Building Automated Revenue Streams

It’s easy to assume that landing clients and building your portfolio are the hardest parts of freelancing. However, the numbers paint a different reality. More than half of new freelancers never make it past their first six months, not because of a lack of talent, but because their money management falls apart before the business can grow.​ Here’s what the data actually shows. According to Bonsai’s 2025 freelancer survey, over 60% of independent workers admit to starting without a budget or financial plan in place. Industry-wide reports back this up: most new freelancers do not separate business and personal finances early on, nor do they consistently track cash flow, res…

Towards the end of 2025, we circulated a survey to our members, asking how they as freelancers will be affected by the expiration of the Affordable Care Act enhanced subsidies. Of the over 600 respondents, 58% said that they purchase their healthcare plan through the state marketplace. Seventy-seven percent of freelancers said that without the ACA enhanced subsidies, they would lose coverage, downgrade their plans, or need to cut back on essential spending, like housing, groceries, and transportation. Freelancers are overwhelmingly in support of the Affordable Care Act subsidies, with 91% of respondents saying they want to see the ACA subsidies extended. Whether or not f…

At the end of last year, we put a call out to the Freelancers Union community, asking our members for their favorite accomplishments of 2025. It didn't necessarily have to be the "biggest" or "best" accomplishment — though it certainly could be — but whatever their favorite accomplishment was. Read on below for these achievements shared by our members; hopefully their proudest moments of the year will inspire you to celebrate of your own, and consider what you want to achieve in 2026. "My favorite accomplishment of 2025 was finally turning twenty years of research into something tangible. I've spent my career exploring how health (mental, physical, chronic conditions, lif…

Many freelancers believe inflation is just a distant line in government reports, something that barely dents their day-to-day hustle. If you find yourself thinking, “It’s just a few extra dollars at the store,” you are not alone. Yet behind those small changes is a slow but steady force that can quietly chip away at your financial security, often without immediate warning signs. Here’s a fact that may surprise you. Data from the 2025 Freelancer Rates Report shows that while rates have gone up slightly on average, many freelancers adjust their pricing less than once per year, often falling behind the real cost of living. If you skipped a rate adjustment, you are already ma…

This article is courtesy of our partner Solo Health Collective. Learn more about Solo at: https://freelancersunion.org/solo. For freelancers, independence isn’t just about clients or schedules. It’s about control — over income, time, and long-term stability. Healthcare should work the same way. For years, the conversation has focused on one question: Do you have coverage? But freelancers are asking better questions now: Can I see the doctors I trust?Can I predict what healthcare will actually cost?Do I have any real say in how my plan works?Coverage alone isn’t enough. Freelancers want control. Control Over Doctors: Choice Still MattersTraditional insurance keeps narrowi…

Ah, the holiday season — filled with joy, festive cheer, and maybe just a pinch of family drama! Let’s be real: navigating holiday interactions can sometimes feel like a game of emotional dodgeball. But fear not! Setting boundaries is like having a trusty shield that helps you enjoy the festivities without the stress. What is a boundary? A boundary is a limit you set regarding other people’s words or actions towards you. You can set different boundaries with different people. Good boundaries can: Create positive rapportPromote mutually productive collaborationsEnsure smooth, effective communicationDefine and clearly communicate expectationsProtect your time and energyPr…

There’s never been more freedom for freelance professionals to build businesses around e-commerce sales and remote work. The globalization of client and work opportunities has revolutionized the freelance market, and opened up unprecedented access for business owners to expand their reach across states and even countries. However, this newfound flexibility comes with its own set of challenges—particularly when it comes to tax compliance. Multi-state and multi-country operations can expose your freelance business to complex tax nexus rules, creating audit risks and potential liabilities. Sales tax, in particular, has become a critical area of concern as jurisdictions tigh…

This post was produced in collaboration with Hustle Culture, a free Substack newsletter. Every freelancer brings a unique mix of technical and creative expertise to the table, but most of us share two key skills: self-discipline and time management. Without those, working for yourself can look like long, slow days on the couch or weeks jam-packed with endless tasks. I’ve fallen into both of those modes, but over time I’ve developed a formula that helps me create a manageable and productive weekly schedule. It’s difficult for me to sit and focus on one task for many hours at a time. Instead, I break up my days and weeks into dedicated blocks for each of my weekly obligati…

“I just get really anxious saying no, sometimes,” a client shared with me recently. As a career coach I often hear this sentiment from clients who are struggling to maintain their professional boundaries. Past experiences where saying ‘no’ was met with rebuke or criticism, have made many of us very cautious with this word. Some of us avoid it altogether. For us freelancers, this disconnect from our ‘no’ can be especially destabilizing: we’ll take on projects we know are not a good fit, appease clients who make unreasonable requests, or accept unethical behavior from our associates. As this kind of misalignment grows, our energy drains. And as these burdens lead us into p…

Effective bookkeeping is the basis of any thriving small business. Correct financial records offer crucial insights into a business’s financial health, enabling sustainable growth and the ability to make informed decisions. However, numerous small business owners, managing several responsibilities, usually make common bookkeeping mistakes that could create cash flow problems, financial discrepancies, and tax issues. Knowing these mistakes and understanding how to avoid them is vital for preserving the financial integrity of your small business. #1 Mixing Business and Personal Finance Let’s begin with one of the worst common mistakes of DIY small business accounting: mixi…

From Leo Aquino, founder and financial coach, at Queer & Trans Wealth With the cost of living, health insurance and taxes all rising, saving for retirement as a freelancer can feel impossible. In part, that’s because as a freelancer or small business owner, you’re wholly responsible for creating your own retirement savings. Workers at large companies have some notable advantages in this area: many employers offer 401(k) or 403(b) accounts to full-time workers. This lets employees automatically contribute portions of every paycheck before that money hits their account. These contributions are often tax-free, and some match workers’ contributions up to a certain amou…

