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Small Business Mid-Year Check-In: Do You Actually Know Where You Stand?

June 29, 2026

Small Business Mid-Year Check-In: Do You Actually Know Where You Stand?

You're halfway through the year.

Do you know how your business is actually doing?

Not how it feels.
Not what your bank account looks like.
Not whether you're busy.

Do you know?

A lot of business owners are so focused on serving clients, managing employees, and keeping everything moving that they don't stop to look at the numbers until the year is almost over.

By then, there isn't much you can do.

Mid-year is different. You still have six months to make adjustments.

Review Your Business Profitability

Revenue gets the attention.

Profit is what matters.

Pull up your year-to-date income statement as part of your overall business owner financial planning and ask yourself a few simple questions.

  • Are your margins where you expected them to be?
  • Have expenses quietly crept up?
  • If you keep going exactly as you are today, will you hit your year-end goal?

That last question matters.

Too many business owners assume the second half of the year will take care of itself.

Sometimes it does.

Sometimes it doesn't.

Knowing the difference is where better decisions come from.

Don't Let Taxes Surprise You

Here's something I see catch business owners all the time.

The business has a great year.

Then April shows up with a much bigger tax bill than expected.

Why?

Because estimated tax payments were based on last year's income, not this year's.

If profits are up, there's a good chance your estimates need to change too.

Now is the time to sit down with your CPA, update your projections, and adjust your Q3 and Q4 payments if necessary.

It's a simple conversation that can save a lot of frustration later.

Are You Paying Yourself First?

Business owners are usually great at taking care of everyone else.

Employees get paid.

Vendors get paid.

The business gets reinvested.

Then retirement contributions become whatever is left over.

That's backwards.

Whether you have a SIMPLE IRA, SEP IRA, Solo 401(k), or another retirement plan, now is a good time to see if you're on pace to maximize your contributions.

Waiting until November doesn't leave you many options.

Starting now gives you time to make intentional decisions instead of scrambling at year-end.

It's also worth asking whether your current retirement plan still fits your business.

What worked three years ago may not be the best fit today.


Three Questions Every Business Owner Should Be Able to Answer

Before summer is over, you should know:

  • Is my business as profitable as I thought it would be?
  • Am I setting enough aside for taxes?
  • Am I taking advantage of the retirement plan available to me?

If you can answer all three without hesitation, you're probably in good shape.

If one of those questions makes you pause, that's worth looking into.

They usually don't get better by waiting.

That's the advantage of a mid-year check-in. You still have time to do something about it.

The Second Half Starts Now

The business owners who finish the year strong aren't always the ones who had the best first half.

They're the ones who stopped, looked at the numbers, and made adjustments while they still had time.

There's no magic bullet.

Just better information.

And better decisions.


Ready to see where your business really stands?

Let's have a conversation.

We'll review your profitability, tax strategy, retirement planning, and overall financial picture to help you head into year-end with greater clarity and confidence.

David Drumhiller, CFP®, BFA™, AAMS®is a financial advisor with nearly 20 years of experience helping individuals and families prepare for retirement. He specializes in tax-efficient retirement income planning and comprehensive wealth strategies. David holds Series 7 and 66 registrations and is licensed in WA, OR, and ID, and across the nation. A Washington State University graduate, he lives in Pullman with his wife and enjoys travel, barbecue, and Cougar Athletics.