An Honest Retrospective by Ryan Cole
Last Updated: May 2026 | Reading Time: 29 Minutes
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 of them worked beautifully. Some of them failed completely. Most of them fell somewhere in between — they kind of worked, kind of didn't, taught me something, and then evolved into something else.
In all that time, I've never sat down and written an honest, comprehensive accounting of those experiences. The successes and the failures. The things that surprised me and the things that confirmed what I already suspected. The strategies that generated real money and the ones that generated nothing but frustration. Until now.
This article is going to be different from the others I've written. It's more personal. It's more retrospective. It's me looking back across years of trial and error and pulling out the lessons that actually mattered. I'm going to walk you through the side hustles I tried, what worked and what didn't, what I made from each one, and — most importantly — what I learned that you can apply to your own journey. Some of these stories are encouraging. Some are embarrassing. All of them are true.
My hope is that by sharing the full picture — not just the highlight reel — I can save you from some of the mistakes I made and point you toward the approaches that have the best chance of working. Let's get into it.
The Context: Where I Started and What I Was Working With
Before I dive into the specific side hustles, I think it's important to give you context about where I was starting from. Because success stories without context can be misleading. They can make things seem easier than they actually were, or harder, depending on what details get left out.
When I started my first online side hustle, I was in my mid-twenties. I had 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, a reliable internet connection, and a lot of nervous energy. I had no audience. No email list. No social media following. No mentor. 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 that I should acknowledge. I'm a native English speaker, which opened doors in the global freelance marketplace that aren't equally available to everyone. I had a stable day job that covered my basic expenses, which meant I wasn't under pressure to generate income immediately — I could experiment and fail without catastrophic consequences. I had some writing ability from my marketing work. And I had a stubborn, maybe slightly obsessive personality that made me keep going even when things weren't working.
If your circumstances are different — if you're not a native English speaker, if you need income urgently, if you have less time available — some of what I share may need to be adapted. But the underlying principles of what worked and what didn't should still be valuable regardless of your starting point.
Side Hustle #1: Freelance Writing — The One That Actually Worked
Let me start with the side hustle that became the foundation for everything else. Freelance writing was the first thing I tried that generated consistent, meaningful income. It's also the one I stuck with the longest and the one that taught me the most about how online business actually works.
How I Got Started
I started on Upwork in late 2017. I created a profile, filled it out as completely as I could, and started applying to writing projects. My first few proposals went nowhere. I was competing against writers with established profiles, portfolios, and reviews, and I had none of those things. My early proposals were probably also terrible — too generic, too focused on what I wanted rather than what the client needed.
My first break came when I applied to a project that other writers seemed to be ignoring. It was a small, unglamorous project: writing short product descriptions for an e-commerce site. The pay was modest — maybe $30 for a batch of descriptions. But I wrote a personalized proposal that addressed the client's specific needs. I mentioned that I had marketing experience and understood how product descriptions affect conversion rates. I didn't try to sound impressive. I tried to sound helpful.
The client hired me. I delivered the work on time. They were happy with it. They left me a five-star review. That single review — my first — unlocked everything else. With one positive review on my profile, my proposals started getting responses. Clients could see that at least one person had trusted me with work and been satisfied with the result. That social proof made all the difference.
What I Earned
My first month, I made about $200. My second month, $400. By month six, I was consistently making $1,500 to $2,000 per month writing part-time — evenings and weekends around my day job. By year two, writing had become my primary income, and I had raised my rates multiple times. 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
Several things contributed to this working. I specialized. Early on, I wrote about anything anyone would pay me to write about. But over time, I narrowed my focus to topics I understood well — marketing, business, productivity, and later, personal finance and online income. Specialization meant I could write faster and better than generalists. It meant I could charge more. It meant clients came to me rather than me having to chase them.
I built relationships, not just transactions. I treated every client like a potential long-term partner. I communicated proactively. I met deadlines religiously. I made revisions cheerfully. When projects ended, I stayed in touch. Many of my best clients came back to me months or even years later with new projects. Some referred me to colleagues. Relationships compound in freelancing in a way that one-off transactions never can.
