Earlier this year, I had the good fortune of seeing my name as an available domain to purchase (!).

My very first website was Dragonsinn.net, a dragon resource website that was first launched in June 1999.

I’ve had several others since then.

At one point, I had three smaller websites floating around that I wasn’t updating too often. Two of them were hobby websites.

These three sites were:

• InnerLifeGoals.com (a mixture of astrology and introvert related topics)
• JessChuaBooks.com (for my creative writing), and
• JessVirgo.com (this is what I was using as my professional portfolio when JessChua.com wasn’t available)

Dragonsinn.net: My Self-Hosted WP Site

Dragonsinn.net used to be on html/css for over a decade. The design was cute but it looked a little outdated and was not optimized for mobile viewing (if you’re interested, scroll down this page to see some old screenshots of the website).

Over 2 to 3 years, I sporadically worked on it on and off to migrate the old site over to its self-hosted WordPress platform.

Dealing with third party page settings and some plugin incompatibilities took a lot of my leisure time. It took methodical thought to troubleshoot what had gone wrong (a frustrating one was losing access to my login page, which I later discovered was through an old plugin setting).

While successful troubleshooting is fun, I definitely didn’t want to deal with more than one self-hosted WordPress website when it came to personal projects.

Thoughts About Merging Into One Website

I spent some time thinking about whether I should merge my personal writing site with my portfolio. 

I was a bit worried that it might look unprofessional, or that it would be confusing to visitors.

Andy Crestodina at Orbit Media has an interesting and helpful article on whether you should merge or open a separate website.

According to Andy: “Having another website means more work: more time spent managing and promoting.”

That really stood out to me. My daily work involves online writing and editing because that’s what I enjoy doing. I didn’t want to spend my limited free time constantly troubleshooting various technical issues that are multiplied the more websites you have.

Andy mentions that there are two questions you should ask yourself when considering creating a separate website:

1. Is the site for a different audience?
2. Does the site have a different goal?

If you answer “yes” to both of these questions, that’s when he recommends thinking about building a separate site.

Pros and Cons of WordPress.org

3 Pros of WordPress.org:

1. More freedom to customize. You can install a plugin like Yoast SEO to refine the SEO data associated with your blog posts. You can easily embed forms and other items which could be necessary depending on the type of email marketing or ads monetization you have set up.
2. More choice with plugins. You can try out whatever plugins you want to customize your site. You can use plugins via WordPress.com on the business and higher plans. Compared to a self-hosted WP site, the plans are more costly, so they may not be the best option if you’re a very small business with a tight budget or you just want to keep a blog for fun.
3. Free from WordPress.com limitations. If you’d like to monetize your site through affiliate links and ads, a self-hosted WP is the way to go. Your blog won’t be subjected to the WordPress.com guidelines or terms of service.

3 Cons of WordPress.org:

1. More maintenance with updates and security. I enjoyed doing these things when I was younger and had more time to spend on a learning curve. Nowadays I’m aiming to spend my time more wisely, and dealing with the tech side of things isn’t my idea of what I want to spend my free time on. 
2. It can be difficult if you’re not technically inclined. Some of the things I’ve worked on for a self-hosted site include optimizing page speed, adding page rules on CloudFlare, updating the site to https, researching for a suitable theme without too many bells and whistles, and editing the .htaccess and other files on the backend. BlogAid has helpful info if you DIY a good portion of your self-hosted WP site. A more hands-off option does look attractive with the amount of time it could save.
3. Webhosting. You’ll have to do your research on finding a good web host to host your website on. Are they set up to manage WordPress sites? Do they have security measures in place? What’s the standard of their customer service?

Pros and Cons of WordPress.com

3 Pros of WordPress.com:

1. Hands-off with maintenance and security updates. You won’t need to update core WordPress files or fiddle around with your settings all that much in these areas. This allows you to spend more time on your content.
2. Access to WordPress.com Reader. When you add a relevant tag to your blog post, your post should show up in the “Reader” feature. I met a close online friend many years ago through a WordPress.com tag! It’s something I’m looking forward to using now and then to see what other members of the WordPress.com community are up to.,
3. Option to map a domain (under personal plan and up). At the moment, I’ve mapped JessChua.com to this WordPress.com domain. The domain is actually dragonsinn.wordpress.com, but JessChua.com looks sleeker.

3 Cons of WordPress.com:

• Limitations with customization. If you need to make lots of customizations, then WordPress.com may be too limiting. For example, I couldn’t embed a signup form because I’m not on the Business or eCommerce plan. These are some of the code restrictions on a Premium plan or below. The Business plan is $25/month for access to better SEO customization and other features you may need.
• Ads are placed on all free websites. These are distracting so you’d have to look at the personal plan at least if you want to remove the ads.
• WordPress.com does not offer integrated eCommerce features unless you upgrade to the eCommerce plan. This article on WPBeginner has more pointers on the pros and cons of WordPress.org vs. WordPress.com.

AND A BIG THING TO CONSIDER (for either WP option): Having to use the Gutenberg block editor.

I tried switching back to Classic Editor on WordPress.com, and some text couldn’t be retrieved when I went back to the block editor (and why is the “excerpt” feature missing on Classic Editor?).

I’ve been using Classic Editor on my self-hosted site, but I don’t know if I can continue doing it forever based on WordPress full site editing plans.

I can see how a block editor looks more modern…but seriously, the Classic Editor worked fine for blogging purposes. It was simple and easy to use.

It’s frustrating when I have to fight with the text formatting via the block editor.

Thoughts on My Merged Website

These articles were very interesting to read and influenced my decision:

• The Pros And Cons Of Merging Two Websites (bounteous.com)
• 5 Challenges Plaguing The WordPress Security Ecosystem (torquemag.io)
• WordPress.Com Sitebuilder: Can You Still Love It? (digital.com)

At the end of the day, my main goal was to streamline my three small writing-related websites and save time on site maintenance.

I didn’t have plans for any complex eCommerce options, so I felt that WordPress.com was something I could try out for the time being.

I’m prepared to move back to a self-hosted site if I need to in future.

Until then, I’m happy to see if I can work within WordPress.com.

It frees me up from dealing with time-consuming maintenance issues, which means I have more time for more purposeful pursuits like reading, sketching, or continuing education.