With tax season officially underway, here are several ideas to make filing your return as stress-free as possible:
Gather your tax information for filing. Items you’ll need include K-1s, W-2s, 1099s and other forms you receive from your business, employers, brokers, banks, and others. If you find any errors, contact the issuer immediately to request a corrected copy. And if you have tip or overtime income, be prepared to break this income out to take advantage of tax-free savings as this will not necessarily be broken out on your W-2.
Organize your records. Once you’ve started gathering your information, find a place in your house and put all the documents there as you receive them, or consider scanning documents to store on your computer. You can also take pictures of the documents with your phone as backup. Missing information is one of the biggest reasons filing a tax return becomes delayed.
Create an April 15th reminder. This is the deadline for filing your 2025 individual income tax return, completing gift tax returns, making contributions to a Roth or traditional IRA for 2025, and for paying the first installment of 2026 individual estimated taxes.
Know the deadlines for business returns. If you are a member in a partnership or a shareholder in an S corporation, the deadline for filing business returns for these two entities is March 16th. Calendar-year C corporation tax returns are due by April 15th.
Review your child’s income. Your child may be required to file a 2025 income tax return. A 2025 return is generally required if your child has earned more than $15,750, or has investment income such as dividends, interest, or capital gains that total more than $1,350.
Contribute to your IRA and HSA. You can still make 2025 IRA and HSA contributions through either April 15th or when you file your tax return, whichever date is earlier. The maximum IRA contribution for 2025 is $7,000 ($8,000 if age 50 or older). The maximum HSA contribution is $4,300 for single taxpayers and $8,550 for families.
Calculate your estimated tax if you need to extend. If you file an extension, you’ll want to do a quick calculation to estimate your 2025 tax liability. If you owe Uncle Sam any money, you’ll need to write a check by April 15th even if you do extend.
Plenty of tax changes are lining up as the calendar turns toward 2026, and knowing what’s coming can help you stay a step ahead. Before then, there’s also several moves to make filing your 2025 tax return as easy as possible.
Preparing to file your 2025 tax return
Gather records to support deductions for no tax on tips and no tax on overtime. Review the approved occupations for qualified tips and confirm the amount of this benefit you expect to claim in 2025. You will need proof of these claimed amounts. The same holds true for overtime pay. Employers are not required to issue W-2s or 1099s with this information in 2025, but they should provide you with the necessary confirmation of the dollar amounts. Compare these employer-provided amounts with your records to ensure they match prior to filing your tax return.
Look for new Form 1099-DA. If you own cryptocurrency or other digital assets, you may see this new form. Starting with the 2025 tax year, exchanges and brokers must report certain cryptocurrency and digital asset transactions, so you should track cost basis, sale dates, and wallets used to avoid mismatches or questions from the IRS.
1099-Ks may still be issued. You shouldn’t see a Form 1099-K from a payment processor such as PayPal or Venmo unless you have 200 or more transactions amounting in more than $20,000 in payments from the processor. But because of the many tax law changes in this area you may still receive a Form 1099-K in error. If you receive one, don’t throw it away! Include it with your other tax documents for proper reporting on your 2025 tax return.
Review IRA and HSA accounts. If you have an IRA or HSA account, you can make 2025 contributions up until either April 15, 2026 or the date you file your return, whichever is earlier.
What’s new in 2026
Above-the-line charitable contributions. You can deduct $1,000 of charitable contributions if single or $2,000 if filing jointly. This is available to you whether you use the standard deduction or itemize your deductions. There’s also the introduction of a 0.5% floor for itemizing charitable contributions.
Itemized deduction phaseout is back. If you’re in the top 37% tax bracket, your itemized deductions could be reduced. This phaseout of deductions is being re-introduced beginning in 2026.
Gamblers take a loss. Losses from wagering transactions are now limited to 90% of such losses. Under the previous law you could claim deductions up to the amount of your winnings. For example, if you won $10,000 and incurred $15,000 in losses over the course of a tax year, you could deduct $10,000 using the previous law. Under the new law you can only deduct 90% of your losses, or $9,000 in this example.
Mortgage insurance premiums can be reported as an itemized deduction.
Elimination of many energy credits. This includes the credit for purchasing electric vehicles after September 30, 2025 and the elimination of many residential energy efficient purchase credits at the end of 2025. So plan accordingly.
Every January brings a familiar ritual. We promise to eat better, exercise more, and finally organize the garage. These are fine goals, but if you want a resolution that delivers real, measurable value, fewer taxes paid over your lifetime is about as concrete as it gets. Here are three possible resolutions to consider:
Resolution #1: Maximize use of your retirement accounts
One of the simplest ways to lower your current tax bill is by maximizing contributions to 401(k)s, IRAs and similar accounts. You can also defer taxes by maximizing contributions into 401(k)s and Traditional IRAs or reduce your taxes in the future by considering Roth accounts. Some other great tips:
Ensure you are taking advantage of catch-up contributions.