I continuously raised my rates. Every few months, when my pipeline was full and I was turning down work, I would increase my rates for new clients. This was terrifying every single time. I was always convinced no one would hire me at the higher rate. I was always wrong. The market will tell you what your work is worth if you're willing to test higher prices.
I developed efficient workflows. I created templates for common article types. I built systems for research, outlining, drafting, and editing. What used to take me four hours eventually took me two. Efficiency meant I could take on more work without working more hours, or earn the same amount in less time.
What Didn't Work
I spent too long on low-paying platforms. Upwork was great for getting started, but I stayed there longer than I should have. The platform takes a significant percentage of earnings, and the client base skews toward lower budgets. When I eventually moved to finding clients directly — through LinkedIn, through referrals, through my own network — my income increased significantly while my effort decreased.
I undervalued my work for too long. Even as my skills improved and my clients grew, I was slow to raise my rates. I had a scarcity mindset — I was afraid that if I charged more, the work would dry up. That fear cost me thousands of dollars in potential earnings during my first two years.
I didn't build my own assets. For the first few years, I was purely trading time for money. I wasn't building an audience. I wasn't creating products. I wasn't developing anything that would generate income without my direct involvement. When I eventually started my blog and began creating digital products, I realized how much opportunity I had been leaving on the table by focusing exclusively on client work.
Key Lessons
Freelance writing taught me that you can build a real income from scratch with no audience and no credentials. It taught me that specialization beats generalization. It taught me that client relationships are the most valuable asset in a service business. And it taught me that trading time for money has a ceiling — a comfortable ceiling, but a ceiling nonetheless. Those lessons shaped everything I did afterward.
Side Hustle #2: Affiliate Marketing — Slow Burn That Eventually Paid Off
While I was building my freelance writing business, I also started experimenting with affiliate marketing. This was a very different experience — much slower to produce results, much more frustrating in the early stages, but ultimately very rewarding once it gained momentum.
How I Got Started
I started a blog — this blog, actually. The one you're reading right now. I began publishing articles about topics I knew well from my freelance work: productivity tools, online business strategies, ways to make money online. Within those articles, I included affiliate links to products and services I genuinely used and recommended.
For the first six months, almost nothing happened. I was publishing consistently, but my traffic was tiny — maybe a few hundred visitors per month. Affiliate commissions during that period totaled perhaps $50. It was deeply discouraging. I questioned whether the blog was worth the effort. The only thing that kept me going was that I genuinely enjoyed writing the articles, and I told myself that even if they never made money, they were serving as a portfolio for my freelance work.
What I Earned
Around month eight, something shifted. A few articles started ranking in Google for specific search terms. Traffic began to grow — slowly at first, then more steadily. By month twelve, the blog was generating $300 to $500 per month in affiliate income. By year two, it was $1,000 to $1,500 per month. Today, several years in, affiliate income from this blog and related content properties generates several thousand dollars per month, relatively passively. The articles I wrote three years ago still generate commissions today.
What Worked
SEO was the engine that drove everything. I didn't have a social media following. I wasn't running ads. My traffic came almost entirely from search engines. I learned the basics of keyword research, on-page optimization, and content structuring. I focused on answering specific questions that real people were typing into search engines. Articles targeting long-tail, low-competition keywords performed far better than broad, general topics.
I focused on genuine recommendations. Every product I promoted as an affiliate was something I had actually used and could honestly recommend. This built trust with readers. It also meant I could write detailed, authentic reviews and comparisons that were genuinely helpful, not just thinly veiled sales pitches. Authentic content converts better than generic promotional content, and it's more satisfying to create.
I was patient. Affiliate marketing through content is not a quick-win strategy. It takes months for content to rank, gain traffic, and start generating meaningful commissions. Many people quit during the slow early period. I almost did. Sticking with it through the initial drought was the single most important factor in eventual success.
I diversified income sources. I didn't rely on a single affiliate program. I promoted a range of products across different categories — hosting services, software tools, online courses, freelance platforms. Diversification protected me when individual programs changed their commission structures or when specific products declined in popularity.
