate you following me on this journey.

      • Carl Weitzel

        That’s great!

  • CB

    Thanks for sharing Jesse. Although I don’t do copyrighting as a profession…your copywriting advice still continues to echo in my head when I write for my business. I totally agree, freelance/online business running is lonely. Great to have the freedom but the reality is your life is really moving at a different pace than so many people around you. But good on you for going to Ching Mai. A change is sometimes what is needed. Best, Timothy

    “The world is a book, and those who don’t travel only read one page.”

    ― Augustine of Hippo

  • Wayne Rosa

    Hello Jesse,

    I am Wayne Rosa – Gold Coast Qld.

    I loved the blog post, I also have had a bad few years,

    Double Heart Bypass
    Huge downturn in the mining industry (the industry I have worked for 25 years)
    House broken into 3 times (Harley stolen)
    Father passed away.

    So it’s definitely time for a change for the better

    My 2017 hopefully looks like this – I also would like to become a digital nomad, I have worked in engineering for the past 25 years however I’m over it and over traveling to work and sitting in a cubicle for 8-10 hours a day. I am single and my youngest son has just turned 18. I plan on becoming a copywriter even though I have not worked in this position before.

    I have completed the AWAI Copywriting course and am also going through – John Carltons “Simple Writing System” I have been around the Internet since 1994, I have done an advanced diploma in C/C++ programming and have done the Linux RHCE (RedHat Certified Engineer). So I know my way around a computer so to speak, I have also been using WordPress for many years. I am also in the process of setting up a membership site and an online course.

    Chiang Mai sounds great and is one of my picks as I am also wishing to relocate to another country this year. I have lived in Brazil for 7 months so South America is also appealing to me.

    The one problem I have with Copywriting (which I would like to do) is confidence or “lack there of” as I have not worked in this industry before.

    So after all that I might see you in Chiang Mai some time and would love to be part of you Copywriting/Digital nomad community.

    Wayne Rosa

    • Hi Wayne, thanks for sharing your journey with me. Sounds like you’ve had some interesting experiences throughout your life. If you’ve already done a few copywriting courses, then I’m sure you’re ready to get started. And the best way to do that, is to get out there and actually offer your services to other businesses. You have a wealth of life experiences to draw on. You simply need to ‘get started’ and learn as you go! Best of luck and let me know if you end up coming to Chiang Mai!

  • Steve Sheldon

    Hi Jesse,
    I I told you once, I took Ray Edwards’ “Copywriting Academy” course. Good stuff, but I’m not doing anything with it yet. I’m looking forward to seeing what you put out for us this year.

  • Thia Licona

    Hello Jesse, Don’t remember how we crossed paths but! Perhaps you been to ? Regardless, if you haven’t, I sense a connection in your future content. Would you please check the site and let me know what you think? 🙂

  • James Clark

    Great post. Which websites would you suggest for renting apartments in Chiang Mai?

  • Joe Reynolds

    Welcome back Jesse! Getting a message from you in my Inbox was like reconnecting with an old friend. I’m looking forward to your posts for this year with eager anticipation. I see good times ahead!

    • Hi Joe! Thanks for the lovely message 🙂 Its people like you that inspire me to continue creating and sharing content. Hope you are well and here’s too a successful 2017!

  • Roxanne McDonald

    Proud of you Jesse for claiming your presence as an entrepreneur & most of all: as a spiritual being having a remarkable human experience! Do continue to inspire yourself & others. Peace & Blessings. Roxanne.

  • Sunneva Birgisdottir

    I just “met” you for the first time today and I am so excited! You are spot on with exactly what I want in life. I just could´t find anyone like you to look up to. So thank you! Were have you been. Great way to finish out what I have always wanted.

    • Thank you Sunneva! I’m glad you’re enjoying my blog. I’ll be posting lots of new updates soon.

  • Sabrina P

    Hi Jesse. I’m so happy that you’re doing well. I’m a newer member to the copywriting world and I just wanted to thank you for all your advice and encouragement. I may still be in the practicing stage, but I never would have gotten there without your help.

    • Hi Sabrina, thank you for the kind message. I really appreciate it. And I’m going to be creating and posting more content in the near future!

  • Griffin

    Hey Jesse,

    Like you, my 2016 was full of ups and downs (and probably more downs than ups). I graduated from university in the summer of 2016 and took a sales job a few months after. You know those annoying telemarketers? Yeah…that was me. I absolutely hated it so I quit soon after.

    And also like you, I decided to move to Thailand! I’ve been here since January 5, 2017 and I’ve been liking it so far. It’s very different from America but it’s good to experience another culture.

    I am an English teacher here and the compensation is enough to live off of, but I still need to be a bit careful with my spending.

    So my goal for 2017? Become a digital nomad (in the copywriting niche). I’d love the freedom and peace of mind that would come with being able to make a living anywhere in the world with little more than an internet connection and a laptop. I have no copywriting experience at the moment, but by the end of 2017, I hope to be at the point where I can at least match my teaching income.

    And by the way, I’m very new to your content–I just learned about you yesterday–but hopefully can help me achieve my goal!

    PS. I live about 30 minutes from Pattaya and about 2 hours from Bangkok so if you ever find yourself down this way and want to meet up, let me know!


    • Hi Griffin,

      Thanks for sharing your story with me. Funnily enough, I used to be one of those annoying telemarketers too! I went from telemarketer, to high-end phone sales and then finally, copywriting. I have a few friends who are English teachers here in Chiang Mia too.

      So you want to become a freelance copywriter? Even though you live in Thailand, you should market your copywriting services to companies and businesses in more affluent countries, like America.

      I’ll let you know next time I’m in Bangkok! Send me a message if you’re ever in Chiang Mai. There is a thriving Digital Nomad community here.

      • Griffin

        Thanks for replying! Yeah, I haven’t been to Chiang Mai yet but I definitely would like to visit sometime.

        So what would you recommend I focus on to get me going as a copywriter?

        I’m already learning about the subject and I’m starting with a book you recommended (Influence: Psychology of Persuasion). After I study more about copywriting and begin to practice, how should I go about getting experience? I don’t know anyone in my social circle who needs any copywriting services, so how do I build up a body of work in the initial stage?


        • Hi Griffin,

          There are a number of ways to get copywriting experience. Here are a few solid ways I would recommend.

          1) Write for a business owner friend for free, in exchange for a reference / testimonial and a portfolio example.

          2) Practice writing for products / services you already know and love to use. It might be your local gym, restaurant or even your favorite shampoo! The idea isn’t finding the “perfect” product to write about, its just getting in the habit of writing often.

          How did I get experience? By following the first method. Once I’d written for a friend twice, I was then confident and ready to start writing for paying clients.


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  • Tracy Bousfield

    Hi Jesse,
    Just wanted to say hello as I met you today! I like your honest style and will look forward to hearing more from you.

  • Luisa

    Hello Jesse, so glad to find you. I´m just starting my life as a freelance copywriter and I want to keep learning more and more about this beautiful profession! I discovered your videos in Youtube and here I am now! Thanks for sharing all this experience and your useful advices.

    Greetings from Malta.

    • Hi Luisa, thank you! It’s an exciting journey and I look forward to hearing more about your progress 🙂