12 May We Asked Women Business Owners One Financial Question. Here’s What You Said.
At the NAWBO Chicago Women Mean Business Conference, we set up something simple at our booth: a board, some sticky notes, and one question for the women business owners in attendance.
“What is the hardest financial part of running your business right now?”
No multiple choice. No prompting. Just whatever came to mind first.
Thirty-plus women wrote something down. And what came back wasn’t what you might expect from a room full of accomplished business owners. It wasn’t polished, or strategic. It was honest.
And it was, frankly, a little bit of a mirror.
Taxes topped the list; but taxes are rarely really about taxes
“Taxes!” showed up four times. More than any other answer.
But here’s what I’ve learned after years of working with service-based business owners: when someone says taxes are their biggest financial struggle, they usually don’t mean they need a better CPA. They mean they feel unprepared. They’re not sure if they’ve set aside enough. They mean tax season feels like a threat instead of a routine event.
That’s not a tax problem. That’s a cash management problem in disguise.
When you’re running your finances reactively — categorizing expenses in a rush, not reviewing your P&L monthly, estimating your tax liability instead of tracking it — April feels like a surprise every single year. The Profit First methodology solves this directly: when you allocate a percentage of every deposit to a dedicated tax account, the money is already there. You know what you have. The anxiety disappears because the preparation already happened.
Tax stress is usually the symptom. Inconsistent financial systems are the disease.
“Understanding my financials” — the quiet confession hiding in plain sight
Several women wrote some version of this: Understanding my financials. Understanding the numbers. Know your numbers.
I want to sit with this one for a moment, because I think it’s the most important thing on that board.
These are smart, driven, successful women. They built businesses. They manage teams, serve clients, negotiate contracts, and make payroll. And yet many of them don’t fully trust their own financial reports.
That’s not a personal failing. That’s a systems failing.
If your bookkeeping is weeks behind, your reports don’t match your bank balance, and your P&L looks like a foreign language — of course you can’t “know your numbers.” The data isn’t working for you.
This is exactly what we mean at Reconciled Solutions when we talk about financial clarity over financial complexity. Current, accurate books aren’t a nice-to-have. They’re the foundation of every good business decision you’ll make this year. When you have a clean monthly close and reports you can actually read, “understanding your financials” stops feeling like a vulnerability and starts feeling like a superpower.
Cash flow: the gap between profitable and paid
“Cash flow.” “Working capital.” “Collecting from clients!” “Getting clients to pay on time.”
Different sticky notes. Same underlying problem.
You can run a genuinely profitable business and still feel broke. The culprit is almost always timing: money owed to you that hasn’t arrived yet, expenses due before revenue comes in, payroll on Friday when the client invoice is still outstanding.
This is one of the most emotionally exhausting parts of running a business, because it makes you question whether the whole thing is working — even when it is.
The tools to fix it exist. A simple rolling cash flow forecast can tell you what your bank balance will look like 30, 60, 90 days from now. A Profit First account structure (ideally paired with a bank like Relay that makes it easy) means you’re not mixing operating expenses with owner’s pay with tax reserves in one account and hoping it all works out. And a consistent accounts receivable process — clear terms, early invoicing, prompt follow-up — eliminates most of the “clients who don’t pay on time” problem before it becomes a problem.
Cash flow doesn’t have to be a mystery. It’s one of the most plannable parts of your business when you have the right systems.
“Getting clients” showed up, and that tells us something
A number of respondents didn’t write down a bookkeeping problem at all. They wrote: Landing new paying clients. Keeping my pipeline full. Getting clients.
I think this is one of the most revealing patterns in the whole data set.
When revenue is inconsistent, every expense feels dangerous. You scrutinize every line item because you’re not sure if you can cover it. Then, you hesitate on investments that could actually grow the business. You feel financially anxious even in months when you’re technically ahead.
Revenue instability doesn’t just create a sales problem. It creates a financial psychology problem.
This is where Fix This Next, the framework built by Mike Michalowicz, is incredibly useful. It helps you identify what’s actually holding your business back at this stage — because sometimes the answer isn’t better bookkeeping or a bigger tax reserve. Sometimes it’s that the sales floor needs to be repaired first before any other financial work can stick. Knowing which problem to solve, in the right order, changes everything.
Finding reliable help: the trust problem in small business
“Finding the right trusted help.” “Getting reliable help.”
Two notes, but they echoed loudly.
Handing over any part of your business finances requires trust. It requires confidence that whoever has access to your books, your accounts, your financial data, will handle it with the same care you would — probably more. And for a lot of business owners, that trust has been broken before. By a bookkeeper who disappeared mid-year. A contractor who did the bare minimum. Someone who processed transactions but never helped you understand what they meant.
This is why we don’t describe ourselves as bookkeepers who keep the records. We describe ourselves as financial partners who help you make decisions.
The right financial support isn’t just accurate. It’s proactive. It answers questions before you know to ask them. It shows up for a monthly call not just to review numbers but to help you understand what those numbers are telling you about your business.
The answer nobody talks about
And then there were a few responses that stopped me completely.
“Everything.”
“Being responsible for EVERYTHING.”
“Boundaries.”
“Separating the strategic tasks from the tactical ones.”
These aren’t really financial answers, they’re ownership answers.
When you’re the founder, the CFO, the salesperson, the service provider, and the one who handles the QuickBooks login — all in the same week — the financial chaos isn’t separate from the personal overwhelm. They’re the same thing.
One of the core principles behind our work at Reconciled Solutions, and behind frameworks like Clockwork (Mike Michalowicz) and the Buyback Loop (Dan Martell), is that your highest value as a business owner is your vision and your judgment, not your ability to handle every tactical task yourself. The goal isn’t just accurate books. It’s getting the right things off your plate so you can actually do the work only you can do.
When you outsource your bookkeeping to people who handle it consistently, proactively, and with genuine care, you get back something more valuable than time. You get back mental space.
What all of these answers have in common
Looking at every sticky note together, a clear theme emerges: financial stress in small business isn’t usually about one missing skill or one missing tool.
It’s about operating without a system.
Without a system, taxes are a surprise. Cash flow is a guessing game. The books fall behind and the reports stop making sense and the whole financial picture blurs into something you’d rather not look at.
Our job at Reconciled Solutions is to build that system with you and then run it, so you don’t have to carry it alone.
The sticky notes at NAWBO this year weren’t just a fun booth activity. They were a reminder that you are not alone in the financial challenges you’re navigating. And for us, they were an important reminder of why this work matters.
Most of the women in that room wrote something that made the person next to her nod.
That’s worth something.
Which one of these challenges resonates most with you right now? Hit reply — I’d genuinely love to hear.
And if “understanding your financials” or “cash flow” would have been on your sticky note, let’s talk. A Financial Clarity Call is a good place to start.
