Groundhog Day and Your Taxes: Why Repeating the Same Mistakes Costs You Every Year

Groundhog Day shows up every year and, somehow, a lot of us act surprised. Same date. Same storyline. Same little burst of hope that this year will be different.

Taxes can feel like that too.

If you’re a high-income medical professional, you probably do “fine” with taxes. You earn well. You file on time. You pay what you owe. You move on.

And then you repeat the same tax mistakes next year.

That’s what I mean by “Groundhog Day and your taxes.” You keep making the same choices because they feel normal, or busy life gets in the way, or you assume your CPA has it handled. No shame in that. It’s common. I’ve watched smart people do it for years. I’ve done versions of it myself in other parts of life.

The problem is simple.

Repeating the same tax mistakes keeps costing you real money. Every year. Quietly.

This post breaks down what that looks like in plain language. No jargon. No “advanced strategy” talk. Just practical ways physician tax planning and high-income tax planning help you stop doing the same thing each year and hoping for a different result.

The “Same Mistake” Loop Most High-Earning Clinicians Fall Into

Let’s start with the pattern.

Most high-income clinicians don’t make tax mistakes because they’re careless. They make them because their days are packed and their tax decisions happen in the margins. At night. Between cases. During charting. On a Sunday when you should be doing anything else.

So the default becomes:

• File the return

• Pay the bill

• Tell yourself you’ll plan earlier next year

• Repeat

Here’s what that “loop” often looks like in real life for physicians and practice owners:

• You wait until March or April to ask, “Is there anything I can do?”

• You treat tax planning like a once-a-year event instead of a year-round process

• You don’t connect career moves to tax impact

• You assume your withholding covers it, then get hit with a surprise balance due

• You run side income without a clear structure and hope it “sorts itself out” later

That last one shows up a lot, especially now. More physicians build extra income streams, which is smart. It just needs clean planning. If you’ve been exploring that route, you’ll probably relate to this: how physicians are increasing income with non-clinical side businesses.

None of these are dramatic mistakes. They’re quiet. They’re routine. That’s why they repeat.

And when they repeat, your taxes start to feel like a penalty for being successful.

Why “Tax Filing” Isn’t the Same as Physician Tax Planning

I’m going to say something that might sound obvious, but I think it’s where things break down.

Tax filing reports what happened.

Physician tax planning shapes what happens.

Filing is backward-looking. Planning is forward-looking.

If you earn a high income, your return can look fine on paper while you still overpay. That’s the annoying part. Nothing looks “wrong.” You just never built the system that keeps more of what you earn.

Here are a few medical-industry examples that show the difference:

• You pick up extra call or a bonus shifts your income up
  Filing: you report it
  Planning: you adjust withholding or estimated payments so you don’t get blindsided later

• You start 1099 moonlighting
  Filing: you pay self-employment tax and whatever else shows up
  Planning: you set up a structure that fits your income and reduces waste

• You buy equipment for a practice or side business
  Filing: you hand receipts over and hope they land in the right place
  Planning: you time purchases and categorize them in a way that supports real tax savings

This is where high-income tax planning becomes less about “finding deductions” and more about making decisions on purpose.

If you’ve ever looked at a tax bill and thought, “I mean… I guess that makes sense,” that’s a sign you’re filing, not planning.

And planning doesn’t need to be complicated.

It needs to be consistent.

The Big Repeat-Offenders: 4 Mistakes That Add Up Fast

Let’s talk about the mistakes I see over and over with high-income earners in medicine. Not all of these will hit you. Maybe only one does. That’s enough.

1) Waiting Until Tax Season to Think About Taxes

This is the classic Groundhog Day move.

You can’t change much in March or April for last year. Some things, sure. But most meaningful options require time.

Try this instead:

• Do a quick planning check-in in February or March for the current year

• Do another one mid-year (June or July)

• Do one more in the fall before year-end closes the door

That’s three touchpoints. Not twelve. Not “monthly strategy calls.” Just enough to catch problems early.

If you’ve ever been hit with an underpayment surprise, this ties in with safe harbor rules. If you want a plain-English refresher, this link lays it out well: safe harbor rules and IRS penalties for business owners.

2) Treating Your Income Like It’s “One Thing”

Physicians often have layered income:

• W-2 income from an employed role

• 1099 income from locums or moonlighting

• Practice income if you own a group

• Real estate income

• Side business income

Each layer behaves differently for taxes. Different withholding. Different deductions. Different timing issues.

If you treat all income like one bucket, you end up with:

• Under-withholding on 1099 income

• Missed deductions because you didn’t track expenses correctly

• Confusion about what’s “business” vs “personal”

A simple habit helps a lot: keep clean separation.

• Separate accounts for side income

• Track expenses monthly, even if it’s quick

• Decide early how you’ll pay taxes on that income

That’s not fancy. It just prevents chaos.

3) Ignoring Business Structure Until It’s “Worth It”

I hear this a lot: “I’ll think about that when the side income gets bigger.”

I get it. You don’t want complexity.

But structure decisions often take time to do right. And when your income rises fast, you can miss the window.

One common structure physicians explore is an S corporation. It’s not always the answer. It depends on your numbers and your situation. Still, it comes up often enough that it’s worth reading a clear breakdown:the benefits of an S corporation for physicians.

Here’s the key point.

Physician tax planning works best when you decide structure before your income spikes, not after you feel the pain.

4) Missing “Hidden” Deductions and Timing Opportunities

Let’s keep this simple.

