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Year-End Financial Moves for the Self-Employed

Self-employed workers face many decisions at year-end: Should they make deductible purchases now or in the New Year, model income/tax differences from one year to the next, open an HSA or new retirement account, or change their business structure altogether? These are important decisions to sort before New Year’s Eve.

The end of the calendar year is a hectic time for many Americans who work full-time. But for the self-employed who compose at least 30% of the workforce, there’s typically extra pressure during the holiday season. Decisions made now can impact retirement investment options, tax brackets, and tax liabilities for both the current and coming year.

Financial planners say many decisions that the self-employed make this time of year involve a combination of reviewing this year’s business performance and thinking ahead toward preliminary tax preparation. It’s a good time to check in with both an accountant and a planner, particularly with respect to investment moves that could soften the tax impacts of income fluctuations.

Launch a tax review

“During late fall we find ourselves working with clients on what I’d call ‘tax review,’” says Wade Chessman, a certified financial planner with Chessman Wealth Strategies in Dallas, Texas. Roughly 10% of his clientele is self-employed.

“We try to maximize clients’ tax brackets,” he says, explaining that this involves strategizing so that clients don’t drift into a higher bracket or face an unanticipated jump in tax bills. This can involve reviewing investments in a Healthcare Savings Account, tax-advantaged retirement accounts such as SEP IRA or Individual 401k (or “Single(k)” as it’s called), which can lower taxable income, and many other maneuvers.

Establish self-employed retirement accounts

If you haven’t yet established a self-employed person’s retirement account, you’ll need to do that by December 31, 2017. Both Single(k) and SEP IRA plans need to be open in 2017, even if you don’t make donations for tax year 2017 until first quarter of next year.

You have until the date you submit returns (meaning April 18, 2018—or October 15, 2018 for those with extensions) to contribute for the prior calendar year.

If you’re planning to open a SIMPLE IRA, you missed the deadline of October 1 for 2017. But you can open this IRA type during 2018, any time between January 1 and October 1.

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Review income with an eye toward taxes

Unlike many full-time employees whose salaries are predictable, the self-employed may see ebbs and flows in income due to unforeseen circumstances like client demand for services during a given year or clients paying earlier (December) or later (January) than expected.

The self-employed are responsible for making quarterly tax payments to the IRS throughout the year, and these payments are often calculated against recent-year income—meaning payments made in 2017 were based off CPA or software projections built from 2016’s actual numbers or other somewhat unpredictable estimates.

This means that if the current year’s stew of income sources, business deductions, and investments in retirement accounts vary widely from year to year, the individual in question may be stuck wondering whether to tuck more money in an IRA in order to lower taxable income or keep their cash liquid for the coming year’s tax bills.

“I often have to remind my clients to pay attention to their cash flow and keep sufficient reserves for estimated taxes,” says Brett Fellows, a certified financial planner with Oak Capital in Mount Pleasant, South Carolina, who counts 20% of his clients among the self-employed.

Fellows’s clients—software developers, independent business owners, and contractors—typically fall into higher tax brackets, which means they’re eligible to contribute toward the top end of these retirement accounts’ limits ($53,000 in 2017 for a SEP IRA). That’s a lot of money to tie up should liquid resources need to remain nearby in the event of a tax bill.

Accelerate or decelerate deductions, and use charitable giving and your HSA

If calendar 2017 was a great year, financially speaking, but you earned more than anticipated and risk owing taxes beyond any estimated quarterly payments you made to the IRS, consider what Chessman calls “accelerating” deductions accordingly and taking business expenses during December rather than after the New Year to capture the deductions in 2017.

(Of course, he notes, any dollar spent is not equivalent to a dollar deducted; this depends on tax brackets.) Similarly, if you pulled in less revenue than usual during 2017 and expect things to bounce back in 2018, it might make sense to push deductible spending into the next calendar year where it can do a better job counteracting the tax bill.

Aside from business deductions, year-end sees many adults (self-employed or not) making charitable deductions. The nonprofit sector is well aware that donors not only want to support charitable work but also claim tax deductions for their gifts, and as a result charitable organizations frequently make appeals this time of year for that reason. If you’d rather give your money to an alma mater or humanitarian endeavor than to the IRS, do it before December 31.

You have until tax filing time to fund your Healthcare Spending Account (HSA) for the prior year, but its maximum $3450 contribution can also play a role in lowering taxable income.

Make your employee contributions to retirement plans now

Many self-employed people use a SEP IRA or Single(k) for retirement savings. Even if you’re a sole proprietor, these plans are set up for an employee contribution and employer contribution—and for accounting and tax purposes, you play both of these roles. If you’re lucky enough to be able to make the maximum contribution ($53,000-$54,000) to either of these account types, you need to fund the $18,000 employee portion of this investment by Dec. 31, 2017, notes Fellows.

Depending on your concerns about how your financial picture will look at tax time, you can reserve the remaining $35,000 of employer (or profit-sharing) contribution until you see how your returns look, then invest the money into accounts by mid-April.

The end of the year doesn’t have to be traumatic for self-employed workers. But for maximum success, it’s best to track income and expenses during the year and compare them against the prior year’s in order to have a sense of how the current year is tracking against the prior. With some self-awareness about your business’s trends, and some strategic conversations with a tax preparer and planner, you can make end of year adjustments that serve your goals and help you keep as much investable cash as possible.

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