Writing

The answers I give clients most often.

Three subjects, because they're the three things that actually determine whether a service business feels stable: getting paid, choosing tools that don't fight you, and staying ready for tax season.

Getting paid

Invoicing & cash flow

The mechanics of getting money in the door on time.

Getting paid Clients who won't pay: the playbook I give every business owner

The exact sequence, from invoice terms through the final demand letter, that gets most overdue invoices paid without a lawyer and without torching the relationship.

Reviewed September 2026 · 8 min read

PLANNED FOR THIS PILLAR, write these next, roughly in this order: (1) What to put on every invoice, and the omission that delays payment two weeks. (2) Late fees: what's enforceable, what to charge, how to automate. (3) Recurring invoices: the 20-minute setup that ends monthly billing. (4) Should you accept credit cards? The real math on processing fees. (5) The weekly five-minute cash-flow check.

Software

Tools & setup

Honest comparisons, including when the answer is "neither."

Comparison FreshBooks vs. QuickBooks: a bookkeeper's honest comparison

QuickBooks does more. FreshBooks does less, better. Here's how I decide which one a client actually needs, including the cases where I tell people to skip FreshBooks entirely.

Reviewed September 2026 · 9 min read Review FreshBooks review: what it does well, and where it falls short

An honest review after setting clients up on it, including the four real limitations you should know about before you subscribe.

Reviewed September 2026 · 7 min read

PLANNED FOR THIS PILLAR: (1) FreshBooks vs. Wave, when free is enough and when it costs you. (2) The best invoicing setup for contractors and trades. (3) Spreadsheets vs. software: the real cost of the free option. (4) How to switch accounting software without losing your records.

Taxes

Taxes & compliance

Written for business owners, not for accountants.

PILLAR NOT YET STARTED. Highest-value posts to write, in order: (1) Quarterly estimated taxes explained for contractors, publish two weeks before a deadline. (2) The expense categories freelancers miss. (3) 1099 and W-2 income in the same year. (4) What "tax-ready books" actually means. (5) A Queens, NY-specific freelancer tax guide, this is your least competitive, highest-authority post. (6) Receipts: what the IRS actually requires you to keep.