Freelancing Side Hustles
94 episodes track people who packaged their skills as freelance services — writing, design, development, consulting, and dozens of niches in between. Freelancing is one of the most accessible side hustles: you set your rate, choose your clients, and work on your schedule.
- Failure Friday: “My virtual assistant was a fan of quiet quitting…”
What happens when your virtual assistant practices quiet quitting and you stop paying attention. Side Hustle School Ep. 3324.
- First $1,000: Comedy Podcast Editor Creates Recurring Income
Freelance comedy podcast editor builds recurring income with strategic pricing and efficient editing systems. Side Hustle School Ep. 3292.
- Google Employee Makes $100,000 Using Fiverr
Google product manager earns $100,000 on Fiverr offering marketing services. His platform hacks revealed. Side Hustle School Ep. 3196.
- Q&A: “How can a freelancer pay herself a stable salary?”
How freelancers can pay themselves a stable salary with a three-bucket system. Turn lumpy income into predictable paychecks. Side Hustle School Ep. 3192.
- Q&A: “How do I stop every freelance project from starting in chaos?”
How to build a repeatable freelance onboarding system that eliminates chaos from Day 1—no assistant needed. Side Hustle School Ep. 3178.
- TBT: Selling Ads for Medical Conferences on Commission
Freelance marketer sells medical conference ad placements on commission. Builds consistent income with sponsorships. Side Hustle School Ep. 3169.
- First $1,000: Musician Creates Loop Packs for Video Editors
Musician sells loop packs to video editors, earning first $1,000 with twelve audio loops and community posts. Side Hustle School Ep. 3124.
- First $1,000: AI Agency Writes Execs’ LinkedIn Posts
AI agency writes executive LinkedIn posts with ChatGPT—how one freelancer built a subscription model. Side Hustle School Ep. 3103.
- Q&A: “How do I manage last-minute requests without burning out?”
Manage last-minute client requests without burning out. Set boundaries and build buffer time into your schedule. Side Hustle School Ep. 3020.
- Q&A: “How do I create passive income from a skill-based service?”
How to turn consulting skills into passive income streams without taking on more clients. Side Hustle School Ep. 2988.
- TBT: Solo Nutrition Practice Offers Corporate Wellness Service
Freelance nutritionist pivots from personal meal plans to corporate wellness programs for stable recurring income. Side Hustle School Ep. 2987.
- First $1,000: Social Media Captions Turn Into Passive Income
Arizona writer earned $1,000 writing social media captions for freelancers. Side Hustle School Ep. 2977.
- TBT: Turning Late-Night Edits into a Niche Agency
Freelance video editor turned fitness creator agency in Toronto with sustainable monthly income. Side Hustle School Ep. 2973.
- TBT: How SEO Support Became a Reliable Monthly Payday
Freelance SEO auditor transforms one-time reports into monthly subscription with ongoing keyword and competitive insights. Side Hustle School Ep. 2966.
- Q&A: “When should I hire a virtual assistant?”
When should you hire a virtual assistant? Learn how to assess readiness, find affordable help, and delegate tasks effectively. Side Hustle School Ep. 2946.
- Failure Friday: The Multi-Platform Freelance Overload
Why expanding to Fiverr backfired for a freelance graphic designer with Upwork success—and what she learned. Side Hustle School Ep. 2918.
- Q&A: “How to use LinkedIn to find freelance clients?”
Use LinkedIn to find freelance clients: profile optimization, strategic connections, and outreach tactics. Side Hustle School Ep. 2878.
- Failure Friday: Overworked Freelancer Gets Stressed Out
Freelance writer takes on too many clients and burns out from poor scheduling. What went wrong and how to avoid it. Side Hustle School Ep. 2876.
- Q&A: “How can I diversify my side income streams?”
How to diversify freelance income streams and protect against client loss. Strategies for building a resilient side hustle. Side Hustle School Ep. 2838.
- First $1K: 3D Modeling Skills Leads to International Business
3D modeling freelancer on Upwork earns first $1K from international clients. Engineer in Bangalore leverages rendering skills. Side Hustle School Ep. 2788.
- TBT: Charging Higher Rates Through Content Strategy Consulting
Freelance writer transforms business with content strategy consulting using AI tools for higher-paying client work. Side Hustle School Ep. 2756.
- Q&A: “My clients aren’t paying my invoices on time…”
How to handle late-paying clients and set payment boundaries as a freelancer. Contract terms and communication strategies. Side Hustle School Ep. 2713.
- First $1,000: Accountant Balances Books for Freelancers
How an accountant earned her first $1,000 offering bookkeeping services to freelancers. Side Hustle School Ep. 2711.
