Side Hustles I Tried What Worked and What Didn't – A 7-Year Honest Retrospective
Look, I'm Ryan Cole. I've been building online side hustles for over seven years now. That's long enough to have made a lot of mistakes, learned a lot of lessons, and developed some pretty strong opinions about what works and what doesn't. Over those years, I've probably tried somewhere between thirty and forty different ways to make money online. Some worked beautifully. Some failed completely. 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. For tools that helped me build everything, I've compiled the best online tools and resources to work smarter.
The Context: Where I Started
When I started my first online side hustle, 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.
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, continuously 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.
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 make money 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, relatively passively. 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.
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 passive. 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.
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.
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.
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.
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 extremely difficult without driving my own traffic.
What I Would Do Differently If Starting Over Today
Start with a service for quick cash flow while building toward scalable products from day one. Build an audience immediately 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.
Final Thoughts: What Seven Years Have Taught Me
Consistency is the closest thing to a superpower. 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 sustainable strategy. When you focus on solving real problems for real people, the money follows naturally. 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.
