Vol. 01 · Issue 04

The Smart Money — Weekly personal finance dispatches

Personal finance for people who want to be great with money — written by the friend who already is.

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Side Hustle DeskIssue #25 · Jun 28

Your first 1099 year: the four moves nobody teaches you.

The tax bill is coming. The retirement account is easy. The bookkeeping is boring. The mindset is the hard part.

Move one: the day a client pays you, sweep 30% into a separate high-yield savings account labeled TAXES. Don't touch it. That money isn't yours; you're just holding it for the IRS.

Move two: open a Solo 401(k) before December 31 of your first profitable year. You don't have to fund it yet — but the account has to exist. This one deadline separates the people who get to save $60K+ tax-advantaged from the people stuck at $7,000 in an IRA.

Move three: get boring bookkeeping software and reconcile it every Friday for fifteen minutes. Not monthly. Weekly. This one habit prevents 90% of the panic in April.

Move four: pay yourself an actual salary from the business to your personal account on a schedule. Stop letting the business account be your checking account. The mental separation is the whole game.

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