Why this decision is harder than it looks
Every year, millions of people sit down with tax software, open a folder of receipts, and ask the same question: is this the year I finally hire someone? The answer depends less on how much money you make and more on how complicated your financial life has become.
Filing your own taxes makes sense when your income comes from one or two clear sources and your deductions are simple. Hiring a professional makes sense once your situation has moving parts: a business, rental property, investments across multiple accounts, or income from more than one state or country. The line between those two categories is where most people get stuck.
Start with a complexity count, not a dollar figure
A common mistake is deciding based on income alone. A salaried employee earning a high salary with no side income can often file cleanly on their own. Meanwhile, someone earning far less but running a small business, freelancing across state lines, or holding a mix of investment accounts may already be past the point where software alone is reliable.
Count your complexity points instead of your income:
- More than one source of self-employment or 1099 income
- Rental property, even a single unit
- Stock sales, crypto transactions, or equity compensation
- A move between states during the tax year
- A life change: marriage, divorce, a new child, an inheritance
- Any foreign income or foreign accounts
One or two points and you’re probably fine on your own. Three or more, and the time you’d spend getting it right yourself starts to cost more than a professional’s fee.
What software actually catches, and what it doesn’t
Tax software is built to ask you questions and apply the answers to a form. It’s good at catching math errors and standard deductions you might forget. It is not good at catching the deduction you didn’t know existed because you never got asked the right question.
This is the real gap between filing yourself and hiring someone. A person with expertise in tax planning isn’t just filling in boxes; they’re looking at your full financial picture and asking what you could be doing differently next year, not just this one. Armik Aghakhani, a CPA and managing partner at Chartered International LLP in Los Angeles, works with clients on exactly this kind of forward-looking planning, tax strategy that accounts for a business, an investment portfolio, or income that crosses borders, rather than a single year’s return in isolation.
Questions to ask yourself before you decide
Did last year’s return surprise you? If you owed more than expected or missed a deduction you found out about later, that’s a sign your situation has outgrown a do-it-yourself approach.
Do you have income you’re not sure how to categorize? Gig income, crypto gains, and rental income each have their own rules. If you’re guessing, you’re at risk.
Would an audit worry you? Not because you did anything wrong, but because you’re not confident you could explain every line if asked. A professional’s file notes and documentation habits make that conversation much easier.
Is your time worth more elsewhere? Some people enjoy the process of doing their own taxes. Most don’t. If a weekend of frustration is the actual cost of saving a preparer’s fee, that math doesn’t always favor doing it yourself.
A middle path exists
You don’t have to choose all or nothing. Many people file their own straightforward return most years and bring in a professional only in the years something changes, a home sale, a new business, an inheritance. Others use a professional once to set up a system and then handle routine filing themselves after that.
The point isn’t that one approach is universally better. It’s that the decision should follow your actual financial complexity, not a vague sense of which stage of life you’re supposed to be at. Look at your own list of complexity points, be honest about how much time you have, and let that decide it.