What Didn't Work
I tried social media promotion and it mostly failed. I spent months trying to build a following on various platforms, sharing content, engaging with others. The return on time invested was terrible. My personality and content style didn't translate well to short-form social content. Eventually, I stopped trying to force it and focused on what was actually working — search traffic. That was the right decision.
I chased trending topics that had no lasting value. Early on, I wrote several articles about trending products and services that were popular at the moment but had no staying power. Those articles generated a spike of traffic and then faded into irrelevance. Evergreen content — articles that remain useful and relevant for years — generates far better long-term returns than trend-chasing.
I spread myself too thin across too many topics. In the beginning, I wrote about everything remotely related to online business. My content lacked focus. It wasn't until I narrowed my niche significantly that traffic and conversions started to improve. Depth beats breadth in content, almost every time.
Key Lessons
Affiliate marketing taught me patience. It taught me that content compounds — the articles you write today will generate returns for years if they're valuable and well-optimized. It taught me to focus on channels that actually work rather than trying to be everywhere. And it taught me the immense value of building your own platform — a blog, an email list, a content library — that you control, rather than renting attention from social media platforms that can change their algorithms at any time.
Side Hustle #3: Digital Products — The One I Wish I'd Started Sooner
After a few years of freelancing and blogging, I finally started creating digital products. This was a side hustle that grew out of my existing work — I had developed expertise and an audience, and digital products were the natural way to leverage both. Looking back, I wish I had started this years earlier.
How I Got Started
My first digital product was a simple template bundle — a set of freelance proposal templates, contract templates, and invoice templates that I had developed for my own use. I had refined these documents over years of freelancing. I knew they were valuable because I used them constantly myself. I cleaned them up, added instructions, and packaged them as a downloadable product.
I listed the product on my blog and on Gumroad. I priced it at $27. I wrote a blog post explaining how to write winning freelance proposals and naturally mentioned the templates as a resource at the end of the article. That blog post still ranks well today, and it drives consistent sales of the template bundle.
What I Earned
The template bundle generated maybe $200 in its first month — modest, but encouraging because it was genuinely passive. I had created the product once, and it was selling without ongoing effort on my part. Over time, I created additional products: more template bundles, a guide to starting a freelance business, and eventually a comprehensive course. Digital product income has grown to represent a significant portion of my total online income — somewhere between $2,000 and $4,000 per month, depending on launches and promotions.
What Worked
I created products based on demonstrated demand. I didn't guess what people might want. I looked at the questions readers asked in comments and emails. I looked at which blog posts got the most traffic. I looked at what services my freelance clients requested most often. The template bundle came directly from seeing how many people asked me about proposal writing. Every successful product I've created has been an answer to a question my audience was already asking.
I started small and validated before investing heavily. The template bundle took me maybe a weekend to create. If it had failed, I would have lost very little. Only after it succeeded did I invest more time in larger products. This approach of starting with minimal viable products and scaling up based on real demand saved me from the common mistake of spending months building something nobody wanted.
I built an email list and used it effectively. Email subscribers are far more likely to purchase products than casual blog visitors. I offered a free resource in exchange for email addresses, then nurtured those subscribers with helpful content. When I launched new products, I promoted them to my list first. The list became the engine of my digital product business.
I treated product creation as an ongoing process, not a one-time event. Each product taught me something about what my audience valued, what price points worked, what marketing approaches converted. I applied those lessons to each subsequent product. My products got better and sold better over time because I treated the whole thing as a learning process.
What Didn't Work
I tried creating a product in a new niche where I had no audience and no established credibility. It failed completely. I had assumed that general marketing principles would transfer, but without the trust and audience that came from years of content creation, I couldn't get traction. Building an audience first, then creating products for that audience, is almost always the right sequence.
I underpriced my early products out of insecurity. The template bundle at $27 was probably worth closer to $47 or even $67 based on the value it provided. I was afraid higher prices would kill sales. When I eventually raised prices, sales volume didn't decrease meaningfully, and revenue increased significantly. I had been leaving money on the table because of my own pricing anxiety.
