I have a small side business. Does that mean I need a CPA?

Not automatically. One 1099-NEC, a short list of expenses, no equipment purchases, and no employees is still mostly data entry, and software handles a Schedule C at that scale. It changes when you buy assets that have to be depreciated, when profit gets large enough that an S-corp election is worth modeling, or when nobody has been sending the quarterly Form 1040-ES payments due April 15, June 15, September 15, and January 15, and the underpayment penalty has been accruing all year.

Can I prepare it in software and just have you review it?

I would rather prepare it than review it. Reviewing a finished return means checking the answers to questions I never got to ask, and the expensive errors usually live in whatever the interview never raised. If there is one specific position you want a second opinion on, that is a conversation, and it starts with the contact form.

My return was complicated one year and now it is simple again. Do I still need a CPA?

Maybe not, and I will say so. Check first whether anything carries forward: a capital loss carryover, a suspended passive loss on Form 8582, a depreciation schedule, basis in an entity, IRA basis on Form 8606. Consumer software will not reconstruct those from a prior-year PDF, and a carryforward that quietly disappears is a deduction you already paid for.

When You Need a CPA, and When You Honestly Don't

Plenty of returns do not need me. If you have one W-2, you take the standard deduction, and the most complicated thing that happened all year was a savings account paying interest, good consumer software will get that return right. Paying a CPA for it buys you a tidier PDF.

Better to hear it here than after you have signed an engagement letter. So here is the line as I actually draw it, including the half of it that points away from me.

When the software answer is the right answer

The standard deduction is what makes most simple returns simple. For 2025 it is $15,750 for a single filer and $31,500 for married filing jointly, per the IRS, and those figures move every year. If your mortgage interest, state and local taxes, and charitable giving are nowhere near that number, you are not itemizing, and there is no strategy hiding in your return. There is a total, a withholding figure, and the difference between them.

Software handles that. It also handles the parts of a return that look intimidating and involve no judgment at all: a 1099-B that imports cleanly, one state, student loan interest, a child tax credit with no custody question attached to it.

$15,750Standard deduction, single filer, 2025
$31,500Standard deduction, married filing jointly, 2025
$23,625Standard deduction, head of household, 2025

Returns I would tell you to keep doing yourself

None of these need a CPA in an ordinary year.

One W-2, the standard deduction, and some bank interest
A joint return where both spouses are employees and nothing changed from last year
A brokerage account that imports cleanly and holds nothing exotic
A first job, one state, one employer, no dependents
Social Security, a pension, and an IRA distribution that shows up on a 1099-R every January

What the software is actually doing

Consumer software is an interview. It asks a long list of questions and then optimizes the return you describe to it. Answer accurately and it computes a correct result for the facts you supplied. That is worth what it costs.

The gap is everything you did not know to mention. It does not know you rolled an old 403(b) into a traditional IRA in March, which is why the backdoor Roth conversion you did in April came out mostly taxable under the pro rata rule, and it does not ask whether Form 8606 was ever filed for the year you first had basis. It does not know a colleague told you to open a Schedule C so you could run CME, license renewals, and society dues through it, and that because those costs belong to your W-2 job, that Schedule C is an invented business rather than a deduction. It will let you file it. It has no reason to object.

Software optimizes what you describe. A preparer earns the fee by noticing what you left out, and asking about it before it becomes a number on a filed return.

Where a return stops being data entry

Returns get hard in one particular way. They stop being transcription and turn into a series of choices where two defensible answers produce two different tax bills. Depreciation method on Form 4562. Reasonable compensation for an S-corp owner. Which state gets to tax income you earned in three of them. Whether a rental loss is suspended on Form 8582 or deductible this year. None of those have a lookup answer.

The situations that turn a return into a set of decisions

Self-employment income, including 1099-NEC work picked up alongside a W-2 job
An entity in the picture: an S-corp, a partnership, or a K-1 that shows up in September and withholds nothing
Rental property, where basis, depreciation, and the passive loss rules all interact
Filing in more than one state, or moving between states mid-year
Equity compensation: RSUs vesting, an ISO exercise reported on Form 3921, an ESPP sale with a holding period attached
A life event that changes filing status, dependents, or residency
An IRS notice, an exam, unfiled years, or a balance sitting in collections
Any year that looks materially different from the one before it

Change is the trigger, not income

Income level is a poor reason to hire a CPA. Change is a good one. The year you started the business, sold the rental, exercised the options, moved states, got married, or took your first K-1 is the year the return contains real decisions. The year after that, once the structure has settled, may be routine again, and you should feel free to treat it that way.

Change also comes with a calendar problem. Most of what saves money has to happen before December 31. By April 15 the year is closed and the arithmetic is already fixed, whoever is doing it. That is why planning and preparation are separate services, and planning is the one people skip.

What hiring me does not buy you

A CPA does not make a weak position strong. If a deduction will not hold up, my signature on the return changes nothing except the number of people who were wrong about it. I will tell you when something is solid, when it is genuinely arguable, and when it is not worth the exposure.

A CPA also cannot go back in time. If the property sold in June and we first speak in March, the planning window closed nine months ago, and no amount of preparation skill reopens it.

Here is the one thing a CPA can do that no software does: file a Form 2848 and deal with the IRS directly on your behalf. A notice, an exam, six unfiled years, a lien. Those are representation problems, and re-running an interview does not solve them.

Hunter did my taxes last year. Super professional, straightforward, prompt, and fair. I will never do my own taxes again.

Josh

If you land on my side of the line

Then the next question is what it costs, and I would rather answer that before you commit to anything. The fee comes from objective factors, all of them countable things: income sources, states filed, schedules and forms required, entities involved, transaction volume, prior-year cleanup. You get a written estimate before any work begins, and the final fee is set when the return is complete, up or down, with the reason shown. The scoring and the sequence are laid out in full.