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How to Survive a Job Without Benefits: DIY Health Insurance, Retirement & Vacation


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The gig economy is a big, diverse, and growing field. It includes short-term, part-time, temporary, contract, and freelance workers, from office temps to Uber drivers.

All these workers have one thing in common: They lack the employee benefits that come with traditional jobs. If you’re part of the gig economy, you have to provide perks such as health insurance, retirement plans, vacation time, and even sick leave on your own. 

As a freelancer, I know from experience that this is tricky, but not impossible. It only takes a bit of effort to buy your own health insurance and fund your own retirement plan. And with a little creativity, you can even take vacations and sick days without breaking your budget.

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1. Do-It-Yourself Health Insurance

One of the biggest problems for workers in the gig economy is health insurance coverage. The health care system in the United States has the quirk of being built around employer-sponsored benefits. That makes it tough to get coverage if your job doesn’t provide it.

The Affordable Care Act, popularly known as Obamacare, required more employers to provide health insurance for their workers. However, that applies only to permanent, full-time employees. Temporary, contract, and part-time employees are still on their own.

Fortunately, there are several health insurance options for the self-employed and other workers in the same boat. These choices often cost more than employer-sponsored plans, but they’re a better option than going without insurance and risking having your savings wiped out by a health crisis.

Benefits From Your Spouse, Partner, or Family Members

If you’re married and your spouse works full-time, see if you can get covered as a dependent on their health plan. If you can, it will probably give you better coverage at a lower price than you could get on your own.

Employers often pick up part of the tab for their employee’s insurance premiums, and sometimes for family members as well. And even if the company doesn’t do this, a group plan through a large employer is likely to have lower rates than an individual plan.

If you’re not married but you live with your partner, there’s a chance you could get insurance benefits under their plan as a qualified domestic partner. However, since federal law doesn’t recognize domestic partnerships, this option is only available in some states.

Typically, to get coverage as a domestic partner, you must state that:

  • You and your partner are a couple.
  • You share your home and living expenses.
  • Neither of you is married to anyone else. 

In some cases, you may need to produce documents to back up your claims. For instance, your employer might ask to see your lease agreement or bank statements.

Finally, if you’re age 26 or younger, you can get coverage under a parent’s health plan. You don’t have to live with this parent — or even in the same state — to use their insurance. 

However, if you live out of state, you might pay more to see doctors who aren’t in your parent’s local network. Check the details of the plan before signing up.

The Health Care Marketplace

If you can’t get coverage on a family member’s plan, your next best bet is to shop for an individual plan on the official health insurance marketplace. In most states, you can simply visit to look for insurance. However, some states have their own marketplaces.

Typically, you can only buy insurance here during the annual open enrollment period. For 2022, this period runs from November 1, 2021, through January 15, 2022. You can also apply after a change in your life that affects your coverage, such as losing your job or the birth of a child. 

Marketplace health plans can be expensive. According to eHealth, the average monthly premium for an individual plan in 2020 was $462. For a family of four, the average cost was $1,437 per month.

However, if your income is below a certain level, you get subsidies that cover a large share of this cost. In 2020, the average worker who got a subsidy paid only $199 per month.

All plans available in the marketplace cover certain basic preventive care, such as vaccines and basic screening tests. However, the plans vary widely in what else they cover and how much they cost. 

According to, there are five levels of health care coverage available on the exchanges:

  • Catastrophic. These plans have the lowest monthly premiums, but they also have high deductibles — $8,150 for the year 2020. They’re available only to people under 30 and people who can’t afford a regular plan. Subsidies don’t apply to this type of plan.
  • Bronze. After catastrophic plans, bronze plans have the lowest premiums. However, their deductibles can come to thousands of dollars, and they don’t cover most routine care. All in all, they will probably cover only 60% of your health care costs.
  • Silver. These plans have moderate premiums and moderate coverage. They cover more routine care than bronze plans and have lower deductibles and copays. They should pay about 70% of your costs overall.
  • Gold. These plans have high premiums and low costs for care. A gold plan should pay for about 80% of your health care costs. That makes it a good choice for people who need a lot of care.
  • Platinum. This is the most expensive type of plan. Platinum plans have low deductibles and cover around 90% of all your health care costs.

When you shop for insurance through or your state’s health exchange, you enter information about yourself, your dependents, and your income.

First, the site lets you know whether you qualify for Medicare, Medicaid, or a health care subsidy. Then, it shows you a list of plans you can buy. It provides details such as their monthly premiums, annual deductibles, and the maximum you might have to pay out of pocket in a year.

You can purchase a plan through the site and automatically apply your subsidy, if you have one, to cover part of the cost.


If you’ve just left a full-time job to join the gig economy, you can get short-term health coverage through COBRA. This allows you to keep your health insurance from your old job for up to 18 months. You must sign up for coverage within 60 days of leaving your job.

