Building Automated Revenue Streams

After years representing creatives, consultants, producers, designers, strategists, photographers, developers, agencies, and the companies hiring them, I can tell you something with confidence: most freelance disputes are not caused by “bad people.” They are caused by vagueness. Vague scope. Vague expectations. Vague timelines. Vague approval processes. Vague communication. Vague boundaries. And vague almost always becomes expensive. Freelancers understandably focus first and foremost on the craft itself — the creative work, the technical execution, the strategy, the design, the production. But the business infrastructure surrounding the work is often treated as secondary…

Now that tax season for the 2025 tax year has wrapped up, it is time to plan ahead and get your 2026 tax strategy in order, especially if you earn tips or overtime income that qualifies you for a deduction based on the latest IRS guidance released in April 2026. Which types of freelance work qualify for the overtime and tip deductions? Below is a detailed breakdown of the rules on tip and overtime income and to whom they apply. Remember, your local and state taxing authorities may not conform with the internal revenue code, so it is prudent to check with a qualified tax professional to see how these deductions interact with your full tax picture. Freelancers should pay sp…

Ten years ago, the New York City Council passed the Freelance Isn’t Free Act, guaranteeing freelancers the right to a contract, full payment in 30 days, and protection against retaliation. Since then, the law has been passed in the cities of Los Angeles, Columbus, Minneapolis, Seattle, and statewide in New York, California, and Illinois. Yet there are still scores of freelancers who aren’t paid on time, threatening their livelihoods and making independent work too precarious for many to enter into. 75% of freelancers, roughly 150,000 people each year, experience late pay in New York City alone. That’s why New York City Council Member Chi Ossé recently introduced a bill to…

You did a scope of work, you may have shared and signed a contract, agreed to terms, you did all of the work for the client, finally you sent your invoice when it was all wrapped up, and then… Nothing. No response from the client. No payment. The client no longer responds to your calls, emails, or texts. You have a creeping realization. You’ve been stiffed, and it feels like now there’s nothing you can do about it. Every day across the country freelancers go without payment for their owed invoices. Clients act with impunity. Whether clients are unaware of what they’re doing, don’t care, or somehow believe they are acting appropriately – the consequences of not paying t…

You know what they say (or, ok, what I say): If you’re in business long enough, you’re going to hit some bumpy times. It’s part of the entrepreneurial/human experience. If you’re feeling we might be in the midst of one of those bumpy times, you’re not alone. Between economic uncertainty that leads to longer sales cycles, a challenging political landscape, AI, or simply aging as a creative, it seems there are no shortage of things to keep us up at night. Yet, experience tells me that if you can stay calm, get your mind right, and keep moving your feet (even if it feels like a shuffle rather than a sprint), you will make it through to the next, inevitable, upswing. Here a…

May 1 marks May Day, also known as International Workers Day, a chance to celebrate and recognize the contributions of workers and the labor movement. Freelance is a vital part of the workforce, yet often goes underpaid and undervalued. Yet there’s power in numbers. And there are lots of us, all across the country. In advance of May Day — and Freelance Isn’t Free month — these are the top ten states where Freelancers Union members are living, working, and organizing. View the full article

This post originally ran on Sarah Duran's blog, Fruition Initiatives. Scarcity slips in through the cracks of a slow month, whispers during client negotiations, and sits heavy in your chest when you check your bank balance. For freelancers, scarcity thinking feels both rational and suffocating; a voice that claims to protect you while slowly eroding your potential. Under scarcity's influence, every decision becomes a survival calculation. You say yes to projects that drain your soul because “money is money.” You undercharge because something is better than nothing. You hoard opportunities, clients, and even knowledge, afraid that sharing might somehow diminish your slice…

Are you a freelancer yearning to break free from the expectations of others and truly embrace who you are? The freelance journey is an open field for creativity, self-direction, and the chance to shape your professional identity. Or it's supposed to be — but sometimes it can feel like you need to fit a certain mold to succeed. We freelancers often feel pressured to fit into boxes—whether it’s matching a certain style, following industry trends, or projecting the persona we think clients expect. Maybe you’ve seen bold personalities like me, Hardy Brooklyn, and wondered if you need to be loud or extreme to succeed. The truth is, you don’t need to be flamboyant to attract…