- Q&A: “How can I compete against AI content??”
How can freelance writers compete against AI content? Differentiate through niche positioning and client relationships. Side Hustle School Ep. 2705.
- Failure Friday: The Co-Working Conundrum
Why a freelancer's coworking space gamble backfired and what it reveals about solo work expectations. Side Hustle School Ep. 2680.
- Q&A: “How can virtual assistants find high-paying gigs?”
How virtual assistants can find high-paying clients, position themselves as top-tier, and command premium rates. Side Hustle School Ep. 2678.
- Q&A: “How can I get started as a busy parent?”
How can busy parents start a side hustle? Time management tips for e-commerce and freelance writing. Side Hustle School Ep. 2670.
- TBT: Independent Book Editor Turns Over New Leaf
Independent book editor left publishing to work freelance after having a child. What's changed since we last featured her? Side Hustle School Ep. 2665.
- Q&A: “Should I use the Profit First model?”
Is the Profit First financial model right for your freelance business? Learn how it applies to service-based income. Side Hustle School Ep. 2618.
- TBT: Virtual Assistant for Nomadic Employees
Virtual assistant for digital nomads carves niche between DIY freelancing and full-service platforms. Side Hustle School Ep. 2595.
- TBT: Freelance Grant Writer Expands Offerings
Freelance grant writer expands services into nonprofit sector. How she's growing beyond traditional proposals. Side Hustle School Ep. 2588.
- Q&A: “How to hustle when the world is hard?”
How to stay motivated with your side hustle when global crises feel overwhelming. Strategies to maintain focus and momentum. Side Hustle School Ep. 2579.
- First $1,000: Data Specialist Whips Up Custom Reports
Freelance data visualization expert turns raw data into custom reports. How Vijay in Vancouver earned his first $1,000. Side Hustle School Ep. 2529.
- First $1,000: Video Editor Upgrades from Low-Paying Clients
Video editor in Columbus earns first $1,000 by moving from low-paying Fiverr gigs to higher-value clients. Side Hustle School Ep. 2508.
- Q&A: “Tax advice for new freelancers…”
Tax advice for new freelancers: what side hustlers need to know before tax season. Side Hustle School Ep. 2489.
- First $1,000: Comedy Podcast Editor Creates Recurring Income
Freelance podcast editor specializes in comedy shows, builds recurring income with pricing strategies and efficient systems. Side Hustle School Ep. 2487.
- TBT: Turning LinkedIn Connections into Fashion Collections
Freelance clothing designer earns $6,000/month finding clients on LinkedIn. Where are they now? Side Hustle School Ep. 2448.
- First $1,000: Virtual Assistant Specializes in Email
Virtual assistant specializes in managing startup founder inboxes. How Daniel earned his first $1,000 with email management. Side Hustle School Ep. 2431.
- First $1,000: Freelance Animator Makes Snappy Commercial Videos
Freelance animator specializes in snappy short commercial videos. Financial analyst Tom shares how he earned his first $1,000. Side Hustle School Ep. 2403.
- Q&A: “What should I sell on Fiverr?”
Choosing profitable Fiverr services as a digital nomad with multiple skills. Specialization strategy for freelance success. Side Hustle School Ep. 2388.
- Q&A: “Should I build a website for my freelance coding hustle?”
Website strategy for freelance coders: do you need one, and how to build it effectively. Side Hustle School Ep. 2381.
- TBT: Copyeditor Proofreads Tech Reports & Marriage Proposals
Copyeditor proofreads tech reports and marriage proposals as a side hustle. Her story has evolved since we first featured her. Side Hustle School Ep. 2378.
- First $1,000: “Logo Lady” of Upwork Builds Design Speciality
Logo design speciality on Upwork: HR specialist earns side income focusing only on logos. Niche focus drives efficiency. Side Hustle School Ep. 2375.
- Q&A: “How should I handle freelance contracts?”
How should freelance writers handle client contracts? Learn what terms to include, manage revisions, and protect your rights. Side Hustle School Ep. 2356.
- Q&A: “How to offer content strategy services…?”
Transitioning from freelance copywriting to content strategy. Rebrand and attract clients. Side Hustle School Ep. 2339.
- Q&A: “Structuring a freelance writing program…”
Structuring a freelance writing coaching program in an AI-driven market. How to price and differentiate your services. Side Hustle School Ep. 2313.
- Q&A: “It’s hard to separate work from personal life…”
How to maintain work-life balance as a freelancer and stay motivated working from home. Practical tips to avoid burnout. Side Hustle School Ep. 2293.