Key Lessons
Digital products taught me the power of leverage. Creating something once and selling it many times is fundamentally different from trading time for money. It taught me to listen to my audience — the best product ideas come from paying attention to what people are already asking for. It taught me that an email list is one of the most valuable business assets you can build. And it taught me that pricing is more about perceived value than about cost — charge what the product is worth to the customer, not what it cost you to create.
Side Hustle #4: Dropshipping — The One That Failed Completely
I need to tell you about this one because I think it's important to share failures alongside successes. Too many online business narratives only show the wins. That creates a distorted picture. So here's one of my most complete failures.
What I Tried
Around 2019, I decided to try dropshipping. For those unfamiliar, dropshipping is an e-commerce model where you set up an online store, list products from suppliers, and when a customer buys, the supplier ships the product directly to them. You never hold inventory. The appeal is obvious: low upfront investment, no warehousing, no shipping logistics.
I set up a Shopify store. I found products through Oberlo. I ran Facebook ads to drive traffic. I had watched countless YouTube videos of people claiming to make thousands of dollars per day with this model. It seemed straightforward. It was not.
What Happened
I spent about $500 on ads over the course of two months. I generated maybe three sales, totaling around $120 in revenue. After ad costs, Shopify fees, and product costs, I lost about $450. More importantly, I lost dozens of hours that I could have spent on freelance work or content creation — things I already knew worked.
Why It Failed
The problems were numerous. The products I chose were generic and unremarkable — the same phone cases and trendy gadgets that thousands of other dropshippers were promoting. I had no unique value proposition. I was competing purely on ad targeting, and I wasn't good enough at it to be profitable.
Shipping times were long — two to four weeks in many cases — because products were coming from overseas suppliers. Customers were unhappy with the wait. I received complaints and refund requests that ate into my already-negative margins. The customer experience was poor, and I felt bad about it. Selling products I had never seen, from suppliers I had never met, with quality I couldn't verify, felt dishonest in a way that made me uncomfortable.
The Facebook ads landscape had already become competitive and expensive by the time I entered it. The golden era of cheap Facebook ads that dropshipping gurus referenced in their videos was largely over. I was late to a party that was already winding down.
Perhaps most fundamentally, I had no genuine interest in e-commerce or physical products. I was doing it because I thought it might be profitable, not because I cared about the products or the customers. That lack of genuine interest showed in everything — the store design, the product descriptions, the ad creative. You can't fake enthusiasm, and customers can tell when you're just going through the motions.
Key Lessons
Dropshipping taught me some expensive but valuable lessons. First, if a business model is being heavily promoted by YouTube gurus as an easy path to wealth, it's probably saturated and far harder than they're making it seem. Second, don't chase business models you're not genuinely interested in. The work required to succeed at anything online is significant. If you don't actually care about the thing you're doing, you won't sustain the effort required. Third, customer experience matters. If you can't deliver a genuinely good experience to the people who buy from you, you're building on a foundation of sand. Fourth, being early to a trend matters enormously. Late entrants to competitive markets face an uphill battle that early entrants didn't have to fight.
Side Hustle #5: YouTube — The One I Never Fully Committed To
This isn't really a success story or a failure story. It's a story about partial commitment and partial results. I'm including it because I think many people can relate to having a side hustle they dabble in without ever fully committing, and wondering what might have happened if they had.
What I Tried
Around 2020, I started a YouTube channel in the personal finance and online business space — similar topics to my blog. I published videos sporadically. Some were well-researched and edited. Some were rushed. I never developed a consistent publishing schedule. I would publish three videos in a week and then nothing for two months.
What Happened
The channel grew slowly. After about a year and maybe thirty videos, I had around 2,000 subscribers. Some videos got a few thousand views. Most got a few hundred. The channel generated a small amount of affiliate and ad revenue — perhaps $100 per month on average.
Why It Never Took Off
The reason is simple and I'm honest about it: I never fully committed. YouTube rewards consistency — both in publishing frequency and in content quality. The algorithm favors channels that upload regularly and keep viewers on the platform. My sporadic approach meant I never built the momentum that YouTube requires. I was treating the channel as an experiment, not as a serious business. The results reflected that level of commitment.
