Journey 20 · Running a businessgrindingbuildingstewarding
The Money Side
“I got a tax bill in April that I had no way of paying.”
You become: Someone who is never surprised by a bill again
Bookkeeping, quarterly estimated tax, mileage, 1099s, and knowing when to stop doing it yourself. The unglamorous half of a trade business — and the half that decides whether it survives.
Understand
Which taxes apply to you, and when they are actually due.
Practice
Weekly bookkeeping and quarterly set-asides.
Create
Clean books and a funded tax account.
Evidence
A quarter paid on time, out of money you had ready.
Know what is coming
The April ambush happens to people who were never told there were four deadlines, not one.
- Understand30m
Learn why self-employment tax exists
As an employee, your employer paid half your Social Security and Medicare — 7.65% you never saw. Self-employed, you pay both halves: 15.3% on net earnings, on top of income tax. Write that number down. It is the single biggest reason a profitable-feeling year produces a shocking bill.
You’ll have:The 15.3% written down with what it covers.
- Understand25m
Find the four quarterly deadlines
Estimated tax is not annual. Search 'IRS estimated tax due dates' and write all four in your calendar for the year, each with a two-week warning. They are not evenly spaced quarters, which catches people out every single year.
You’ll have:Four dated calendar reminders.
- Practice45m
Work out your quarterly number
Take your expected profit, apply self-employment tax and your income tax bracket, divide by four. Recalculate each quarter against what actually happened rather than what you hoped would happen.
You’ll have:A quarterly figure you can transfer.
8 more actions · 4h 50m of work
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Keep books you can trust
Fifteen minutes a week, or a lost weekend next April. It is genuinely that binary.
- Practice20m
Book the fifteen minutes and keep it
- Practice30m
Start tracking mileage today
- Understand40m
Learn which expenses are actually deductible
- Understand35m
Handle 1099s for anyone you paid
Make it stop being your job
The point is not to become an accountant. It is to stop being ambushed.
- Understand30m
Separate profit from your pay
- Understand45m
Work out whether an S-corp election saves you anything
- Practice1h
Get a CPA before you need one
- Evidence30m
Pay one quarter on time, from money you had ready
Tools this journey uses
Several actions above run straight through these. All free, no signup.