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The way we work is changing, with more and more individuals building careers and earning income through the gig economy and side hustles. But with this flexibility comes a new set of tax responsibilities that can feel overwhelming. At Lightening the Load, we specialize in guiding individuals through complex tax situations, and that includes helping you turn your side hustle into a financially savvy operation. 

Your tax journey as a gig worker is fundamentally different from that of a traditional employee. Here’s what you need to know. 

The Importance of Tax-Conscious Record Keeping 

Unlike a W-2 employee, taxes aren’t automatically withheld from your gig income. This means you are responsible for keeping detailed records of both your income and your expenses throughout the year. 

• Track Your Income: Keep a log of all income, even if it’s not reported on a Form 1099. Every dollar earned from a side hustle is considered taxable income. 

• Deduct Your Expenses: The biggest opportunity for tax savings lies in properly deducting your business expenses. This includes costs for things like: 

• Business mileage for a rideshare driver 

• Supplies for a freelance artist 

• Internet and phone bills used for work 

• Software subscriptions and professional fees 

Estimated Quarterly Taxes 

Since taxes aren’t taken out of your paychecks, you are likely responsible for paying estimated quarterly taxes. Failing to do so can result in penalties from the IRS. We can help you calculate and schedule these payments so you can stay ahead of your tax obligations and avoid a large tax bill at the end of the year. 

The Self-Employment Tax 

Another key difference is the self-employment tax. This includes both the Social Security and Medicare taxes that would typically be split between an employee and employer. As a self-employed individual, you are responsible for paying both portions, which adds an additional layer to your tax planning. 

Your side hustle deserves a smart tax strategy. Let us at LTL help you turn your gig into a financially savvy operation. 

he new year is upon us, and with it comes the start of tax season. Instead of waiting for a last-minute scramble, getting a head start on your tax preparation is a move that can save you time, stress, and money. At Lightening the Load, we believe in a proactive approach, and this checklist is designed to get you organized and ready for a smooth tax filing experience. 

Your Essential Tax Season Checklist 

1. Personal and Family Information 

Start with the basics. Having this information ready at the beginning of the process ensures a seamless flow. 

• Social Security numbers for you, your spouse, and any dependents. 

• Dates of birth for everyone on your return. 

• If you were issued one by the IRS, your Identity Protection PIN. 

2. Income Documents 

This is the cornerstone of your tax return. Gather all documents that report your income from the prior year. 

• W-2s from all employers. 

• 1099 Forms (1099-NEC for independent contractor work, 1099-INT for interest, 1099-DIV for dividends, etc.). 

• SSA-1099 for Social Security benefits. 

• Any other forms reporting income, such as from rental properties or side hustles. 

3. Deduction & Credit Documentation 

To ensure you’re taking advantage of every tax break you qualify for, you need to have the proper documentation. 

• Records of charitable contributions, including cash, checks, and donated items. 

• Homeownership records, such as your Form 1098 for mortgage interest and records of real estate taxes paid. 

• Receipts for medical expenses not covered by insurance. 

• Records of education expenses, including Form 1098-T from educational institutions. 

• Business expenses, including mileage logs and receipts for supplies, travel, and meals. 

4. Tax Payments Made 

Don’t forget to account for the taxes you’ve already paid. This can significantly reduce or eliminate your final tax bill. 

• Records of estimated tax payments made throughout the year. 

• Any payments made with a prior-year extension request. 

5. Business and Self-Employment Documents 

For small business owners and those in the gig economy, your record-keeping is vital. 

• Profit and Loss statement for your business. 

• Records of all business expenses, categorized by type. 

• Documentation for assets purchased for business use, which may qualify for depreciation. 

Don’t wait until January! Use this checklist to get a head start on your tax preparation. And if you need help, we’re just a call away. 

Healthcare and taxes have always been intertwined, but new tax legislation has made the connection even more significant. For individuals and families with Health Savings Accounts (HSAs) or those considering one, understanding these changes is crucial to maximizing your tax savings. At Lightening the Load, we’re here to help you make sense of these new rules and ensure your tax strategy is as healthy as you are. 

The New Rules for HSAs 

The new tax bill loosens some of the restrictions around HSAs, making them a more flexible and powerful tax-advantaged tool for healthcare expenses. 

• Expanded Telehealth Access: The new law makes permanent the ability for high-deductible health plans (HDHPs) to cover telehealth services before you meet your deductible, without jeopardizing your HSA eligibility. 

• Direct Primary Care: A major change is the new ability to participate in Direct Primary Care Arrangements (DPCAs) and still be HSA-eligible. You can also now use your HSA funds to pay for DPCA fees. This opens up new ways to use your HSA to pay for a more comprehensive healthcare experience. 

Other Health-Related Tax Changes 

Beyond HSAs, the new legislation introduces other tax-related provisions for healthcare and dependents. 

• Increased Dependent Care FSA Limits: The annual exclusion from taxable income for dependent care Flexible Spending Arrangements (FSAs) has increased from $5,000 to $7,500. This is a significant benefit for families with childcare expenses. 

