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What should you delegate?

Jan 28, 2026

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10 min read

What should you delegate?

Delegating sounds great... on paper. But it’s not always easy.

Jill James
Jill James
No, you can’t wait until the midterms

Jan 21, 2026

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11 min read

No, you can’t wait until the midterms

We were already dealing with a lot. This week is different.

Jill James
Jill James
Important 1099 & W-2 tips for Feb. 2 deadline

Jan 15, 2026

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9 min read

Important 1099 & W-2 tips for Feb. 2 deadline

If checking boxes calms, this tax task has got you

Jill James
Jill James
Is it just a rough patch?

Jan 7, 2026

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14 min read

Is it just a rough patch?

You’ve got more going out than coming in... what now?

Jill James
Jill James
Kicking this one into the rearview

Dec 31, 2025

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9 min read

Kicking this one into the rearview

2025, we punt you toward a black hole

Jill James
Jill James
Jill James Wrapped

Dec 24, 2025

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9 min read

Jill James Wrapped

The “urgent” email you need to make your escape

Jill James
Jill James
It’s my 50th birthday

Dec 18, 2025

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11 min read

It’s my 50th birthday

When enough things change at once, you don’t get to stay on autopilot.

Jill James
Jill James
Marriage, moving, delegation, and panic

Dec 10, 2025

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10 min read

Marriage, moving, delegation, and panic

‘Tis the season to answer your biggest questions.

Jill James
Jill James
Love deductions? File your 1099s

Dec 4, 2025

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6 min read

Love deductions? File your 1099s

Keep January running on rails

Jill James
Jill James
Your 401(k) deadline is Dec. 31

Nov 26, 2025

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7 min read

Your 401(k) deadline is Dec. 31

This is one of those decisions that pays you back in ways your future self will actually feel.

Jill James
Jill James
Can you save on taxes as an S-corp?

Nov 19, 2025

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9 min read

Can you save on taxes as an S-corp?

Good tax move, bad tax move edition

Jill James
Jill James
Should you wait to buy health insurance?

Nov 13, 2025

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6 min read

Should you wait to buy health insurance?

Cut through the nonsense

Jill James
Jill James
...
The Jill James

The Jill James

It’s time to move from founder to CEO.


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