Tax What If Doctor

As weather interrupts some parts of the country and business owners have to scramble and fill in the gaps of employees, supplies, deliveries and the like, it’s easy for them to worry about taxes later, after all, there’s “plenty of time.” That often comes back to bite them though, sometimes hard. If they run their business as a sole proprietorship then yes, they have until mid-April to file, and until mid-October if they file an extension.  However, the majority of small businesses under pay tax estimates, if they pay them at all, and the first filing date (mid-April) is when the taxes are due, even with an extension to file. The penalties and interest are based on what’s owed and[…]

There are many ways a tax return can be done that are all OK with the IRS, but only one of those ways nets the largest refund! People need to understand this across America, and we talk about tax planning constantly. We blog, tweet, post, email and on and on, yet we as an industry are not even getting 10% of the public to take on tax planning! The clients who do are often thrilled at the outcomes, and yet it’s just hard to get people to want to spend half the time that they spend planning their vacations on planning their own tax outcomes, even though larger refunds would pay for those vacations! Tax planning offices often don’t look like a franchise such[…]

Have you worked toward losing weight in the past because you want to look more attractive, or fit into an expensive wardrobe you already own? When you lose weight you often also lower your blood pressure and/or cholesterol as a bonus. It might not be the primary motivation, but the extra benefit is of course welcome! If you are a business owner, then we pose this question. Some time ago you had an idea. Over the years your turned that idea into a successful and profitable business. Have you properly protected what you worked so hard to build? An unexpected turn of events could put your biggest asset at risk. Did you know that moving business earnings into a qualified plan[…]

People try, but “adulting” is hard!  Kids, pets, job, relatives, friends, bills, medical problems, car problems, work problems all in the last day, so when I have time I will start tax planning.  Same as….so when I have time I will start estate planning, it’s just so far down on most peoples’ day to day list of things to do that all the other issues just cycle in some complex order that nobody understands and the last two items never seem to bubble up to the top…UNTIL THEY DO! If you are a business owner, thoughts of tax planning might bubble to the surface a couple times a year, perhaps March 15th and April 15th (or later if you have[…]

Dear Santa, I feel like you put me on the naughty list every year. When I file my tax return you impose taxes on me that I don’t want to pay. It feels like tons of coal are being unfairly put into my very little stockings. I try to be a good person all year, so I’m not sure why you are singling me out and treating me this way. Dear Suzie, You are not on the naughty list. In fact, you’re not on any list at all. You’re not being watched by me or my elves, unless you are doing things you ought not be doing. Every year I actually provide you with lots of presents, the following just[…]

People who are worried about the 10 year rule, requiring beneficiaries of inherited IRAs to withdraw the entire balance within 10 years, can double that time with a CRT beneficiary in front of inheritors. What if you really have a big IRA and the 10 year rule just isn’t enough of a stretch to help your beneficiary stay out of the top tax bracket? Or any other reason you care about reducing the negative tax impact from the 10-year rule? You could use other remaining tax rules to your benefit by setting up a charitable trust. A charitable trust allows the retirement assets to continue growing tax-deferred, even once the assets are distributed from the retirement account into the CRT.[…]

Most people feel like their taxes are a sleeping giant. They tiptoe around them as if staying away from the topic will keep it from waking up. Then at tax time when the giant awakens, they often act as if the final tax refund or bill is a surprise. Many working people try to change their withholding to get their tax outcome “dialed in”, but that joy of having a refund of “XYZ” coming is so often way off from what was expected and they are shocked. That’s because taxes are dealt with one time a year for most and their scenarios that lead to a consistent outcome change. For example, they go from no kids, to having kids. Children[…]

Many people have the intention of doing a better job of “tax planning” in order to start having more favorable outcomes, but busy lives and life interruptions can leave them little time.  If this is you, you’re not alone.  Time flies even in normal times, but with the current stressful environment, everyone is scrambling even more, so you look at the calendar and think, “I can go see my accountant or financial advisor, or I can get my shopping done”, and the next thing you know it, it’s Thanksgiving and the end of the year is upon us. Most advanced tax planning requires communication about concepts, takes reams of paperwork and time to submit to custodians, so it would be[…]

Many people in the tax planning industry were expecting a democratic win and big changes in tax policy. With Trump’s victory, many of those same tax planners are expecting no changes and extensions of the policies that were going to expire in 2025. Although some things will likely continue as they are now, it will not be as simple as an automatic extension of all policies. The reason that the policies were going to expire at the end of 2025 is that any time the government reduces projected revenues (tax reduction) they have to also have planned in a replacement to that revenue or have plausible growth because of tax policy that will balance the budget. When Trump placed the[…]