Always contribute to take advantage of any employer matching programs.
Take full advantage of SEP IRAs as a small business owner.
Look to create additional accounts when possible through spousal retirement accounts or youth accounts when children have earned income.
This resolution can be rich with tax saving ideas.
Resolution #2: I will keep my tax records organized.
If tax season feels like a scavenger hunt through old emails and crumpled receipts, organization should be high on your list. Remember, if you can’t support a deduction, you can’t take it. This is especially true if you run a small business, if you want to take advantage of things like the new $1,000 ($2,000 joint) charitable contribution deduction, or claim the teacher out-of-pocket expense deduction. The same is true with educational expenses.
Resolution #3: Commit to paying health costs tax efficiently
A health savings account (HSA) is one of the most powerful tax saving tools in the tax code. Contributions are often deductible, with earnings on funds in the account usually tax-free. Plus qualified medical withdrawals are also tax-free. So try to maximize your eligible donation into your HSA each year, including catch-up contributions. Then invest your unused funds to grow tax-free. Leaving the HSA untouched allows it to function like a stealth retirement account. Years down the road, those funds can be used for healthcare costs that almost everyone faces, often with significant tax advantages.
Making taxes a year-round conversation
Taxes are not a once-a-year event. Life changes like income shifts, business activity, investments, or family milestones can all affect your strategy.
This year, choose a resolution that quietly compounds, rewards consistency, and pays you back every April.
The U.S. tax code is constantly changing. What saved you money last year might cost you this year. Between shifting income thresholds, changing deduction rules, and overlooked credits, you now need to stay focused on your tax plan throughout the year. Here are several bits of tax wisdom that can help you lower your bill to the IRS.
Phaseouts matter (a lot). A lot of tax breaks, such as child tax credits, tax benefits for college costs, or the new senior deduction don’t disappear all at once. Instead, they phase out slowly as your income rises. This means earning a bit more could quietly cost you some of these benefits.
What you can do: Keep an eye on how much income you’re showing on paper and how it will impact these phaseouts. You might be able to stay in the sweet spot so you don’t lose the value of your deductions or credits by putting more into your retirement account or timing when you receive certain payments.
Are itemized deductions going the way of the dinosaur? Not so fast! Yes, the standard deduction is now higher than ever ($31,500 for married couples, $15,500 for singles in 2025), which has made itemizing less common. But with an increase of the state and local tax (SALT) deduction from $10,000 to $40,000, you may be shifting back to itemizing your deductions without realizing it.
What you can do: Don’t assume you’ll be taking the standard deduction again this year. Add up your potential itemized deductions, especially if your expenses vary, to see how close you are to being able to itemize. Consider bunching charitable contributions or property taxes into one year to clear the standard deduction hurdle.
Timing is everything (especially with capital gains). If you sell assets held longer than a year, you’ll likely qualify for long-term capital gains rates (0%, 15%, or 20%). But miss that time by even a day and you could pay ordinary income rates, which can be nearly double. Strategic timing can also help you harvest losses to offset gains and reduce your overall tax bill.
What you can do: If possible, hold investments that are profitable for at least one year and a day before selling to qualify for lower tax rates. Use end-of-year tax-loss harvesting to offset gains, and stagger sales across tax years if needed.
Don’t sleep on the Qualified Business Income deduction. If you’re a small business owner, self-employed, or even a gig worker, you may be eligible for a 20% deduction on your qualified business income. Planning how and when revenue hits your books could make or break your eligibility for this significant deduction.
What you can do: Review how your business is structured and how much income you’re reporting. You may be able to reduce taxable income through retirement contributions, shifting income between years, or reclassifying your business activities.
Tax-deferred doesn’t mean tax-free. Traditional 401(k)s and IRAs offer tax deferral, not tax elimination. When you withdraw funds in retirement, you’ll pay ordinary income tax on the distributions. If you expect to be in a high tax bracket in retirement, it may be a better idea to contribute to a Roth account now and pay taxes up front.
What you can do: Schedule a planning session to discuss whether diversifying your retirement accounts between traditional and Roth makes sense for your situation. Also consider planning for the timing of distributions from these accounts to be as tax efficient as possible. Run long-term tax projections to decide which type of contribution makes sense today. Consider partial Roth conversions during lower-income years. Tax planning isn’t a once-a-year scramble, but rather a year-round strategy. And with these pieces of prevailing tax wisdom, you can be better prepared to cut your tax bill. Please call if you have any questions about your tax situation.
Tax myths can spread quickly, leading to costly mistakes or missed opportunities. Here are several common tax myths along with best practices to help you stay grounded in reality.
