Trending
I started my first financial planning business back in 2013. Overnight, I became a small business owner and pretty quickly, I found myself working with female small business owners as part of my clientele. When I launched my RIA (registered investment advisor) firm, I was one of the first virtual firms in the country at the time. This was pre-covid and pre-the-industry-paying-attention-to-millennials. What can I say? I was on the cutting edge.
I launched my business, found a cohort of other female business owners to grow and build alongside, and quickly realized that I was good at the money portion of running a business because I majored in money and specialized in it as a career. Working with creatives, therapists, coaches, online entrepreneurs of many shapes and sizes showed me that just because I love the numbers, it doesn’t mean all small business owners do.
Most of us got into our line of work (whatever that may be) because we love our craft. And while I was surrounded with women who were building and growing, the numbers didn’t necessarily keep up. And I wanted something different for them.
When it comes to money, there are no stupid questions in my opinion. That said, avoiding your numbers because they feel scary doesn’t make them less scary. It just delays a conversation you’re more than capable of having.
The good news is it doesn’t have to be overwhelming, and there are plenty of women out there who dive deep into their numbers, make strategic decisions, and navigate the ups and downs of business cycles like absolute pros. You can be one of them.
We’re 6 months into the year and I’m having conversations with my small business owner clients that are important. My clients are on top of their numbers, revenue, cash reserve, insurance, what happens if they need to step away, because a mid-year check-in like this one is built into how we work together.
Here are the questions I review with them, and the conversation I’d have with you if you sat down across from me today, six months into the year, with your actual numbers open.
Read Your P&L Like Someone Outside the Business Would
Your profit and loss statement tells you the shape of the business, not just the size of it. Pull the last six months. Look at three things:
-
Gross revenue
-
Your largest expense categories and how they’ve moved compared to the first half of last year
-
Your net revenue
Most owners read their P&L to confirm what they already believe. I’d ask you to read it instead to find what surprises you. What vendor costs have crept up? What revenue or client segments bring in money, but also eat up a disproportionate amount of your time? How does Q2 look vs. Q1 and what is the story behind it? The number at the bottom of the page tells you if you made money. The lines above it tell you why.
Cut What Doesn’t Make Sense Anymore
Every business accumulates costs that were right for a different version of itself. It’s happened in the businesses I’ve run, both large and small. It’s happened with my clients as they’ve moved through business cycles. Think: the software built for a team size you no longer have, contractors that have scope creep or that you’re overpaying for work that is no longer needed, office space sized for growth that hasn’t come yet, or has already outpaced it.
Go through your expense list line by line and ask one question of each: would I approve this today, knowing what I know now? Anything that gets a no, or even a maybe, is worth a phone call or email, either to renegotiate or to cancel. Think of this less like austerity measures and more like making sure the money leaving your business is aligned with your values and that of the business.
Check Your Cash Reserve Against Real Months
Pull up your business bank balance and answer this question:
If income stopped tomorrow, how many months could you cover payroll, fixed overhead, and your own pay before you’d have to make a hard decision?
For most owners, three months is the floor that you should have and six is where it starts to feel steady instead of tight.
If you’re under three months, you’ll want to start addressing the problem. Slow or reduce owner distributions if possible, hold off on the next hire, or route a fixed percentage of every invoice straight into reserve until you catch up.
Already at six months or more? This is where you want to make sure that cash is actually working for you. Money sitting in a checking account earning nothing isn’t a reserve strategy. It’s an idle asset with your name on it. Check out locations where you can open a high-yield savings account in the name of your business and at a minimum get yourself some interest on the money you have sitting.
Are Your Estimated Taxes Accurate?
Your Q2 estimated payment was based on a projection you or your CPA / Accountant made months ago. This could have been before the client you didn’t expect, the slower spring, or the price increase that finally stuck. A lot can change in six months and if your business is on an upward or downward trend, your tax payment likely isn’t aligned.