I also found video creation uniquely draining. The filming, editing, thumbnail design, and optimization process took far more time and energy than writing equivalent content for my blog. I didn't enjoy it enough to sustain the effort required to succeed. Some people love making videos. I learned that I'm not one of them.
Key Lessons
YouTube taught me that platform selection should align with your natural strengths and preferences. If creating video content feels like pulling teeth, you're probably better off focusing on written content or audio. The best platform is the one you'll actually use consistently. It also taught me that half-commitment produces half-results. If you're going to pursue a platform, either commit fully or don't bother. Dabbling rarely produces meaningful outcomes.
Side Hustle #6: Coaching and Consulting — High Value, Low Scale
As my blog grew and my freelance reputation developed, people started asking if I offered coaching or consulting. At first, I said no — I didn't feel qualified. Eventually, I realized that I had accumulated knowledge and experience that was genuinely valuable to people who were a few steps behind me on the same path. So I started offering one-on-one consulting.
What I Offered
I offered hourly consulting sessions focused on freelance business strategy, blogging, and online income generation. I charged $150 per hour — a rate I chose because it felt slightly uncomfortable, which I've learned is usually a sign that you're in the right range. Sessions were conducted over video call or sometimes just voice call. I prepared for each session by reviewing the client's situation in advance and thinking through specific recommendations.
What I Earned
Consulting was very profitable on an hourly basis. A few clients per month at $150 per hour generated $600 to $1,200 in additional income for relatively little time investment. The work was also genuinely satisfying — I enjoyed helping people think through their challenges and seeing them implement the advice successfully.
The Limitation
Consulting doesn't scale. My income was directly tied to the number of hours I was willing to spend on calls. There was no way to serve more clients without personally investing more time. I could have raised my rates — and I did, over time — but that only changes the ceiling, not the fundamental constraint. Consulting is a high-value service, but it's not a scalable business model unless you eventually transition to group programs or courses, which I partially did.
Key Lessons
Consulting taught me that direct, personalized help commands premium pricing. People will pay significantly more for one-on-one access to expertise than for generic information. It also taught me that high hourly rates can be a trap — the income is good, but it's still trading time for money. If scalability is your goal, consulting should be a stepping stone, not the destination. Use it to generate income, build relationships, and develop deeper understanding of your audience's needs, then transition that knowledge into scalable products.
Side Hustle #7: Print on Demand — The Middle Ground
After the dropshipping failure, I was wary of e-commerce. But print on demand seemed different. The model is similar — you create designs, list them on products, a third party handles printing and shipping. But the key difference is that the products feature your original designs. There's a creative element. The products are, in some small way, unique to you.
What I Tried
I created designs related to niches I understood — freelance life, writing humor, productivity themes. I listed them on t-shirts, mugs, and notebooks through Redbubble and Merch by Amazon. The designs were simple text-based graphics, which I could create in Canva without advanced design skills. I didn't run ads. I relied entirely on organic discovery within the platforms.
What I Earned
This was never a major income source. At its peak, print on demand generated $100 to $200 per month — a nice supplement, but not something I could have lived on. Individual product margins were small — $3 to $7 per sale after the platform took its cut. Making meaningful income required volume that I never achieved.
What Worked and What Didn't
The low-maintenance nature of print on demand was appealing. Once a design was uploaded and listed, it required no ongoing effort. Sales trickled in passively. But the passive nature of the income was also the limitation — passive for me meant passive for the platforms too. They had no particular incentive to promote my designs over anyone else's. Standing out among millions of products was extremely difficult without driving my own traffic.
My designs were probably too simple. Text-based designs are easy to create, which means they're easy for competitors to replicate or approximate. More complex, illustration-based designs tend to perform better because they're harder to copy and feel more premium. But I lacked the design skills to create them, and I wasn't interested enough to develop those skills.
