As families prepare for the new school year, many states are once again offering sales tax holidays —limited-time periods when shoppers can purchase certain items without paying state sales tax. While these tax-free events can lead to meaningful savings, the rules vary widely by state. Some holidays last only a weekend, while others span several weeks. Eligible items also differ, with some states exempting only clothing and school supplies while others include computers, emergency preparedness equipment, or energy-efficient appliances. Source: Sales Tax Institute. What Is a Sales Tax Holiday? A sales tax holiday is a designated period during which states temporarily suspend sales tax on specific purchases. Most are timed around the back-to-school shopping season, although some states also hold tax holidays for hurricane preparedness, hunting supplies, or energy-efficient products. Source: Sales Tax Institute. Which States Are Participating? Where Are Back-to-School Sales Tax Holidays Happening? The following states are offering statewide back-to-school sales tax holidays or similar tax relief programs during the 2026 shopping season. Keep in mind that dates, eligible items, and price limits vary by state. Arkansas (Aug. 1–2): Clothing, school supplies, instructional materials, and many electronics. Connecticut (Aug. 16–22): Clothing, footwear, backpacks, and qualifying school supplies under applicable limits. Florida (July 20–Aug. 20): Clothing, school supplies, learning aids, and computers meeting price thresholds. Illinois (Aug. 7–16): Reduced state sales tax rate on qualifying clothing, footwear, and school supplies. Iowa (Aug. 7–8): Clothing and footwear under $100 per item. Maryland (Aug. 9–15): Clothing and footwear priced at $100 or less. Massachusetts (Aug. 8–9): Most retail items priced up to $2,500 qualify, with certain exclusions. Missouri (Aug. 7–9): Clothing, school supplies, computers, software, and calculators within price limits. New Mexico (July 31–Aug. 2): Clothing, school supplies, computers, backpacks, calculators, and related technology. Ohio (Aug. 7–9): Qualifying clothing, school supplies, and instructional materials. Oklahoma (Aug. 7–9): Clothing and footwear under $100 per item. South Carolina (Aug. 7–9): Clothing, school supplies, computers, printers, software, and select household items. Tennessee (July 31–Aug. 2): Clothing, school supplies, and qualifying computers. Texas (Aug. 7–9): Clothing, footwear, backpacks, and most school supplies under $100 per item. Virginia (Aug. 7–9): Clothing, school supplies, emergency preparedness items, and qualifying Energy Star products. West Virginia (July 31–Aug. 3): Clothing, school supplies, laptops, tablets, and qualifying sports equipment. While back-to-school shopping receives the most attention, it's not the only type of sales tax holiday taking place throughout the year. Several states also offer temporary tax exemptions on items such as hurricane and emergency preparedness supplies, Energy Star® appliances, hunting and fishing equipment, firearms and ammunition, severe weather preparedness products, and even certain purchases made by members of the National Guard. These holidays are designed to encourage preparedness, support conservation efforts, or promote specific industries, and the qualifying items and dates vary widely by state. Before making a major purchase, it's worth checking whether your state offers a tax holiday that could help you save. Source: Sales Tax Institute; Federation of Tax Administrators. Read the Fine Print One of the biggest misconceptions about sales tax holidays is that everything is tax-free. In reality, each state establishes its own eligibility rules. Many programs include price limits, exclude luxury goods or accessories, or apply only to certain categories of merchandise. Some states also have different rules for online purchases, layaway transactions, coupons, and shipping charges. Source: Sales Tax Institute; Federation of Tax Administrators. Are the Savings Worth It? For families already planning back-to-school shopping, timing purchases to coincide with a sales tax holiday can reduce costs . With back-to-school expenses continuing to rise, even modest tax savings can make a difference, especially when purchasing clothing, backpacks, school supplies, or computers that qualify under your state's rules. However, shoppers shouldn't buy items simply because they're temporarily tax-free. The greatest benefit comes from purchasing items you were already planning to buy while understanding your state's specific requirements. Sales tax holidays can provide valuable savings, but they aren't one-size-fits-all. Before heading to the store, or placing an online order, check your state's rules to confirm the dates, eligible items, and any purchase limits that apply.  If you own a retail business, remember that sales tax holidays also create additional compliance responsibilities. Your tax professional can help ensure you're applying your state's rules correctly and collecting the appropriate amount of sales tax throughout the year.