Deductions don’t matter if you don’t document them. Timing doesn’t matter if you decide too late.

This is where physicians get tripped up because your spending patterns don’t look like the average person’s. A few examples:

• CME, licensing, boards, professional dues

• Travel tied to legitimate business activities

• Home office use for admin work if you qualify

• Vehicle use that may support deductions in certain situations

Even if you don’t think these apply, it’s worth understanding what’s real and what’s not. For example, this is a good reference point if you’ve ever wondered about vehicle and home office rules: heavy vehicle and home office tax deductions.

And for business travel questions, this is timely:tax deductions for doctors on business vacations.

I’ll be honest. Some of these topics feel annoying. They’re detail-heavy. People avoid them because they don’t want to “mess it up.”

That’s why they keep repeating the same approach: ignore it, then hope the return captures it.

How Tax Advisory Helps You Break the Pattern Without Living in Spreadsheets

If you’re a high-income physician, you don’t need more tasks. You need fewer surprises.

That’s where tax advisory comes in.

Tax advisory is not just someone preparing your return. It’s someone helping you make choices during the year that affect your taxes.

A decent tax advisory rhythm can look like:

• One planning call early in the year
  You set targets for income, savings, retirement, and tax payments

• A mid-year check
  You adjust for bonuses, new contracts, side income, big purchases, or practice changes

• A year-end review
  You lock in final moves before December 31 and clean up anything that drifted

The benefit isn’t some dramatic “hack.” It’s control.

You stop asking these questions too late:

• “Why do I owe so much?”

• “Should I have changed my withholding?”

• “Did I miss a deduction?”

• “Should I have set up an entity earlier?”

• “Is my practice structured in a way that supports tax savings?”

And yes, this is still true if you have a great CPA. Some CPAs do advisory. Some don’t. Some want to, but your file lands on their desk in March when it’s too late.

High-income tax planning works best when planning happens before filing.

Also, there are moments in a medical career where planning matters a lot more than normal. Selling a practice is one of them. Even if you’re not close to that, it’s the kind of event that’s hard to “wing.” This is a helpful read if it’s on your horizon:minimize taxes when selling a medical practice.

A Simple “Stop the Repeat” Checklist for This Year

If your taxes feel like a yearly replay, try this checklist. It’s small on purpose.

Step 1: Pick one date for a planning check-in

Put it on your calendar. Seriously.

• Late February

• Or early March

You don’t need to do everything. You need to start.

Step 2: List your income sources for the year

Just write them down.

• W-2

• 1099

• Practice profit

• Real estate

• Side business income

This list alone changes how you approach your taxes.

Step 3: Decide how you’ll handle tax payments

Ask:

• Do I need estimated payments?

• Should I adjust withholding?

• Do I want a buffer so I don’t stress in April?

Even a rough plan beats guessing.

Step 4: Track a short list of deductible categories

Pick the ones that match your reality:

• CME, boards, dues

• Business travel

• Home office use

• Equipment

• Business-related mileage

Don’t track everything. Track what you actually spend.

Step 5: Check one “structure” question early

Not ten questions. One.

• Does my side income justify a structure change?

• Do I need cleaner separation between personal and business spending?

• Should I talk through entity options?

If you want a quick grounding in official IRS basics, this page can help you sanity check the basics without getting lost:IRS tax tips.

This checklist isn’t perfect. It won’t cover every scenario. But it stops the automatic repeat cycle.

That’s the point.

Where This Leaves You

If you’re a high-income medical professional, you already know how to manage complexity. You do it all day. Taxes just hit you in a different way. They feel distant until they aren’t.

Groundhog Day and your taxes happens when you rely on last-minute filing and hope it covers everything.

Physician tax planning and high-income tax planning break that cycle by shifting decisions earlier, tracking what matters, and building a basic system that stays steady even when your income changes.

If you want a next step that feels reasonable, do this:

• Choose one planning date this month

• Write down your income sources

• Bring those two things to a tax advisor and ask for a simple yearly plan

You don’t need perfection. You need fewer repeats.

And maybe, just maybe, next April won’t feel like the same scene again.

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FAQ

What does “Groundhog Day and your taxes” mean in plain terms?

It means you repeat the same tax habits every year, then get the same results. Often that looks like waiting until tax season to think about taxes, then feeling surprised by the bill.

I make a high income. Isn’t overpaying taxes just part of the deal?

Paying taxes is part of the deal. Overpaying because you didn’t plan is optional. High-income tax planning focuses on choices you can control, like timing, structure, and tracking.

What’s the difference between tax preparation and tax advisory?

Tax preparation files your return and reports what happened. Tax advisory helps you make decisions during the year so you owe less, avoid surprises, and create a plan for tax payments.

What are the most common tax mistakes physicians repeat?

Common repeats include waiting until tax season, underpaying on 1099 income, ignoring entity structure until income grows, and missing deductions because tracking stays messy.

Do I need physician tax planning if I’m W-2 only?

Maybe. If you have only W-2 income and no side income, planning can still help with withholding, retirement contributions, and year-end moves. The biggest need usually shows up once you add 1099 income, a practice, real estate, or a spouse with complex income.

How often should I meet with a tax advisor for planning?

A simple cadence works for most people:

• Early-year planning

• Mid-year check-in

• Year-end review

If your income changes a lot, you might add one extra touchpoint.

What’s one thing I can do this week to improve my taxes?

Pick a date for a planning check-in and list your income sources. That’s it. Those two steps set up a real conversation and stop the “last-minute scramble” pattern.