3 Wealth Planning Tips for the Self-Employed

3 Wealth Planning Tips for the Self-Employed

We could talk for days about the perks of being your own boss. But have you considered how a self-employed lifestyle could impact your long-term financial plan? Don’t overlook these three key areas if you’re working for yourself.

Published by Motley Fool Wealth Management Originally posted on Tue, Sep 6, 2022 Last updated on January 10, 2024

read time 6 min read

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If you are considering going out on your own, or you’re already your own boss, you are part of a growing trend. Roughly 64.6 million Americans reported some degree of self-employment in 2022.1 

If you take this big step, don’t overlook that some important perks of a traditional job—such as retirement savings plans and insurance—will no longer be provided to you. But because these could be key components of your long-term security, neglecting them could cause you hardship down the line that may diminish the joy and success of your self-employed lifestyle.

Fortunately, they are not hard to put in place. We think enjoying both freedom and long-term financial security while being self-employed comes down to three key areas.

The key areas to shore up as a self-employed individual

Long-term financial security hinges on planning for your wealth later in life, including Social Security, retirement savings, and insurance protection. Here are the ins and outs of each.

1. Social Security

In traditional jobs, the employer and employee each pay 6.2% of the employee’s net income into Social Security and 1.45% into Medicare. This is taken from each paycheck before it comes to an employee. Assuming working individuals make 10 years of these payments (40 quarters), they’ll receive Social Security checks in retirement based on their contributions.

But how does it work for self-employed people?

If you continue to pay into the system (and make at least 40 quarters of payments in your lifetime), you will receive checks based on your highest 35 years of reported wages.

But since you are now your own employer, you need to make the payments on your own (instead of having them automatically withdrawn from your paycheck). Many self-employed people do this at the end of the year—in their tax returns—instead of with each paycheck. This is fine but requires a bigger payout all at once, so consider paying more often if you want to budget better.

Another difference is, that self-employed workers must pay both the employer’s and employee’s portion, or 15.3% of taxable income. The employer’s portion is a deductible expense, somewhat lowering this cost.

Remember an important tradeoff: While the self-employed are often encouraged to claim every business expense possible to lessen taxable income each year, this also reduces your Social Security payment later in life. Should you report fewer expenses now to get more benefits later? It’s hard to calculate, but the benefit of doing this is greater for those with lower incomes than those with higher incomes.2

2. Retirement savings

Another big change when self-employed is funding your retirement.

In a traditional job, many employers offer a retirement plan that automatically takes pre-tax contributions from workers’ paychecks. They may also provide a matching contribution.

Now that you are self-employed, you need to do this yourself. Our advice—don’t stop contributing! You can set up your own plan or contribute to various retirement accounts. Here are a few to consider:

  • Individual 401(k). One of the best options for self-employed people working alone is an Individual 401(k). As with Social Security, you are now considered both the employee and employer. But this time, it works to your advantage.

    As a self-employed “employee,” you can contribute the same amount as those with a company 401(k)—$22,500 pre-tax earnings per year plus a $7,500 catch-up if you're 50 or older. But as the “employer” also, you can now make an additional contribution of 25% of your salary, for a total contribution of up to $66,000 per year (or $73,000 for those 50 and over).

    If you have employees, though, this may not be your best option, as your contribution will be limited to how much you contribute for your employees.
  • SEP IRA. This type of individual retirement account (IRA) offers similar benefits as Individual 401(k)s. While both allow contributions up to $66,000 per year, SEP IRAs make sense for individuals but not small businesses because only an employer can contribute.
  • Simple IRA. These IRAs are available for individuals but generally are not recommended because the contribution limits are low ($15,500/year and $3,500 catch-up) and require a contribution every year. Early withdrawal penalties are also high.
  • Personal Defined Benefit Plan (aka Pension plan). Like defined benefit plans in general, a personal defined benefit plan is rare today. This type of plan is typically best reserved for very high-earning individuals without other employees associated with their business. To set it up, you must declare how much you want to receive each year in retirement. This establishes a required annual contribution while working to stay properly funded. A required and unwavering annual contribution does not fit well with the variable cash flow of many self-employed people.
  • Roth and Traditional IRA. Setting up and managing these has always been the responsibility of the individual, so being self-employed does not change this. Roths tend to be better suited for younger people and those with lower incomes, while traditional IRAs are usually owned by individuals with higher incomes. While both are excellent vehicles for retirement savings, the maximum contribution to all your IRAs in one year is $6,500 ($7,500 if you’re 50 or older), so they won’t fund your retirement to nearly the degree other savings vehicles could.3

However you decide to save for retirement as a self-employed individual, it’s important not to delay doing so. Delaying even a few years can result in much lower retirement savings later due to a loss of long-term compounding. For example, if you fail to contribute even as little as $5,000 per year into a diversified stock portfolio earning 7% a year from ages 28 through 33, you could give up the opportunity to amass over $200,000 30 years later.4

What about if you have a side “hustle” and an employer-based retirement plan?

Well, like Hannah Montana sang, “You’ve got the best of both worlds!” You can still contribute up to the max of your employer-sponsored retirement plan (like a 401(k)) and your own business’ 401(k), simple IRA, or SEP plan. For example, if you are under the age of 50, you can contribute $22,500 to your employer 401(k) and 25% of your net earnings from self-employment up to $66,000 for your SEP plan for 2023. (There are restrictions like you cannot be an owner of your employer’s business, so consult with a tax professional.)


Another aspect of your long-term security that changes with self-employment is insurance. In traditional jobs, many employers provide health and sometimes life insurance. When you’re self-employed, you need to get these for yourself.

Don’t underestimate the importance of insurance. It’s protection against an emergency that could result in financial ruin but, more importantly, hurt your health and well-being.

There are many options for health insurance, from low to high deductibles, and even plans that allow you to save more in a Health Savings Account. Consult an insurance broker or your state’s health insurance marketplace via healthcare.gov to help you make the choice that best fits your circumstances. As a bonus for self-employed individuals, costs associated with health insurance premiums for yourself, your spouse, and your dependents are considered tax-deductible expenses.

Life insurance is another important consideration for a self-employed person. If you don’t have dependents, you may not need it. But if you do, we believe it’s important to have a mechanism for replacing your income in case of premature death. There are a lot of ins and outs of life insurance, so consult with an insurance professional to learn more about your options.

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1Statista, data through 2022

2Investopedia, April 7, 2022

3Schwab, Sept 24, 2021

4SmartAsset investment calculator


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