If you’re planning a move—or you already split time between two states—you should understand the term domicile. Domicile is one of those legal concepts that can quietly change your tax picture in big ways. It helps decide which state can tax you on all your income, which state’s estate rules apply when you die, how community-property rules treat income with a spouse, and even whether you qualify as a bona fide resident for the foreign earned income exclusion. The good news: domicile is mostly about facts you can document. The better news: with a little planning and good recordkeeping, you can significantly reduce tax risk. This article explains what domicile is, how it differs from other residency tests, the practical evidence courts and tax agencies look for, and a step-by-step checklist to protect your position. What is Domicile? Domicile is your permanent legal home—the single place you intend to live for an indefinite or unlimited period and to which you intend to return when absent. Unlike a mailing address or where you happen to spend most of your days in a given year, domicile is a legal conclusion based on both intent and conduct. A person can only have one domicile at a time, even if they maintain houses in more than one state. Key Point : Physical presence alone doesn’t determine domicile. Moving into a new state for a short time without clear intent to remain can leave your old domicile intact. Conversely, a brief but genuine move with intent to stay can establish a new domicile quickly in some circumstances. How Domicile Differs from Other Residency Tests: States and federal tax rules use several different tests that are easy to confuse: Domicile (Common Law) : Your permanent legal home (intent + conduct). Only one domicile at a time. Statutory Residency/Day-Count Rules : Many states use a day-count (commonly 183 days) or a combination of “permanent place of abode + 183 days” to determine tax residency for the year, regardless of domicile. Federal Tax Residency for Aliens : Tests like the green card test and Substantial Presence Test are separate statutory rules for noncitizens and do not equate to common-law domicile. Because these tests are different, you can be domiciled in State A while also being a statutory resident of State B if you spend enough days there. That creates potential double-filing and taxation unless carefully planned and documented. Why Domicile Matters for Taxpayers : State Income Tax : Most states tax domiciliaries on worldwide income. If you’re domiciled in State X, that state expects a full resident return, even for income earned elsewhere. Part-Year Status : If you change domicile during the year, most states treat you as a part-year resident and apportion income between resident and nonresident periods. The exact date you changed domicile is often heavily contested in state audits. Nonresident Source Taxes : States typically tax nonresidents only on income sourced to the state—wages earned there, rents on in-state real estate, business income, or gains from sale of in-state property. Federal Issues : Domicile can influence whether you qualify as a bona fide resident for the foreign earned income exclusion (FEIE) when you work overseas, because the bona fide residence test looks to intention to make a foreign country your home. The alternative FEIE physical presence test is purely days-based. Estate and Gift Tax : Domicile is important for determining which state’s estate or inheritance taxes apply, if any, and can be a focal point when a decedent moved shortly before death. Community Property and Spouse Issues : The characterization of income as community or separate property often depends on spouses’ domiciles and applicable state law. What Courts and Tax Auditors Look For : Objective, contemporaneous evidence! Because domicile is a question of intent proved by conduct, agencies and courts evaluate the totality of the facts. No single item is dispositive—collect them all and keep dates clear. Useful evidence includes: Home Occupancy : Closing statements, lease, move-in dates, utility start and stop bills, photographs showing you lived in the new home. Family Location : Where your spouse/partner and dependent children reside; school enrollments; pediatrician or other medical records. Official Registrations and IDs : Voter registration and voting records, driver’s license or state ID issuance, vehicle registration. Tax Filings and Addresses : Address used on your federal and state returns, payroll withholding, and 1099s. Employment and Business Ties : Employer transfer letters, principal place of business, business registrations, professional licenses. Financial Ties : primary bank accounts, safe-deposit boxes, mortgage or loan documents. Social and Community Ties : Church membership, club memberships, subscriptions, local volunteering. Actions Severing Old Ties : Sale or long-term rental of prior residence, closure of local bank