Who I help
Ask me the thing you’ve been carrying around.
Usually one they’ve been carrying around for a while, and usually one they’re slightly embarrassed to ask. Most of them aren’t really tax questions at all. They’re questions about whether things are going to be all right.
Here are the ones I hear most. If yours is on this list, that’s a perfectly good reason to get in touch. If it isn’t, ask anyway.
“Am I even doing this right?”
Am I overpaying, and would I ever know?
No, you wouldn’t. Nobody sends a letter telling you that you paid too much. You file, you hope, and the year closes. That’s why the first thing I usually do for someone is read last year’s return and tell them plainly what I’d have done differently, including when the answer is nothing.
Is there a form I’m missing?
Possibly, and it’s usually not an exotic one. Missing forms cluster around a handful of ordinary things. A foreign account you barely use. A retirement plan election nobody filed. A state you now owe a return to because you bought a rental there. The software didn’t ask, so you didn’t answer.
My taxes got complicated and I can’t tell when that happened.
It’s usually one specific year. You started a business, or bought a property, or got equity in a company, or someone died and left you something. The return was simple in March and wasn’t in April, and nobody marked the moment. That’s the point where software stops being enough, and most people carry on with it for two or three more years before they notice.
My preparer files it and I have no idea what any of it means.
Then you’re paying for a document rather than for understanding. Before I file anything, I go through the return with you on a call. What the numbers are, why they are what they are, what changed, and what we should do differently next year. Half an hour, and you’ll understand your own finances better than you did.
“Something arrived and I don’t want to open it.”
What do I do about this letter from the IRS?
Find the notice number in the top right corner and send it to me. Most of these are generated by a computer matching what was reported about you against what you filed. Nobody read your return and decided you looked suspicious, and the number printed on it is frequently wrong. There’s a whole page on this if you want to understand it before you call anyone.
I’m never going to be able to pay this. What happens to me?
Less than you’re imagining. There are established ways to handle a balance you can’t clear, and none of them require money you don’t have. A payment plan set at a level you can sustain. Collection suspended entirely if paying anything would stop you meeting basic living expenses. Penalties removed where you have a clean history. The frightening scenarios you’ve been running at three in the morning are mostly not how this works.
I haven’t filed in years and I’m too embarrassed to tell anyone.
One year or fifteen, it’s the same conversation and I’ve never once been surprised by a number. IRS policy generally treats six years of returns as enough to bring someone current, not every year since you stopped. Some of those years may even owe you a refund. More here, and there’s nothing on that page designed to frighten you into calling.
They say I owe an amount that can’t possibly be right.
It probably isn’t. When you don’t file, the IRS eventually files for you, using only the income reported about you and allowing nothing else. No business expenses, no dependents, no credits, worst filing status. Filing an accurate return for those years usually drops the balance sharply, sometimes to nothing.
“The business is eating my life.”
Am I actually making money, or does it just feel busy?
Most owners genuinely can’t tell, because the bank balance goes up and down for reasons that have nothing to do with profit. I ran a laundromat before I did anyone’s taxes and I couldn’t tell either, for longer than I’d like to admit. The answer is a profit and loss statement that separates things properly, and the ratios that mean something for your particular business rather than for businesses in general.
I never have time for the paperwork and it’s costing me.
It is, and this is the part I understand from the inside. There is always something more urgent than reconciling last month. So it waits, and waiting costs money quietly, in deductions nobody took and decisions made a year later than they should have been. Handing it over isn’t laziness. It’s the highest-return thing most owners can do with an hour.
Should I be an S-corp? Someone at a barbecue said I should.
Maybe. Below a certain profit it costs more in payroll administration than it saves, and above that level it saves real money. And there’s a second question nobody mentions at the barbecue, which is what you then have to pay yourself. That figure is expected to be defensible, and most owners have never had anyone document it.
Is this business worth buying, or will I regret it?
Bring me the numbers before you commit, not after. Sellers show revenue that includes an account about to walk, deferred maintenance described as recently serviced, and cash figures nobody can verify. And how the purchase is structured decides your tax position for years afterwards, which is settled before signing rather than at tax time.
I think I want to sell, but I don’t know where to start.
Start eighteen months out, with the books. Clean books raise your multiple, and a buyer’s first request is the thing most owners can’t produce quickly. Then the structuring, because what you keep after tax is usually affected more by how the deal is shaped than by negotiating harder on price. I’ve sold a business. The tax planning mattered more than the haggling did.
“Are we going to be all right?”
Will I have enough to retire?
You want a straight answer and most people won’t give you one, because a forty page projection built on assumptions nobody can defend is easier to produce than a clear sentence. What I can tell you is what you have, which account it should come out of first, what each of those choices costs in tax, and how long it lasts under sensible assumptions. That’s usually the conversation people actually wanted.
I’m afraid to look at the numbers at all.
That’s more common than anyone admits, and avoiding the numbers is almost always worse than the numbers. Nearly everyone who finally looks finds the situation is somewhere between “manageable” and “better than I thought,” and the small number who find it genuinely difficult at least now have time to do something. The fear is generally worse than the arithmetic.
Will there be enough for my children’s education?
