How to Get the Biggest Tax Refund in 2025: The 2025 Tax Guide for Founders & Freelancers

The average US tax refund in 2024 was $3,167. 

And guess what, with smart strategy and the right tools, your refund in 2025 could be even bigger.

But here’s the truth: most founders, freelancers, and small business owners either leave money on the table, or worse, end up overpaying, because they don’t realize how much of the tax code is designed to reward them.

Whether your income shifted, you launched a business, or you worked a patchwork of gigs and clients, your 2025 refund potential has everything to do with what you claim and how you file.

Here’s the 7-part playbook to get the biggest tax refund in 2025, no guesswork needed.

We’ll walk you through:

• How to know if you qualify for a refund

• Deductions and credits you actually qualify for

• The best timing and filing tactics

• Common refund-killing mistakes

And most importantly, how doola can help you optimize it all, stress-free. Let’s unlock that bigger refund.

Step 1: Confirm You’re Eligible for a Refund

Let’s bust a common myth right away: 

Getting a refund isn’t about how much you earn, it’s about how much you overpaid.

Too often, founders, freelancers, and gig workers skip filing or rush through it without realizing they’re actually owed money back.

Whether you’re running a business or juggling multiple income streams, the key to unlocking a refund starts with understanding your eligibility.

Quick Refund Eligibility Quiz

Let’s take a quick quiz to find out if you’re eligible for a refund this year:

✔️ Did you have federal income tax withheld from a paycheck?

If you worked a W-2 job at any point and didn’t adjust your withholdings after a raise, bonus, or side hustle income, chances are you overpaid, especially if your employer used default withholding settings.

✔️ Did you make quarterly estimated tax payments as a self-employed person?

Freelancers and solopreneurs often overestimate their quarterly taxes to avoid underpayment penalties.

If your actual net income was lower than expected, you might be entitled to a refund on the difference.

✔️ Did you qualify for any refundable tax credits?

Unlike non-refundable credits (which just reduce your tax bill), refundable credits can increase your refund even if you owe zero in taxes. These include the Earned Income Tax Credit (EITC) or Child Tax Credit. 

You could qualify for a refund even with low or negative taxable income.

✔️ Did your business operate at a loss?

Founders who invested heavily in their business during the year, but didn’t turn a profit, can often carry losses forward or offset other income.

If taxes were prepaid (via estimated payments or payroll), you may be entitled to some of that money back.

Step 2: Pick the Right Filing Status (and Update It If Needed)

Your filing status is a major factor that influences how much tax you owe, which credits you qualify for, and ultimately, how big your refund could be.

Choosing the wrong filing status, or forgetting to update it after life changes, can cost you thousands. But when selected strategically, it can unlock credits, boost deductions, and shrink your taxable income.

Let’s zoom into each situation with examples. 

Common Filing Statuses (and Why They Matter)

1. Single: This is the default filing status for individuals who aren’t married and don’t qualify as a Head of Household. It offers the lowest standard deduction compared to other statuses.

• 2025 Standard Deduction (Projected): $14,600

• Best for: Unmarried individuals with no dependents

2. Married Filing Jointly (MFJ): Married couples can choose to file together, which typically results in lower combined tax liability and increased credit eligibility.

• 2025 Standard Deduction (Projected): $29,200

• Access to: Higher income phase-out limits for Child Tax Credit, Earned Income Tax Credit (EITC), and IRA contributions

• Best for: Couples where one spouse earns significantly more, or both want to access broader tax benefits

3. Head of Household (HOH): Designed for unmarried taxpayers supporting dependents, this status offers a larger standard deduction and better tax brackets than “Single.”

• 2025 Standard Deduction (Projected): $21,900

• Best for: Single parents or caregivers who pay more than half the cost of household expenses

4. Qualifying Widow(er): This status applies for up to two years after a spouse passes away, if you have a dependent child and haven’t remarried.

• Offers the same standard deduction and tax benefits as MFJ

• Best for: Recently widowed individuals with children

Real-World Examples of Refund-Boosting Status Changes

Let’s now see how updating your filing status (or business structure) can directly impact your tax outcome, and your refund.

