8 Tips to Avoiding Financial Woes This Tax Season

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December 1, 2023

This article is Tax Professional approved

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Tax season is like that uninvited guest who shows up every year, adding just a little more spice and stress to our already bustling lives. Whether you're a small business owner, freelancer, or just managing personal finances, the complexities of tax laws and the fear of making errors can be overwhelming.

This article aims to alleviate some of that stress and provide practical, easy-to-understand tips to navigate tax season efficiently and avoid common financial pitfalls. That way, you can breeze through the paperwork and get back to running your business. 

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1. Understand your tax obligations

Before diving into anything else, you need an understanding of your tax implications. Unfortunately, taxes aren’t one-size-fits-all — different income sources each have their own tax implications. Let’s explore what you need to know below. 

Why understanding tax obligations matters

Your tax obligations vary depending on your financial situation. Are you a full-time employee, a freelancer juggling gigs, or a small business owner? Each role comes with its own set of tax rules. 

For instance, if you're employed, your employer handles much of your tax calculations, but as a freelancer, you're the captain of your tax ship. Knowing your obligations helps you steer clear of penalties and, possibly, save money.

Common tax forms and their purposes

Understanding tax forms and their purposes is the bedrock of financial success during tax season. Common tax forms to familiarize yourself with are: 

  • W-2 Form: This is your annual wage and tax statement if you're an employee. It shows how much you've earned and the taxes withheld from your paycheck.
  • 1099 Forms: There are many types of 1099 forms, but they're generally used to report income other than wages, salaries, and tips. For example, 1099-MISC is for freelance or independent contractor income, and 1099-INT is for interest income.
  • Schedule C: If you run a business or are self-employed, this form is used to report income or loss from your business operations.

2. Organize your financial documents

We get it; it can be hard to keep up with the slew of receipts and records that accumulate over the year. But, well-organized financial documents are the cornerstone of efficient tax preparation. They not only make it easier to file your taxes accurately but also to defend your deductions in case of an audit. It’s like having a well-organized toolbox; when you need a specific tool (or document, in this case), you know exactly where to find it.

How to implement an efficient document management system

  • Start Early: Begin organizing your documents at the start of the financial year, not just when tax season approaches. This proactive approach prevents last-minute scrambles.
  • Categorize Wisely: Group your financial documents by category — invoices, receipts, bank statements, etc. Tools like the Expensify Card automatically categorize expenses, so you can sort in your sleep. 
  • Go Digital: In this digital age, having a paperless system is not just convenient but also a necessity for easy access and storage. Expensify’s receipt scanner app is perfect for this. Snap a photo of your receipt, and the app digitizes and categorizes it for you.
  • Update Regularly: Make it a habit to update your document system regularly. This could be weekly or bi-weekly, depending on your business volume.

With these tools and strategies, your financial documents will be so well-organized that even Marie Kondo would be proud. More importantly, you'll be setting the stage for a smoother, more efficient tax filing process.

3. Keep track of deductions and credits

Understanding tax deductions and credits is essential for minimizing your tax liability. Deductions reduce your taxable income, while credits reduce your tax bill directly. Let’s walk through the definitions of each below: 

  • Tax deductions are expenses you can subtract from your taxable income. Think of them as discounts on your income. For instance, if you earn $50,000 a year and have $10,000 in deductions, you only get taxed on $40,000. Common deductions include business expenses, home office costs, and charitable donations.
  • Tax credits are more like gift vouchers against your tax bill. They directly reduce the amount of tax you owe, dollar for dollar. If you owe $1,000 in taxes and have a $300 tax credit, your tax bill drops to $700. Credits can be for things like education expenses or energy-efficient home improvements.

The benefits of maximizing deductions and credits

Maximizing these opportunities can significantly reduce your tax liability. This can lead to substantial savings, reducing the overall amount of taxes you pay or potentially increasing your tax refund.

