Making Tax Time Less Terrible: A Year-Round Approach

When I talk to business owners, there's one time of year that consistently stresses them out: tax season. They're already juggling their business and personal life, and suddenly they need to add "do my taxes" to their endless to-do list.

I get it. When I worked as a freelance sign language interpreter, I thought tax season had to be a stressful rush to gather documents and total my profits.

But here's the thing: it doesn't have to be. It really doesn't!

 

A Different Approach

Imagine this: It's January, and your books are already ready for your accountant. No rushing around finding old receipts in your email inbox. No late-night spreadsheet sessions. Your P&L is just... ready.

This isn't a fantasy - it's what happens with regular bookkeeping. If your business is newer, quarterly bookkeeping might be enough. But for most businesses, monthly is the way to go. Here's why:

  • You record income and expenses while they're fresh in your mind (so you actually remember what that Walmart purchase in February was for)

  • You see your profits throughout the year instead of getting surprised next tax season

  • Your records stay organized naturally instead of becoming a year-end project

 

The Hidden Benefits of Year-Round Bookkeeping

Regular bookkeeping doesn't just make tax time easier - it opens up opportunities:

 

Tax Planning:

  • Your accountant can estimate taxes before year-end

  • You have time to plan for tax payments

  • You might find ways to reduce your tax bill

  • No surprises during an already busy season

 

Professional Collaboration:

  • Your bookkeeper and accountant can work together

  • Tax preparation becomes smoother

  • Everyone has what they need before busy season

  • You get better support from your financial team

 

 

Making the Switch

Ready to turn tax season from a stressful mess to a peaceful period? You have options:

  • DIY monthly bookkeeping (if you have the time and interest)

  • Outsource to a bookkeeper (if you'd rather focus on running your business)

 

The key is starting now, not waiting until next tax season.

Author | Aneisha - Writer and Bookkeeper

Aneisha Velazquez is a bookkeeper and clarity guide who helps neurodivergent-led businesses stop fighting their numbers and start trusting themselves.

Having experienced firsthand the pressures different-brained entrepreneurs face in systems not built for them, she brings compassion to money conversations and normalizes the mess — making finances feel less overwhelming and far more manageable.

She’s the founder of Yellow Sky Business Services and writes the newsletter The Peaceful Pocket, where she explores making business more neurodivergent-friendly, money tips with context, and stories and behind-the-scenes as an AuDHD founder.

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