Side Projects I Tried: What Worked and What Didn't A 7-Year Retrospective
I've been building online side projects for over seven years now. That's long enough to have made a lot of mistakes, learned a lot of lessons, and developed some strong opinions about what works and what doesn't. Over those years, I've probably tried somewhere between thirty and forty different ways to earn online. Some worked. Some failed. Most fell somewhere in between. In all that time, I've never sat down and written an honest, comprehensive accounting of those experiences, until now. Results vary from person to person, and what worked for me may not work the same way for you. For tools that helped me build everything, I've compiled a list of online tools and resources to work smarter.
The retrospective format matters because it's honest in a way that most side project content isn't. The typical article presents a single success story as if it were inevitable, omitting the failures and false starts that came before. That's misleading. It makes readers feel like failures when their own journeys don't match the polished narrative. The truth is messier. Success online is almost always the result of multiple failed experiments, each one teaching something that made the next attempt slightly more likely to work. That's the real story, and it's the one I'm going to tell.
The Context: Where I Started
When I started my first online side project, I was in my mid-twenties with a day job in marketing that paid the bills but didn't excite me. I had a bachelor's degree in communications, nothing technical, nothing that directly qualified me for any particular online work. I had a laptop, reliable internet, and a lot of nervous energy. I had no audience, no email list, no social media following, no mentor, and no insider knowledge about how online business worked. I was as close to starting from zero as it's possible to be. I also had some advantages: I'm a native English speaker, I had a stable day job covering basic expenses so I could experiment without catastrophic consequences, and I had some writing ability from my marketing work.
Those advantages mattered more than I realized at the time. The stable day job was particularly important. It gave me the psychological freedom to experiment without desperation. When you're desperate for money, you make short-term decisions that undermine long-term progress. You take low-paying work. You abandon strategies before they've had time to mature. You chase short-term wins that don't compound. Having my basic expenses covered meant I could afford to be patient, and patience turned out to be one of the most valuable assets in my entire journey.
Freelance Writing: The One That Actually Worked
Freelance writing was the first thing I tried that generated consistent, meaningful income. I started on Upwork in late 2017 with no portfolio and no reviews. My first break came when I applied to a small, unglamorous project, writing short product descriptions for an e-commerce site, that other writers seemed to be ignoring. I wrote a personalized proposal addressing the client's specific needs. They hired me. I delivered on time. They left a five-star review. That single review unlocked everything else.
My first month, I made about $200. By month six, I was consistently making $1,500 to $2,000 per month part-time. By year two, writing had become my primary income. At my peak as an individual writer, I was charging $100 to $150 per article and making $4,000 to $5,000 per month while working around 25 to 30 hours per week.
What worked: specializing in topics I understood well, building long-term client relationships rather than one-off transactions, raising my rates every few months, and developing efficient workflows with templates and systems. What didn't: staying too long on low-paying platforms, undervaluing my work due to scarcity mindset, and not building my own assets like an audience or products alongside client work. For more on the specialization principle that changed everything, my guide on skill stacking for online work covers it in depth.
Affiliate Marketing: Slow Burn That Eventually Paid Off
While freelancing, I started this blog and began publishing articles about productivity tools, online business strategies, and ways to work online, including genuine affiliate recommendations. For the first six months, almost nothing happened. Traffic was tiny. Commissions totaled perhaps $50. It was deeply discouraging.
Around month eight, articles started ranking in Google. By month twelve, the blog was generating $300 to $500 per month. By year two, $1,000 to $1,500. Today, several years in, affiliate income generates several thousand dollars per month, with minimal ongoing effort. Articles I wrote three years ago still generate commissions today.
What worked: SEO targeting long-tail, low-competition keywords, genuine recommendations of products I actually used, patience through the initial drought, and diversifying across multiple affiliate programs. What didn't: trying to force social media promotion when my content style didn't translate to short-form platforms, chasing trending topics with no lasting value, and spreading too thin across too many unrelated topics. For more on this model, my guide on non-traditional text services with real demand covers related strategies.
Digital Products: The One I Wish I'd Started Sooner
My first digital product was a freelance template bundle, proposal templates, contract templates, and invoice templates I'd developed for my own use over years. I cleaned them up, added instructions, listed them on Gumroad for $27, and wrote a blog post about writing winning proposals that naturally mentioned the templates. The bundle generated maybe $200 in its first month, modest, but genuinely automated. Over time, I created additional products. Digital product income now represents $2,000 to $4,000 per month.
What worked: creating products based on demonstrated demand from audience questions, starting small with minimal viable products before investing heavily, building an email list as the engine of product sales, and treating product creation as an ongoing learning process. What didn't: trying to create products in a new niche with no audience, and underpricing early products out of insecurity. For a complete walkthrough, my guide on creating digital products with Canva covers the entire process.
Dropshipping: The One That Failed Completely
Around 2019, I set up a Shopify store, found products through Oberlo, and ran Facebook ads. I spent about $500 on ads over two months, generated maybe three sales totaling $120 in revenue, and lost about $450. More importantly, I lost dozens of hours I could have spent on things I already knew worked.
