You're here because your 9-to-5 feels like a cage. You know you can do more. That itch you feel? It's the founder’s itch, and I know it well. You have the drive, but the path from your desk to your own business seems foggy. Good news: you don’t have to leap without a net. The best side business to start is one you can build right now, in the evenings and on weekends.
Think of this as your blueprint, not just another list. We're skipping the "follow your passion" fluff. Instead, I'm giving you a real breakdown of 12 business models, from e-commerce brands to tiny software products. For each one, I’ll tell you:
- Startup Costs: What you’ll actually spend.
- Time Commitment: The honest weekly hour count.
- Revenue Potential: A realistic look at your first-year earnings.
- Action Plans: Your exact steps for the first 30 and 90 days.
This isn’t about dreaming; it's about building. We'll explore real paths for hardworking people like you who want to create something that matters. Let's find the business that won’t just add to your income but will make you feel alive again. It’s time to stop wondering "what if" and start building.
1. E-commerce Brand (Shopify/Print-on-Demand)
Launching an e-commerce brand is one of the easiest and most scalable ways to start a side business. You create a brand and sell physical products online, usually on a platform like Shopify. You don’t need a warehouse full of stuff to start. Models like print-on-demand (for shirts, mugs, posters) let you sell products without ever touching them yourself.
This works because you can start small, test ideas cheaply, and talk directly to your customers. Think of it like a band starting in a garage. They play for a small, passionate crowd first. You do the same. Maybe your brand becomes the go-to for sustainable pet toys or witty t-shirts for Chicago coders. The key is to find your people and serve them well.
Actionable Tips for Success
- Niche Down: Don't sell "coffee." Sell "organic, single-origin coffee for cold brew lovers." Being specific makes marketing way easier.
- Build an Email List Immediately: Your email list is yours forever. Offer a small discount for a signup on day one.
- Master Organic Social: Use TikTok and Instagram Reels to tell your story. Show your products. Be real. Do this before you spend a dime on ads.
- Focus on the Post-Purchase Experience: A handwritten thank-you note can turn a one-time buyer into a fan for life.
For a deeper dive, my guide on how to start an e-commerce business gives you a step-by-step roadmap. This is a great side business to start if you have a creative spark and want to build a brand people love.
2. Content Creator/Personal Brand (YouTube, TikTok, Newsletter)
Being a content creator means you build an audience around your expertise or personality. Instead of selling a product, you are the product. You build a community on YouTube, TikTok, or a newsletter by sharing valuable stuff. You make money later through sponsorships, affiliate links, or by launching another business to your audience.
This is a powerful side business because your effort compounds over time with almost no startup cost. It's like planting a tree. Your first few posts or videos might feel like they do nothing. But over time, they grow into a huge asset. You could be the go-to YouTube channel for Midwest gardeners or the must-read newsletter for Chicago's tech scene. Your unique view is the whole business.
Actionable Tips for Success
- Pick Your Platform: Don't try to be everywhere. If you write well, start a newsletter. If you're good on camera, do YouTube or TikTok. Play to your strengths.
- Document, Don't Create: Don't pretend to be a polished expert. Just document your journey. Share what you learn, your mistakes, and your wins. It’s authentic and builds a strong community.
- Engage with Your First 100: Treat your first 100 followers like gold. Reply to every comment. These people will become your biggest fans.
- Repurpose Everything: One long YouTube video can become 10 TikTok clips, five Instagram posts, and a newsletter. Work smart, not hard.
If you want to build a real audience, this is the best side business to start. It’s a marathon, not a sprint, but the payoff is huge.
3. Freelance Services (Design, Writing, Development, Marketing)
If you have a skill people will pay for, freelancing is the fastest way to make side money. You offer your expertise in things like design, writing, or marketing directly to clients. You can start on sites like Upwork, but your real goal is to build direct relationships.
This model works because you invest your time, not your money. You’re just selling the skills you already have. It’s like being a talented chef who starts by cooking for private parties before opening a restaurant. Your first few projects are your "tasting menu"—they prove what you can do and help you land bigger clients. The key is to stop selling hours and start selling results.
Actionable Tips for Success
- Specialize Ruthlessly: Don't be a generic "writer." Be a "B2B SaaS copywriter for email onboarding sequences." This focus gets you better clients and lets you charge more.
- Build Case Studies, Not Just a Portfolio: A portfolio shows what you did. A case study shows the value you created, like "I increased their lead conversions by 35%."
- Create Productized Services: Offer a fixed-price package, like a "$2,500 Website SEO Audit." This makes your services easy to buy and avoids endless back-and-forth.
