How to De-Stress Estimated Taxes with One Simple System
A calming 4-step ritual for small business owners, creatives, and coaches.
Let’s talk about one of the least sexy — and most stress-inducing — parts of running your own business: estimated tax payments.
If you’re a sole proprietor, single-member LLC, coach, creative, or side hustler… and you’re earning consistent income, chances are you’re required to make quarterly estimated tax payments. But if the thought of those deadlines gives you a little anxiety spike, you’re not alone.
The good news? There’s a calm, repeatable way to handle your taxes without panic, confusion, or last-minute scrambling.
Let’s break it down.
The Truth About Estimated Taxes
Roughly 83% of U.S. small businesses are taxed as “pass-through” entities — which means the income from your business flows through to your personal tax return. This includes sole proprietors, most LLCs, and S-corp owners.
The IRS expects you to “pay as you go” throughout the year — via quarterly estimated tax payments — so you’re not hit with a big surprise (and big penalties) when you file your annual return.
And yet…
The Reality? Many Business Owners Are Getting Penalized
In 2023 alone, nearly 15 million taxpayers were penalized for underpaying or paying their estimates late.
That’s millions of dollars wasted in fees and interest — not because people were irresponsible, but because they were overwhelmed, confused, or simply didn’t have a system in place.
Why We Avoid It (Even When We Know Better)
If you’ve found yourself skipping a payment or pushing it to the last minute, it’s probably not a lack of discipline — it’s a lack of structure.
Common reasons we avoid quarterly tax payments:
It feels too complicated
We forget the deadlines
We don’t have the cash ready when the payment is due
And this is exactly where the Zen Money Method can help.
The Zen Money 4-Step Estimated Tax Ritual
This is the what I recommend to all my private clients and teach inside the Zen Money Map program — and it works, beautifully.
1. Print your quarterly payment slips when you get your tax return. Most tax prep software (or your accountant) will give you Form 1040-ES with payment vouchers. Download them, print them, and keep them visible.
2. Pre-write your checks and address the envelopes. Yes — even before you’ve earned the income. Dated appropriately, these act as gentle placeholders and reminders. Place them somewhere visible or keep them with your calendar.
3. Set aside 25–30% of each income deposit into a dedicated tax savings account. This ensures the money is there when it’s time to send the check — and keeps it mentally and emotionally “off-limits” from everyday spending.
4. Mail each quarterly payment a week before the due date. Use your calendar to set a reminder the week prior. You can even use automatic bank bill pay if you prefer a digital route.
Why This System Works
You avoid stress and penalties
You don’t have to scramble for cash
You create a reliable rhythm that builds trust with your business and your money
Instead of trying to outguess the IRS or waiting until the last minute, this ritual lets you handle your taxes with confidence — and then get back to doing what you love.
Ready to Make Your Tax Work Feel Lighter?
If you’re ready to set up systems like this for your income, offers, and client flow — the Zen Money Biz Bundle is for you. It’s designed to help you simplify your business finances, price your brilliance, and keep your cash flowing with less effort and more clarity.
→ Learn more + grab the Biz Bundle here for just $7.
(Why so little? I wanted to make it as easy as possible for you to get your hands on my 5 best resources so you can jumpstart your biz asap!)
Talk soon,
Liz
