As the April 15 deadline approaches, many individuals and business owners find themselves scrambling to get everything in order. But tax season doesn’t have to feel overwhelming—especially if you know what to expect and prepare early.

While there’s no way to make tax season enjoyable, it can become less stressful by taking a more methodical, informed approach. Whether you’re filing a relatively simple return or coordinating with an accountant for a more complex situation, there are a few key areas worth reviewing carefully before you file.

Organize Your Documents First

One of the most common causes of tax-time frustration is disorganization. Gathering your documents in one place—before starting your return or visiting your CPA—can prevent costly mistakes and reduce the likelihood of needing to amend a return later.

You’ll want to make sure you’ve collected:

• W-2s from any job you held in the past year

• 1099s for investment income, contract work, or retirement withdrawals

• 1095-A if you used a Marketplace health insurance plan

• Mortgage interest and property tax forms if you own a home

• Any K-1s if you’re involved in partnerships or private placements

Some tax documents are delayed for valid reasons. For example, K-1s often don’t become available until March or even later. If you’re missing a key form and the rest of your return is ready, it may make sense to file an extension. That’s not uncommon, especially for taxpayers with more complex holdings.

It’s also easy to overlook duplicate documents. If you changed jobs during the year, you may have more than one W-2. Similarly, if you rolled over or withdrew from multiple retirement accounts, each institution may send a separate 1099-R. Missing even one of these can lead to inaccurate income reporting.

Health insurance is another area that occasionally causes confusion. If you had coverage through the Marketplace, you’ll receive a 1095-A that’s needed to reconcile any advance premium tax credits. Filing without it, or filing with incorrect information, can lead to rejected returns or adjustments from the IRS.

It’s frustrating when everything seems ready but one document is missing. But rushing to file without complete and accurate paperwork can create more trouble than it’s worth.

Don’t Miss Contribution Deadlines

Another area worth paying attention to is contributions—specifically, those you can still make for the 2024 tax year, even though we’re now in 2025.

Many people are surprised to learn that they can contribute to retirement accounts like Traditional IRAs and Roth IRAs up until the tax filing deadline. The same applies to Health Savings Accounts (HSAs), which offer a unique set of tax advantages if you qualify.

These deadlines give you an additional opportunity to assess your tax situation before it’s final. If you find that your income is pushing you into a higher tax bracket or triggering phase-outs for certain deductions or credits, making a deductible contribution—where applicable—can be a smart way to soften that impact.

Traditional IRA and HSA contributions may offer a deduction, depending on your income and other factors. Roth IRAs, while not deductible, still allow you to put money away in a tax-advantaged account for future use.

It’s also worth revisiting any credits you may be eligible for. Education-related credits, clean energy incentives, and adoption-related expenses are just a few examples. Some of these are reflected in standard tax forms, but others may require documentation that isn’t automatically provided unless you know to look for it.

Contribution windows and tax credits are often missed because people assume the window closed at year-end. But in many cases, you still have time to make those decisions count for last year.

Consider How Life Changes Might Affect Your Return

Life changes have a direct effect on your tax return, sometimes in subtle ways. Whether it’s a new job, marriage, or home purchase, these events can alter your filing status, deductions, and credit eligibility.

Take marriage, for example. Getting married changes your filing status, but it doesn’t automatically mean you should file jointly. While joint filing usually results in a lower tax burden, that’s not a guarantee. Couples with widely different incomes or those who itemize differently may want to compare both filing options to see what works best.

A home purchase may open the door to itemizing, especially when combined with other deductible expenses. Still, with today’s elevated standard deduction, fewer people find itemizing to be worthwhile unless mortgage interest and property taxes are substantial.

Inheritances can also complicate things. If you inherited an IRA or other retirement account, it’s important to confirm whether the decedent took their required minimum distribution (RMD) in the year of their passing. Missing that step could result in penalties that are avoidable with proper coordination.

Even job transitions come with tax implications. Multiple W-2s are the most obvious result, but there could also be changes in benefits, retirement plans, or withholdings that affect your return in less obvious ways.

For Business Owners: Plan Ahead, Don’t React

Tax season for small business owners is about more than reporting numbers—it’s an opportunity to assess your strategy. If your business generated more income than expected in 2024, there’s still time to make decisions that could impact your return.

One of the most impactful is contributing to a retirement plan. Depending on your business structure, you might still be eligible to contribute to a SEP IRA, SIMPLE IRA, or Solo 401(k) and claim a deduction for the prior year. These contributions not only help reduce taxable income but also build long-term savings for yourself and your employees.

When a business owner tells me they had a strong year, I immediately start looking at how retirement contributions could help offset the added tax burden. These aren’t one-size-fits-all decisions, but they’re almost always worth reviewing.

Another important area is entity structure. If you’re still operating as a sole proprietor or single-member LLC, now might be the time to explore whether an S Corporation designation could result in tax efficiencies—especially as income scales.

The right entity structure depends on multiple variables, including income level, payroll, and long-term business goals. It’s not always about immediate savings; sometimes it’s about positioning your business for growth while managing liability and compliance efficiently.

Avoid Surprises with Estimated Taxes

Estimated taxes are often misunderstood, but they can have serious consequences if ignored. If you’re self-employed or have significant income outside of W-2 wages, the IRS expects you to make quarterly tax payments. Failing to do so—even if you pay your full tax bill by April—can result in underpayment penalties.

These penalties have become more severe in recent years as interest rates have risen. What might have once been viewed as a minor nuisance is now a more noticeable financial setback.

There used to be a mindset that skipping quarterlies and investing the cash might generate a better return. That doesn’t hold up anymore—penalties are higher, and the margin for error is much thinner.

If your income has increased significantly over the past year, it’s a good idea to talk with your tax advisor about setting up quarterly payments for the current year. This kind of forward planning not only keeps you compliant but can also smooth out cash flow throughout the year.

Final Thoughts

There’s no substitute for good preparation. Tax season may never be simple, but it doesn’t have to be chaotic either. By organizing your documents, reviewing key contribution deadlines, and staying aware of how personal or professional changes affect your tax profile, you can take control of the process.

For business owners, especially, this season is more than just a deadline—it’s a chance to review your broader financial strategy. Contributions, structure, estimated taxes—these aren’t just tax topics; they’re planning conversations that can shape your year ahead.

As always, this article is for informational purposes only and does not constitute tax advice. Every situation is different, and it’s important to consult with a qualified professional before making decisions related to your tax return.