- Focus on Building Direct Relationships: Use platforms to get started, but aim to move clients off them. This builds long-term partnerships and avoids fees.
For a deeper look, my guide on how to quit your job for your business shows you how to plan the leap. Freelancing is the best side business to start if you want to use your skills for fast cash and build a foundation for something bigger.
4. Digital Product/Course Creation
If you're an expert at something, you can package that knowledge into a digital product and sell it forever. Think online courses, e-books, or design templates. This is the ultimate "create once, sell forever" model. Platforms like Gumroad or Podia make it simple to upload your product and start selling.
This is like writing a hit song. You do the hard work of writing and recording it once, and then it can earn you money for years while you sleep, work, or vacation. Your product could be a course on "Excel for Chicago Real Estate Analysts" or Lightroom presets for Midwest wedding photographers. You’re just solving a painful problem for a specific group of people.
Actionable Tips for Success
- Solve a Niche Problem: Don't create a course on "marketing." Create one on "LinkedIn Content Strategy for B2B Tech Sales Reps." Specificity sells.
- Validate Before You Build: Pre-sell your course to see if anyone cares. Don't spend months building something nobody wants.
- Start with a 'Tripwire' Product: Create a low-cost, high-value product like a checklist. This builds trust and makes it easier to sell your big course later.
- Leverage Testimonials: Social proof is everything. Show off success stories from your first few customers to build credibility.
If you have valuable skills and want a scalable, low-overhead business, creating a digital product is one of the best side business ideas to start. You build a real asset that generates passive income.
5. Niche Affiliate Marketing (Content + Recommendations)
Instead of making your own product, you can become the most trusted guide in a specific niche. This is affiliate marketing. You create helpful content (blog posts, YouTube videos) that solves a problem, and you earn a commission when your audience buys products you genuinely recommend. You're not a salesperson; you're a trusted advisor.
This works because you focus on building trust, not managing inventory. Think of it like being the one friend everyone asks for movie recommendations. You've seen everything, you know their taste, and you give honest reviews. Your credibility is your most valuable asset. A Chicago blogger could become the expert on "the best running gear for the lakefront trail in winter" and earn income from those recommendations.
Actionable Tips for Success
- Solve Problems, Don't Push Products: Your content should answer specific questions like "What's the best podcasting mic under $100?" instead of just listing features.
- Be Radically Transparent: Always tell people you're using affiliate links. Trust disappears the second your audience feels tricked.
- Test Everything You Recommend: The best recommendations come from your own experience. People can spot generic advice from a mile away.
- Create Comparison Content: "Best Of" lists and "X vs. Y" articles work incredibly well because they help people make a final decision.
If you love teaching and helping people make smart choices, this is an excellent side business to start. It rewards your expertise and the trust you build.
6. Local Service Business (Coaching, Consulting, Tutoring)
You can turn your expertise into a powerful side business by selling it as a service. This means offering one-on-one coaching, consulting, or tutoring. You can work with local Chicago clients or serve people anywhere online. Your brain is the product. No inventory needed.
This model is a rocket ship powered by your reputation. You start by solving problems for a few people, and their success becomes your marketing. Think of it like a personal trainer. They help one client get amazing results, and suddenly, everyone wants to train with them. You could be a career coach for tech professionals or a GMAT tutor for MBA hopefuls. Your value is tied to the results you deliver, making it one of the most fulfilling side businesses you can start.
Actionable Tips for Success
- Specialize Intensely: Don't be a generic "life coach." Be a "productivity coach for first-time founders juggling a day job." This specificity makes you a magnet for the right clients.
- Document Every Win: Your first clients are your best marketing. Track their progress and turn their success into powerful case studies.
- Price for Commitment: Charge premium rates. This attracts serious clients who will do the work and get results.
- Scale to a Group Model: Once you're fully booked one-on-one, launch a group program. You can help more people and increase your income without working more hours.
If you’re ready to turn what you know into a high-impact business, my guide on how to build a personal brand is the perfect place to start.
7. Software as a Service (SaaS) Product
Building a Software as a Service (SaaS) product is one of the most scalable side businesses you can start. You create a software solution for a specific problem and sell access through a recurring subscription. Think of it less like building a skyscraper and more like designing a single, perfect key that unlocks a big frustration for a small group of people.
You don't have to be a coding genius. Many successful SaaS companies started because the founder just wanted to solve their own problem. The real power here is recurring revenue. It’s like getting paid rent every month instead of selling a house once. This creates predictable income that grows over time, making it a powerful engine for building real wealth.