accounts, cancellation of memberships. Estate Planning Updates : Revising wills, trusts, beneficiary designations and filing them where appropriate. Special Rules and Common Exceptions: Rapid Domicile Establishment : In estate and gift tax contexts, a person may quickly acquire domicile if they move and show no definite present intent to leave. Military and Certain Government Personnel : Special protections often preserve a prior domicile despite moves. The Servicemembers Civil Relief Act (SCRA) protects military members from losing or acquiring domicile solely due to change-of-station orders. Federal laws (MSRRA and VAEIA) let a civilian spouse elect to use the servicemember’s domicile for state tax purposes in many situations. Noncitizens : Don’t confuse statutory tax residency tests for aliens with domicile; they’re analytically separate and have different consequences. Common Audit Issues : Auditors commonly challenge the claimed effective date of a domicile change. Typical red flags include: Inconsistent dates across records (e.g., driver’s license updated after tax filing date). Retention of strong ties to the old state—especially voter registration, vehicle registration, and bank accounts. Failure to occupy the purchased home as your primary residence. Lack of contemporaneous documentation (e.g., collecting evidence only after an audit starts). Practical, Taxpayer-focused Checklist for Changing Domicile: If you intend to change your domicile and want to reduce audit risk, act deliberately and create contemporaneous records. Steps to follow: Create a dated timeline - Document every relevant event: move date, property sale or lease, employment change, family moves, and any major actions with exact dates. Update official records promptly Apply for a driver’s license and state ID in the new state as soon as you establish residency there. Register to vote and actually vote in the new state. Register vehicles where required. Update professional licenses if you are required to be licensed in the new state. Make your new home your primary residence Move personal belongings and occupy the home. Start utility service in your name at the new home. Use photographs, receipts, and service start dates to show occupancy. Change financial and legal ties Move primary bank accounts and close old local accounts when practical. Update beneficiary designations, wills, and trusts to reflect new domicile. Transfer professional licenses, business registrations, and professional memberships if applicable. Shift social and community ties Join local organizations, churches, and clubs; maintain membership records and dates. Enroll children in local schools; keep enrollment and medical records. Sever ties to the old domicile Sell or rent the former residence (long-term leases are stronger evidence than occasional rentals). Cancel local club memberships or transfer them. Close or consolidate local accounts. Update tax and employment records Update your address with your employer’s payroll department and adjust withholding to reflect the new state. File part-year returns when appropriate and be consistent about the claimed date of domicile change. Keep contemporaneous, organized documentation Maintain a one-page chronology and a file of exhibits (tabbed and dated) for each relevant year. Draft a short, signed contemporaneous declaration of intent to make the new state your permanent home and keep it in your file. Practical Tips and Final Thoughts : Consistency Matters: Conflicting dates or addresses in different documents are a red flag. Make sure your driver’s license, voter registration, tax returns, and employer records tell the same story. Be Mindful of Statutorily Based Residency Rules: Even if you change domicile, you can still trigger tax obligations in other states if you spend enough days there. Don’t Ignore Estate and Community-Property Implications: A move late in life, or different domiciles between spouses, can create complex tax and property issues.  When in Doubt, Consult: Domicile disputes are fact-intensive and often litigated. If your circumstances are complicated (e.g., cross-border moves, multi-state income, military service, or imminent estate issues), contact this office for guidance before engaging with an auditor. Bottom Line : Domicile is about where you truly intend to make your home—not just where you sleep a few nights a year. Because it is decided by the totality of your actions and documented intent, proactive planning and thorough, contemporaneous recordkeeping are your best defenses. If you’ve moved or plan to move, follow the checklist above, keep clear records, and coordinate changes to IDs, financial accounts, tax withholding, and estate documents as soon as practical. Those steps will help you minimize surprises and be ready to defend your chosen domicile if a tax agency asks questions. If you are contemplating a move it may be appropriate to consult with this office in advance.