Key Lessons
Print on demand taught me that low-maintenance income streams are appealing but often limited. True passivity often comes with low earning potential unless you have a unique advantage — distinctive designs, an existing audience, or marketing capabilities that other sellers lack. It also reinforced the lesson that you need to either develop the skills required to compete or choose a different playing field. Half-hearted design effort produced half-hearted results.
What I Would Do Differently If I Were Starting Over Today
After seven years of trial and error across multiple side hustles, I've developed some strong opinions about what I would do if I were starting from zero today. Here's the advice I would give my younger self.
Start with a Service, Build Toward Products
If I were starting over, I would begin with freelance services — writing, virtual assistance, whatever aligned with my existing skills. Services generate cash flow quickly. They build relationships and testimonials. They teach you what the market actually values. But I wouldn't stay in services forever. From day one, I would be thinking about how to productize what I was learning. What templates could I create? What systems could I package? What knowledge could I turn into a course or guide? Services fund the exploration phase. Products build long-term wealth.
Build an Audience from Day One
I waited too long to start building my own platform. I was so focused on client work that I neglected the asset that would eventually become most valuable: my blog and email list. If I were starting over, I would publish content from the very beginning. Not with the expectation of immediate returns, but with the understanding that content compounds. Every article, every email subscriber, every piece of value I put into the world is an asset that appreciates over time.
Focus on One Thing Until It Works
I spread myself too thin in the early years. Freelancing, blogging, YouTube, e-commerce, consulting — I was doing too many things at once, and none of them were getting my full attention. The businesses that succeeded were the ones I focused on most intensely. If I were starting over, I would pick one thing — probably freelance services — and commit to it fully for at least six months before adding anything else. Depth before breadth. Mastery before diversification.
Invest in Skills Before Platforms
Platforms come and go. Algorithms change. But skills are permanent. The time I spent learning to write well, to understand SEO, to communicate with clients, to manage projects — that investment has paid dividends across every side hustle I've attempted. If I were starting over, I would prioritize skill development over platform optimization. Master a valuable skill, and you'll always be able to find a way to monetize it, regardless of what platforms are popular at the moment.
Take Bigger Swings Once You Have a Foundation
I played it too safe for too long. I was so focused on reliable, incremental income that I avoided opportunities with higher risk and higher potential reward. Digital products, for example — I waited years to start creating them when I could have started much earlier. Once you have a stable income foundation from services, give yourself permission to experiment with more leveraged opportunities. The downside is limited. The upside can be transformative.
Final Thoughts: What Seven Years of Side Hustles Have Taught Me
Seven years is a long time to do anything. Looking back across all the projects, all the successes and failures, all the money earned and money lost, a few themes stand out.
The first is that consistency is the closest thing to a superpower in online business. The freelance writing worked because I showed up every day and applied to projects and delivered work. The blog worked because I published articles regularly for years. The products worked because I kept creating and improving. Almost nothing worked immediately. Almost everything that eventually worked required sustained effort over periods that felt uncomfortably long. The people who succeed are not necessarily the most talented. They're the ones who keep going when others quit.
The second is that genuine value creation is the only sustainable business strategy. The dropshipping store failed because I was trying to extract value without creating any. I was a middleman adding nothing to the transaction. The freelance work succeeded because I was genuinely helping clients solve problems. The blog succeeded because I was genuinely helping readers learn things. The products succeeded because they genuinely made people's lives easier. When you focus on creating real value for real people, the money follows. When you focus on the money first, you usually end up with neither money nor satisfaction.
The third is that there is no single right path. The online business world is full of people telling you that their way is the only way. Dropshipping gurus say e-commerce is the answer. SaaS founders say software is the only thing worth building. Content creators say audience-first is the only approach. The truth is that there are many paths to building a sustainable online income. The right path is the one that aligns with your skills, your interests, and your goals. My path — freelance services leading to content leading to products — worked for me. Yours might look completely different. That doesn't mean either of us is wrong.