Most freelancers don't have a time management problem. They have a time allocation problem. You're booked solid, but your bank account doesn't reflect it. You're working constantly, but the numbers don't add up. You wake up looking at your calendar and think, "How did I get here?" You're not bad at managing time; the problem is what you're spending those hours on. You're replying to Slack messages that don't move projects forward. You're formatting client deliverables for three hours when the actual strategy work took one. You're on your fifth "quick call" of the day that wasn't on the original scope. You're spending Tuesday afternoon learning a new project management too…

The deadline for filing your personal tax return as a freelancer (including your Schedule C if you are reporting your income as an LLC on your Form 1040) is just around the corner on April 15, 2026. As you may be aware, being a freelancer means that you face a unique tax landscape. Unlike traditional employees, you may juggle multiple income streams, diverse tax obligations and a wide range of deductible expenses. This complexity is part of the reason why your tax return may contain moving parts that put you at higher risk than the average tax filer of triggering the red flags that can lead to an IRS audit. To be clear, a tax audit notice is not an accusation of wrongdoi…

At SXSW, the future of music and culture is always on display. From packed showcases to surprise sets and branded activations, the festival offers a glimpse of what’s next. But behind every viral moment and seamless event is a workforce SXSW rarely acknowledges: freelancers. They are the sound engineers running live sets, the videographers capturing performances that travel the world, the stage managers keeping showcases on schedule, the photographers, producers, and crew who turn ideas into experiences. SXSW depends on them. I saw this up close at a Latino Victory Fund event during the festival, where filmmaker Robert Rodriguez took the stage to celebrate Los Lobos — an …

As businesses grow, financial decisions become more complex. Cash flow planning, forecasting, hiring, pricing, and long-term strategy all start to matter more, yet many small and mid-sized businesses are not ready to hire a full-time Chief Financial Officer (CFO). That’s where fractional CFO services come in. A fractional CFO can give businesses access to high-level financial expertise without the cost or commitment of a full-time executive. For many companies, it’s the missing link between basic bookkeeping and true financial leadership. What Is a Fractional CFO?A fractional CFO is a senior financial professional who works with a business on a part-time or contract basis…

As an independent worker, you shouldn't have to choose between flexibility and security. Freelancers Union is designing a new portable benefits program, and we need your input to get it right. We know that in the months following the expiration of the Affordable Care Act subsidies, access to healthcare has narrowed dramatically, with basic plans out of reach for many freelancers. The demand for flexible healthcare will only continue to grow, particularly as more and more workers across the country go independent. New portable benefits proposals seek to remediate this, clearing barriers for clients to disperse money into an independent worker’s account to use for healthc…

For many business owners, bookkeeping is one of those things you know you need, but may not fully understand until something goes wrong. Late invoices, confusing bank balances, missed deductions, or surprise tax bills often trace back to one issue: poor bookkeeping. Whether you’re launching a new company or running an established business that’s never had consistent financial tracking, understanding the basics of bookkeeping is essential. What Is Business Bookkeeping? At its core, bookkeeping is the process of recording and organizing your business’s financial transactions. Every dollar coming in and going out of your business needs to be tracked properly. This includes:…

Deductions are a key part of the tax preparation process for freelancers. It’s important than freelancers consider all of the potential deductions available to them, as to ensure they don’t inadvertently pay more in taxes than needed. To that end, we’ve put together some career-specific tax deductions, to help you brainstorm as you look to capture all possible expenses for your records. Keep in mind that the lists below are not necessarily meant to be exhaustive, and that many of the deductions can apply to multiple professions. WriterWebsite hosting fees Writing competition fees Lit journal submission fees Business cards Printing ActorHeadshots Printing headshots Ticke…