To effectively track deductions and credits, you should: 

  • Stay Informed: Tax laws change, and so do the details of deductions and credits. Keep yourself updated on these changes to maximize your benefits.
  • Keep Detailed Records: Document every expense that could qualify as a deduction or credit. Store receipts, invoices, and relevant documents.
  • Categorize Expenses: When you track your expenses, categorize them according to the type of deduction or credit they may qualify for. This makes it easier to calculate your total deductions at the end of the year.
  • Leverage Technology: Take advantage of apps and expense software to simplify tracking and catch expenses that could qualify as deductions. 
  • Consult with Professionals: If you’re unsure about what you can claim, consulting with a tax professional can help. They can provide advice tailored to your specific financial situation.

By harnessing the power of deductions and credits and tracking them meticulously, you're setting yourself up for a more financially rewarding tax season. Remember, every dollar you save in taxes is a dollar that can be reinvested in your business or personal life.

4. Plan for tax payment

It's crucial to plan and budget for your tax payments well in advance. Approaching tax payments with a plan is like preparing for any major life event — it requires foresight, organization, and a bit of financial know-how. This isn't just about avoiding surprises; it's about ensuring your financial stability throughout the year.

How to plan for this year’s tax payment 

  • Review last year's return: A good starting point is to look at your previous year's tax return. It can give you a baseline of what to expect.
  • Consider changes in income: If your income has increased or decreased significantly, adjust your expectations accordingly.
  • Use online calculators: There are numerous online tax calculators available that can help you estimate your tax liability based on your income and deductions.
  • Create a tax savings account: Open a dedicated savings account for your tax payments. This separation from your regular accounts reduces the temptation to use these funds for other purposes.
  • Set up regular transfers: Treat your tax savings like a recurring bill. Set up automatic transfers to your tax savings account each month.
  • Adjust your budget: Review your budget to identify areas where you can cut back to allocate more funds to your tax savings.

By adopting these practices, you’re not just preparing to meet your tax obligations; you’re also fortifying your overall financial health. When tax season rolls around, you'll be ready to face it head-on without any last-minute financial panic.

Essential reading: How to Get Your Business Ready for Tax Season

5. Consider professional help

There are times when you can rock tax season on your own — but it’s also totally fine (and encouraged!) to seek professional help. You should consider professional help if you have a complex financial situation, have recently undergone a major life or career change, or if you have time and/or knowledge constraints.  

Types of tax advisors and accountants

There are a variety of tax professionals to choose from. We’ll break down a few helpful resources for those seeking a hand with their taxes below.

  • Hire a Bookkeeper: Bench is an online service that pairs you with a dedicated bookkeeper and provides intuitive software for managing your financials. They're an excellent option for small businesses looking for comprehensive bookkeeping and tax assistance. 
  • Certified Public Accountants (CPAs): CPAs are highly qualified in accounting and tax preparation. They can provide comprehensive tax planning and advice, especially for complex financial situations.
  • Enrolled Agents (EAs): EAs are federally licensed tax practitioners specializing in tax preparation and representation before the IRS.
  • Tax Attorneys: A tax attorney is the go-to professional for legal tax issues or disputes with the IRS.

When considering your options, it’s important to check credentials, consider the tax professional’s specialization, and always ask for references. Also, don’t be afraid to discuss fees upfront — you don’t want to be surprised with a hefty bill down the road. 

Insert Related Reading: https://www.bench.co/small-business-tax and bench.co/pricing

6. Avoid tax scams

Stay vigilant against tax scams, which are unfortunately common during tax season. Scammers tend to prey on the stress and confusion that can come with tax filing, aiming to steal money or personal information. 

The IRS compiles an annual list of the "Dirty Dozen" tax scams, highlighting the most common and dangerous tactics scammers use. Let’s break down some of these tactics to help you stay aware during tax season. 

  • Phishing: These scams involve fake emails or websites aimed at stealing personal information. They often mimic the IRS in appearance, urging you to provide sensitive data.
  • Phone Scams: Scammers may call posing as IRS agents, demanding immediate payment or personal information. They may threaten arrest, deportation, or license revocation.
  • Identity Theft: This involves using someone else’s personal information to file a tax return and claim a fraudulent refund.