Actionable Tips for Success
- Solve a Micro-Problem: Don't try to build the next Slack. Build a tool that helps freelance designers in Chicago manage client feedback. A narrow focus is your superpower.
- Validate Before You Build: Use no-code tools to create a simple version first. See if people will pay for it before you write a single line of code.
- Talk to 20+ Potential Users: Before you build anything, interview people. Understand their pain points. Ask them what they're using now.
- Charge From Day One: Even a small price proves you're solving a real problem. Your first paying customer is a bigger deal than your first 1,000 free users.
For more on this, check out my guide on how to start a product business. If you love solving problems with tech and want to build a business with massive potential, a SaaS product is the best side business to start.
8. Amazon FBA (Fulfillment by Amazon) Business
An Amazon FBA business is when you find and brand a physical product, then let Amazon handle all the storage, shipping, and customer service. You find a product people want, put your brand on it, and send it to Amazon. When someone buys it, Amazon does the rest. It's like having an e-commerce store where your warehouse is run by one of the biggest companies in the world.
This model lets you tap into Amazon’s millions of customers and Prime shipping without needing your own warehouse. Your job is to be a smart detective. You hunt for an underserved product category, find a way to make it better, and then create the perfect Amazon listing to attract buyers. This is the best side business to start if you love market research and want to use a massive existing platform to your advantage.
Actionable Tips for Success
- Master Market Research: Use tools like Jungle Scout to find products with high demand but low competition. Don't guess; use data.
- Target 40%+ Gross Margins: After all the costs and Amazon fees, you need a healthy margin to afford advertising and actually make a profit.
- Optimize Your Product Listing: Your title, bullet points, and images are your digital storefront. Obsess over every detail to get more sales.
- Learn Amazon PPC: Paid ads on Amazon are how you get your first sales and start ranking. Start with a small daily budget to learn the ropes.
For a detailed walkthrough, Jungle Scout's Million Dollar Case Study is a fantastic free resource that shows you the entire process.
9. Membership Site / Community Platform
Building a membership community means creating a digital space where people pay a recurring fee for exclusive access to content, networking, or you. This isn't just a Facebook group. It's a private club built on platforms like Circle or Mighty Networks where members connect around a common goal.
Think of it like building the ultimate clubhouse for a specific niche. You're not selling a one-time product; you're providing ongoing value and connection. Maybe you create a community for Chicago founders navigating their first year, or one for Midwest woodworkers to share techniques. The goal is to make the community so valuable that the members themselves become the main attraction. This is an incredible side business to start if you love connecting people.
Actionable Tips for Success
- Build the Audience First: Don't build a community and then look for people. Start a newsletter, podcast, or social media account to gather your future members first.
- Start Free, Then Go Paid: Launch a free version to prove your idea. Once you have a core group of active members, introduce a paid tier with premium benefits.
- Facilitate Member-to-Member Connections: Your job is to be the host of the party, not the center of attention. Create events and spaces that encourage members to connect with each other.
- Charge a Price That Attracts Commitment: A low price attracts lurkers. Charge enough to ensure everyone in the room is serious about being there.
For inspiration, look at how local groups like Chicago Brandstarters build trust. A strong community is a long-term asset that can become the core of a thriving business.
10. Content Agency / Productized Content Services
Starting a content agency means you turn your creative skills—writing, video, design—into a scalable business. Instead of trading hours for dollars, you create "productized" services. This means you offer fixed-scope packages with clear prices, like "Four Blog Posts Per Month for SaaS Companies." This gives you predictable revenue and your clients get clear results.
This is one of the best side business to start because you're building a machine, not just a job for yourself. It’s like a restaurant that offers a set menu instead of a custom dish for every guest. It’s more efficient and can serve more people. You can start solo, prove your process with a few clients, and then hire other creatives to do the work while you focus on growing the business.
Actionable Tips for Success
- Productize One Core Offer: Don't sell everything. Start with one specific, high-value package, like a "Monthly SEO Article Pack," and master it.
- Document Your Process: Create a step-by-step checklist for everything. This is your playbook for hiring people and keeping quality high.
- Focus on Retainers: Prioritize clients who need ongoing monthly work. Recurring revenue is the key to stability.
- Build Case Studies: Show the business impact of your work. Don't say "we wrote four blogs." Say "we increased their organic traffic by 40% in three months."
This side business is perfect for you if you're a skilled creator who wants to build a real business with systems, not just another freelance gig.
11. Reselling/Arbitrage (Thrift Flipping, Dropshipping Variation)
Reselling is the art of buying low and selling high. You find undervalued stuff at thrift stores or online and resell it for a profit on platforms like eBay or Facebook Marketplace. This is one of the fastest ways to generate cash with very little upfront money.