Frequently Asked Questions About Employment Practices Liability Insurance What is employment practices insurance? Employment practices insurance is another way people refer to Employment Practices Liability Insurance, or EPLI. It helps protect a business from certain claims tied to employment decisions and workplace treatment. These claims may involve wrongful termination, discrimination, harassment, retaliation, failure to hire, or failure to promote. Employment practices insurance is not designed for physical injuries or property damage. It is designed for employment-related allegations. Do I need employment practices liability insurance? If your business has employees, former employees, or job applicants, Employment Practices Liability Insurance is worth considering. Small businesses often think they are too small to face an employment claim. But even small teams make hiring, pay, discipline, promotion, and termination decisions. Any of those decisions can lead to a dispute. EPLI may be especially important if your business is hiring quickly, adding managers, handling terminations, expanding into new states, or operating without HR support. What is the difference between E&O and EPLI? Errors and Omissions insurance, often called E&O, is different from Employment Practices Liability Insurance. E&O insurance generally helps protect a business from claims that it made a professional mistake. That may include poor advice, missed deadlines, or failure to deliver services as promised. EPLI focuses on workplace claims. It helps protect against certain allegations from employees, former employees, or job applicants. A simple way to separate them is this: E&O is about the professional work your business does for clients. EPLI is about how your business treats employees and applicants. What is the difference between EBL and EPLI? Employee Benefits Liability, or EBL, is different from Employment Practices Liability Insurance. EBL generally helps protect a business from certain mistakes in employee benefits administration. For example, it may apply if an employee was left off a benefits plan by mistake or given incorrect information about eligibility. EPLI focuses on broader workplace claims. These may include wrongful termination, discrimination, harassment, retaliation, failure to hire, or failure to promote. A simple way to separate them is this: EBL is about benefits administration mistakes. EPLI is about employment-related claims and workplace treatment. Sources [1] Insurance Information Institute, "Employment Practices Liability Insurance." The III explains that EPLI protects businesses against claims that workers' legal rights as employees were violated. It also lists common claim types and notes that policies generally do not cover punitive damages or civil or criminal fines. https://www.iii.org/article/employment-practices-liability-insurance [2] Equal Employment Opportunity Commission, "EEOC Highlights Record-Breaking Results in Agency Reports." The EEOC reported securing $660 million for 17,680 victims of employment discrimination in fiscal year 2025. https://www.eeoc.gov/newsroom/eeoc-highlights-record-breaking-results-agency-reports [3] International Risk Management Institute, "Employment Practices Liability Insurance." IRMI identifies common EPLI claim types, including wrongful termination, discrimination, sexual harassment, and retaliation. It also notes that EPLI policies contain shrinking limits provisions, meaning defense costs reduce the policy's available limits. https://www.irmi.com/term/insurance-definitions/employment-practices-liability-insurance [4] Equal Employment Opportunity Commission, "Best Practices for Employers and Human Resources/EEO Professionals." The EEOC outlines general best practices for preventing workplace discrimination, including training, neutral and objective criteria for employment decisions, and open communication. https://www.eeoc.gov/initiatives/e-race/best-practices-employers-and-human-resourceseeo-professionals [5] Equal Employment Opportunity Commission, "Small Business Resource Center." The EEOC provides free guidance for small business owners on hiring, training, evaluating, disciplining, and terminating employees. https://www.eeoc.gov/employers/small-business [6] National Association of Insurance Commissioners, "Small Business Insurance." NAIC explains that small business insurance needs vary based on business factors such as employees, products, services, and operations. https://content.naic.org/consumer/small-business.htm [7] International Risk Management Institute, "Claims-Made Policy." IRMI explains that under a claims-made policy, coverage applies to claims first made during the policy period, and that EPLI is typically written on this basis. https://www.irmi.com/term/insurance-definitions/claims-made-policy