- TBT: Corporate Exec Ditches Job for Side Hustle
Corporate auditor leaves office job for freelance consulting side hustle—now running it full-time. Where are they now? Side Hustle School Ep. 2280.
- First $1,000: Health & Wellness Writer Establishes Side Income
Freelance health and wellness writer earns her first $1,000. How Susan Petersen in Indiana built sustainable part-time income. Side Hustle School Ep. 2270.
- TBT: Successful Screenwriter Becomes Screenplay Consultant
Freelance screenplay consultant in Hollywood built a sideline editing scripts during the pandemic. Side Hustle School Ep. 2266.
- First $1,000: Bali Nomad Writes Copy for Local Businesses
How Jack earned his first $1,000 writing copy for Bali businesses. Australian digital nomad's initial paycheck. Side Hustle School Ep. 2249.
- TBT: “I put in long hours and worked hard to deliver quality work…”
Web developer transitions from corporate job to Upwork freelancing, earning nearly as much in two years. Side Hustle School Ep. 2217.
- TBT: “The monthly retainer was a huge confidence-booster…”
Freelance commercial animator on TV shows worldwide shares what's changed since we first featured them. Side Hustle School Ep. 2196.
- Failure Friday: “My virtual assistant was a fan of quiet quitting…”
What went wrong when an advisory service founder hired his first virtual assistant without staying involved. Side Hustle School Ep. 2169.
- Q&A: “Can you still make $10,000 with voiceover work on Fiverr?”
Can you still earn $10,000 doing voiceover work on Fiverr? Yes—here's how to compete in today's marketplace. Side Hustle School Ep. 2166.
- First $1,000: “Six people signed up, including two at the higher rate…”
Web designer earns first $1,000 with standardized website audit service. Six clients signed up, two at premium rate. Side Hustle School Ep. 2165.
- Q&A: “Can you still make $10,000 with voiceover work on Fiverr?”
Can you still earn $10,000 doing voiceover work on Fiverr? Tips for competing in a crowded marketplace. Side Hustle School Ep. 2150.
- Q&A: “Where’s the best place to hire contractors?”
Where to hire virtual assistants and contractors: Upwork vs. Fiverr and beyond. Advice for scaling your second side hustle. Side Hustle School Ep. 2122.
- TBT: Online Yoga for People with Chronic Illnesses
Kayla Kurin builds sustainable income teaching yoga to chronic illness patients. Toronto-based evolution. Side Hustle School Ep. 2091.
- TBT: Filipino Virtual Assistant Hub Serves Millions
Filipino virtual assistant hub reaches 2 million profiles. OnlineJobs.ph connects employers with remote workers. Side Hustle School Ep. 2042.
- First $1,000: “I cold-pitched 10 brands and got my first 2 clients…”
Freelance apparel designer in Seattle lands first $1,000 with cold pitches to menswear brands. Her strategy and early wins. Side Hustle School Ep. 2011.
- Failure Friday: “I acted like an inexperienced order-taker…”
Freelance writer Alli Hill learns why order-taking mentality cost clients—and how communication built her six-figure business. Side Hustle School Ep. 1987.
- Q&A: “’Spaced repetition’ practice with overseas tutors?”
Spaced repetition tutoring with overseas instructors: validate your "Upwork meets Coursera" idea. Earn $500/month. Side Hustle School Ep. 1946.
- First $1,000: “I sold my day job skills to a client after-hours…”
How Joel Runyon earned his first $1,000 freelancing with day job skills after-hours in Austin. Side Hustle School Ep. 1892.
- Freelance Writer Publishes Sixty Articles Each Month
How freelance writer Rebecca Lake earns $300/week writing 60 articles monthly in finance. K-Pop fan turned niche expert. Side Hustle School Ep. 1814.
- Failure Friday: “A bad hire will set you back six months…”
Bad hire setbacks: Davis Nguyen's $90K/month consulting firm lost months to a poorly-vetted virtual assistant. Side Hustle School Ep. 1721.
- The $30,000/Month Women’s Fitness Website
How Tami built a women's fitness blog earning $30,000/month through affiliate reviews. Side Hustle School Ep. 1718.
- Designer Makes Magnificent Menswear
Menswear designer goes freelance after becoming a mom, pitching direct-to-consumer brands for flexibility. Side Hustle School Ep. 1683.
- TBT: Romance Novel Editor Goes All-In
Romance novel editor Jessica Snyder went full-time after 800+ days building her freelance editing business. Side Hustle School Ep. 1657.
- Food Scientist Cooks Up Juicy Profits
Food science PhD earns $4,500/month writing specialized content for clients. Freelance writing with expertise pays off. Side Hustle School Ep. 1632.