The fourth and perhaps most important lesson is this: start before you feel ready. Every side hustle I ever started felt uncomfortable at the beginning. I never felt fully qualified. I never felt like I knew enough. The discomfort is not a sign that you're on the wrong track. It's a sign that you're doing something new. Competence comes from action, not from preparation. You learn by doing. You build confidence by shipping work and getting feedback. The people who wait until they feel ready never start. The people who start despite feeling unready are the ones who figure it out.
I hope this honest accounting of my side hustle journey has been useful to you. I've tried to share the full picture — the wins, the losses, the things I'm proud of, and the things I'd do differently. If even one of these lessons saves you from a mistake I made or points you toward a path that works for you, then this article was worth writing.
Now I'd genuinely love to hear from you. What side hustles have you tried? What worked? What didn't? What lessons have you learned that others could benefit from? Drop a comment below. These conversations are always the best part of publishing these articles, and I read and respond to as many as I can.
As always, I'm Ryan Cole. Thanks for reading this far. Here's to the next seven years.
Disclaimer: This article reflects my personal experiences with various side hustles over approximately seven years as of May 2026. All income figures, timelines, and results described are my actual experiences and are not guarantees of what any individual will achieve. Your results will depend on your skills, effort, market conditions, timing, and numerous other factors. Some of the platforms and services mentioned — Upwork, Shopify, Amazon Merch, Gumroad, and others — are third-party services over which I have no control. Their policies, fee structures, and market conditions may have changed since my experiences with them. This article is for informational and educational purposes only. It does not constitute professional business or financial advice. Always conduct your own due diligence before investing time or money into any business venture.
FAQ ⬇️
What was Ryan Cole's most successful side hustle?
Freelance writing was the foundation of everything. Starting on Upwork with no portfolio, Ryan made $200 in his first month and scaled to $4,000 to $5,000 per month within two years by specializing in marketing, business, and personal finance topics. The key factors were specializing rather than remaining a generalist, building long-term client relationships instead of one-off transactions, and continuously raising rates as demand grew.
How long does it take for affiliate marketing to generate meaningful income?
Affiliate marketing through content is a slow burn. Ryan's blog generated only $50 in the first six months. Around month eight, articles began ranking in Google, and by month twelve, income reached $300 to $500 per month. After several years, affiliate income grew to several thousand dollars per month passively. The most important success factor was patience—sticking with it through the initial drought when most people quit.
Why did Ryan's dropshipping side hustle fail?
The dropshipping store lost $450 over two months due to several critical mistakes. The products were generic items that thousands of other sellers offered. Long shipping times from overseas suppliers led to customer complaints and refund requests. Facebook ad costs had already become expensive by the time he entered the market. Most fundamentally, he had no genuine interest in e-commerce or physical products, and that lack of authentic enthusiasm showed in everything from store design to ad creative.
What are digital products and how much can they earn?
Digital products are downloadable assets like templates, guides, and courses that you create once and sell repeatedly. Ryan's first product was a freelance template bundle priced at $27, created over a single weekend. It generated $200 in its first month. Over time, with additional products and an email list, digital product income grew to $2,000 to $4,000 per month. The key insight was creating products based on demonstrated demand from audience questions, not guessing what might sell.
Is YouTube a good side hustle for everyone?
Not necessarily. Ryan's YouTube channel grew to only 2,000 subscribers and $100 per month because he never fully committed to consistent publishing. Video creation was also uniquely draining for him compared to writing. The key lesson is that platform selection should align with your natural strengths and preferences. If creating video content feels exhausting, written content or audio may be better fits. Half-commitment produces half-results; either commit fully or focus your energy elsewhere.
What would Ryan do differently if starting over today?
He would start with freelance services for quick cash flow while building toward scalable products from day one. He would begin building an audience immediately through a blog and email list, understanding that content compounds over time. He would focus on one thing for at least six months before diversifying, invest in permanent skills like writing and SEO before chasing specific platforms, and take bigger swings on leveraged opportunities like digital products once a stable income foundation existed.
What is the most important lesson from seven years of side hustles?
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 before producing meaningful results. The people who succeed are not necessarily the most talented; they're the ones who keep going when others quit. Additionally, genuine value creation is the only sustainable strategy. When you focus on solving real problems for real people, the money follows naturally.