• Enhanced Adoption Tax Credit: The tax credit for adoption assistance has also been improved, becoming partially refundable, which can provide much-needed relief for families. 

Healthcare and taxes are now more intertwined than ever. We can help you understand the new rules and maximize your health-related tax savings. 

The tax landscape is in constant motion, and for individuals and couples, keeping up can feel like navigating a complex trail without a map. At Lightening the Load, we’re committed to being your tax basecamp, guiding you through every new twist and turn. Recently, new tax legislation has introduced some significant changes that could directly impact your tax return, offering incredible opportunities for tax savings. 

Let’s break down some of the key provisions in the new bill that affect individuals and families. 

Tax Relief for Tips and Overtime 

In a major change designed to help a wide range of workers, the new tax bill introduces a temporary deduction for both tips and qualified overtime pay. This is a game-changer for many service industry professionals and hourly workers. 

• Tips: You may now be able to deduct up to $25,000 of qualified tip income for tax years 2025 through 2028. This is a special, “above-the-line” deduction, meaning you can take it even if you don’t itemize. 

• Overtime: For qualified overtime compensation, a deduction of up to $12,500 is available for single filers, and up to $25,000 for married couples filing jointly. This applies to the “half” portion of “time-and-a-half” pay and is also an above-the-line deduction. 

Both of these deductions have income phase-out rules, so it’s essential to understand your specific situation to know your full eligibility. 

Changes to the Child Tax Credit 

For families, the Child Tax Credit is a critical source of tax relief. The new legislation has made a few important modifications that could increase the credit amount for many households. 

• Increased Value: The credit has been increased from $2,000 to $2,200 per eligible child for the 2025 tax year. This amount will also be indexed for inflation in subsequent years. 

• Work-Eligible SSN Requirement: There is a new requirement that the child and at least one filer on a joint return have a work-eligible Social Security Number. 

These changes are designed to provide more support for working families and are a key consideration as you prepare for tax season. 

Introducing TRUMP Accounts 

The new bill also creates a new savings vehicle for children, often referred to as “Trump Accounts.” These tax-advantaged accounts aim to encourage long-term savings for a child’s future. 

• Government Contributions: An eligible child born between 2025 and 2028 will receive a one-time $1,000 contribution from the government. 

• Tax-Deferred Growth: Like some other popular accounts, contributions and earnings can grow tax-deferred. 

• After-Tax Contributions: Individuals and employers can make after-tax contributions up to a combined annual limit. 

This new account adds another layer to family tax planning, providing a way to build a nest egg for the next generation. 

For many high-net-worth individuals, the annual question of whether to itemize or take the standard deduction has become increasingly complex since the 2017 tax law. With the new tax bill, signed into law in July 2025, the debate has been reshaped entirely, especially for homeowners in high-tax states. At Lightening the Load, we understand that a one-size-fits-all approach to tax strategy doesn’t work for you. We are your steadfast partners, here to provide the clarity you need to make the right decision. 

Understanding the New Rules of the Game 

The new tax bill is a game-changer because it directly addresses the State and Local Tax (SALT) deduction cap, a provision of the 2017 law that significantly impacted many taxpayers. 

The new, temporary change increases the SALT deduction cap from $10,000 to $40,000 for single and married filers. This is a significant shift that will be in effect through 2029, with a gradual phase-out for those with modified adjusted gross income above $500,000. For context, the standard deduction for the 2025 tax year is $15,750 for single filers and $31,500 for married couples filing jointly. 

How the New SALT Cap Changes Everything for Homeowners 

Before this new legislation, homeowners in high-tax states often found that their combined property and state income taxes quickly exceeded the $10,000 SALT cap. This left them with a total of itemized deductions that was often less than the standard deduction, making itemizing a non-starter. 

The new $40,000 cap fundamentally changes this math. For many high-net-worth individuals, the higher cap means their property taxes and state income taxes alone may now be enough to make itemizing a more advantageous strategy. When you add other common itemized deductions to the equation, such as: 

• Mortgage Interest: The new law makes the $750,000 mortgage interest deduction cap permanent. For those with mortgages below this threshold, every dollar of interest paid adds to their potential itemized deduction total. 

• Charitable Contributions: Significant donations to charities can be a major component of a high-income individual’s itemized deductions. 

• Medical Expenses: While subject to an income threshold, large, uninsured medical expenses can also contribute to your total. 

When these deductions are combined with the new, higher SALT cap, the total may easily exceed the standard deduction. This can result in a lower overall tax liability and greater tax savings. 

Don’t Guess, Get a Professional Analysis 

The decision to itemize is no longer a simple one. The new tax bill, with its temporary provisions and phased-out benefits, requires a careful, personalized analysis. The right choice depends on your specific circumstances, including your income, home value, and state of residence. 

Don’t guess on your filing strategy. Let us run the numbers to see if itemizing still works for you under the new rules. Schedule your consultation today! 

Let us lighten your load.