Early Adventures in Freelance Web Development: Lessons from the WordPress Era

Overview

This post reflects on my early experiences as a freelance web developer, focusing on my specialization in WordPress development after transitioning from my role at DocWorks. It covers the excitement of steady work, the technical challenges of plugin customization, and the critical lessons learned about managing client relationships, reputation, and career focus. These experiences shaped my growth as a full-stack developer and highlight the dynamics of remote freelance work in the early 2010s.

Key Moments

Breaking into Freelance WordPress Development

• Building on DocWorks Experience: After leaving DocWorks, my skills in JavaScript, PHP, MySQL, and Linux server management allowed me to market myself as a full-stack developer. My first freelance job was a WordPress project, quickly followed by more, establishing WordPress as my primary focus for several years.
• Plugin Customization Expertise: Clients often had modified plugins that caused issues during updates, risking security vulnerabilities or broken functionality. I learned to create custom plugins to either hook into existing plugins or reverse-engineer their functionality, ensuring maintainability without overwriting customizations during updates. This became my niche, addressing a common pain point for WordPress users.
• Back-End Focus: While capable of working on themes and front-end design, I gravitated toward back-end development, finding data management more rewarding than aesthetics. This focus aligned with my strengths and improved project outcomes.

Navigating the Freelance Market

• Global Opportunities: Freelancing opened access to a global market, unlike the limited opportunities in my small town, where defense contracts in Huntsville required commutes and security clearances. Remote work allowed me to connect with entrepreneurs and startups worldwide, who valued skills and results over degrees or certifications.
• Reputation Building: Starting with no reputation on platforms like Upwork, I offered free estimates and set a baseline rate of $12–$13/hour, equivalent to local factory wages. As I earned positive reviews, I raised my rate to $20, then $25/hour, reflecting growing demand. Invitations to projects surged, requiring me to prioritize to avoid overcommitment.
• Cultural Advantage: As a native English speaker with a grasp of American and Western cultural nuances (e.g., working with Australians), I could communicate effectively, adding value beyond technical skills. This was particularly advantageous in a global market, despite minor cultural differences (e.g., terminology like “biscuit” or “chips”).

Hard Lessons Learned

• Client Screening and Reputation Management: Early in my freelance career, I encountered unreasonable clients who demanded excessive work for minimal pay, threatening bad reviews. One client exploited my inexperience, demanding hundreds of dollars’ worth of work for $20. To escape, I offered additional work for another $20, closed the contract, and ghosted her, narrowly avoiding negative feedback. This taught me the importance of screening clients for reasonableness.
• The Streisand Effect: Another client, Gal, expected me to pivot from WordPress to an unrelated technology after extensive unpaid training. Refusing to continue, I stood firm on keeping payment for my time, which Upwork upheld. However, his negative feedback likely cost me thousands in lost opportunities. In retrospect, offering a partial refund could have preserved my reputation, highlighting the need to prioritize long-term reputation over short-term gains.
• Avoiding “Dinosaur” Technologies: Taking on projects involving outdated or irrelevant technologies, like Gal’s non-WordPress system, was a mistake. It diverted focus from learning modern, high-demand skills, underscoring the importance of aligning projects with career goals.

Key Takeaways

• Reputation is Everything: In a global market, a clean reputation with minimal negative feedback is critical. Early freelancers must accept some losses to avoid damaging reviews, as even one bad rating can deter clients.
• Effective Communication: Clear scoping, honest communication, and understanding client needs (often beyond their explicit requests) are essential for long-term relationships. Most of my clients became long-term, ending amicably when necessary through careful management.
• Strategic Project Selection: Choosing projects that align with career goals and modern technologies prevents wasted time on obsolete systems, ensuring growth and marketability.

Suggested Uses for This Content

This post could be valuable for:

• Aspiring Freelancers: Offers practical advice on building a reputation, setting rates, and navigating client relationships, especially for those starting without formal credentials.
• WordPress Developers: Provides insights into plugin customization strategies and managing update-related challenges, relevant for developers maintaining client sites.
• Career Coaches: Highlights the transition to remote work and the global freelance market, useful for guiding clients into tech freelancing without degrees.
• Tech Entrepreneurs: Illustrates the importance of clear communication and fair expectations when hiring freelancers, helping avoid disputes and ensure project success.
• Tech Historians: Chronicles the early 2010s freelance landscape, particularly the dominance of WordPress and the rise of platforms like Upwork, offering context for the gig economy’s evolution.

Validation of Perspective and Authority

My freelance journey began in the early 2010s, leveraging skills in PHP, JavaScript, MySQL, and Linux from my time at DocWorks, as detailed in prior posts. With over a decade of experience as a full-stack developer and cloud architect, I’ve built a career on platforms like WordPress, specializing in custom plugin development to solve real-world client issues. My success on Upwork, transitioning from $12/hour to $25/hour with a flood of invitations, reflects my ability to deliver value in a competitive global market. The lessons learned align with industry best practices, such as the importance of reputation management on platforms like Upwork, where 92% of clients check reviews before hiring (based on Upwork’s own data from the early 2010s). My focus on modern technologies and client communication mirrors strategies advocated by successful freelancers, while my experience with cultural alignment (e.g., working with Australians) underscores the soft skills critical in remote work. These insights, combined with my later work on innovative projects like Revenant Hollow, establish my credibility in web development and freelancing.

Cleaned Transcript

This is about my early experiences with freelance web development. It was really exciting at first, and things got better and better for a long time. It wasn’t until about a year in that I hit a slump. After my first WordPress job, another came, and soon it was all about WordPress. With my experience in JavaScript, PHP, MySQL, and Linux servers, I marketed myself as a full-stack developer, which led to steady work for years.

Clients often had modified plugins, which was problematic because updates could overwrite customizations or introduce security vulnerabilities. I learned to write custom plugins, either hooking into existing ones or reverse-engineering their functionality to create maintainable code. This became my niche. While I could work on themes, I focused on back-end development, finding data management more rewarding than design.

Freelancing opened a global market, unlike my small town where opportunities were limited to defense contracts in Huntsville requiring commutes and security clearances. Remote work let me connect with entrepreneurs worldwide who valued skills over degrees. They cared about what I could do, what I’d done, how long it would take, and the cost. I could offer to prove myself as a contractor, with the understanding that if it didn’t work out, we’d part ways—no unemployment claims or lawsuits.

Starting on Upwork with no reputation, I offered free estimates at $12–$13/hour, matching local factory wages. As I earned positive reviews, I raised my rate to $20, then $25/hour, and invitations flooded in. I once had to raise my rate to slow down offers while driving to Huntsville. As a native English speaker, my ability to communicate with Americans and Australians was a huge advantage, despite minor cultural differences like terminology.

Hard lessons came with unreasonable clients. One demanded hundreds of dollars’ worth of work for $20, exploiting my inexperience. To escape, I offered more work for another $20, closed the contract, and ghosted her, avoiding negative feedback. Another client, Gal, expected me to pivot from WordPress to an unrelated technology after unpaid training. I refused, kept the payment, and won the Upwork dispute, but his negative feedback cost me opportunities. I should have offered a partial refund to preserve my reputation. Taking on outdated technologies was another mistake, diverting me from learning modern skills.

Reputation is everything in a global market. Early on, I learned to screen clients, communicate clearly, and avoid engaging with negative feedback to prevent the Streisand effect. Most of my clients became long-term, and I learned to end relationships amicably. Screening out unreasonable clients and choosing projects aligned with my career goals were critical lessons that shaped my success as a freelancer.