Episode Details

Filing taxes is one of those things we’re all expected to figure it out on our own. Unfortunately, this often means it can be confusing, frustrating, or even downright terrifying.In this episode, we pull back the curtain on their real-life tax experiences, from our first terrified attempts at TurboTax to navigating the complexities of self-employment taxes. 

We’ll also:

Bust common tax myths, including what a “write-off” actually is and how tax brackets work

Share personal stories of surprise tax bills

Offer practical advice for building confidence during tax season 

Help you figure out when it’s time to outsource 

Whether you're an employee or business owner, a DIY filer or a CPA enthusiast, this honest conversation will help you approach tax season with less anxiety and more clarity.

✨ Episode Highlights ✨

• [02:00] Our tax journeys over the years, from nervous first-time filers using TurboTax to business owners who outsource
• [10:00] Common tax filing mistakes, including those we’ve made over the years
• [12:00] How procrastination and anxiety affect our approach to tax season, and how organization can help you get a hold on tax stress
• [16:00] Tax myths and misunderstandings, including why a big refund isn't always good, how tax brackets actually work, and why “tax write-offs" aren’t what most people think
• [25:00] DIYing your taxes vs. getting professional help 
• [30:00] Talking about taxes with partners, friends, and other business owners, and how to build confidence in tax-related conversations

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