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Benefits basics for self-employed workers

Key takeaways

  • When you're self-employed, you can put together a do-it-yourself (DIY) benefits package, but you need to be proactive.
  • Use the open enrollment period to find a health insurance policy, and fill coverage gaps where necessary. If your health plan is eligible for a health savings account (HSA), you can use the account to save and pay for qualified medical expenses on a pre-tax basis.
  • A retirement plan, such as a SEP IRA or self-employed 401(k), can help you save for the future with some tax advantages.
  • Consider buying a term life insurance policy to help protect your dependents.

When you’re self-employed, you can get many of the same benefits that W-2 employees receive, including health coverage, life insurance, and a retirement plan. And you can even deduct some of these expenses and lower your taxable income. The challenge is sorting through all the available options to build a DIY benefits package that meets your needs. Here are some of the factors you should take into consideration along the way.

Health insurance when you're self-employed

"The mistake a lot of us make is that we don't think about health insurance benefits until we're driven away in an ambulance," says Benjamin Isgur, vice president of health care thought leadership at Fidelity Investments. That can be especially true for contractors and freelancers, who don't have an employer to help them choose and pay for a plan. So it's important to be proactive and get your health insurance lined up well before you need it.

In certain circumstances, you may have relatively straightforward options:

  • If you've recently left a full-time job, you may be entitled to extend your previous employer plan through COBRA. But you'll likely pay more out of pocket every month, as you'll be responsible for any employer contribution. You can only extend COBRA for 18 months.
  • If you have a spouse or domestic partner who gets coverage through their employer, find out if you can be added to the plan, and if so how much it would cost. Compare that cost and coverage to what you'd get with buying your own plan.
  • If neither of those apply or are feasible, investigate health insurance plans on the state or federal exchange during open enrollment, typically in the fall—or immediately upon losing job-based coverage, which qualifies you for special enrollment.

When evaluating a plan, consider your specific health needs, and whether your current providers and local hospitals are in-network. Marketplaces like Stride5 can help to find affordable options: on their site, you can search and compare public and private health insurance plans, and get recommendations based on your health concerns, preferred doctors, budget, and other needs.

At the very least, you'll need a plan that will cover catastrophic health issues. One option is to pair a high-deductible health plan (HDHP) with a health savings account (HSA). HDHPs tend to be inexpensive in terms of monthly premiums, but their high deductibles mean that, should you face any health issues, you'll have to pay a large amount out of pocket before your coverage kicks in.

The HSA is designed to take the sting out of some of those out-of-pocket expenses. You can make tax-deductible contributions to the HSA and then draw from it tax-free to pay for qualified medical expenses. You may also be able to use funds in your HSA to pay COBRA premiums. Because funds roll over year to year, can be invested, and can be withdrawn beginning at age 65 for any purpose, HSAs can also be a useful retirement savings vehicle.

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Retirement plans when you're self-employed

While contractors don't have access to a typical 401(k) plan, you may be able to save in a retirement account built specifically for small business owners with a high contribution limit. In other words, you get the opportunity to save a lot of money in a tax-advantaged account each year.

The ability to defer taxes offered by retirement savings accounts is among the biggest tax benefits available to most investors. Deferring taxes may help your money grow by keeping more of it invested and potentially growing.

"The key with saving for retirement is consistency," says Roger Morrissette, vice president of small-business retirement products at Fidelity Investments. "Choose a plan and start making automatic contributions."

Here is an overview of a couple of those plans. For help picking the right plan for you, try our 5-minute quiz: Small Business Plan Selector

SEP IRA A SEP IRA is one way for a self-employed worker to save more aggressively for retirement. As with a traditional IRA, contributions are tax-deductible and withdrawals in retirement are taxed as income. A key advantage of the SEP IRA is a potentially higher annual contribution limit. As the employer, you're allowed to make contributions of up to 25% of your annual compensation, not to exceed a given dollar amount—$66,000 in 2023.

Self-employed 401(k) With a self-employed 401(k), you can make contributions as both the employee and the employer. As the employee, you can make tax-deductible contributions of up to 100% of your compensation, not to exceed $22,500 ($30,000 if you're 50 or older). As the employer, you can make tax-deductible contributions of up to 25% of your compensation, up to a total amount of $66,000 in 2023—$73,500 if you're 50 or older.

