Writer
Theo Whitfield
Former CPA, freelance bookkeeper · Asheville, NC
Theo spent twelve years as a CPA at a regional firm in North Carolina before leaving in 2020 to work directly with small operators. He now manages monthly bookkeeping and tax planning for about two dozen solo businesses. He writes about money topics for people who would rather not think about them.
6 articles
Articles by Theo
The 2026 freelance tax reset, decoded
The One Big Beautiful Bill Act took effect this January. Here is what actually changes for a one person business, and what looks big but is mostly noise.
The ACA subsidy cliff is back. Here is what to do about it.
Enhanced premium tax credits expired at the end of 2025. For self employed earners above 400% of the poverty line, the cost of insurance just doubled or tripled. Here is the practical playbook.
Quarterly taxes for US freelancers, in plain English
What estimated taxes are, who owes them, when they are due, and how to stop being terrified of the IRS.
Sole proprietor or LLC: which one actually makes sense
A practical look at the two most common business structures for solo operators in the US, and how to choose between them without overthinking it.
Bookkeeping for one person businesses, without the tears
A minimum viable bookkeeping system you can actually keep up with, and the few habits that make tax season a non event.
The freelance financial buffer: how much cash you actually need
Why three months of expenses is the wrong target for freelancers, and what to aim for instead.