✅ Single → Head of Household

Sarah, a freelance designer, for example, is raising her nephew and paying more than half the household expenses. For years, she filed as Single out of habit. 

But when she switches to Head of Household, her standard deduction increases by over $7,000.

Refund Impact:

• Deduction boost: $14,600 → $21,900

• Tax savings: Up to $1,000–$3,000, depending on income and credits unlocked

• Credit eligibility: HOH opens access to higher EITC and Child Tax Credit limits

✅ Married Filing Separately → Married Filing Jointly

Let’s say, a couple, Jason and Maya are married but filed separately last year because of student loan concerns. 

However, by filing jointly this year, they unlock $4,000 in education tax credits and qualify for the full Child Tax Credit for their two kids.

Refund Impact:

• Access to credits: American Opportunity Credit + EITC

• Tax liability: Reduced by $2,000–$5,000

• Refund boost: Joint filing also qualifies them for a larger standard deduction

✅ Sole Proprietor → S Corporation (S Corp)

Suppose, Alex, a software consultant, earns $120,000/year as a sole proprietor and pays around $17,000 in self-employment tax. 

In 2025, he elects S Corp status, pays himself a reasonable salary of $70,000, and takes the rest as distributions.

Refund Impact:

• Self-employment tax saved: ~$6,000

• Overpayment via prior estimates: $3,500

• Refund potential: $3,000–$5,000 due to lower tax liability

Filing Status Scenarios & Refund Impact 

Think Beyond Filing Status, Consider Entity Status Too

Thinking of switching to an S Corp in 2025? It might lower your overall taxes and increase your refund, especially if you’re earning more than $80,000/year as a solo founder.”

S Corps aren’t technically a filing status, but the way you elect to structure your business (LLC vs. S Corp) has a direct effect on your personal tax return. 

With the right CPA guidance (like doola offers), you can file with the right status and the right structure, maximizing your refund from both ends.

Step 3: Maximize Your Deductions With These Strategies 

Every dollar you deduct reduces your taxable income, and that directly impacts how much you owe or how much you get back.

Think of deductions as strategic levers: the more legitimate expenses you track and claim, the higher your potential refund.

For Freelancers & 1099 Workers

You’re essentially running a business. So every tool, trip, or gig-related expense can count.

Here’s how to make every dollar work for you:

📌 Pro Tip: Use mileage tracking apps like Everlance or MileIQ to auto-log trips and stay audit-ready.

For Startup Founders

Starting up means spending upfront, and if you’re tracking those costs right, the IRS lets you deduct up to $5,000 in your first year (phases out if startup expenses exceed $50K).

🔍 Audit Alert: If the IRS ever comes knocking, they’ll want more than just a receipt. They’d need clear records that explain the “who” and “why” behind each business meal or expense, especially when deductions are involved.

So, always keep itemized receipts for business expenses, and go one step further by “documenting the context”.

For W-2 Employees With Side Hustles

Even if you work a full-time job, the IRS sees your freelance gigs as a separate business. That means you’re eligible for 1099 deductions too.

📌 Reminder: Even if your side hustle didn’t make much, those deductions still lower your total income, which can boost your refund or reduce tax owed.

2025 Deduction Insight: Standard vs. Itemized

Itemize only if your total deductions exceed these thresholds. Common itemized expenses include:

• Medical bills (if >7.5% of AGI)

• Mortgage interest

• Charitable donations

• State and local taxes (up to $10,000 cap)

But wait, are you still juggling spreadsheets and receipts? doola Bookkeeping replaces all that with intelligent categorization, clear reports, and expert-backed accuracy, minus the hassle:

✔️ Auto-sync your bank accounts

✔️ Categorize expenses in real time

✔️ Export IRS-ready reports anytime

✔️ Track tax-deductible mileage, subscriptions, and more

Whether you’re full-time freelance or side-hustling on the weekends, doola keeps your finances sharp and refund-friendly.

🔖 Related Read: 7 Smart Habits for Maximizing Savings Next Tax Season

Step 4: Claim All Refund-Boosting Credits

While deductions reduce your taxable income, credits reduce your actual tax bill, dollar for dollar. And here’s the thing: some are refundable, meaning even if you owe $0 in taxes, you still get the full value back as a refund.

