Importance of Document Organization During Tax Season

Tax Perceptions Among Generations Revealed

Every generation has unique learning preferences, even when learning about taxes. These generational differences can significantly affect how individuals approach and navigate tax season each year.

For Gen Zers, news outlets and social media platforms proved to be key sources for tax learning. Conversely, millennials rely heavily on online forums and communities and professional advice for their tax knowledge. Gen Xers still prioritize traditional news sources, while Baby Boomers lean towards government publications and seek professional guidance.

Notably, 53% of Baby Boomers prefer to manually organize their tax documents in physical files, while younger generations embrace the digital era by organizing their documents digitally. Further awareness among older generations about digital document platforms like Adobe Acrobat can help streamline the tax preparation process, providing convenience and efficiency for taxpayers of all ages.

Only 1 in 3 Freelancers and Small Business Owners Feel Confident and Prepared For Tax Season

For freelancers and small business owners, tax season carries distinct challenges. Navigating through business expenses, deductions, and the intricate web of tax regulations can be daunting.

1 in 10 small business owners admit to feeling overwhelmed and stressed when tax season rolls around, and 2% feel utterly lost and need help figuring out where to start regarding taxes. The top challenges faced by small business owners during tax season include general financial stress (42%), understanding tax laws (41%), and keeping up with changing regulations (37%).

The top three challenges faced by freelancers during tax season include filling out tax forms accurately (49%), understanding tax laws (48%), and managing general financial stress (42%). Freelancers often navigate a complex landscape of deductions, estimated taxes, and varying income sources, making tax preparation even more challenging.

Navigating tax season requires small businesses and freelancers to stay informed, seek assistance when needed, and adopt tools and strategies that suit their needs. Developing a proactive approach towards tax planning and utilizing available resources, such as Adobe Acrobat, can help both groups overcome challenges and ensure a smooth tax season each year.

54% Of Gig Workers Cite Filling Out Forms As A Top Challenge

Tax season can be a challenging time for gig workers, including delivery drivers and independent contractors, who face their own set of unique obstacles. Many gig workers have recently been relieved by the tax delay on the new payment platform tax, where they won't have to report amounts below the upcoming $600 limit for the 2023 tax year. Despite this, gig workers must be aware that they may still need to file any income received, even if they don't receive a 1099 K.

Regarding the upcoming tax season, our findings show that gig workers are most concerned about filling out tax forms accurately, navigating the news of future taxation of payment platforms like Venmo and CashApp, and understanding complex tax laws.

Gig workers can greatly benefit from incorporating digital document organization tools such as Adobe Acrobat into their tax preparation routine, especially as they gear up for the impending implementation of the new tax reporting law on cash income within platforms such as Venmo. With the deferral of the law to the 2024 tax year, gig workers have a crucial window to adapt and leverage digital solutions effectively to prepare for the following tax season; by harnessing the capabilities of tools like Adobe Acrobat, gig workers can seamlessly edit, combine, and organize their tax-related documents.

This strategic use of digital tools simplifies the tax preparation process and empowers gig workers to proactively address the forthcoming changes in reporting requirements. As gig work continues to rise and digital transactions become increasingly prevalent, embracing such tools becomes essential for gig workers to navigate tax season easily, ensuring accuracy, compliance with evolving regulations, and ultimately alleviating the stress associated with their tax obligations.

Best ways to organize tax documents

Digital document organization during tax season becomes increasingly more important every year. Adobe Acrobat is here to help you prepare for tax season in 2026. Check out these tips to keep your tax documents organized this year:

1. Create a simple digital folder system

   Organize folders by category:

   • Income
   • Expenses
   • Deductions
   • Receipts
   • 1099s
   • W‑2s
   • Business Expenses (if self‑employed)

2. Digitize everything

   • Scan paper documents using Adobe Acrobat
   • Save files as searchable PDFs
   • Rename files with clear labels (e.g., “2024‑1099‑NEC‑ClientName.pdf”)

3. Track expenses consistently

   • Keep a monthly expense log
   • Save receipts immediately by snapping a photo
   • Store digital receipts in a dedicated folder
   • Use Acrobat to combine receipts into a single PDF for each month

4. Prepare documents before meeting with a tax preparer

   You should bring:

   • All income forms
   • Expense summaries
   • Receipts
   • Identification
   • Last year’s return
   • Any IRS notices

These tips demonstrate the value of digital document organization and PDFs for tax season. Utilizing PDFs promotes efficiency, accessibility, and organization, making the tax preparation process smoother and more effective.