Building Automated Revenue Streams

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…

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…

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…

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…

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…

Artists are freelancers — among the most underpaid and structurally unsupported. What happens in the arts is a mirror of what happens across the entire freelance economy. Why Art Matters Without art, we lose what makes us human. Art generates meaning, but what is less acknowledged is that meaning is the foundation of what we choose to invest in. Without meaning, any possibility of sustainable profit collapses. Growth Requires Resources Making art demands growth. Growth requires resources. Ask a corporate worker to leave a stable 9–5 to start their own business and see how destabilizing that transition can be. Ask an author what it takes to write a book. Art requires this…

The U.S. Department of Education (DOE) recently announced a delay in resuming wage garnishment for borrowers with defaulted federal student loans. This offers temporary breathing room if you are a freelancer with such a loan. The following summarizes this new development and how freelancers can use this delay student loan garnishment to get ahead of potential financial strain and avoid the negative implications of garnishment. As you may be aware, when garnishment hits your radar it has strong potential to disrupt cash flow, jeopardize your tax planning and create other financial challenges. What’s Behind the DelayThe Department of Education has been working to transitio…