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Chris Brindle

tax mistake


A client got $19,915 back on his taxes. Three life events made it possible. TurboTax would have missed all three.

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FINANCE


The $19,915 Difference

Filing your taxes and planning them are not the same thing.

Read time: 4 min

I told a client to stop using TurboTax. He got $19,915 back on his taxes.

He got married last year. His wife started working. They paid off their student loans.

Three things changed in his life. TurboTax would have processed the inputs and moved on. His CPA knew what each one was worth. That difference -- the gap between a tool that files and a professional who plans -- showed up as a number on his return: $19,915.


What TurboTax does (and doesn't do)

TurboTax is a documentation tool. You answer questions about what happened, it runs the math, you file. Clean, fast, reasonably accurate.

What it doesn't do is tell you that getting married last year changed your withholding situation. Or that your spouse's income stacking on top of yours may have pushed you into a higher bracket -- and that adjusting your W-4 mid-year could have reduced what you owed come April. Or that paying off your student loans freed up $800 a month that could have gone into a tax-advantaged account before December 31.

Those aren't filing decisions. They're planning decisions. And by the time you open TurboTax, it's already too late to make them.

Why life events are the biggest planning triggers

Every major life change comes with a tax implication. Most people either don't know that, or they find out about it a year too late.

Tax Planning for Sales Reps

Life Events That Change Your Tax Picture

Life Event What It Affects The Opportunity

Getting married

Filing status, standard deduction, combined bracket, withholding

MFJ standard deduction is $30,000 -- nearly double the single rate. Update W-4 immediately or you'll owe at filing.

Spouse starts working

Withholding accuracy, combined tax bracket

Default W-4 assumes each spouse is the only earner. Two incomes on one return almost always means one of you is under-withheld.

Paying off debt

Freed-up cash flow, tax-advantaged account capacity

You lose the student loan interest deduction, but you gain cash flow. That money is most valuable redirected to a 401(k), IRA, or HSA before December 31.

These aren't edge cases. They're the normal milestones of life in your 20s and 30s. Every one of them is a planning window -- and every one of them closes.

What proactive tax planning actually looks like

Tax planning happens during the year. Not in April.

By the time you're answering TurboTax's questions, the decisions that determined your tax bill have already been made. What you're doing in April is recording them, not changing them.

The way I think about it:

  • Your CPA handles what already happened. They're looking back at the year and filing an accurate return.
  • A financial planner handles what's coming. Reviewing withholding when your income changes. Deciding how much goes into traditional vs. Roth. Timing contributions before year-end. Coordinating the strategy so your CPA has something to work with.
  • When both are working the same case, you stop leaving money on the table.

My client left $19,915 on the table because no one was looking ahead.

Now someone is. And it shows up in the numbers.

Other things worth reviewing now

A few other situations where proactive planning tends to pay off:

  • Big commission year. If you're on pace to earn significantly more than last year, your withholding may not reflect your actual bracket. Getting ahead of that now avoids a large bill in April.
  • New job or company switch. Old 401(k) sitting at a former employer? That's a rollover opportunity, and potentially a Roth conversion opportunity if the timing is right.
  • First year earning real income. Most new AEs default their 401(k) to Roth because someone said Roth is always better. At $200K+ income, that may be exactly backward. The deduction on a traditional contribution at 32% is real money today.
  • Having kids. Child tax credits, dependent care FSA, childcare deductions -- most people find out about these after the fact instead of before.

The year is almost halfway through. Whatever changed in the last 12 months, now is the time to make sure someone is looking at what it means for the rest of this one.


If you had a major life change in the last 12 months -- new job, marriage, a big comp year, paid off debt -- it's worth a conversation now while there's still time to act before year-end.

I work alongside a CPA to cover both sides of the equation: proactive planning during the year and clean filing when April comes. Book a call if you want to talk through what saving on taxes for next year could look like for you.

Book a call to talk about your tax picture →

-Chris Brindle

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Chris Brindle

I'm a Financial Planner and Investment Advisor for Sales Reps. I create financial content to help people live a better life without the stress that comes with variable income.

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