Credits are refund game-changers.

Let’s break down some of the most powerful credits available in 2025 and who can qualify.

Key Credits: Do You Qualify?

Step 5: Time Your Filing (and Income) Strategically

Timing is key in maximizing your refund, unlocking credits, and keeping your tax liability in check.

Tax optimization isn’t just about what you report, it’s also about when you report it.

✔️ Why Filing Early Pays Off

Filing your return as early as possible isn’t just about getting it over with, it’s a smart financial move.

For one, it dramatically reduces the risk of tax identity theft, where fraudsters try to file using your name and claim your refund. The earlier you file, the less window they have to act.

Secondly, you get your refund faster, especially if you e-file and opt for direct deposit. 

And lastly, early filing can help you qualify for income-based credits (like the EITC or Saver’s Credit) before phase-outs kick in due to additional income earned later in the year.

Important IRS Deadlines for the 2025 Tax Year

• Filing Opens: January 27, 2025 (projected)

• Filing Deadline: April 15, 2025

• Extension Deadline: October 15, 2025 (if you file for an extension)

Missing these deadlines can mean penalties, delays, and missed opportunities, so mark your calendar right away.

📅 Refund Optimization Calendar

⚡ doola Tip for Do’ers

Income-based credits like the Earned Income Tax Credit are calculated based on your total income for the year. 

But if you’re a gig worker or freelancer with inconsistent income, filing early, before your year-end income spikes, may help you lock in a better refund. 

Just be sure your reported income is accurate and documented.

Step 6: Avoid These 7 Refund-Killing Mistakes

Founders need more than software, they need strategy. Because even small oversights can lead to major refund losses.

Don’t let your software think for you. Founders need strategy, not shortcuts.

Here are the top mistakes that quietly drain your refund potential, and how to fix them like a pro: 

⚠️ Important: Tax software can file, but strategy can win. Smart founders don’t leave money on the table, they work with pros (like the ones at doola) who know where to look.

Step 7: Use Expert Tools Like doola to Maximize Without the Headache

For founders juggling clients, income streams, and compliance across borders, tax filing is table stakes. Besides checking boxes, it’s more about uncovering every credit, deduction, and treaty benefit you’re actually owed.

That’s exactly where doola Tax Filing wins, offering the perfect mix of automation, strategy, and human expertise.

Here’s why smart entrepreneurs file with doola:

✅ Real CPAs + Smart Automation

✅ Year-Round Tax-Saving Strategy

✅ Entity-Based Filing (LLCs, S Corps, & Beyond)

✅ Designed for Non-Residents with US LLCs

✅ Transparent Pricing: No Hidden Fees, No Guesswork

Don’t Let Your Refund Slip Away: Just doola It

A tax refund isn’t a bonus, it’s your money. 

To unlock the biggest possible refund in 2025, you need more than software. You need a team that understands your unique setup and guides you like a partner. 

And with doola, you don’t just file taxes, you optimize them.

Sign up with doola today. Your refund-maximized future starts right now.

FAQs

Can I get a refund if I’m self-employed or a founder?

Yes, especially if you overpaid estimated taxes or qualify for credits like QBI or EITC.

How do I know if I’m missing out on deductions or credits?

Use a CPA-backed service like doola Tax Filing to review your full tax picture.

Will using doola guarantee I get the biggest refund possible?

While no provider can “guarantee” a refund, doola ensures you don’t miss deductions, credits, or filing strategies that could increase it.

What if I’m not based in the US but operate a US LLC? Can I get a refund?

Yes, if you overpaid or qualify under a tax treaty. doola can help determine eligibility.

Is it worth filing early? Will that actually increase my refund?

Filing early reduces fraud risk and gets your refund faster. It can also help with income-based credits.

How does the IRS issue refunds?

Via direct deposit, paper check, or U.S. Treasury debit card.

Can I amend my tax return if I find a missed deduction later?

Yes! You can file a Form 1040-X for up to 3 years after your original return.