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The 2025 Version of Why It’s Time For an Annual Checkup For You and Your Company

Beginning in 2014, many of you probably read my blog regarding having a checkup for you and, if you have one, your business. This does not involve the doctor, but it does involve all the other professionals in your personal and business life. Based on positive feedback, I have made this an annual tradition. I originally made this post about the week between Christmas and New Year’s but that’s too late, which is why I now share this a few weeks prior to the end of the year to give you time to act and look into possible changes before year end.

It’s good to check in with various professionals you or your company work with, be they attorneys, accountants, insurance professionals, financial planners, investment professionals, etc. The list depends on you and your business.

Some of you said “What a great idea. I am going to do that.” Others said, “Sounds like a good idea, maybe I will look into that.” Another response was “I wish I had thought about this before the end of the year or when certain contracts automatically renewed.”

I’ll bet in most years many of you were busy with or recovering from the holidays and probably did nothing in response to my push for you to do this type of “annual checkup.” To be honest, this response is okay and ignoring my advice may not have had negative effects on you or your business.

The point of the advice is that you only know what you know. For example, I always check in with my accountant prior to the end of the year to ensure that all is right with taxes and withholding because I don’t want a big surprise that I owe more money or am being assessed penalties for under-withholding.

A few years back I had a reminder related to a different item you should check on annually, auto insurance. We had teenagers on our policy at the time and several vehicles, and the premiums always seemed so high to me. But my insurance person knows me and shops the policy every year looking for the best rates for similar coverage from quality insurers. He did that for me, and we ended up with a new insurer, with significant savings.

Does your insurance person do this? If not, why not? You should ask. Or you should switch to a new insurance person who cares as much about you as they do about the commissions and income you represent to them.

With life being so busy, sometimes it’s hard for me to move beyond the higher-level checkup, but when I do, I usually end up with some benefit. Unfortunately, in our time-crunched world, the question of who to check in with at year end is broad; from your estate planning attorney to your investment person, from your insurance person to vendors you may use such as a yard or pool maintenance company, from your cell phone carrier or to your Internet provider. You may be surprised by what a company will do in lowering monthly costs to satisfy or keep a current or long-term customer. Try it and see what happens. Start with your cell phone provider.   There always is a promotion that will lower your monthly costs.

I know, I know, who has the time? None of us do, which is why the choices are yours. Are your contracts up to date? Did you pay enough estimated taxes or withholding? Are you paying too much for the cleaning service at your office or your lawn service for your home? The choice of what professionals to consult, what costs to check or compare, and what services to put out to bid is yours. Choose wisely.

As always, this post and others can be found on my blog, Business Law Guy

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