Think of yourself as a modern-day treasure hunter. The thrill is finding a vintage Coach bag for $10 and reselling it online for $150. You need to develop an eye for a specific niche, whether it's vintage band tees, first-edition books, or mid-century furniture. This is a fantastic side business to start if you love the hunt and have a knack for spotting hidden value.
Actionable Tips for Success
- Specialize in One Category: Start with what you know. If you love fashion, focus on designer denim. If you're a gamer, hunt for retro video games. Specializing helps you spot gems faster.
- Systematize Your Process: Batch your tasks. Have a sourcing day, a photography day, and a listing day. Efficiency is how you scale.
- Master Photography and Listings: Your photos are everything. Use good light and write detailed, keyword-rich descriptions.
- Track Your Margins Religiously: Use a spreadsheet to track your costs, selling price, fees, and shipping for every item. Profit is the only thing that matters.
If you want to build a brand around your finds, check out my guide on how to build a brand on social media. You can turn this hustle into a recognized name.
12. Micro-Influencer Marketing / Brand Partnerships
Instead of chasing millions of followers, you can build a profitable side business by becoming a trusted voice for a small, engaged audience. This is micro-influencer marketing. You build a community (usually 10k-100k followers) in a niche and partner with brands for sponsored posts and affiliate deals.
Think of it as being the most trusted foodie friend in your group, but on a bigger scale. Brands will pay you a premium to reach your audience because your recommendation carries more weight than a celebrity's. A Chicago creator with 50,000 TikTok followers who reviews local breweries can charge more than a general influencer with 500,000 followers. You’re selling trust, not just eyeballs. This is a powerful side business because your authenticity is your greatest asset.
Actionable Tips for Success
- Pick a Niche with Buyers: Focus on a topic where brands already spend money, like personal finance, B2B software, or beauty.
- Obsess Over Engagement Rate: Your engagement rate (likes, comments, shares) matters more than your follower count. It proves your audience is real.
- Create a Media Kit: Build a simple PDF showcasing your stats and past work. This makes you look professional.
- Pitch Brands Directly: Don't wait for brands to find you. Find companies you love and send them a pitch explaining how you can help them.
For a great example of how you can monetize your influence, check out the tools offered by platforms like Kajabi, which helps creators build entire businesses around their audiences.
Top 12 Side-Business Ideas Comparison
| Business Type | Implementation (🔄) | Resources & Efficiency (⚡) | Expected Outcomes / Impact (📊) | Ideal Use Cases (💡) | Key Advantages / Quality (⭐) |
|---|---|---|---|---|---|
| E-commerce Brand (Shopify / Print-on-Demand) | 🔄🔄 Medium — store, branding, supply chain setup | ⚡ Low–Medium capital (POD low; inventory raises costs); marketing-intensive | 📊 Scalable revenue over months → years; variable margins | Makers, product designers, consumer goods with brand focus | ⭐ Direct brand control; omnichannel sales; passive potential after automation |
| Content Creator / Personal Brand (YouTube, TikTok, Newsletter) | 🔄 Low — content process + consistency required | ⚡ Very low capital, high time commitment; platform-dependent efficiency | 📊 Compound audience growth (6–18+ months to monetize meaningfully) | Storytellers, educators, niche experts building audience-first businesses | ⭐ Defensible personal moat; multiple monetization paths |
| Freelance Services (Design, Writing, Dev, Marketing) | 🔄🔄 Low–Medium — client workflows and delivery systems | ⚡ Low capital; high time/skill; quick to start, harder to scale without team | 📊 Immediate income potential; scalable via price increases or outsourcing | Skilled professionals selling time/skill to clients | ⭐ Fastest path to revenue; direct client feedback builds reputation |
| Digital Product / Course Creation | 🔄🔄🔄 Medium — course creation + funnel setup | ⚡ Low capital, high upfront time; highly efficient after launch | 📊 Passive, high-margin sales possible; weeks→months to first sales | Subject-matter experts wanting scalable digital offerings | ⭐ High margins and authority-building; evergreen revenue when marketed well |
| Niche Affiliate Marketing (Content + Recommendations) | 🔄🔄 Low–Medium — content + SEO/placement systems | ⚡ Low capital; time to build content and audience; efficient once indexed | 📊 Passive commissions from past content; 3–6+ months to traction | Reviewers, niche bloggers, product-focused creators | ⭐ No inventory; low operational overhead; easy to combine with other streams |
| Local Service Business (Coaching, Consulting, Tutoring) | 🔄 Low — direct client delivery and scheduling | ⚡ Low capital, high time; premium hourly or package rates | 📊 Fast revenue (days→weeks); limited scale without group products | Coaches, consultants, tutors serving local/remote clients | ⭐ High per-client pricing; quick validation and referrals |
