Tax Season Ready: Smart Strategies for New and Established Businesses

HVWiB Lunch and Learn Recap (February)

Tax season has a way of sneaking up on even the most organized business owners. That is exactly why Hudson Valley Women in Business hosts a monthly Lunch and Learn series: real talk, real tools, and real women supporting each other. These virtual sessions are designed to make business feel a little less isolating and a lot more doable, with practical guidance you can actually use.

This month’s topic, Tax Season Ready: Smart Strategies for New and Established Businesses, was led by Rebecca Johnson, owner of Black Diamond Bookkeeping, a boutique accounting support firm based in Hudson, New York. Rebecca and her team provide bookkeeping and operational support for more than 75 businesses and organizations, with a strong commitment to championing local women owned and LGBTQIA plus owned enterprises.

And in true Lunch and Learn fashion, Rebecca came in with a few key slides, then opened the floor for a grounded, helpful conversation focused on the real stuff that trips business owners up year after year.

The theme: Don’t make your accountant cry

Rebecca framed the conversation with a simple truth: most tax season stress is avoidable, but only if you build habits before you are in crisis mode.

Her core reminders were refreshingly straightforward.

Pick a system and actually use it.
Whether you are in QuickBooks, a spreadsheet, or something in between, the “right” system is the one you can maintain consistently. QuickBooks is a tool. A spreadsheet can be a tool. The problem is not the tool. The problem is paying for a tool and never using it, or using a system you do not understand and then avoiding it entirely.

Gather paperwork early.
This is the time of year to track down the forms, statements, and documentation you always end up hunting for at the last minute. The more complete and timely your paperwork is, the easier it is for your tax professional to assess your situation and flag changes that matter.

Communicate with your tax preparer like it is part of the job.
Rebecca encouraged attendees to establish expectations early: how often you should connect, how documents should be submitted, and what your tax preparer will and will not proactively flag. If they use a secure portal, use it. Emailing sensitive documents and banking info creates unnecessary risk for everyone involved.

Ask the “dumb” questions.
There are no dumb questions, only expensive misunderstandings. If your accountant is using terminology that goes over your head, ask them to translate it into language you can act on. If you do not understand your P and L or balance sheet, you are not alone. You are also not stuck.

Key takeaways from the Q and A

The Q and A covered the exact topics business owners tend to wrestle with when they are growing fast, hiring help, or juggling multiple ways to get paid.

Contractor vs employee matters more than people think.
Rebecca walked through the IRS’s general framework for determining whether someone is a contractor or an employee. The way you direct the work, the financial relationship, and the type of benefits involved can all shift that classification. Misclassifying a worker can create major headaches later.

1099s feel intimidating, but they are manageable with good habits.
The best habit is simple: collect W 9s from vendors providing services so you have what you need when it is time to issue forms. Rebecca also spoke about how payment methods can complicate things now that many platforms and payment rails exist.

Bartering should still be tracked.
Even if no cash changes hands, trading services is still an exchange of value. Rebecca recommended tracking barter activity as you would any other income or expense so your records reflect reality.

Spreadsheets can work, until they don’t.
If your business is very simple, a spreadsheet may be enough to track income, expenses, and cash balance. But as soon as you add complexity like equipment purchases, loans, multiple accounts, or growth goals that require better reporting, accounting software becomes less optional and more protective.

You should have access to your own financial system.
One of the most important moments in the conversation was the reminder that you, as the business owner, should have ownership and visibility. Even if you hire someone to manage your books, you should still have access to your QuickBooks or accounting file, be the primary admin when possible, and understand what roles and permissions others have.

Why these Lunch and Learns matter

This session was not about perfection. It was about reducing stress, protecting your time, and setting your business up for sustainable decision making. Tax season does not have to feel like a panic spiral if you build a system you can actually stick to and communicate before deadlines show up.

Free to attend, and open to all women in business

HVWiB Lunch and Learns are always free to attend, and they are held virtually on the first Wednesday of every month. Come as you are, bring your questions, and leave with clarity you can use right away.

Want to speak at a future Lunch and Learn?

If you would like the opportunity to present as a featured speaker for an HVWiB Lunch and Learn, you must be an Invested Member. This series highlights expert voices inside our community and is reserved for members who actively support HVWiB’s mission and growth.

Coming up next

Next month, we will be joined by Dana Hammond for a session on how to use color to build trust, influence, and signature.

If you have not attended a Lunch and Learn yet, this is your sign. Grab your lunch, hop on Zoom, and come learn with us.