Protecting yourself from tax scams

By staying informed and vigilant, you can significantly reduce the risk of falling victim to these scams. Remember, when it comes to taxes, erring on the side of caution is always the best policy. Here are a few ways you can steer clear of scams this tax season: 

  • Be Skeptical of unsolicited contacts: The IRS doesn't initiate contact with taxpayers by email, text messages, or social media to request personal or financial information.
  • Protect personal information: Don’t give out your Social Security number or bank details unless you know who you're dealing with and why they need it.
  • Use secure networks: When filing taxes electronically, ensure you're on a secure network. Avoid using public Wi-Fi for financial transactions.
  • Verify the IRS contact: If you're unsure whether a communication is legitimate, contact the IRS directly through their official channels.

7. File on time

While it might be tempting to postpone your tax payments, missing tax filing deadlines can result in penalties and interest, which means you have to pay more money in the long run. Let’s walk through everything you need to know to ensure you never miss a payment. 

Understanding tax filing deadlines and extensions

Be aware of the key dates and consider using tax software or professional services to ensure timely filing. For most individuals, Tax Day usually falls on April 15. For businesses, deadlines vary depending on the type of entity.

If needed, you can request an extension, which generally gives you until October 15 to file. Just remember that this is an extension to file, not an extension to pay any taxes you owe.

Strategies to avoid last-minute filing stress:

  • Start early: Begin gathering your financial documents well before the deadline. This gives you ample time to organize your information and address any issues.
  • Use tax software or seek professional help: Software like Bench Accounting can help guarantee accuracy. If you're using a local professional, book their services early as they get busier closer to the deadline.
  • Set personal deadlines: Aim to complete your tax filing at least a week before the actual deadline. This buffer can be a lifesaver if unexpected issues arise.


By understanding and respecting these deadlines and by implementing these strategies, you can have a smoother, penalty-free tax season.

8. Review and adjust your financial strategy

After tax season, review your financial strategy. This review can provide insights for setting goals and making informed decisions for the upcoming year. Reflect on what worked, what didn’t, and how you can make next year even smoother. 

Here’s how you can leverage this tax season to improve the next. 

Assess your financial strategy:

Take some time to reflect on the past year. Look at your tax return to understand where most of your income came from and where your major expenditures lay. Did you maximize your deductions? Were there any unexpected liabilities?

Then, assess how well you managed cash flow throughout the year and identify any patterns or areas for improvement.

Setting financial goals for the upcoming year

Let’s explore some tactics to set (and nail!) your financial goals in the upcoming year: 

  • Create a budget: Based on your insights from the tax return, adjust your budget to better align with your financial goals.
  • Set savings goals: Whether it’s for retirement, an emergency fund, or a major purchase, define clear savings goals and create a plan to achieve them.
  • Investment planning: Consider how you can better leverage investments to optimize for tax advantages.
  • Make proactive financial decisions: If you anticipate significant changes like buying a home, changing jobs, or starting a business, factor these into your financial planning.

How Bench can help 

Navigating tax season doesn't have to be a source of dread. By following these tips, you can take control of your finances, minimize stress, and potentially improve your financial situation — for years to come. With the right knowledge, technology, and professional help, you’ll be on the road to a smoother, more financially secure tax season.

At Bench, we understand the complexities of starting and running a business and that blending personal and business finances is sometimes inevitable even if it’s not in line with your business structure. Our seamless solution caters to your unique needs, providing the tools to still maintain proper and compliant books. Whether you operate as a sole proprietorship, partnership, LLC, or corporation, Bench has you covered.

Bookmark this resource: 

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This post is to be used for informational purposes only and does not constitute legal, business, or tax advice. Each person should consult his or her own attorney, business advisor, or tax advisor with respect to matters referenced in this post. Bench assumes no liability for actions taken in reliance upon the information contained herein.
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