Why it failed: generic products with no unique value proposition, long shipping times from overseas suppliers leading to customer complaints, expensive and competitive Facebook ads, and most fundamentally, I had no genuine interest in e-commerce or physical products. You can't fake enthusiasm, and customers can tell when you're just going through the motions. The lesson wasn't that dropshipping doesn't work. It was that dropshipping didn't work for me because it didn't align with my skills or interests. That distinction matters a lot when evaluating which side projects to pursue.
YouTube: The One I Never Fully Committed To
I started a YouTube channel around 2020, publishing sporadically. After about a year and thirty videos, I had around 2,000 subscribers. Some videos got a few thousand views; most got a few hundred. The channel generated perhaps $100 per month. The reason is simple: I never fully committed. YouTube rewards consistency, and my sporadic approach meant I never built momentum. I also found video creation uniquely draining compared to writing.
The YouTube experience taught me something useful about energy management. Different creative formats require different kinds of energy. Writing comes naturally to me. Video production, with its lighting, editing, and performance demands, drains me quickly. Recognizing which formats suit your natural energy patterns is important. Forcing yourself into a format that doesn't fit leads to inconsistency, and inconsistency is fatal on platforms that reward regular publishing. For more on finding formats that match your temperament, my guide on quiet work without camera calls covers related strategies.
Coaching and Consulting: High Value, Low Scale
As my blog grew, people asked if I offered coaching. I started offering one-on-one consulting at $150 per hour. A few clients per month generated $600 to $1,200 in additional income for relatively little time. The work was genuinely satisfying. I enjoyed helping people think through their challenges. The limitation: consulting doesn't scale. Income was directly tied to hours spent on calls.
Coaching taught me the difference between income that scales and income that doesn't. A consulting hour earns you money once. A digital product earns you money repeatedly without additional time investment. Both have value, but they serve different purposes. Consulting provides high hourly rates and deep satisfaction from direct client interaction. Products provide leverage and automated income. The most consistent earners I know combine both: consulting for the connection and immediate income, products for the leverage and growth over time.
Print on Demand: The Middle Ground
I created simple text-based designs for niches I understood and listed them on Redbubble and Merch by Amazon. At its peak, this generated $100 to $200 per month, a nice supplement, but not major income. Individual margins were small, $3 to $7 per sale, and standing out among millions of products was difficult without driving my own traffic.
Print on demand occupied a middle ground: not a failure like dropshipping, but not a success like freelance writing or digital products. It worked well enough to justify the time I put into it, but never became a primary income source. The key insight was that print on demand, like dropshipping, requires a pre-existing audience or marketing budget to scale. Without those, you're competing with millions of other sellers in a marketplace where standing out is genuinely difficult.
What I Would Do Differently If Starting Over Today
Start with a service for faster cash flow while building toward scalable products from day one. Build an audience early through a blog and email list. Content compounds. Focus on one thing for at least six months before diversifying. Invest in permanent skills like writing and SEO before chasing specific platforms. Take bigger swings on leveraged opportunities once you have a stable income foundation.
The sequence matters more than most people realize. Freelance writing provided the cash flow that reduced financial pressure. Reduced financial pressure allowed me to be patient with the blog. The blog built the audience that made digital products viable. Each step created the conditions for the next one. Trying to skip ahead, launching products before building an audience, or scaling before establishing cash flow, leads to frustration and wasted effort. The path is sequential, and each phase teaches lessons that make the next phase possible.
Final Thoughts: What Seven Years Have Taught Me
Consistency is one of the most powerful factors. Almost nothing worked immediately. The freelance writing, blog, and digital products all required sustained effort over uncomfortably long periods. Genuine value creation is the only strategy that holds up. When you focus on solving real problems for real people, the money tends to follow. There is no single right path. The right path aligns with your skills, interests, and goals. And most importantly: start before you feel ready. Competence comes from action, not from preparation. The people who wait until they feel ready never start.
The seven-year retrospective has taught me that the journey is less about finding the perfect side project and more about becoming the kind of person who can do well at whatever side project they choose. The skills that mattered most, writing, patience, consistency, genuine curiosity about solving problems, weren't specific to any single platform or business model. They transferred across everything I tried. That's the real asset you're building. Not a specific income stream, but a set of capabilities that can generate income in multiple ways over time.
Results vary by person. What worked for me may not work for everyone. The income figures mentioned are from my personal experience and are not typical or guaranteed.
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Disclaimer: The information provided in this article is based on personal experience and research and is intended for educational and informational purposes only. It does not constitute financial, investment, or business advice. Income figures and results described are real examples from my own experience but are not guarantees of what any individual will achieve. Your results will depend on your skills, effort, market conditions, location, and numerous other factors. Always conduct your own research and consult with a qualified professional before making any financial decisions.
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This article is a personal retrospective based on my own seven years of testing online side projects. Your experience may differ depending on your skills, the time you invest, and market conditions. Take your time, start small, and let real results guide your next step.
