A 10 Year Journey Through the World of Blogging

Lessons learned from a decade trying multiple blogging platforms, failing as an online publisher, and refining my direction as a creator and solopreneur.

A 10 Year Journey Through the World of Blogging

Blogger: The Starting Point

February 2008 marked my eleventh year living in Tokyo (I'm originally from Australia), and I had obtained permanent residence status. In the summer of that year, I graduated from yoga teacher training and started on Google’s Blogger service to provide information about my first classes. It was easy to use, but eventually, I found it too limiting, so searched for options.

WordPress.com: More Features & Possibilities

By the time 2009 started, I had moved to WordPress.com. It gave me a lot more possibilities and served my needs for around eight months or so.

Meanwhile, I had started using the blog to help spread the word about yoga workshops and events in Tokyo. I then branched out into interviews. Eventually, I created a crudely implemented studio and teacher directory. Since there was already a lot of local sites giving information, I decided to focus on providing information in English about classes, workshops, and events offered in English.

A girlfriend came up with the name, HelloYoga. Working through an intermediary hired on Elance, I managed to secure the .com domain name from a Chinese entrepreneur. I also got a freelancer to design a logo.

WordPress.org Attempt I

Wanting to offer my yoga class students an easy way to check my teaching schedule and sign up for classes, I looked around for options.

Facebook had an events feature, but the social network was only just starting to gain traction in Japan, and so not all my students were on it. Furthermore, its event reservation system was a bit lacking. People would click to join the event but not show up. Others would show up without having made a reservation. Facebook wasn't it.

There was no suitable web-based service available at the time, and WordPress.com didn’t allow plugins, so I migrated to WordPress.org and hired a series of Indian developers via Elance (now Upwork) to build the features I needed.

We found a plugin that was the closest possible to what I wanted and had the developers modify it. It was incredibly buggy and never quite worked. Whenever the WordPress core was updated, it would break the site. We had constant problems with the plugins too. On top of that, I kept having new ideas and changing the scope of the developers. The project was a bloated mess, and nobody was happy.

WordPress.org Attempt II

I made friends with a small creative agency, Pikkles, and worked with them on refining the site's concept. We worked out an arrangement to fit my shoestring budget. They moved the site to their servers, gave it a slick new design, and continued working on the scheduling system.

I established a company in Spring 2010 as a vehicle on which to build the business and found a local accountant to do my annual tax filings. This, I hoped, would help me do business with brands and perhaps serve well if I wanted to sell the operation later.

The scheduling system never did quite work out – I hadn’t realized what a massive undertaking it would be. Today, there are WordPress themes and plugins that would have reduced the development work to just minor customization, but it was the only course of action at the time.

I attempted to work with a series of interns to work on the site, especially the scheduling system. However, despite their valiant efforts, the result was a growing pile of spaghetti code, and each intern eventually moved on to a real job, leaving me in the lurch. Finally, I reached the reluctant decision to throw in the towel and just make the site an online magazine with a directory of teachers and studios.

Trying to Go Bilingual

Discovering the site’s visitors were mainly Japanese, I recruited volunteers to translate the site’s content into Japanese. We got mixed results. Since I’m not a native speaker, I couldn’t judge the quality or accuracy. Some Japanese told me that, while several translations were incredibly well done, most were average, and several were quite poorly done.

I adapted and added another layer of volunteers so that for each article or profile, it would be translated into Japanese, and then another would check and edit it. However, even this failed to produce consistent results, and we ended up with a variety of writing styles and tone across the Japanese side of the site.

I ended up ditching the attempt at making the site bilingual. To do it properly would have required a huge budget to hire professionals, which was not feasible. Another lesson learned the hard way.

WordPress.org Attempt III

By the time we entered 2012 smartphones had proliferated to the point where it was becoming embarrassing not to have a responsive website. HelloYoga.com had been limping along with an old custom theme that would break whenever the WordPress core or plugins were updated.

By this time, the content of the site had lost focus, and there were multiple genres and categories. It was a mess, and I needed to do a full renewal. I took the site offline and just put up a “Coming Soon” page. Meanwhile, I worked with Adam T. Perry, who drafted a stunning new design in Photoshop.

In 2013, I moved to a new WordPress-specialized host that took care of all layers below the core CMS. That took care of many of the technical issues, but a few months later, the host went down for an extended time, so I decided to leave them and move to WP Engine, one of the top hosts in the business.

