Tax Season 2025 – an annual tradition as inevitable as Texas’ chilly cold in winter, and yet somehow just as strangely invigorating.
At TheWiseBook, we know tax and its deadlines can feel like trying to untangle Christmas lights for your Holiday tree: tedious, overwhelming, and somehow full of surprises … from last year! But don’t worry, we’re here to simplify the complexity, one question at a time.
Below, we’ve rounded up the top five questions we hear every tax season, along with answers that’ll help you stay ahead of the IRS and maybe even laugh a little. Whether you’re already neck-deep in all kinds of tax forms or just starting to dust off last year’s receipts, we are here to answer all your questions.
Content list:
1. Do I need to file taxes at all?
2. Should I take the standard deduction or itemize?
3. What happens if I owe taxes but can’t pay right away?
4. What forms and documents do I need?
5. How Do I File for a Tax Extension?
*Bonus Question: What’s the deadline to file my taxes?
1. Do I need to file taxes at all?
If your income exceeds the IRS filing threshold for your age and filing status, you’re required to file a return. For instance, for Tax Year 2024 filing in 2025, here’s the breakdown:
– Single filers under 65: You must file if your income exceeds $14,600.
– Married couples filing jointly: You must file if your combined income exceeds $29,200.
Many taxpayers mistakenly assume they don’t need to file because they’re under the threshold. However, several factors might trigger a filing requirement, even if your income is lower than the amounts listed above. Here’s where your tax situation can get a little tricky:
- Self-Employment Income: Whether you’re a freelancer, contractor, or side hustler, if you earned more than $400 from self-employment, you must file. The IRS requires you to report this income for both tax purposes and to calculate your self-employment tax, and yes, that’s separate from your regular income tax.
- Investment Gains: Did your stock portfolio do better than expected? Or maybe you sold some property or cryptocurrency? Those gains – whether from stocks, bonds, or even the sale of collectibles – must be reported. Investment income can also include dividends, interest, and capital gains, which are taxable even if your total income falls under the filing threshold.
- Government Benefits: Certain government payments, like unemployment benefits, Social Security benefits, or stimulus checks, can also affect whether you need to file. Even if you’re receiving these payments at lower income levels, the IRS requires you to report them, and you may even be eligible for deductions or credits to reduce your tax burden.
- Refundable Credits: If taxes were withheld from your paycheck because you had a W-2 job, filing a return could actually mean a refund, even if your income is under the threshold. You might be eligible for credits like the Earned Income Tax Credit (EITC), which could put cash back in your pocket – but only if you file.
Surely, you could skip filing tax, but is that really a good idea? Even if you’re not sure whether you need to file, just don’t ignore it. A little paperwork now can save you big headaches down the road. And if in doubt, we’re here to help you navigate the filing threshold like a Texas-sized breeze.
2. Should I take the standard deduction or itemize?
This is a top concern and also a million-dollar question for many taxpayers. For Tax Year 2024, the standard deduction is $14,600 for singles and $29,200 for joint filers.
The standard deduction tends to be the easiest and most beneficial route. However, if you’ve made significant charitable donations or have high medical expenses or paid a substantial amount in mortgage interest, itemizing deductions could save you more – especially if your eligible deductions exceed the standard deduction amount.
We’re all about maximizing your tax savings. Whether you’re cruising through with the standard deduction or diving deep into the world of itemized deductions, TheWiseBook has the expertise to help you make the right choice.
3. What forms and documents do I need?
Gathering W-2s, 1099s, receipts for deductions, and health insurance forms like 1095s is crucial. For business owners or contractors, January 31, 2025, is the deadline to issue 1099-NECs for non-employee compensation to recipients. We know, gathering those documents feels like you’re preparing for a scavenger hunt – but don’t worry, we’ve got your back! Here’s a quick rundown of what you’ll need to gather:
- W-2 forms: for employees)
- 1099 forms: for contractors, self-employed folks, or those earning investment income
- 1095 forms: proof of health insurance coverage
- Receipts for deductions: think medical, charity, or business-related expenses
The IRS has a checklist, and you don’t want to be caught without the right paperwork. We’ll guide you every step of the way, ensuring your tax season runs smoother than a Texas BBQ.
4. What happens if I owe taxes but can’t pay right away?
We’ve all been there: you open that tax bill, and it hits harder than a Texas thunderstorm. The good news is the IRS offers options to help you pay, but there’s a catch: interest and penalties start accruing after April 15, 2025, if you don’t pay in full.
Here are your options:
- Pay what you can by April 15 to reduce penalties.
- Apply for an IRS Payment Plan – either short-term (up to 120 days) or long-term (spread over several months or years).
- Consider financing or loan options, but be mindful of high interest rates.
Don’t ignore the IRS! Let’s work together to create a plan that minimizes costs and keeps you in good standing. We’re here to help before things get messy. Then you’ll see, with the right planning, you can handle the IRS without breaking a sweat.
5. How Do I File for a Tax Extension?
Filing an extension gives you until October 15, 2025, to submit your tax return – but your taxes are still due by April 15, 2025. So the purpose of filing an extension is to buy you more time to file. You could consider this if you need a little extra time to get your paperwork together.
An extension can relieve some of pressure, but it won’t save you from penalties if you owe money and don’t pay by April. Planning ahead is still key.
Here’s the tip: remember your deadlines. And we’ll help you stay on track so you don’t end up paying more than you need to.
*Bonus Question: What’s the deadline to file my taxes?
We’ve got an entire post dedicated to deadlines and extensions – click <here> to get all the details.
Let’s Simplify Your Taxes Together
Tax season doesn’t have to be a beast. At TheWiseBook, we believe in the power of clear advice, strategic planning, and of course, a good sense of humor. So, let us help you tackle 2025 with confidence, without the last-minute panic.
Ready to get started? Whether you’re a seasoned taxpayer or still figuring out where to even start, don’t wait until April 14th to figure things out – let’s make tax season your easiest one yet!