Sometimes “tax planning” can be easy: “Open an IRA and it reduces your taxable income.” Other times it can be quite complex: “Cost segregation” on a building means hiring an engineering firm and having a structure broken down into its many components on paper, with each value separately listed; the frame, wiring, heating systems, etc., and taking write-offs, generally much faster than simply taking a standard approach. These are both ways to lower federal or state taxes.   For the people who have made large amounts of money or have larger estates, the year to year tax bill is not as much of a concern as the “Death Tax Bill.” Planning for them can be simple or complex as well,[…]

In a few months the U. S. will begin filing tax returns again, and at tax firms all over the country people will be making the “E-Trade” Shocked Baby Face (remember him?) when they see they are being charged penalties and interest for under paying their taxes due. Even if they made a 941 payment in the last quarter to cover ALL the tax due for the year, they can still find themselves fined by Uncle Sam as a penalty for not paying equally over the four quarters of the year. A last quarter over-payment simply means they underpaid for three quarters and overpaid for one quarter, and no, it’s not “good enough” for the IRS. People also argue that[…]

We talk a lot about people not doing tax planning and not spending more time creating the tax outcomes they want. We urge people to understand that it’s within their own control and that tax outcomes can be legally and ethically manipulated. We go on and on about the benefits.  But…we understand why it’s so rarely done! It is because almost nothing in people’s lives has more constant change than taxes, and keeping up with all the changes can be an overwhelming challenge. What if every four years your banking rules changed, “Oh I’m sorry John, we no longer pay you interest, now you pay us interest to keep money here.” Or “Now you have to send in your mortgage payment daily,[…]

Most business owners in any five year period can answer yes to at least one of these life event questions that would cause them to need to know what their company is worth. 1. Are you contemplating the sale of your business? 2. Are you working with or bringing in a partner? 3. Are you contemplating or currently going through divorce proceedings? 4. Are you potentially going to have to defend yourself or your company in court? 5. Are you looking for financing? There are other possible reasons of course, but the point is that there are many times a business owner finds himself or herself needing to obtain a proper business valuation for their company. Unfortunately, it’s often an[…]

People who earn more than a certain amount and who are enrolled in Medicare Part B or Medicare Part D, or both, will face additional premiums, called The Medicare Income-Related Monthly Adjusted Amount (IRMAA). IRMAA “surcharges,” which is a replacement word for a tax, are based on income earned two years prior to the coverage year. So, for example, a client enrolling in Medicare in 2024 would pay an IRMAA surcharge based on their 2022 tax return. Generally there are two types of people that pay IRMAA surcharges: Those who might be affected and those who will always be affected. Because it is income based, people with an unusual income event may only be affected once, while people with higher incomes may always[…]

With signs of fall in the air, it’s time to start thinking about things that need to be done to prepare for winter. The garden harvests are rolling in, fresh vegetables are everywhere and it’s really, really great. Time to fill up your oil tanks before the price change, and at least know where those snow tires are in the back of the garage. It’s also time for tax planning. There are so many things in the tax code that have time limitations. It’s really time to check in with yourself if you want to actually participate in your bill with the IRS. Taxes can be very much within people’s control, even though they don’t feel that way. If you’re[…]

All around the country, there are people in an absolute panic because the real tax deadline for personal tax return extension filers is approaching and they are running out of time. The exception would be for those who have been affected by flooding or other natural disasters and may be given an extended deadline by the IRS. Those people may now have additional time to file, but would need to check the IRS website to see if they are in an affected area recognized by the IRS and would be covered by the exception. For the rest of us extension filers, there are some choices that need to be made quickly. The deadline is just a few weeks away. You’re not ready. What do you do?  The[…]

This last wave of tax filers are quite often the most productive people in our economy. Many are business owners, some with more than one business, or at least in some ways just have a lot going on, which means they usually add and not subtract from the tax base. That said, if your taxes are not done yet, then you’re in a rush (or should be) to get everything ready for filing, which usually means you’re not getting everything done accurately, and very often means you’re not getting any real tax mitigation advice either. It’s a vicious cycle. You wait to file because you are so busy getting ahead and just plain getting things done, then comes the fear[…]

This is the time of year when people often start taking personal inventory of how fortunate they are and start considering charitable contributions as a way to “give back” a little. For some, it’s an automatic budget item in their day to day lives, but for others it’s a new activity. For many years the IRS has helped people give by allowing charitable contributions to be deducted on schedule A when they file their taxes. The tax deduction value of those gifts changed with the Trump tax code simplification, as many people no longer need to file a Schedule A due to the higher standard deduction. Many people are still ingrained in their old charitable giving habits and aren’t aware[…]

Ask anyone if they “pay too much income tax” and the knee jerk reaction is almost always, “Yes!” and without much hesitation. Why do we call that a knee jerk reaction? Because if you then follow the question up with two more questions, “What did you pay in federal tax last year? And/or what bracket are you in?” they almost as quickly say, “I don’t remember, or I’m not sure.” Or they might guess at a bracket percentage, but usually not correctly. We’ve even had people profess the pain of paying too much in tax only to discover that not only did they get back all of their withholdings, but they were given tax credit refunds of money they did[…]

