Quarterly Taxes for High Earners: What, Why and How To Plan Ahead

Tax season might be in the rearview mirror, but if you're self-employed or earn income outside of a regular paycheck, quarterly estimated taxes are still very much on your radar. We're showing you how it all fits together — what they are, who needs to pay them, and how to calculate what you owe. Learn key dates to remember, simple ways to estimate your payments, how to use the IRS's "safe harbor" rule to avoid any unexpected penalties, and simple strategies to avoid underpaying and giving the government an interest-free loan. It's all about staying ahead without stressing out — or paying more than you have to. Key moments: (01:15) W-2 employees have taxes automatically deducted, while 1099 workers must save and plan on their own (06:28) Simple ways to estimate your tax bill without getting lost in spreadsheets or complicated calculations (17:21) The four big tax due dates to circle on your 2025 calendar right now (20:18) The IRS safe harbor rule helps you avoid penalties, even if your estimates aren't perfect Like the show? There are several ways you can help! Follow on Apple Podcasts, Spotify or Amazon Music Leave an honest review on Apple Podcasts Subscribe to the newsletter Feeling helpless when it comes to your student loans? Try our free student loan calculator Check out our refinancing bonuses we negotiated Book your custom student loan plan Get profession-specific financial planning Do you have a question about student loans? Leave us a voicemail here or email us at [email protected] and we might feature it in an upcoming show!