

Estimated Taxes: When Safe Harbor Isn’t Right
Safe Harbor is the simpler way to handle estimated taxes but it isn't the right fit for everyone. If your income has shifted a lot this year, or you're expecting a big change, Safe Harbor can put you in the wrong spot: pay based on a stronger prior year and you could be handing over money you're not actually earning — cash you might need for payroll, taxes, or just running the business. Go the other way, with income up sharply this year, and you could underpay and get hit with penalties. This session is about figuring out whether that's your situation, and what to do about it.
This is the more in-depth, hands-on session. Bring your own numbers and get help calculating live.
Aneisha (bookkeeping & systems) of Yellow Sky Business Services and Megan of (Enrolled Agent and Licensed Tax Consultant) of Crayon Advisory will cover:Megan (tax professional) and Aneisha (bookkeeping & systems) will cover:
When Safe Harbor isn't the right option
How to calculate whether it's a good fit for your specific situation
What to do instead if it's not
Working through your own numbers, live, with support
We're running this in October, at the start of Q4 so you have enough time to calculate and adjust before year-end if you need to.
Information to have ready for this session
Prior Year Tax Return
Prior Year W2(s)
Retirement contributions
Health insurance withholdings
Federal & State income tax withholdings
Current year Paystub(s)
Year to Date Business Income
Year to Date Adjustments (self-employed health insurance & retirement contributions)
A note: This is Part 2 of a 2-part series, and it builds on Session 1. If you haven't been through Session 1 (or watched the replay), you may feel a step behind here.
This session has no replay, so you'll need to attend live to get support.
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How to Join Event
✅ In the event email, click the "Click here to join the meeting". This will take you to the Google Meet to join the meeting.
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