Back Taxes: Myths & Facts (and Why You’re Not Going to Jail)

It's easy to put off taxes---until the years pile up, and suddenly, the task feels impossible. But you don't have to do it alone. What if I told you that catching up on back taxes is simpler than it seems, and getting started today could save you from bigger problems tomorrow?

On this episode of Become Sensible, I introduce my new co-host, Anh, and together we dive into the story of “Samantha”, a graphic designer who came to us with three years of unfiled taxes. We walk through the exact steps I take with clients to prioritize the oldest tax year, minimize penalties, and catch up on bookkeeping. 

"The best time to start is yesterday, and the second-best time is today." 

If you've been avoiding your taxes out of fear or overwhelm, I want to assure you---it's never too late to turn things around. 

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Timestamps

• 0:00 - Introduction to the episode and my new co-host, Anh  
• 2:00 - “Samantha's” story: A graphic designer with three years of unfiled taxes 
• 5:15 - Where do you even start if you haven't filed taxes in years?  
• 8:30 - Should you manage your taxes or hire a CPA?  
• 10:45 - Using AI-powered accounting tools for faster tax prep  
• 14:00 - How does the IRS calculate penalties and interest?  
• 17:00 - Can you request a waiver for penalties?  
• 20:45 - Fixing automatic IRS filings with amended returns  
• 24:30 - How important is keeping up with bookkeeping?  
• 27:00 - Encouragement: "Better late than never"  
• 30:00 - Final thoughts: Don't be ashamed---just start today

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