Depends on what you’re picturing, and a lot of people are picturing the most expensive version without meaning to. There are tax-advantaged ways to save, credits available while they’re studying, rules about what counts as a qualified expense that catch people out, and consequences to how you own the money that affect what they qualify for. Worth planning years ahead rather than in the spring of their senior year.
What happens to all this if one of us gets ill?
A fair question and one people tend to ask late. There’s a tax side to it that’s rarely discussed until it’s happening. What medical costs are deductible and when. How health savings accounts actually work. Medicare surcharges triggered by income from two years earlier. What’s deductible when a parent needs care. None of it is cheerful, and all of it is better understood in advance.
“There’s a conversation I NEED to have but I don’t know how to start.”
These are the ones people are most reluctant to admit they need help with, and they’re some of the most useful work I do. In every one of them, the problem isn’t the money. It’s who has to say the first sentence.
How do I ask my parents about their estate without sounding like I’m counting the inheritance?
You don’t. You blame me instead. Tell them your tax guy says you have to ask, and I’ll run the conversation. From that point they’re my client rather than yours, and I say that to them out loud, which is what makes it honest. It isn’t about what you’ll get. It’s about making sure what they want is what actually happens, and that nobody has to guess later.
I’m about to get married and neither of us will bring up money.
Then let someone else bring it up. Debt, credit, student loans, what happens to your filing status, whether either of you should speak to an attorney. Somebody has to start that conversation and it genuinely doesn’t have to be one of you. I’ll run the agenda so neither of you is the person who made it awkward.
My spouse and I haven’t properly discussed our finances in years.
Very common, and it usually isn’t about secrecy. One person took it on early, the other stopped asking, and now raising it feels like an accusation in either direction. A third person in the room changes that entirely, because the questions come from me and neither of you has to be the one who brought it up.
My child wants to study something that won’t pay. How do I say that?
Honestly, I don’t think that’s quite the question. What you’re really asking is what you can afford to support, for how long, and whether saying so makes you the villain.
That version has an answer. We can look at what it actually costs, what you can commit to without damaging your own retirement, and where the line is. Then you’re not delivering a verdict on their dream. You’re telling them what’s available, which is a different conversation and a far easier one to have.
My parent is getting older and nobody in the family has said anything.
Somebody usually has to go first, and everyone’s waiting for somebody else. If it’s becoming clear that decisions need making and nobody wants to be the one raising it, that’s exactly the situation the parents conversation is for. And if it turns out a parent isn’t able to make these decisions any more, I’ll tell you plainly and point you to an elder law attorney, because that’s a different problem.
“I own things I don’t fully understand.”
My investments are complicated and I don’t think my preparer follows them.
Then they probably don’t, and it isn’t really their fault. Bond premium, market discount, basis on shares bought before brokers tracked it, partnership units with ordinary income buried in the disposal. These get missed constantly because most preparers have never worked on the investment side. I spent fifteen years there before I came to tax.
I bought a rental and everyone said it was a tax shelter. It doesn’t feel like one.
Usually one of three things. Depreciation that was never set up properly, losses suspended by the passive activity rules without anyone explaining why, or the split between land and building done badly at the start and quietly costing you every year since. All three are checkable in about five minutes on your last return.
I have crypto and my accountant said they’d rather not.
Most won’t. I hold a certificate in digital assets and I do this work deliberately rather than reluctantly. The usual finding is that people have been over-reporting, because transfers between their own wallets were counted as sales and basis was abandoned as too hard to find.
I got stock from work and now there’s a tax bill I wasn’t expecting.
Equity compensation catches almost everyone, because the tax arrives at exercise or vest rather than at sale, and the withholding is often set well below what a high earner actually owes. The mistakes are expensive and they happen before the return is prepared, which is why this is worth a conversation in the year it’s happening rather than the following April.
I live abroad and I’m not sure I’ve been doing this right.
Almost nobody is told before they leave that the US taxes its citizens wherever they live. If you’re behind, there’s a defined programme for exactly that situation and it usually ends with no penalty at all. More here, and nothing on that page is written to make you feel worse.
If you’d rather see it by category
Some people find it easier to start from where they fit rather than from what’s worrying them. Either works.
IRS letters and audits
Notices, examinations, collections, payment plans, penalty removal.
Unfiled returns
One missed year or fifteen. Catching up, and what it actually involves.
Laundromat owners
Coin and card reconciliation, machine packages, multi-store numbers, buying and selling.
Business owners
Bookkeeping, entity structure, S-corp questions, quarterly estimates, buying and selling.
Investors
Stocks, bonds, funds, K-1s, equity compensation, cost basis nobody can find.
Rental property
Depreciation, passive losses, 1031 exchanges, cost segregation, selling.
Americans abroad
Foreign income and accounts, catching up if you’re behind, state residency.
Estates and trusts
Executor support, trust and estate returns, inherited accounts, the parents conversation.
Crypto and digital assets
Cost basis reconstruction, staking and airdrops, DeFi, exchange reporting.
What if my question isn’t here?
Ask it anyway. Nobody’s situation fits a category neatly, and working out which box you belong in is my job rather than yours. If it turns out to be something I don’t do, I’ll tell you who does.