Myth: Moving into a higher tax bracket means you’ll take home less money
Reality: The U.S. tax system is progressive, meaning your income is taxed in layers. There are currently 7 different layers, with tax rates ranging from 10% to 37%. When you enter a higher tax bracket, only the portion of income above the bracket threshold gets taxed at the higher rate, not your entire income.
Best Practice: Know your marginal tax rate! This is the tax rate of the next dollar you earn. By understanding this you can do your own calculations on the impact of any additional income you earn.
Myth: Getting a tax refund means you did something right.
Reality: A tax refund means you overpaid your taxes. It’s your money, coming back to you – without interest. Getting a big refund might feel great, but from a cash flow perspective, you’re better off adjusting your withholding so you keep more of your paycheck each month.
Best Practice: Review last year’s tax return, then update the numbers to reflect your situation for the current year. Factor in the latest changes such as tax-free tips, tax-free overtime, and increased standard deductions, including the new $6,000 deduction for seniors. Once you’ve made these adjustments, revisit your paycheck withholdings to make sure they’re on track.
Myth: You can deduct all your expenses if you’re self-employed.
Reality: Not quite. While being self-employed certainly opens up more deduction opportunities, not every expense qualifies. Only ordinary and necessary business expenses can be deducted. That family trip overseas doesn’t qualify unless it was genuinely work-related (and even then, only parts of it might qualify).
Best Practice: Set up a dedicated business bank account to handle all income and expenses related to your work. Then establish a regular schedule to transfer funds into your personal account for all non-business spending. And don’t commingle funds with your personal expenses. The IRS may be quick to throw out ALL expenses if they see this occurring.
Myth: You don’t have to report income if you didn’t receive a Form 1099.
Reality: If you earn money, the IRS expects to hear about it, regardless of whether you received a Form 1099. Many people assume that if a client or gig platform doesn’t send you a 1099, then that income doesn’t need to be reported on your tax return. But that’s not how it works. The tax code requires you to report all income, no matter how it’s documented – or if it’s not documented at all.
Best Practice: Keep a list of past 1099s to help you remember which clients or platforms have paid you before, and to double-check if you earned income from them again this year.
Please call if you have any questions about your tax situation.
As a freelancer or contractor, at some point you may wish to incorporate and be taxed as an S corporation. Here’s a closer look at the process of becoming an S corporation and when switching might make sense for you.
The main benefits of S corporations
Self-employment tax savings. As a sole proprietor, you’re required to pay a 15.3% self-employment tax (which includes Social Security and Medicare) on your entire income. However, with an S corporation, you can split your income into two parts: a reasonable salary (which is subject to Social Security and Medicare taxes) and distributions (which are subject to income taxes but not Social Security and Medicare taxes).
Pass-through taxation. Similar to sole proprietorships, S corporations are considered pass-through entities. This means that the business itself doesn’t pay income taxes. Instead, profits and losses pass through the business to the owner’s personal tax return. Profits of a C corporation, on the other hand, are taxed twice – once at the entity level, and again on the owner’s tax return.
Legal protection. If there is a risk of possible legal action, an S corporation can potentially help protect your personal assets from your business assets. For example, this can be especially helpful if you are in the contractor trade and the customer makes a claim against the fulfillment of your contract.
While transitioning from a sole proprietor to an S corporation can certainly result in significant tax savings, there are a few trade-offs to consider.
Trade-offs to consider
Most of the trade-offs are centered around administrative requirements and potential costs. These include:
Running payroll. Even if you’re the only employee, you’ll need to set up payroll and withhold taxes. Many business owners use a payroll service to handle this.
Separate tax filing. Your business will now need to file a Form 1120-S tax return with a March 15th due date in addition to your personal tax return.
Accountants or bookkeepers are typically used. Most S corporation owners work with professionals to handle bookkeeping and tax filings.
Reasonable salary requirement. The IRS expects owners to pay themselves a fair market wage. Underpaying yourself to avoid taxes can lead to penalties.
State-level requirements. Some states have minimum franchise taxes or annual fees for corporations and LLCs, regardless of income.
When it makes sense to switch
Switching to an S corp generally becomes worth considering when your net income (after expenses) is in the range of $75,000 to $100,000 or more per year.
Here’s an example: Assume you earn $120,000 in net income as a consultant.
As a sole proprietor, you’d pay self-employment tax on the full amount, about $18,000.
As an S corp, if you pay yourself a reasonable salary of $60,000, you’d only pay payroll taxes on that amount, roughly $9,200. The remaining $60,000 in profit would be subject to income taxes but not payroll taxes.
That’s a potential tax savings of nearly $9,000 per year.
Switching from a sole proprietor to S corp can offer real tax advantages, but it’s not a one-size-fits-all solution. It’s usually best practice to review your situation once per year to ensure your business is organized properly.