In 2014, I worked to separate the content into several genres and categories. It made sense to split into different blogs to sever the different audiences. I worked with a Serbian-based agency to build my new family of blogs, including adding a new schedule system based on recently released plugins and themes. Finally, I was set to achieve my dreams!

Unfortunately, due to my lack of experience, knowledge, and constant revising of the scope, the project went in circles, and I burned a ton of money again. Frustrated, I decided to wait for a while.

Migrating to Medium

In 2016, Medium began presenting itself as a free, easy-to-use CMS that serious publishers could use. To prove their worth, they had worked out deals with several independent publishers and migrated them to their platform. These were powerful case studies.

It was an incredible offering. I could walk away from the smoldering wreckage of my WordPress mess and migrate to a platform that was minimalist, clean, free to use, and unlimited in scope. No more WordPress, no trying to customize it, and no hosting or development costs.

It was a lot of work to migrate, but I was able to do it myself without developers. Once it was done and I got into a rhythm with the content production workflow, I fell in love with Medium. After wrestling with WordPress for so long, it was such a pleasure to use. My legacy content never looked better, and they even had a slick mobile app.

Medium had announced that various ways for monetizing publications would be forthcoming, and I, along with many other online publishers patiently waited. We enjoyed the effortless publishing experience and focused on our content until potential income means such as subscriptions, advertising, and donations were released. Meanwhile, nothing was stopping us from using affiliate links in our posts. I found Skimlinks to be a particularly convenient system for this.

Medium Pivots Multiple Times

In early 2017, Medium famously pivoted again. They dumped their advertising options and continued delaying allowing publications to offer subscriptions.

Over time, Medium shifted away from serving publishers' interests. The monetization tools never came, and they discontinued support for adding custom domains. There was an exodus of publishers, many of whom went back to WordPress and other self-hosted CMS.

Uncertain of what to do, I persisted for a while but failed to find ways to monetize my portfolio of publications. I naively thought that if I just built up a big enough audience then avenues for monetization would eventually present themselves and everything would work itself out. But, that never happened.

The Epiphany Phase

I had been paying guest writers, many of whom submitted shoddy work. In most cases, I would spend vast amounts of time editing, and sometimes wholly rewriting their work. I would also edit their photos and supplement them with stock images. Once their work was published, I would promote it via social media, including paid Facebook post "boosts."

Looking at all the work I was doing for these guest writers; it just didn’t make sense. The affiliate income I was generating was negligible, and I had no other revenue streams.

The irony was that I had become a lean and mean content machine. I was doing better than the marketing departments of many companies. A yoga brand should have bought me out or brought me onboard. However, the content was too grassroots and non-commercial. It wouldn't have worked well to market yoga products well.

Bowing Out

In Autumn 2018, this project which had started with a humble blog back in 2008 ended. As much as I enjoyed the many aspects of the work, it just wasn’t a sustainable venture. I had sacrificed vast amounts of time and money over the years without ROI.

Many motivational speakers will tell you never to give up, but, if, after ten years you still can’t see the light at the end of the tunnel, you need to ask yourself if it is worthwhile continuing. I felt shattered, disappointed, and embarrassed at my failure. But, at the same time, there was also some relief in there and the knowledge that I was opening myself up to new opportunities which would be built on what I had learned from this failure.

New Beginnings

I decided to start again from scratch. Sometimes it’s better that way because there is no legacy structure holding you back. It took me a while to figure out what to do next, but I had come up with several conditions on which to base my next venture.

  1. No Development: While I can understand the concepts, I am not a coder or engineer, so prefer to use SaaS that I can just sign up for.
  2. No Collaboration: Guest writers cost time and money while demanding full creative control over the final product. Interviewees can be hard to get a hold of to review drafts. After the interview is approved, they may come back later, after having a change of heart, and ask for it to be pulled. I’d rather just make my own original content and have full creative freedom.
  3. No Outsourcing: I have blown obscene amounts of money on developers, writers, designers, and artists over the years with nothing to show for it. Better to focus on my strengths instead of trying to fill in the gaps with hires. That said, I will still do it when absolutely necessary. For example, I use an accountant for my company.
  4. No Deadlines: One key to becoming a successful content creator is publishing regularly. That said, if you raise the frequency too high and put yourself under too much pressure, you suffer burnout. Furthermore, for the time being, I’ll have to prioritize earning money to pay my bills before my creative ventures.
  5. Privacy: I prefer to keep my name and face offline. This wasn’t the case even five years ago, but now I know the risks associated with it. I’m not good looking or charismatic, so building a personal brand isn’t going to work for me.
  6. Integrity: If you put something online, you need to be prepared to have it be discovered and come back to you. Not only content but also little comments you leave on different sites. You wouldn’t believe the technologies and techniques that experts can use – and, AI will make this even more possible. So, unlike some anonymous content creators that I know, I’ll be assuming that everyone can figure out who I am and trace anything I do online back to me - and behave accordingly online.
  7. Minimalism: I want to remain lean and mobile, so won’t be renting an office or hiring staff. I don’t want an office/studio full of equipment, so I will be using only mobile devices and accessories.
  8. Mobility: It’s not easy to just up and move to a new place, but I want to simplify my life and shift towards working remotely so that I can be location independent as much as possible. I live in Tokyo, but the city is overdue for a massive earthquake, and you never know when tensions with China or North Korea might erupt. I may need to get the heck out of here fast one day.