When to Consider Employment Practices Liability Insurance The best time to consider Employment Practices Liability Insurance is before a claim happens. Many owners wait until there is a problem. By then, a new policy may not help with an issue the business already knew about. A business should review EPLI when it: Hires its first employee Adds managers Grows quickly Terminates employees Creates an employee handbook Expands into another state Handles workplace complaints Has high turnover Operates without formal HR support The National Association of Insurance Commissioners notes that small business insurance needs vary based on the business, including employee count, products, services, and operations. That is a good reminder that insurance should grow with the company. [6] Employment Practices Liability Insurance is not just about today's team. It is also about where the business is headed. If the plan is to hire more people, open another location, or add supervisors, EPLI should be part of the planning conversation. Take the Next Step Before Your Next Hire Hiring is one of the biggest decisions a small business makes. It affects payroll, taxes, cash flow, workplace practices, and insurance all at once. Those pieces work better when they are reviewed together. That is why Steven Brewer & Company CPAs and Gild Insurance Agency work together. Brewer helps business owners understand the real cost of hiring, plan for payroll and taxes, and protect cash flow as the team grows. Gild helps owners understand which coverages belong in the conversation, from Employment Practices Liability Insurance to workers' compensation and general liability. Request a quote with Steven Brewer & Company to talk through the financial side of your next hire. Then take a few minutes for a free business insurance review through Gild Insurance and get a fast online quote. Two conversations. One stronger plan for growing your business.

Why Growth Increases Employment Risk A business with two employees may feel easy to manage. A business with ten employees needs more structure. A business with twenty employees needs even more consistency. Growth creates more decisions. More decisions create more chances for confusion, conflict, or claims. As a business grows, employment practices can lag behind. The company may add people before updating job descriptions. It may promote a team member into management before training them. It may handle performance issues differently from one employee to another. These gaps are common. They do not always mean the owner is careless. They often mean the business is busy. But employment claims often focus on process. For example: Was the rule applied the same way for everyone? Was the employee warned? Was the complaint reviewed? Was the hiring process fair? Was the manager trained? Was the decision documented? A clear process is easier to defend than memory. The Equal Employment Opportunty Commission advises employers to train managers and employees on equal employment opportunity laws, establish neutral and objective criteria for employment decisions, and monitor practices for consistency. It also recommends fostering open communication and early dispute resolution to keep small issues from becoming legal claims. [4] That is why Employment Practices Liability Insurance works best when it is paired with good workplace habits. Insurance helps protect the business financially. Documentation helps explain what happened. How Small Businesses Can Reduce EPLI Risk Employment Practices Liability Insurance is one layer of protection. Strong employment practices are another. Small businesses can reduce risk by making workplace decisions more consistent. This does not require a large HR department. It does require a simple system. Start with these steps: Use written job descriptions. Create a basic employee handbook. Document performance concerns. Use consistent interview questions. Keep hiring notes professional and job-related. Train managers on harassment, discrimination, and retaliation. Respond to employee complaints promptly. Apply workplace policies consistently. Review termination decisions before acting. Keep payroll and worker classification practices current. These steps help create a better workplace. They also help the business if a claim appears later. The EEOC offers a Small Business Resource Center with free guidance on hiring, training, evaluating, disciplining, and terminating employees. The agency notes that small business owners often do not have legal or HR experts on staff, and the resources are designed to help fill that gap. [5] Owners should be especially careful with terminations. A termination may be valid, but it should still be documented. The business should be able to explain why the decision was made and show that similar situations were handled in a similar way.  Good records do not remove all risk. They make the business more prepared.

