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Raise Your Hand If You Do This
Behind the scenes, founders often fall into a few common patterns when handling their Quarterly Taxes.
See if one sounds familiar.
1. “My accountant gave me a number, so I pay it.”
You trust the expert. You send the money.
2. “I wait until the deadline and send what feels survivable.”
You look at your bank balance.
You do some mental gymnastics.
You send the amount that doesn’t break anything.
3. “I overpay on purpose so I don’t have to think about it.”
You treat the IRS like an involuntary savings account.
It keeps you compliant…
4. “I kind of avoid it and deal with it later.”
You miss a payment.
You promise yourself that next year will be different
If you’re nodding at any of these, good. That’s the point.
Founders don’t struggle with paying quarterlies.
They struggle with confidence.
The One Upgrade Calm Founders Make
Founders who feel calmer about quarterlies don’t do anything fancy.
They don’t model scenarios.
They don’t perfect the math.
They make one upgrade:
👉 They stop guessing each quarter and start using a simple rule.
Not a perfect rule.
A good-enough rule.
Something like:
“I always set aside X% as money comes in.”
“Quarterlies come from that account, not my operating balance.”
“If I need to adjust, I adjust, but I don’t start from zero every time.”
That’s it.
The relief doesn’t come from precision.
It comes from removing the decision.
What This Upgrade Actually Changes
Once you’re no longer reinventing the wheel every 90 days:
Quarterlies stop hijacking your brain
You stop bargaining with your bank balance
You stop wondering if everyone else has this figured out
You stop feeling like taxes are a surprise attack
They become… expected.
Not fun.
But manageable.
And that’s a win.
What This Article Is Not Telling You to Do
Let’s be clear.
This is not about:
Optimizing to the last dollar
Never overpaying again
Becoming a tax expert
Getting it “perfect.”
Quarterly taxes don’t need perfection.
They need containment.
The goal is not to love quarterlies.
The goal is to think about them less.
Community Note
Founder, everyone has a quarterly tax story they don’t put on Twitter.
The payment felt wrong.
The quarter they overpaid.
The one they definitely underpaid.
The system that finally made it tolerable.
Reply and tell us:
Which camp were you in?
What finally made quarterlies easier (even a little)?
What do you wish someone had told you earlier?
We’ll fold the most honest stories into the NestLedger Playbook, so fewer founders feel like they’re doing this alone.
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