Shore Thing

A lot of small business owners treat their pricing like it’s a moral statement about their own worth, which turns a straightforward business decision into an emotional one every single time it needs revisiting. Let’s take the emotion out of it for a minute. Your rates aren’t a referendum on how much you deserve. They’re a number that needs to cover your actual costs, your actual time, your actual expertise, and leave enough left over for the business to be sustainable — inclu

If you’re the only member of your LLC, you might assume an operating agreement is something for businesses with partners — a document to divide equity and settle disagreements between people who aren’t you. Since there’s no one to disagree with, why bother? Here’s why. It’s not really about disagreements. It’s about proof. An operating agreement spells out how your LLC actually operates — ownership, management structure, how decisions get made, what happens if you bring on a

Nobody sits new business owners down and says: hey, you might owe the IRS four times a year now, not once. So let’s have that conversation before the penalty notice does. When you work for someone else, taxes get taken out of every paycheck automatically. You barely think about it. When you work for yourself, nobody’s withholding anything — which means the responsibility for sending that money to the IRS throughout the year now belongs to you. That’s what quarterly estimated

“Monthly close” sounds like something a large company’s accounting department does with a lot of ceremony. For a small business, it’s a much smaller thing — but skipping it is exactly how books quietly drift from accurate to fictional over the course of a year. What it actually is. At the end of each month, you (or your bookkeeper) confirm that every transaction has been recorded, everything is categorized correctly, and your accounts have been reconciled against your actual

Ask a travel agent whether they have errors and omissions insurance and you’ll sometimes get a confident yes, sometimes a confident no, and surprisingly often: “I think my host agency covers that? I’m not totally sure.” That “not totally sure” is the problem I want to address. What E&O insurance actually is. Errors and omissions insurance covers you if a client claims you made a mistake, gave bad advice, or failed to do something you were supposed to do in the course of booki

There’s a specific kind of business advice that circulates endlessly in small business Facebook groups, and some of it is genuinely useful. A lot of it is confidently wrong, delivered by someone who did one thing once and is now certain it’s universal law. I don’t say this to be dismissive of community advice generally — some of it is great, and peer support matters. I say it because “someone in a group told me” is, alarmingly often, the actual foundation of a decision that s

Mention the home office deduction to a small business owner and watch them get nervous, like they’ve said a phrase that triggers an automatic IRS response. I understand where this comes from — it has a reputation as an audit magnet, mostly built on outdated advice. Let’s actually look at it. What it is. If you use part of your home regularly and exclusively for business, you may be able to deduct a portion of your home expenses — a slice of your rent or mortgage interest, uti

Getting your bank account connected directly to QuickBooks Online feels like a small technical step, but it’s the difference between bookkeeping that stays current automatically and bookkeeping that depends on you remembering to do something manually every month. What the bank feed actually does. Once connected, transactions flow into QuickBooks automatically as they happen in your actual bank account — no manual download, no CSV import, no risk of forgetting to do it for thr

Quick, honest question: do you know if your LLC owes an annual filing to the state, and if so, whether you’ve actually done it this year? A lot of business owners don’t, and it’s an easy thing to lose track of — you form your LLC once, in a burst of paperwork and relief, and then assume you’re done with the state unless something changes. But depending on your state and how your LLC is taxed, there can be an ongoing filing requirement that has nothing to do with your income t

At some point, your business might grow enough that you need help — someone to answer emails, manage social media, handle overflow bookings. And the moment you bring someone on, you’ll run into a question that has real consequences if you get it wrong: are they an employee or a contractor? This isn’t a preference question. The IRS and the Department of Labor have actual criteria for this, and misclassifying someone can mean back taxes, penalties, and a much worse conversation

When you form an LLC, one of the boxes you have to fill in is “registered agent.” And for a lot of first-time business owners, this is the moment the whole thing suddenly feels official and slightly intimidating, like you wandered into a legal process you weren’t prepared for. You didn’t. It’s simpler than it sounds. A registered agent is just the official point of contact for your business — a person or service with a physical address in your state who can receive legal docu

When you worked for someone else, retirement savings may have been almost automatic — a percentage pulled from your paycheck, maybe an employer match, a decision you made once during onboarding and mostly forgot about. When you work for yourself, nobody sets that up for you. Nobody matches your contribution. If it’s going to happen, you’re the one who has to build it. I bring this up because it’s easy to postpone indefinitely — not because it’s not important, but because ther

I hear a version of this constantly: “Everyone else seems so much further along than me.” Said by business owners who are eight months in, comparing themselves to accounts and colleagues who’ve been doing this for six or eight years. That comparison isn’t just unkind to yourself. It’s mathematically off. What you’re actually seeing. When you look at someone else’s business — their polished website, their fully booked calendar, their confident social media presence — you’re al

When I tell people I’m a bookkeeper, I get one of two reactions. Either they nod politely and clearly have no idea what that means, or they say “oh, like taxes?” and I have to gently explain that no, not like taxes — adjacent to taxes, relevant to taxes, but not taxes. So let me explain what bookkeeping actually is, because I think a lot of small business owners are either doing parts of it accidentally or skipping it entirely because they’re not sure what they’re skipping. B

Let’s talk about the clients who come to me not because their books are a little behind, but because their books don’t exist. Or they existed in 2023 and then life happened. Or there’s a QuickBooks account somewhere that nobody has opened in fourteen months and the password is a mystery. If that’s you, I want to say two things clearly. First: this is incredibly common. Second: it is completely fixable. There is even a name for the fix — catch-up bookkeeping — because so many

Here’s something most people don’t realize: the moment you start doing business and getting paid, you are a business. The government already considers you one. If you never filed anything, never picked a structure, never made a single official decision — congratulations, you’re a sole proprietor. You didn’t choose it. It chose you. And that’s the part I want to talk about. Because being a sole proprietor by default is not the same as deciding it’s the right structure for you.

I want to give you some permission you didn’t know you needed. You don’t have to enjoy bookkeeping. You don’t have to find it interesting, or satisfying, or anything other than necessary. I work with plenty of people who are great at their businesses and genuinely uninterested in their finances, and that’s completely fine. What’s not fine — what I’m going to push back on gently — is using “I’m not a numbers person” as a reason to not know your numbers. Because here’s the thin

My business setup page says I’ll help you avoid the expensive mistakes I already made for you. People sometimes assume that’s just a clever line. It is not. It is autobiography. Let me actually tell you a few, because the whole reason I do this work is that I learned a lot of it the hard, costly way. I’m not going to pretend I started every venture I’ve run with a perfect foundation. I didn’t. I’ve mixed money I should have kept separate. I’ve put off paperwork that would hav

Nobody starts a business excited about the administrative plumbing. But the plumbing is what keeps the whole thing from leaking, so let’s talk about a handful of unglamorous essentials that are easy to set up early and genuinely annoying to retrofit later. A real business email address. Not yourname1987@gmail.com. An address at your own domain — something like hello@yourbusiness.com. It costs very little, it makes you look established, and it keeps your business correspondenc

At some point in setting up your books, you’ll run into a question that sounds far scarier than it is: do you keep your books on a cash basis or an accrual basis? People tend to nod, pick whichever word they heard last, and move on terrified. Let’s actually understand it, because for some of you — travel agents especially — it genuinely matters. The whole difference comes down to one thing: when you count the money. Cash basis: you count it when it actually moves. Income coun