What EPLI Is Not Employment Practices Liability Insurance is not the same as general liability insurance. General liability usually focuses on third-party bodily injury, property damage, and certain personal injury claims. For example, it may apply if a customer slips and falls at your office. EPLI is different. It focuses on workplace claims. Employment Practices Liability Insurance is also not the same as workers' compensation. Workers' compensation helps cover employees who are injured or become ill because of their work. EPLI helps with certain claims about how employees or applicants were treated. That distinction matters. Many owners assume their business insurance will cover an employee lawsuit. It may not. A claim involving wrongful termination, discrimination, harassment, or retaliation may fall outside general liability or workers' compensation. EPLI is designed to help fill that gap. EPLI also has limits. The Insurance Information Institute notes that EPLI policies may reimburse companies for defense costs, settlements, and judgments. But they generally do not cover punitive damages or civil or criminal fines. [1] Common exclusions may include: Criminal acts Intentional wrongdoing Bodily injury Property damage Workers' compensation claims Certain wage and hour claims Claims known before the policy began Some contract disputes Wage and hour claims deserve extra attention. Some policies exclude them. Others may offer limited defense coverage or an endorsement. The best question is not, "Do we have EPLI?"  The better question is, "What does our Employment Practices Liability Insurance actually cover?"

What Employment Practices Liability Insurance Covers Employment Practices Liability Insurance is built around the employment relationship. It may help cover legal defense costs, settlements, or judgments tied to covered workplace claims. A policy may respond to claims involving: Wrongful termination Discrimination Sexual harassment Retaliation Failure to hire Failure to promote Wrongful discipline Negligent evaluation Employment-related defamation Invasion of privacy The International Risk Management Institute identifies wrongful termination, discrimination, sexual harassment, and retaliation as common EPLI claim types. It also notes that policies may cover other employment-related conduct, such as defamation, invasion of privacy, failure to promote, and negligent evaluation. [3] Here is a simple example. An employee is fired after repeated performance issues. The owner knows the decision was based on the work. But the former employee claims the firing was discriminatory or retaliatory. Even if the business did nothing wrong, it may still need to respond. That could mean attorney fees, agency filings, a demand letter, or a lawsuit. That is one of the most important parts of EPLI. A claim does not have to be successful to be expensive. IRMI notes that EPLI policies contain shrinking limits provisions. That means defense costs, which are often a substantial part of a claim, reduce the policy's available limits. [3] Some EPLI policies also cover claims from job applicants. This matters if someone says they were not hired because of age, disability, pregnancy, race, gender, religion, or another protected category.  Some policies include third-party coverage too. This may help if a customer, client, or vendor claims harassment or discrimination by someone at the business. Not every policy includes it, so owners should ask.

Employment Practices Liability Insurance: What Growing Businesses Should Know Hiring employees is a major step for a small business. It means more help, more capacity, and more room to grow. It also means more responsibility. Most owners plan for payroll, taxes, workers' compensation, and training when they hire. Those costs are easy to see. The harder risk to spot is the one tied to employment decisions. Every business with employees makes decisions about: Hiring Pay Schedules Promotions Discipline Performance reviews Workplace complaints Termination Any of those decisions can lead to a claim. That is where Employment Practices Liability Insurance, often called EPLI, becomes important. Employment Practices Liability Insurance helps protect a business from certain claims made by employees, former employees, or job applicants. These claims may include wrongful termination, discrimination, harassment, retaliation, failure to hire, or failure to promote. In plain English, EPLI helps protect your business when someone says they were treated unfairly at work. This is not only a big-company issue. Small businesses can face employment-related claims too. In fact, they may be less prepared because they often do not have a full HR team, formal records, or consistent employment practices. The Insurance Information Institute explains that Employment Practices Liability Insurance protects employers against claims that workers' legal rights were violated. Those claims can include harassment, discrimination, wrongful termination, failure to hire or promote, wrongful discipline, and negligent evaluation. [1] Why EPLI Belongs in the Small Business Conversation Small businesses often feel personal. Owners know their teams. Managers solve problems quickly. Conversations happen in real time. That can be a strength. It can also create risk. A business owner may believe a decision was fair. An employee may see it differently. A missed promotion may feel like discrimination. A termination may feel like retaliation. A casual comment from a manager may be viewed as harassment. Employment Practices Liability Insurance does not mean a business has done something wrong. It means the business understands that workplace claims can happen, even when leaders are trying to make fair decisions. Small businesses may also have weaker documentation. Performance conversations may happen in person but never get written down. Hiring decisions may not follow the same process each time. Terminations may happen quickly, without a clear paper trail. That can make a claim harder to defend.  The Equal Employment Opportunity Commission reported that it secured $660 million for 17,680 victims of employment discrimination in fiscal year 2025. For a small business, even one claim can create real financial strain.