Underpaying means a penalty when you file and likely getting a surprise bill if you’re not on top of the numbers. Overpaying means you’ve handed the IRS an interest-free loan with cash that could have covered payroll or padded your reserve.
The fix: Compare year-to-date actual profit against your original projection, then reach out to your CPA or Accountant with updated numbers and ask if you should make adjustments to your Q3 payment before it’s due in September.
Protecting Your Assets is Just Smart Business
Business insurance is one of those things owners set up once and rarely revisit, even as the business it’s protecting keeps changing shape around it. Here’s what’s worth asking:
-
Does your liability coverage reflect your current revenue and client base?
-
If you have employees, is coverage current with headcount?
-
Do you carry disability coverage on yourself, given that you are very likely the business’s most important asset?
-
If you have a partner, is there a buy-sell agreement funded by life insurance, so a death or exit doesn’t become a financial crisis stacked on top of an already hard moment?
None of this needs to be resolved today. It needs to be reviewed today, with your broker or advisor, so the gaps get caught before they matter instead of after. This is also the moment to ask about an umbrella policy, especially if your personal net worth has grown alongside the business.
What Happens to This Business if You’re the One Who’s Out?
This is the one owners skip most, because it requires sitting with a version of events nobody wants to picture. But a continuity plan isn’t pessimism. It’s the difference between a business that survives your absence and one that doesn’t.
If you were out for six weeks tomorrow, unplanned, could someone else access your accounts, sign checks, keep client relationships moving? Is there a written record of your key processes, or does it all live in your head? If you have a co-owner, is there a documented agreement for what happens to your share if you can’t run it?
A working plan doesn’t need to be elaborate. At minimum: a second person with account access, a written list of key vendors and passwords stored somewhere other than your own memory, and a clear answer to who decides things in your absence.
Check Whether You, and Your Employees, Are on Track for Retirement
If you’re self-employed with no employees, a SEP IRA or solo 401(k) both let you contribute well beyond a standard IRA, up to $72,000 in 2026 between employee and employer contributions in a solo 401(k), plus a catch-up amount if you’re 50 or older. A SEP IRA caps at the same overall limit but works differently, since contributions come only from the business side. Which one fits depends on your income, whether you want a Roth option, and whether you’re likely to hire.
If you do have employees, this becomes a compliance question as much as a planning one. If you sponsor a SIMPLE IRA or 401(k) with a match, are you actually contributing the amount your plan documents require, on time? Missed or late employer contributions are one of the more common, and more expensive, oversights small business owners run into. Confirm it with whoever administers your plan. Don’t assume.
And separate from all of that: are you, personally, still on pace for the retirement you actually want? A mid-year point is a good moment to check your contribution rate against this year’s income, rather than finding out in December that you left room on the table.
Revisit What You’re Actually Paying Yourself
Owner pay usually gets set once, out of necessity, and then left alone for years while the business around it keeps changing shape. Ask two questions:
-
Is your pay still reasonable for the role you’re actually doing day to day?
-
And is the business healthy enough to support an increase, or does this quarter call for pulling less so the business can breathe?
Neither answer is a failure. An owner who adjusts her own pay based on real numbers, twice a year, is doing exactly what she should be doing. The number you pay yourself is a decision you’re allowed to keep making, not one you set once and owe an old version of the business forever.
What to Do With This
You don’t need to resolve all eight of these in one sitting. Block time this week for the two or three that feel most exposed right now, whether that’s the cash reserve, the insurance gap you’ve been meaning to ask about, or the plan question you’ve never let yourself finish thinking through. Bring the rest to your next conversation with your financial advisor or CPA, so nothing sits untouched until January, when it becomes a scramble instead of a decision.
You built this business to create more room in your life, not less. A clear-eyed look at these numbers now, while there’s still runway left in the year, is what keeps it that way.
Related: My Mom’s Cancer Forced Me To Ask Three Life-Changing Questions