- Software Engineer Publishes Technical Writing Guide
Software engineer writes technical writing guide, makes $20,000 in first week on Hacker News. Side Hustle School Ep. 1534.
- To Find Freelance Work, Look at Full-Time Job Listings
Social media strategist earns $10,000/month finding freelance clients through LinkedIn job listings. Side Hustle School Ep. 1527.
- Graphic Designer Documents Remote Earnings
Graphic designer earns income through Upwork freelance work while traveling nomadically. One rating changed everything. Side Hustle School Ep. 1443.
- Dancer Steps Up With Blinged Out Costumes
Freelance dancer transforms costume-making hobby into profitable business with blinged-out designs for performers. Side Hustle School Ep. 1410.
- Lifelong Freelancer Adds Real Estate Photography to Portfolio
Real estate photography side hustle: how a lifelong freelancer built a new business from a home sale. Side Hustle School Ep. 1310.
- Recruiter Moonlights on HR Jobs Marketplace
HR recruiter launches niche jobs marketplace for talent placement. Fills gap in Upwork-dominated freelance space. Side Hustle School Ep. 1291.
- TBT: Man Makes $100,000, Five Dollars at a Time
Man makes $50,000/month naming businesses after selling $5 jokes on Fiverr. From gig work to six figures. Side Hustle School Ep. 1286.
- Choreographer Moonlights as Voiceover Artist
How a choreographer earns six figures as a voice actress on Fiverr using theatre training. Kate Quinn's Fiverr side hustle. Side Hustle School Ep. 1212.
- Music Teacher Quits Job to Earn $100k on Fiverr
Music teacher turns Fiverr freelance writing into $100k income, leaving her job to go all-in on the platform. Side Hustle School Ep. 1172.
- Marketer Connects Filipino Employees with Global Employers
How a marketer built a $500/month business connecting Filipino employees with global employers. Side Hustle School Ep. 945.
- Fashion-Lover Finds the Right Freelancing Look
How a laid-off PR specialist built LWP PR to $1,500/month freelancing for fashion brands. Side Hustle School Ep. 895.
- Best Buy Employee Moonlights as Online Ad Consultant
Digital marketer builds multi-million dollar PPC agency Granular while working Best Buy nights and weekends in Milwaukee. Side Hustle School Ep. 850.
- Freelancer Starts New Hustle to Help Frustrated Clients
Freelancer builds productivity systems business after noticing clients' workflow struggles. The LAB Creative Co. Side Hustle School Ep. 810.
- Go Vote! Freelance Designer Sells Voter Turnout Postcards
Freelance designer sells voter turnout postcards on Etsy, turning a civic passion into a crafted product business. Side Hustle School Ep. 675.
- Google Employee Makes $100,000 Using Fiverr
Google product manager earns $100,000 on Fiverr with specialized marketing services in one year. His secret: avoid commodities. Side Hustle School Ep. 548.
- Australian Designer Starts Publishing Company, Hires Herself
How an Australian designer earns $10k publishing books for creative women. Pre-order campaigns cover printing costs. Side Hustle School Ep. 441.
- Designer Goes Viral with Playful T-Shirts; Earns $445,000
Graphic designer earns $10,000/month with viral print-on-demand t-shirts. Started with design research and Google Ads testing. Side Hustle School Ep. 424.
- Creative Illustrator Creates Creative Podcast for Creatives
Freelance illustrator who designed for Google and Nickelodeon launches a creative podcast earning $70,000 annually. Side Hustle School Ep. 411.
- Freelance Writer Starts School To Help Writers Start Side Hustles
Freelance writer teaches aspiring writers through an online school after answering the same questions repeatedly. Side Hustle School Ep. 403.
- Writing Duo Makes a Vow To Improve Wedding Speeches
Two writers help couples craft personalized wedding vows and speeches. Built through Yelp and word-of-mouth. Side Hustle School Ep. 271.
- Freelance Illustrator Helps Other Artists Sell Their Work
Freelance illustrator earns $25,000+ yearly helping artists sell their work online through coaching and workshops. Side Hustle School Ep. 81.
- Belgian Fine Chocolate Comes to America
How a Louisiana freelancer earns $8,000/year making Belgian-style chocolate at home. Side Hustle School Ep. 50.
- Hospital Database Programmer Outsources His Skills
Hospital employee earns $125/hour teaching Microsoft Access to healthcare professionals. Uses Wyzant tutoring platform. Side Hustle School Ep. 29.
- How to use your voice and a $100 microphone to make $8,000 on Fiverr
Voiceover services on Fiverr: how an IT manager earns $8,000 with a $100 microphone recording for international clients. Side Hustle School Ep. 5.