New Brand, New Ventures

  • Brand Name: I chose the initials of my full legal name, DLKR, as my brand name. I do use my real name in a few places, but have greatly minimized it compared to before and aim to phase it out altogether eventually.
  • Company: I renamed it to DLKR, Inc.
  • Logo: Whereas I’ll use my profile picture for my personal brand, for my business, I’ll use a simple logo of why initials.
  • Profile Picture: As for profile pictures, I’ll still use my face, but it will be manipulated and obscured to be unrecognizable.

Reinventing My Business

I thought back over my career to remember what exactly it was that (i) I knew I could do well, and (ii) people appreciated. While I’ve become known as a “marketer” over the past decade, marketing is a broad field, and I’m only good at certain things.

Based on much reflection, I put together a menu of services that I often get contacted for out of the blue by people who know me. These were obviously things I did well and people valued. You could loosely fit them all under the category of "content marketing."

My experiences have taught me that I prefer to work with SMEs that are financially stable, open to new ideas, lack a dedicated marketing department, and have few decision makers.


I needed a simple landing page showcasing my content services. After reviewing various options, I chose Strikingly, a website builder best known for its simplicity and reasonable pricing.

It was initially created to specialize in one-page websites and landing pages. However, as with many online services of its kind, had built in many additional features based on customer requests.

After finalizing my landing page, I duplicated it and translated the copy into Japanese. I then made one more copy and reworked it to appeal to companies located outside of Tokyo that I might work remotely with.

However, I was soon about to have a change of heart and start looking at Strikingly in a very different way.

Principles: Free Speech

Until I reached my forties, I didn’t have much interest in politics. Perhaps it was my getting older and developing more of a broader perspective, or maybe it was the 2016 US presidential election. Either way, I have gradually shifted towards following a number of commentators to try and become more aware and educate myself.

I’ve developed a fondness for edgy commentators. Following them on various social media became a form of entertainment and escapism. Over the past few years, several have gotten themselves banned from multiple platforms. This introduced me to the issues surrounding free speech, censorship, and where lines should be drawn.

Most platforms claim to support freedom of expression but within certain guidelines. The problem with this is it gets into a subjective territory and is open to abuse and corruption.

The commentators I follow started joining platforms where they wouldn’t get censored.  These free speech platforms only remove content that breaks US law. The logic is that the solution to bad speech and wrong ideas is more discussion and communication.

We should let ideas compete in the open marketplace. If they lack merit, then their shortfalls will soon be shown up. Conversely, if you censor, repress, and ban, then it has the opposite effect. It can lead to extremism. When you tell somebody they aren't allowed to see something they are more likely to want to see it. This is known as the Streisand effect.

This introduced me to the alt-tech (alternative technology) movement, which is building free-speech alternatives to the mainstream social media.

Principles: FOSS & Privacy

FOSS stands for free and open source software. I had known of high profile examples such as Linux, WordPress, and Gimp.

The CEO of one of the free speech social media platforms, Minds, explained in several interviews about the benefits of open source. One of these is transparency. Since they make their entire platform open source, anybody can inspect its code and make sure that it is only doing what they say it does. You can also use it to set up your own independent instance of Minds.

Another benefit of FOSS is that there is no vendor lock-in. Google and Apple have built convenient and comfortable walled gardens that are almost impossible to leave if you want to function in modern society. The FOSS community is working to produce alternatives to these closed offerings.

Surveillance capitalism, the business model of companies such as Google, Facebook, Microsoft, Amazon, and others has alarmed many. We are being tracked. Our data is being stored, spread to multiple companies around the world, and analyzed. FOSS alternatives provide alternatives that respect privacy.

