Building Automated Revenue Streams

The One Big Beautiful Bill has introduced a series of tax reforms designed to simplify the filing process and provide targeted relief to key taxpayer demographics. One of the most notable changes is the significant increase in the standard deduction for seniors—those aged 65 and older. This adjustment has the potential to make a meaningful difference for retirees and older adults living on fixed incomes, offering a straightforward way to reduce taxable income without the need for the itemization of each deduction. Under previous tax law, seniors received a modest increase in their standard deduction compared to younger taxpayers. While helpful, the bump was relatively sma…

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…

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…

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…

Change is in the air at the Freelancers Union. As Executive Director Rafael Espinal moves on to become the Commissioner of the Mayor’s Office of Media and Entertainment, we’re thrilled to officially announce three new hires. (Some of them are newer than others but if you haven’t met them yet, they’re new to you.) Read on below to learn more about each of them, their path to the Freelancers Union, and the work they’ll do now that they’ve arrived. Jonathan KimJonathan joined us back in June as our Hub Operations Assistant and since then has helped ensure our co-working space is well-maintained and all our events run smoothly. Jonathan is a lifelong New Yorker, who has alway…

This post was produced in collaboration with Hustle Culture, a free Substack newsletter by Olivia Rockeman centered around financial and creative guidance for working writers of all genres. Subscribe here. Last summer, when I quit my corporate journalism job to freelance full time, I thought I’d be lucky to earn enough in the first year to cover my rent. I left the corporate world for the autonomy and flexibility I hoped freelancing would provide, but I worried constantly about my financial prospects. The rates for freelance journalism projects are notoriously low, and I’d heard horror stories about writers being out of work for months at a time. In the months before I q…

The tax rules around how freelance income gets reported are changing again, thanks to the newly passed One Big Beautiful Bill (OBBBA). While the intent is to simplify paperwork and modernize outdated thresholds, the rollout has created plenty of confusion—especially around Form 1099-K and its shifting requirements. For many freelancers, 1099s come in fast and furious during tax season. Understanding these new changes is important so that your records are up to date and you are aware of the tax implications on your freelance income. Key 1099 Updates Under OBBBA The following is a breakdown of the key updates and how to stay compliant under the OBBB. Form 1099-MISC and 1…

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…

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…

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.”…

The recently enacted One Big Beautiful Bill (OBBB) has introduced a wave of tax reforms many of which may benefit freelancers. Among the most impactful changes? A new provision that allows freelancers and gig economy workers to deduct car loan interest when their vehicle is used for business purposes. This marks a significant shift in how self-employed individuals can manage and reduce their taxable income, especially those who rely heavily on their vehicles to earn a living. A few important points in regard to the type of vehicle and loan that qualifies: This deduction is available for new car loans originated after December 31, 2024, used to purchase a qualified vehicl…

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…

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 …

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 …

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…

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:…

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…

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…

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…

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…

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…