Life insurance when you're self-employed

If there are people dependent on your income, then a term life insurance policy is essential. As Jill Maher, head of term life insurance at Fidelity Investments Life Insurance Company, puts it, "Protection is one of the primary pillars of a financial plan."

First, you have to figure out how much coverage you may need. Fidelity suggests purchasing enough life insurance to replace any potential lost income from now until retirement. The amount you need may increase as you earn more and then decrease as you get closer to retirement. A general guideline suggests aiming for 10 to 12 times your annual salary and adjusting that to your personal needs. Our Term Insurance Quote Tool1 can help determine an approximate coverage amount and provide a quote.

Next, you have to decide the policy term that is right for you. A term life insurance policy covers you over a set term, or specific number of years. These policies have a fixed premium during their term period. After the term period ends, you can choose to continue the coverage, but the premiums increase significantly and may change every year. For any policy, check if you have a guaranteed right to renew.

A few things to bear in mind:

  • A term policy is generally cheaper the younger you are when purchasing. Age and any new health issues are risk factors that increase your premiums.
  • Your premium is inflation-proof. Even as prices overall increase over time, you continue to pay the same amount for the duration of your policy term. This isn't true of group plans.
  • You should review your plan when you experience major life events. Do you have more dependents? Did you receive a huge boost in income? If so, it may make sense to consider more coverage.

Beyond the basics

Don't forget about the other benefits an employer would provide, like disability insurance and paid time off. You can set aside funds to create a paid time off "bank" you can use for sick days or an upcoming vacation. Consider your average daily income and the number of days you may need, and set aside a corresponding amount of money. You may want to keep this in a separate account where it will accrue interest.

Disability insurance can be easy to forget but it's a critical piece of your safety net as an independent worker. If something happens that jeopardizes your ability to earn money, disability insurance could kick in to help supplement your income. An important factor to figuring out how much coverage you need is the payout percentage—most policies only offer 60% income replacement.

Short-term disability insurance policies will typically replace a portion of income for a short period of time like 6 months to a year. Long-term disability is designed to help with long-term illnesses or injuries which may take years to recover from.

Getting started

No matter what, taking the time to protect your health, your loved ones, and your future may provide the peace of mind you need to focus on your freelance career—and the rest of your life.

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More to explore

1. Estimates and quotes are subject to change. 2. Estate taxes may apply to insurance proceeds. Consult a financial or tax advisor about your specific financial situation. 3. Only tax-deductible contributions and earnings are taxed upon withdrawal, non-deductible contributions are not taxed a second time upon withdrawal. 4. A distribution from a Roth IRA is tax-free and penalty-free, provided the 5-year aging requirement has been satisfied and one of the following conditions is met: age 59½, disability, qualified first-time home purchase, or death. 5. Stride and Fidelity Investments are independent entities and are not legally affiliated.

The information provided here is general in nature. It is not intended, nor should it be construed, as legal or tax advice. Because the administration of an HSA is a taxpayer responsibility, customers should be strongly encouraged to consult their tax advisor before opening an HSA. Customers are also encouraged to review information available from the Internal Revenue Service (IRS) for taxpayers, which can be found on the IRS Web site at They can find IRS Publication 969, Health Savings Accounts and Other Tax-Favored Health Plans, and IRS Publication 502, Medical and Dental Expenses (including the Health Coverage Tax Credit),online, or you can call the IRS to request a copy of each at 800.829.3676.

Fidelity does not provide legal or tax advice. The information herein is general and educational in nature and should not be considered legal or tax advice. Tax laws and regulations are complex and subject to change, which can materially impact investment results. Fidelity cannot guarantee that the information herein is accurate, complete, or timely. Fidelity makes no warranties with regard to such information or results obtained by its use, and disclaims any liability arising out of your use of, or any tax position taken in reliance on, such information. Consult an attorney or tax professional regarding your specific situation. Keep in mind that investing involves risk. The value of your investment will fluctuate over time, and you may gain or lose money. Views expressed are as of the date indicated, based on the information available at that time, and may change based on market or other conditions. Unless otherwise noted, the opinions provided are those of the speaker or author and not necessarily those of Fidelity Investments or its affiliates. Fidelity does not assume any duty to update any of the information. This information is intended to be educational and is not tailored to the investment needs of any specific investor.

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