It is now official. The U.S. federal government will require nearly all payments to and from federal agencies—including the IRS and Social Security Administration—to be made electronically. Essentially, refunds are being moved to e-refunds for the coming tax season and in the next two years, the IRS is anticipated to phase out accepting payments via check. The IRS provides several electronic payment options for freelance businesses. To prepare for this change in your freelance business, it is important to familiarize yourself with electronic payment methods including IRS Direct Pay, which allows free payments from your bank account, and the Electronic Federal Tax Payment …

The door for Open Enrollment will begin in most states on November 1. If you’re choosing your healthcare through the government’s marketplace, November through January is your opportunity to enroll in one of these healthcare plans. Exact deadlines vary state by state, so be sure to double check the pertinent dates for your location. While we don’t yet know what the outcome will be of the fight to extend the Affordable Care Act tax subsidies, we do know it’s important to be educated and informed of your options, including what health plans are available via our partners. Take this quiz to determine which health plan is right for you and read on below to learn more about ea…

Freelancers across the country face a common challenge: figuring out how to structure their business to minimize taxes without triggering compliance headaches. No matter where you are working, staying on top of the local and state taxes you are responsible for is a critical part of the complex tax trade-offs that can come with forming and operating your freelance business as an entity like an S corporation (S-corp) or limited liability company (LLC). Now, under the new "Big Beautiful Bill" tax provisions, it is more important than ever to understand how you can optimize your tax strategy, taking into account all levels of tax: local, state and federal. Below is a breakdow…

This article is posted with permission from our partner MacPaw. MacPaw makes Mac + iOS apps that have been installed on over 30 million devices worldwide. Freelancers Union members receive 30 days of free unlimited access to CleanMyMacX and Setapp: https://freelancersunion.org/resources/perks/macpaw/ Freelancing often occurs in the digital realm, where safeguarding personal information is essential. National Data Privacy Week, celebrated from January 27 – 31, serves as a timely reminder to take control of our data. Online activities leave a significant digital footprint, so understanding how to manage and secure this data is more important than ever. MacPaw is dedicated t…

This article is posted with permission from our partner MacPaw. MacPaw makes Mac + iOS apps that have been installed on over 30 million devices worldwide. Freelancers Union members receive 30 days of free unlimited access to CleanMyMacX and Setapp: https://freelancersunion.org/resources/perks/macpaw/ There are so many financial obligations to cover as a freelancer, right? You’ve got to handle living expenses, pay for key equipment, and save your dollars all at once. Your goal might be financial freedom, which is all about living comfortably and not being constrained by your financial obligations. But what’s the easiest way to do this? Budgeting apps are ideal. They’re a c…

This article is posted with permission from our partner MacPaw. MacPaw makes Mac + iOS apps that have been installed on over 30 million devices worldwide. Freelancers Union members receive 30 days of free unlimited access to CleanMyMacX and Setapp: https://freelancersunion.org/resources/perks/macpaw/ As a freelancer, your online security isn’t just personal—it’s your livelihood. But with cyber threats evolving daily, staying secure online isn’t just about protecting your data; it’s about safeguarding your career, reputation, and income. Unlike employees in traditional workplaces with dedicated IT teams, freelancers are their first and last line of defense. Cybercriminals …

This article is posted with permission from our partner MacPaw. MacPaw makes Mac + iOS apps that have been installed on over 30 million devices worldwide. Freelancers Union members receive 30 days of free unlimited access to CleanMyMacX and Setapp: https://freelancersunion.org/resources/perks/macpaw/ If you’ve ever bought something from Best Buy, you’re probably familiar with Geek Squad. For those who pick up their freelance gadgets elsewhere, Geek Squad is Best Buy’s trusted tech support service. It’s well-known and reliable, which makes it a prime target for scammers. Some Geek Squad scams trick people into visiting fake websites where they’ll unknowingly enter sensitiv…

Tax season is officially here! Understanding the available tax deductions can help you keep more of your hard-earned income. Be aware, however, that you must claim all of the freelance taxable income you have received and substantiate all of your deductions with proper receipts (not just credit card statements). There are a few new key updates for freelance tax deductions in 2024, including: Form 1099-K Threshold: The threshold for receiving Form 1099-K has increased to $5,000 in gross proceeds. This form reports payments received through online platforms like PayPal, Stripe, and Venmo. It's essential for tracking income from online platforms. Even if you don't receive Fo…

This article is posted with permission from our partner MacPaw. MacPaw makes Mac + iOS apps that have been installed on over 30 million devices worldwide. Freelancers Union members receive 30 days of free unlimited access to CleanMyMacX and Setapp: https://freelancersunion.org/resources/perks/macpaw/ As a freelancer, you’ll need to constantly improve your project management skills to manage your projects smoothly. This constant improvement is important because it can result in effortless transitions between projects and a better output. But there’s another way to handle project management with ease, no matter how many projects you need to take on. With project management…

Studies show that 58% of freelancers find it challenging to manage their time. I have personally experienced this challenge as a freelance writer. I sometimes struggle to maintain productivity and deliver high-quality work while meeting deadlines. My mind tends to become more scattered when I juggle multiple writing tasks or clients. However, I have been in the business for a long time. So, I have learned the art of balancing my clients or tasks quite well. And today, I would like to share some tips on what works for me. Keep a To-Do ListI use a to-do list notebook to write down my tasks for the month because I prefer the manual option. I find it much easier to keep tra…