Lessons learned from tax season

If you're feeling a tax hangover from the filing season that just ended, cure it with a hair of the dog that bit you. Planning and organizing your finances from a tax perspective now may be just the medicine you need to make next year's taxes less stressful—and save you money. Below are some concerns you may have had this time around, plus advice on how to address them.

If most of your income is from a salaried job, you can reduce the shock of April by adjusting your federal income-tax withholding. Use the IRS Withholding Calculator (type "withholding calculator" in the search window at irs.gov). You may have to adjust your state withholding, too.

You may have owed more last year because of investment income. If you receive quarterly investment statements, compare those for 2012 with those from 2011, advises Michael G. Maksymiw, a CPA with Filomeno & Co., business advisers in West Hartford, Conn. If you're receiving significantly more in dividends, adjust your quarterly estimated tax payments accordingly.

If fluctuating income from your small business made your taxes higher than you expected, ask a tax adviser to calculate optimal quarterly tax payments that also avoid IRS underpayment penalties.

Experts we interviewed recommend using Quicken to label and organize taxrelated transactions. (You can import the information to a desktop version of TurboTax and H&R Block At Home.) Other personal-finance programs—the server-based Mint.com and Yodlee MoneyCenter (yodlee.com), and AceMoney (mechcad.net), a download—can also categorize and organize your transactions. Or check whether your credit card or bank's online site auto-labels transactions.

A low-tech way to organize your files is to label the pockets of an accordion folder with tax categories—charitable donations and rental property, for example—then fill them with receipts and statements throughout the year.

Chris Bixby, a financial planner at Key Private Bank in Bellevue, Wash., says he advises his small-business clients to put envelopes for expense receipts in their vehicles to fill on the go. "The hundreds of dollars a year they saved in deductions went to thousands of dollars a year," he says. To calculate business mileage, Bixby likes mileage-tracking apps on GPS devices and smart phones.

Waiting until almost the end of tax season to fund an IRA means you might not have as much to invest as you'd like. Plus, you might end up buying at an investment's peak. By contributing regularly—say, monthly through automatic electronic transfers—you might benefit from dollarcost averaging: getting a lower average price on your investment and avoiding the possibility of overpaying.

If you're funding a Simplified Employee Pension IRA, you might not know until you've done your taxes how much you can invest, since the contribution is a percentage of your earnings. David Walters, a CPA and senior financial planner at Palisades Hudson Financial Group in Fort Lauderdale, Fla., says he tells some clients to estimate their minimum income early in the year, then aim to fund their SEP-IRA based on that amount. "We can add more as needed at tax time," he says.

Even without a change in income, a shift in your family situation or a tweak to the tax laws could affect your eligibility for tax credits, exemptions, or deductions—and even bump you into a higher tax bracket. When a child turns 17, for instance, you'll lose a child tax credit of up to $1,000.

So contact your tax preparer in June or July, when you can review the first half of the year and make educated projections for the second half. You might want to talk again in October to plan year-end sale of investments to harvest losses and time the donation of appreciated stock. Set up your first tax-season visit in early February, when you still have time to find documents your preparer might need.

If you've used tax software to prepare your return, you'll probably get e-mail messages announcing the updated version around Thanksgiving. But who knows? Having taken the steps above, you might find your 2013 tax prep to be all gravy.