The archive
All articles
21 pieces on the craft and business of working for yourself. Sorted newest first.
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.
How to set freelance rates that actually pay your bills
Most pricing advice for freelancers starts with the wrong number. Here is a more honest way to work out what you should charge.
The middle of the freelance market is hollowing out
Freelance writing volume dropped 32% in the last year. The cheap end of creative work is collapsing. The high end is doing fine. Where you land depends on a single question.
When AI makes you faster, hourly billing eats your business
If a 10 hour project is now a 4 hour project, hourly billing means a 60% pay cut for the same outcome. The math behind why value pricing is no longer optional.
The freelance contract checklist
The clauses that actually matter when a project goes sideways, explained in plain English by people who have been on both sides of one.
Working mostly for one client? The rule changed. The risk did not.
The DOL proposed a new independent contractor rule in February. The 2024 rule is still in effect for now. Either way, the pattern that gets freelancers reclassified as employees is the same one.
The cold email is dying. Here is what is replacing it.
Reply rates are at all time lows, AI generated outreach is everywhere, and inboxes are functionally hostile. The outbound channels that still work look almost nothing like the old playbook.
Why scope creep happens, and what to do when it does
Scope creep is rarely about bad clients. It is about unclear scope. Here is how to spot it early and handle it without burning the relationship.
Quiet burnout: the solo business problem you stop noticing
Most freelancer burnout is not the dramatic kind. It is the slow erosion of energy, taste, and judgment that happens when you work alone for too long. Here is what actually helps.
Getting paid on time without becoming the annoying one
Late invoices are mostly a process problem, not a client problem. Here is a calm, repeatable system for collecting on time.
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.
How to find your first five clients without a network
Most advice for finding freelance clients assumes you already know people. Here is what to do when you do not.
Productized services vs. hourly work: which one fits your business
A clear look at three common ways to package freelance services, and when each one is the right fit.
Hiring your first contractor without making a mess of it
The first time you bring in help is harder than it looks. Here is how to do it without destroying your margins, your work quality, or your sanity.
When (and how) to raise your rates
Most freelancers wait too long, then raise rates badly. Here is a calmer way to do it that does not blow up the business.
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.
Marketing for people who hate marketing
If selling yourself makes your skin crawl, the answer is not to push through. It is to pick a strategy that does not require you to.
How to say no to bad clients without burning bridges
The hardest skill in freelancing is not saying yes. It is saying no early enough that you do not regret saying yes.