I was speaking to a new client yesterday and she shared that her overwhelming wish for her business this year was to approach it with more intention. Can you relate? I know I can! Being a creative freelancer or business owner often feels like reacting to things in the moment and doing the best you can. It reminds me of a “fun” game my kids played for a while. It involved them tossing something to me unexpectedly (like an egg!) and triumphantly shouting “too slow” when I didn't react and catch it in time. Basically, 2025 was like an eight-year-old boy tossing an egg and expecting you to catch it! Reactivity is an easy habit to fall into and an especially hard one to bre…

This post is brought to you by our partners at TaxAct. It initially appeared on their blog. There are many similarities between being self-employed and being a small business owner. Both allow you to be your own boss, for one thing! But in the eyes of the IRS, your formal business classification can mean very different things when it comes to filing your taxes and reporting your business income. Here’s how to determine which category you fall under as an entrepreneur and how it will impact your taxes. Self-employed vs small business owner: Understanding the differenceThe simplest way to differentiate between being self-employed and being a small business owner is to look …

Sales tax: What is it and do freelancers have to pay it? Sales tax is a state-level tax imposed on the sale of goods and, in many states, certain services. Unlike income tax, which you pay out of your own earnings, sales tax is something you collect from your customer and then pass along to the state. In other words, you’re acting as a temporary steward of the state’s money, not paying a tax out of your own pocket. However, not every freelancer is required to collect sales tax. Whether you need to collect sales tax depends on what you sell, where you sell it, and whether your state taxes the type of service or product you offer. Sales tax rules vary dramatically from stat…

Did you know that you have free access to the Freelancers Union Legal Clinic? If this is the first you’re hearing about our Legal Clinic, we are excited to share some details with you! The clinic provides free legal support to all independent workers across the country. If you’re a freelancer, that means you. After you submit a complaint form on our website, our legal team will reach out directly to you and provide direct, specialized guidance based on your legal questions and concerns. Even if you have already sought every option for recourse without legal assistance (i.e. direct appeal to the client, demand letters, attempted mediation), the clinic can provide advice …

I’m an artist, so I can say this: Us artists, we can be super weird sometimes. And when we’re around gallerists, we get even weirder. When I was Fine Art Chairperson of ASMP NY, I produced our annual Portfolio Review. My job was to find gallery owners to volunteer their time reviewing photographers’ portfolios. One afternoon I was sitting at a downtown gallery, chatting with the owner for what could not have been more than twenty minutes. In that time, seven different artists barged in trying to show her their work—one even pulled a painting out from under his arm. She replied as kindly as possible: “Sir, this is a photography gallery.” His answer: “Okay, I’ll email you.”…

Freelancers Union is pleased to introduce Elle Toussi as Interim Executive Director. Elle first joined Freelancers Union as a member, helping to organize local LA Spark events that fostered community, collaboration, and connection among independent workers. Her commitment to strengthening the freelancer community led her to serve as a Member Representative on the Board of Directors, after which she was elected as a permanent Board Member and, two years ago, chosen by her peers to serve as Chair of the Board. With more than 15 years of experience in journalism and production, Elle has built her career around storytelling and advocacy for creative and independent professio…

Every year, freelancers unintentionally hand the IRS more money than they need to simply because they overlook deductions they’re fully entitled to claim. This breakdown of the 14 key business deductions to be aware of is designed to help you avoid revenue-boosting blind spots on your freelance business tax return before you file. It’s easy to miss expenses that qualify as business deductions because the tax code is complex and constantly shifting. This is why it is important to be aware of changes that may affect your freelance return and work with a tax professional who can help you identify additional opportunities to reduce your taxable income and maximize any refund…

I remember it clearly: my first freelance gig, back in 2005. On the way there, I’d see Freelancers Union posters in the subway, and it felt like a lowkey way of seeing my future home — that’s exactly what I’m joining, once I get started on my career. I’d look around the train and wonder how many other passengers were also freelancers, building their lives quietly in parallel. That day’s work was low wage street intercept — stopping people, showing them big studio movie trailers, and asking how likely they were to watch the film. It wasn’t the foot in the door I imagined for filmmaking, but like most freelancing, it built real skills: how to talk to strangers, how to trans…