Building Automated Revenue Streams

Next week, the Freelancers Union will mark a major milestone: We’re turning the big 3-0. Obviously, the world is much different than it was 30 years ago, and by extension, so is the business of freelancing. Freelancers are nimble by nature, and just as the last three decades have forced freelancers to navigate a constantly shifting media, tech, and economic landscape, the Freelancers Union, too, has grown and changed. In the spirit of navigating change and getting back up again, even after you’ve been knocked down, we asked freelancers to share some of the “mistakes” they’ve made over the course of their freelance careers. Our members kindly shared their stories, as seen …

Whether you’re self-employed or employed and work in a tipped profession, there is a new opportunity to lower your federal income tax bill—thanks to the newly enacted 'One Big Beautiful Bill Act (OBBBA).' For the first time, qualifying freelancers can deduct up to $25,000 in tips from their taxable income starting in tax year 2025, but as of right now, this deduction only qualifies until 2028. But before you celebrate, let’s unpack what this means and how to make it work for you. What’s New Under 'OBBBA' The “No Tax on Tips” provision applies to federal income tax only. That means while you can deduct tips from your taxable income, they still count toward your self-employ…

Freelancing gives you creative freedom, but it also means you’re solely responsible for your finances. If you’re a designer, writer, consultant, stylist, or any kind of creative solopreneur, the following strategies will help you keep your money working for you — without the fluff. Build a Real Emergency Fund An emergency fund cushions you against surprise expenses such as medical bills, client payment delays, or sudden equipment replacement. A practical guideline is to save three to six months of living expenses. One effective way to build this fund is to treat your contribution like a monthly bill; set aside a fixed amount each month until you reach the target. Aim for …

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…

If you’re like most freelancers, many of your best clients come from referrals, word of mouth, and your network. But this is a recipe for feast-and-famine months. Your network is finite. If something unexpected happens — like a client has to reduce your hours or end a contract early — you could have a dip in income without a warm pipeline of high-quality leads. If you’ve never done proactive marketing and lead generation before, you’re not alone. Freelancers and consultants often come to me after three, five, even ten successful years in business because their referrals dry up and they realize they never built a proactive marketing strategy. Believe me, I’ve heard it all.…

On July 4, 2025, the One Big Beautiful Bill Act (Public Law 119-21) was enacted, introducing significant new deductions that can benefit freelance and self-employed individuals. Below are some key quick tips based on the most relevant provisions, along with some initial guidance for maximizing potential tax benefits. As always, it is best to consult a tax professional if you have questions and to consider adjusting your tax plan when warranted: Tip 1: Deduction for Qualified Tips May Ease Tax Burden for Gig Workers Effective from 2025 through 2028, taxpayers in occupations recognized by the IRS as regularly receiving tips may deduct up to $25,000 annually in qualified tip…

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…

One of the most challenging parts of freelancing is figuring out what you’re going to do about healthcare. Unlike traditional workplaces, which provide employees with healthcare plans, freelancers typically do not receive insurance plans from their clients. This can often leave freelancers in a precarious position, forcing them to pay high out-of-pocket prices for health insurance plans, relying on a partner’s employer healthcare coverage, or in certain cases, forgoing insurance entirely. New legislation seeks to change this, clearing barriers for clients to disperse money into an independent worker’s account to use for healthcare and other benefits like time off. These a…

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…

If you’re a freelancer earning income through a business entity and living in a high-tax state like New York, understanding the Pass-Through Entity Tax (PTET) and its role in offsetting federal tax limitations could directly impact your bottom line. This is especially true with the recent passage of The President’s One Big Beautiful Bill (OBBB) which provides sweeping tax reform and expanded tax advantages at both the state and federal levels. Now is the time for freelancers to explore the benefits of strategic entity structuring and SALT workarounds. What Is PTET?The PTET is a state-level workaround created in response to the State and Local Tax (SALT) deduction cap impl…

If you are a freelancer who gives to charity, there’s good news: recent legislation has reshaped how charitable contributions are treated under federal tax law. The Charitable Act (S.317) and the One Big Beautiful Bill (OBBB), both passed in 2025, introduce new opportunities for tax deductions—especially for those who do not itemize—and new limits for high-income donors. Here is what you need to know to make the most of your giving strategy starting in 2026. A new deduction for non-itemizers: Under the Charitable Act, taxpayers who take the standard deduction can now claim a charitable deduction for cash donations to qualified charities. This is a significant shift from t…

The other day, I was cleaning out my storage unit and I stumbled upon a pile of cassette tapes. All of them were my very first voice over demo that I produced way back in 1995. As I held one of them in my hand, I realized that this piece of plastic is a relic. It also dawned on me that this year marks my 30th anniversary as a freelance voice actor. Thirty years?! Wow. It feels like both a lifetime and the blink of an eye all at once. I’ve gone from booking studio time by the hour to editing mp3 auditions on my laptop from a hotel room closet. The technology has changed, trends have come and gone, but the core principles of building a lasting freelance voice over career? T…

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 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 …

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…

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…

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…

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…

Not sure what to get the freelancer in your life for the holidays? Do you want to show them you support the independent path they’re on? We’ve created for you the Ultimate 2025 Freelancers Gift Guide, with gifts that will help empower the freelancer you’re shopping for in their work, and help them take a well-earned break when they need it. And as a bonus — all of these gifts are created and sold by freelancers and small businesses themselves! For the New FreelancerMutualism written by Freelancers Union founder, Sara HorowitzBreak Up With Your Job hat, from our friends at Freelancing Females99 Classics headphones by Meze AudioFor the Work-From-Home WarriorMain Character C…

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…