Working together

Bookkeeping is the ongoing process of recording and organizing your financial transactions — money coming in, money going out, everything categorized and reconciled so you have an accurate picture of your business finances at any given time. Think of it as keeping score.

An accountant typically uses the records a bookkeeper maintains to do higher-level work: filing taxes, providing financial advice, auditing, and strategic planning. The two roles are complementary. A good bookkeeper makes your accountant's job easier and your tax bill less of a surprise.

Most small businesses don't need a full-time accountant, but they do need their books to be in order. That's where I come in.

You're not alone — this is incredibly common. QuickBooks is powerful software, but it's not particularly intuitive, and most people who sign up for it either use a fraction of its features or avoid it entirely after the initial setup.

The good news is it's fixable. I can audit what's in there, clean up anything that's gotten messy, and either take it over or teach you how to actually use it in a way that makes sense for your business. Some people want to hand it off entirely. Others want to learn. Both are valid, and I can support either path.

If QuickBooks isn't the right fit for your business, there are other options — we can talk through what might work better.

I hear this one a lot, and I get why it seems like it should be simple. But here's what's actually happening behind the scenes.

When I look at a bank feed, I'm not just seeing neat labeled transactions. I'm seeing things like "ACH transfer 4492" or "PYMT 00183 VENDOR" — and my job is to figure out what every single one of those means, whether it's been correctly categorized, whether it matches an invoice or a receipt, and whether anything looks off. Sometimes a transaction is split across categories. Sometimes a business owner paid a personal expense from the business account and we need to address that. Sometimes there's a duplicate. Sometimes there's fraud.

This detective work is the job. It's not inefficiency — it's diligence. When your books are accurate, you can trust them. And when you can trust your numbers, you can actually make decisions based on them.

If you're self-employed, the IRS expects you to pay taxes as you go throughout the year — not just at filing time. These are called estimated quarterly taxes, and a lot of small business owners either don't know about them or ignore them until they get hit with a penalty.

Here's a simple way to think about it: set aside roughly 25–30% of every payment you receive into a separate savings account. Don't touch it. That's your tax money. It belongs to the government; it just hasn't left your account yet.

More precisely, your estimated taxes are based on your net income (revenue minus legitimate business expenses) multiplied by your self-employment tax rate (15.3% for Social Security and Medicare) plus your income tax rate, which depends on your total income and filing status. Vermont has its own income tax on top of federal, so Vermont-based business owners need to file and pay estimated taxes at both the state and federal level.

The quarterly deadlines are typically mid-April, mid-June, mid-September, and mid-January. Missing them doesn't mean you owe more tax — it means you may owe a small underpayment penalty. Still worth avoiding.

If you're not sure where to start, this is exactly the kind of thing I can help you work through in a consulting session.

I understand the impulse, and honestly, there's something almost poetic about it as a form of quiet resistance to a tax system that's structurally designed to benefit the wealthy. You're not wrong that the system is extractive, and I'm not here to lecture you about playing by rules that were never written in your favor.

That said — limiting your income to avoid taxes is usually a way of keeping yourself small in order to avoid giving money to systems you don't like. The math often doesn't work in your favor. If you make $10,000 more, you might owe $2,500 in taxes — but you still have $7,500 more than you did before.

What I'd encourage instead is understanding where your tax dollars go, and making intentional choices from there. If you're interested in war tax resistance — the practice of withholding a portion of federal taxes that would fund military spending, and redirecting that money to causes you believe in — that's a real thing people do, and it's worth learning about. The National War Tax Resistance Coordinating Committee is a good place to start. It's a political act, and it carries legal risk, and it's not something I can advise you on as a bookkeeper — but it's a far more intentional form of resistance than just making less money.

The bottom line: keeping yourself poor to avoid feeding a system you oppose is a sacrifice that mostly hurts you. Let's talk about what you can do with the money you actually earn.

Hold on, dear friend!

The S corp tax strategy is real — but it's widely misunderstood, and it gets promoted online in a way that makes it sound like a no-brainer for anyone who is self-employed. It isn't.

Here's what the strategy actually involves: as an S corp, you pay yourself a "reasonable salary" (which is subject to payroll taxes), and take the rest of your profits as distributions (which are not subject to self-employment tax). The savings come from not paying self-employment tax on the distribution portion. Sounds great, right?

The problem is that running an S corp is significantly more complex and expensive than operating as a sole proprietor or single-member LLC. You have to run payroll. You have to file a separate corporate tax return (Form 1120-S), which costs more in accounting fees. You have to maintain corporate formalities. And if your profits aren't high enough, the savings from avoiding self-employment tax will be completely eaten up by those additional costs and complexity.

Most financial professionals suggest you need to be netting at least $40,000–$60,000 in profit before the S corp election even starts to make sense. Below that threshold, you're likely paying more in accounting fees than you're saving in taxes.

If you're at a point where this is genuinely worth considering, let's talk — and I'll refer you to an accountant who can help you model it out. But please don't do it just because someone on YouTube made it sound easy.

This is one of those questions where the answer is almost always: it depends, and probably not as often as people think.

Nonprofit status (specifically 501(c)(3) status with the IRS) is a legitimate and powerful tool for organizations whose work is charitable, educational, religious, scientific, or otherwise in the public interest. The benefits are real: donations to you become tax-deductible for donors, you don't pay federal income tax on revenue that's used for your mission, and you become eligible for many grants and foundation funding sources that are restricted to nonprofits.

But nonprofit status is not a tax dodge, and it doesn't mean the money isn't real. A nonprofit still pays payroll taxes. Staff still pay income tax on their salaries. And running a nonprofit comes with significant regulatory overhead: annual reporting requirements, board governance obligations, restrictions on how money can be used, and public disclosure of your finances.

The bigger question is whether your work is actually charitable in nature, and whether the structure fits your goals. A lot of mission-driven businesses — social enterprises, worker cooperatives, benefit corporations — do deeply valuable community work without being nonprofits, and that's completely valid. The structure should serve the mission, not the other way around.

If you're genuinely weighing this, I'd encourage you to talk to a nonprofit attorney in addition to a bookkeeper or accountant. It's a decision worth making carefully.

The first step is a free 30-minute discovery call. We'll talk through what's going on with your books, what kind of support you're looking for, and whether we're a good fit. There's no pressure and no commitment — just a conversation. If it makes sense to work together, I'll put together a proposal outlining what I'd recommend and what it would cost. From there, you decide. You can book directly through the website, or just shoot me an email if you'd rather start that way.