While I can’t help but marvel at what Big Tech has built, these issues kept nagging at me and I’ve decided to start working on transitioning towards using FOSS wherever possible. It’s a big undertaking, but I believe in supporting this mission.

Online privacy is a fascinating and broad topic. The average person has no idea just how much these companies know about them.

Privacy enthusiasts include a broad range of people. On one side, you have characters such as the concerned parent who wants to protect his kids to journalists who are putting their lives at risk by revealing truths. On the other side, you have people engaging in illegal activities who want to be untraceable. It’s quite fascinating.

To start with, I adopted a few of the easier choices:

  • Search: DuckDuckGo is a privacy-respecting alternative to Google
  • Browser: Brave is an open source and privacy-oriented alternative to Google Chrome that lets you use the same extensions
  • VPN: Virtual Shield is a virtual private network service which provides some privacy protection

However, these only slightly reduce what privacy experts call your “attack surface.” I have a long way to go and have compiled a list of other Google alternatives and other tools/services that I’m planning on transitioning to.

Why I Had to Leave Strikingly

As much as I enjoyed the convenience and ease of use that Strikingly provided, they had several glaring issues for me:

  1. Closed Source: If they decide to shut down the service, there is no alternative. I can’t just export my content and migrate to another company who uses the same platform. It’s a lock-in situation.
  2. Small Company: Small companies are usually run by one or two individuals. This isn't such a problem if the project is open source because it can live on after the founders or company that originated it disappear. However, if a company operating a closed platform implodes, then their tech goes with them.
  3. A Chinese Company: China is ruled by a totalitarian government. Any Chinese company operating an online platform has to comply with the government’s surveillance requirements, or they cannot operate. Since Strikingly is run by a Chinese company, this makes me wary of using it. Nothing against the good people of China, but I have my principles.
  4. Prohibiting "Hate Speech:" Being against hate speech sounds like a good thing at face value. The problem is that it is vague and subjective. Who gets to decide what constitutes hate speech? What if I published a post that politely and logically argued against their political beliefs and they choose to delete my blog/site without warning?

Open Source Website Platform Options

There is a surprising number of open source blogging platforms, CMS, and website builders. Many require you to have your own server, set it up, and maintain all the various layers of software involved. That wasn’t an option for me because I want to focus on the content. So, I had to limit myself to SaaS offerings.

I came down to three that I liked. The first two were at extreme ends of the complexity spectrum, and the third I liked.

1. WordPress.com is much easier to deal with than WordPress.org, and it has improved a lot since I used it ten years ago. Nevertheless, it is still overkill for my needs. After a day of wrestling with it, I gave up.

2. Write.as is at the other end of the scale. I found it overly minimalistic and bare bones. I experimented with it for a few weeks, but then gave up because so many of the features I wanted were either far off on the roadmap or not planned at all. It wasn't for me.

3. Ghost was somewhere in between these two extremes and felt like a good compromise, so I've chosen to go with it and set up DLKR.life as a place to share what I learn from my business and creative pursuits, along with my art, photography, and videos.

Becoming a Creator

My services are just to pay the bills while I build up my income as a creator to the point where it can support me full-time. This is because (i) at nearly 45, I’m already too old to be employable in the eyes of many companies, and, (ii) my creative work is what I really want to do.

I’ve had the privilege to know a few creators, including one who is able to live off his work full-time. I’ve also been following and studying several creators over the past five years to learn how they do things.

As a creator, I have several ideas for income streams:

  • Patronage: I’ll be offering options for people to contribute one-time or recurring donations. Patreon has been exposed for being censorious and they're really just a middleman. Most platforms either have or are in the process of building in ways to allow fans to support their favorite creators.
  • Print-on-Demand (POD): I’ll use POD sites such as RedBubble and Society6 to let people buy prints of my photos and art.
  • Affiliate Links: I’ll continue using Skimlinks to monetize any links to online merchants.

Peace Out

I was just using this post to organize my thoughts and do some reflecting. Thank you for reading, and I hope it gave you some ideas for your own endeavors.

One of my favorite YouTubers rants and raves for as long as he likes each video. When he has finally run out of steam, he abruptly ends with, "Oh, well, that's about all for now. Peace out!" So, it feels appropriate to end this long and rambling post with the same words.

Peace Out!

Cover photo by Mark Solarski on Unsplash + filter by BeFunky