It may sound odd when you say it out loud, but after considering all the facts, it’s quite true. It’s an emotional but understandable reaction to think you always want to lower your tax bill as much as possible. However, except in the case of death, the tax code is basically a case of “tax me now or tax me later.” In many cases, to lower your current tax bill means that income avoided or deductions taken now are going to come back into your life at some later point. One example would be an IRA. You put money in an IRA and lower today’s tax bill, but those dollars will need to be taxed at some point. When you[…]

In the “old days,” you went to the general store for your dry goods, the blacksmith for your horseshoes or tool repair and likely had your own cow and chickens for milk and eggs.  Fast forward, you went to a lawyer to get a will, an insurance rep to get a policy and an accountant to get your taxes done.  There was no internet, so information was something you had to gather and organize yourself.  You would talk to a few co-workers, a family member, a mentor and then take actions based on the limited intel.  Back then, you would sit with a financial advisor, and if they were a big deal they might have a stock ticker pumping out tape[…]

First, let us make it clear that we aren’t saying that your CPA or accountant is doing anything wrong. The accounting industry is one of the most honorable and respected fields around. That being said, there is a misconception that they are going to be proactive when advising clients about their taxes, and that’s just not part of the training most have received. Certainly some are, but the majority who know things about steps a business could take to perhaps be more aggressive on tax planning for the future, don’t feel it’s their responsibility to pursue a client in engaging in alternative accounting choices or behaviors. A good example is “Bob” who owns a tire shop that has grown from two employees[…]

Most people pay little attention to their tax obligations, which we understand, as we are the richest and most privileged society ever to exist and so are very comfortable and complacent. However, taxes are a matter of political policy and as the economy changes so do tax policies. It would be helpful for everyone to at least take a moment and reflect on why the US separated from England, as when the Pilgrams came here they were heavily taxed in England and they risked life and limb as well as gave up creature comforts because they would then have NO TAXES. Nobody would have their hand out and “take away their money by force” which, framed in a different way,[…]

Well, do they or don’t they, actually? Long debated and often manipulated by the media, the topic of the wealthy and taxation has many, many complex points and counterpoints. First, when people say that, they often don’t define what kind of tax. The people hearing the comment usually go to federal personal income tax in their mind as TAXES. However, if a wealthy person owns 20 C corporations, with each filing their own tax returns, those C corporations pay their own taxes and unless the wealthy person needed to take a dividend or other distribution, then they could pay zero federal income tax, even though their companies paid potentially millions in taxes themselves.   The kinds of taxes people pay depends[…]

Have you ever seen a cat on the side of the road that waits until the very last second and then darts across the road in front of traffic? Ever see one that didn’t make it and think, “Some child is going to be very sad soon.”? I always wonder what makes the cat wait until the last second, but then again that’s what most taxpayers seem to do. They wait until February or March with a filing deadline looming and then dash out in front of a tax preparer and beg, “Is there anything we can do to lower this?”  Like the cat, perhaps the preparer has an idea and they miss getting hit with the entire bill, but[…]

It’s July. In a few short months people will be filing their 2024 tax returns with that familiar recurring moan and groan about paying too much. Now is the time to take your preventative medicine and avoid the pain next time around! Being human, we all form habits. Some good. Most bad. We try to develop good ones to replace the bad ones and often we are successful, but most successes don’t come without a coach, cheerleader or some kind of support. Tax time is usually a time of regret over not being successful at last year’s promise to oneself, “I’m not going to pay this much again. I`m going to keep better records and search out a tax planner or some professional[…]

If you pay attention and plan your tax outcomes proactively, there are many things you can do to reduce your tax bill. But the planning and the resulting activities that you need to engage in to achieve those outcomes are all year-round actions you must take, not just things to do the week before you file. Start by opening your calendar and marking a day each month to spend an hour on your taxes. That’s 12 hours a year. If when you file your taxes those year-round activities saved you $1500, then you were “paid” $125.00 an hour, which is worthwhile! If you saved $10,000.00 in taxes, that would be $833 per hour. Sign me up for that job! Start[…]

Many people who do not deal in the tax preparation or planning business think of taxes as something to deal with one day per year. Like Christmas, only not as good. So perhaps more like “Grinch Day.” Nevertheless, it doesn’t get a lot of attention after April. It drifts into the “Thank goodness that’s over!” mental space and goes away until the new year. It’s different for self-employed small business owners, as tax related issues are dealt with more often, but it’s still mechanical in nature. “I’ve got to go deposit payroll taxes today” or “I need to send in my 941 quarterly payment this week.” But still, their thoughts are not focused on proactive activities, but more so on responsibilities on[…]