| SaaS Product | 🔄🔄🔄🔄 High — product dev, infra, compliance | ⚡ High technical & capital requirements; long build cycles | 📊 Predictable, recurring revenue; large upside but months→years to product-market fit | Technical founders solving repeatable workflow problems | ⭐ Most scalable and defensible model; strong exit potential |
| Amazon FBA (Fulfillment by Amazon) Business | 🔄🔄🔄 Medium–High — sourcing, listing, PPC, inventory ops | ⚡ Significant capital ($10K–$50K+); logistics efficiency via Amazon | 📊 Potential high revenue quickly with right product; margins compressed by fees | Private-label sellers targeting Amazon demand channels | ⭐ Amazon traffic + outsourced fulfillment; proven exit markets |
| Membership Site / Community Platform | 🔄🔄 Medium — community design & moderation systems | ⚡ Medium resources (audience or heavy upfront effort); recurring efficiency with retention | 📊 Recurring revenue; high lifetime value if engagement maintained | Creators/organizations with engaged followings | ⭐ Strong retention via network effects; diversified monetization |
| Content Agency / Productized Content Services | 🔄🔄 Medium — processization, hiring, client ops | ⚡ Moderate resources (team/time); scalable with documented systems | 📊 Reliable retainer revenue; scales with hires and productization | Freelancers scaling to agency; niche content providers | ⭐ Predictable delivery; easier to delegate and grow margins |
| Reselling / Arbitrage (Thrift Flipping, Dropshipping Variation) | 🔄🔄 Low–Medium — sourcing, listing, fulfillment routines | ⚡ Very low capital to start (<$100); labor-intensive but fast turnaround | 📊 Immediate cashflow; volume-dependent scaling (weeks→months) | Thrifts, flippers, bargain-sourcing entrepreneurs | ⭐ Lowest barrier to entry; fastest path to cash |
| Micro-Influencer / Brand Partnerships | 🔄🔄 Low–Medium — content + partnership ops | ⚡ Low capital; time to grow to 10K+ followers; efficient per-campaign | 📊 Sponsorship revenue once engaged audience (10K–50K); variable per post | Niche creators aiming for brand deals | ⭐ High engagement value; premium CPMs for niche, loyal audiences |
The Hardest Step Is the First One. Let's Take It Together.
We’ve just walked through twelve different paths. You’ve seen everything from launching a Shopify brand to building a tiny software product. Each idea has its own mix of startup costs, time, and skills.
It's normal to feel both excited and overwhelmed right now. This is where "analysis paralysis" kicks in—that tricky state where you feel productive researching, but you never actually build anything. You might be stuck weighing the pros and cons, trying to find the one perfect, risk-free option.
Here’s the truth: the real best side business to start isn't the one with the highest potential on paper. It’s the one you actually start.
From Idea to Action: Your Next Move
The journey from a 9-to-5 to a side business isn't one giant leap. It’s a series of small steps. Your goal right now is not to build an empire by next year. Your only goal is to create momentum.
Think of it like pushing a stalled car. The first push takes the most effort. You have to overcome inertia. But once the wheels start turning, it gets much easier to keep it moving. That's what you need to do now.
Forget about a 50-page business plan. Pick the one idea from this list that sparked something in you. Not the one your friend thinks is cool. The one you can’t stop thinking about.
Your next action should be so small it’s almost silly:
- Interested in E-commerce? Buy the domain name.
- Thinking of Content Creation? Create the TikTok account.
- Considering Freelancing? Email one person you know and tell them what you're offering.
- Dreaming of a Digital Product? Outline the first three parts of your course.
This isn’t about being perfect; it’s about proving to yourself that you're serious. You're turning a dream into a real project, no matter how small.
You Don't Have to Build Alone
Starting a business is lonely. You're working late nights, wrestling with problems none of your friends understand. The best asset you can have isn't another course. It's a community of people who are in the trenches with you. People who get the struggle of finding your first customer and the thrill of your first sale.
You've done the hard work of exploring the ideas. You've found a path that feels right. Now, the hardest step is the first one. Go do that one small thing today.
If you're a kind, hardworking builder in Chicago looking for a community that values collaboration over competition, then Chicago Brandstarters was built for you. We are a supportive network of founders helping each other grow from idea to seven figures, without the ego and gatekeeping of traditional networking. Join us and surround yourself with people who will help you take that first step and every one after.