This generation doesn’t wait for a paycheck. They create income on their own terms. Selling products online. Editing videos for clients. Running social media accounts. Picking up freelance work between classes or jobs. It’s flexible. It’s fast. And in a lot of cases, it works. But there’s one part no one really talks about: Most of it isn’t being tracked—or taxed—correctly. And that mistake doesn’t show up right away… it shows up later, all at once. The New Income Reality (That No One Really Explains) For Gen Z, income rarely comes from just one place. It’s usually a mix: A part-time job A few freelance clients Money from a side hustle Payments from apps or platforms Maybe even a little creator income Individually, none of it feels like a big deal. But combined? It absolutely is. Because from a tax perspective, it’s all income—and it all needs to be accounted for. Where Things Start to Go Wrong The problem isn’t effort. It’s that no one really teaches this. So a lot of people assume: “If it’s small, it doesn’t matter” “If I didn’t get a form, I don’t need to report it” “I’ll deal with it when I file” That last one is where most issues start. Because by the time you “deal with it,” the decisions that mattered have already been made. Mistake #1: Not Tracking Income Clearly When money comes in from multiple places, it’s easy to lose track. A few payments here. A deposit there. Something paid through an app that you forget about. But over time, it adds up. And without a clear record: You don’t know what you actually earned You can’t report accurately You’re more likely to miss income At the same time, many platforms are now reporting earnings directly. So if your numbers don’t match what’s reported… That’s when problems start. Mistake #2: Ignoring Estimated Taxes This is where most first-time earners get caught off guard. If you’re making money without taxes being withheld—like freelance work, side gigs, or creator income—you’re expected to pay taxes throughout the year. Not just once at filing. These are called estimated tax payments. And if you skip them, you may end up with: Penalties Interest A much larger bill than expected It’s not obvious—but it’s important. Mistake #3: Misunderstanding Write-Offs Write-offs get talked about a lot online. But they’re often misunderstood. A write-off isn’t: Everything you buy Anything loosely related to your work A way to avoid taxes entirely It has to be both: Ordinary and necessary for what you do. For example: A content creator can deduct editing tools or software A freelancer can deduct business-related subscriptions An online seller can deduct inventory costs But guessing—or copying advice from social media—can lead to mistakes. Mistake #4: Overlooking How Income Is Reported Today The way income is tracked has changed. More transactions are being reported: Payment apps Online platforms Digital marketplaces And in some cases, things like crypto or digital assets can also trigger reporting requirements. In other words: There’s less room for things to go unnoticed. Which makes it even more important to stay organized from the start. Why This Matters Earlier Than You Think Getting this wrong once? Usually fixable. But when it keeps happening, it builds: Back taxes Penalties Stress Missed opportunities to save The good news? Gen Z has an advantage most people don’t: Time to get this right early. The Opportunity: Build Good Habits Now When you understand your income and taxes early, you: Keep more of what you earn Avoid surprises at tax time Make better financial decisions Build confidence as your income grows It doesn’t have to be complicated. But it does have to be intentional. Final Thought Earning money in new ways is a huge opportunity. But without structure, it can also create unnecessary problems. The goal isn’t to overcomplicate things— It’s to get the basics right early, so everything gets easier as you grow. If you (or someone in your family or team) is earning income from multiple sources and is not sure how it all fits together, we're here for you. The earlier you get this right, the easier everything becomes. Request your free quote from Steven Brewer & Company CPAs today!