COBRA can also cover you if you’ve lost access to someone else’s employer-sponsored plan. For instance, you can use it to stay on your spouse’s health plan after a divorce or on a parent’s plan past age 26. In these cases, you can keep your COBRA coverage for up to three years.

However, the benefits you receive from COBRA will probably cost you more than you paid for them as an employee. Most employers pay for part of their employees’ health care costs, but under COBRA, you generally must pay the entire premium yourself.

If you’ve recently lost a job, you’re probably better off looking for a plan in the health insurance marketplace. If you’re already on for COBRA, you can choose to switch to a marketplace plan during the next open enrollment period.

Membership Organizations

Many organizations that charge dues, such as labor unions, offer health insurance as a benefit for their members. Just like businesses, these groups can band together to negotiate better prices for their members than they could get buying individual plans.

Organizations that provide health insurance include:

  • AARP. This organization is open to people over 50. It offers several supplemental health plans for people on Medicare. It also sells life insurance, short-term medical insurance, dental plans, hearing and vision care plans, and a prescription discount card.
  • Affiliated Workers Association (AWA). The AWA is a national association of self-employed people. It offers accident, dental, prescription drug, and vision coverage for its members. It also has a variety of discount plans to reduce the cost of care.
  • Association for Computing Machinery. This association of computer professionals provides several medical plans for members. It also offers dental plans, long-term care insurance, and coverage for accidental death and dismemberment.
  • Freelancers Union. This nationwide organization of freelancers has partnered with a couple of health insurers to offer individual plans in New York only. It also offers Medicare Advantage Plans for freelancers over age 65.
  • Writers Guild of America. This labor union represents writers for movies, TV, and new media. Members who earn a specific amount through their writing in a year can qualify for health coverage through the guild’s Health Fund. Visit the site to check your eligibility.

If you’re not a member of any of these organizations, consider what other groups you belong to that might provide this benefit. Also consider groups that you don’t belong to, but could be eligible to join.

Possibilities include unions, professional and trade organizations, alumni associations, and your local chamber of commerce. Call these organizations or check out their websites to see if any of them can provide you with an affordable health plan.

Other Health Care Coverage Options

Depending on your situation, you may qualify for other sources of health care coverage. For example:

  • If you’re at least 65 years old or disabled, apply for Medicare.
  • If you’re a student, see if your college or university offers a student health plan.
  • If you’re a current or former member of the military, get TRICARE coverage for yourself and your family.
  • Look for part-time jobs that offer health benefits.
  • Look into health care sharing ministries such as Medi-Share. These faith-based health plans are not ACA-compliant and often don’t cover certain health care costs, such as birth control. However, they often have lower premiums than other plans.
  • If you need short-term coverage to get you through, check out eHealthInsurance. Some of its health options cost $99 per month or less.

Bonus Tip: Open a Health Savings Account (HSA)

Some health insurance plans offer you the option to open a health savings account (HSA) This is a tax-free investment account you can use to save money for health care costs. If your plan doesn’t give you this option, you can open an HSA through Lively

An HSA works in conjunction with a high-deductible health insurance plan. The idea is simple: You buy health insurance with low monthly premiums, then put aside money in the HSA as a health emergency fund. This fund covers the high deductible if you incur massive medical bills.

In 2022, you can pair an individual plan with an HSA if its deductible is at least $1,400 and its out-of-pocket costs are capped at $7,050 or less, according to For a family plan, these limits are doubled.

This combo is a compelling option for healthy people with few current medical needs. To make them even more attractive, HSAs offer triple tax protection. Contributions are tax-free, earnings grow tax-free, and withdrawals are tax-free if you use them for medical expenses.

2. Do-It-Yourself Retirement Plans

Along with health insurance, many people rely on their workplaces for retirement benefits. These days, traditional pension plans funded by employers are rare. However, many workers do most of their retirement saving through workplace plans such as a 401(k) or 403(b).

These plans allow you to set aside money out of your pretax income for retirement and pay no taxes on it until you withdraw it. As a plus, many employers match your contributions to these plans, at least up to a certain amount each year.

If you’re self-employed, you can’t contribute to a workplace plan. However, there are other ways to save for retirement on your own. You can’t take advantage of employer matching, but you can still get the same tax advantages you’d get from a workplace plan.

Individual Retirement Accounts (IRAs)

The simplest way to set aside money for retirement on your own is through an individual retirement account, or IRA. These plans have tax advantages that help you build savings faster. IRAs come in two main types: traditional IRAs and Roth IRAs

A traditional IRA has the same tax advantages as a 401(k). You fund it with pretax dollars, and the money accumulates tax-free until you reach retirement age. The IRS currently defines this age as 59½ years old. 

If you withdraw any money before then, you must pay taxes on it immediately, along with a 10% penalty. You’re required to start taking money out — and stop putting money in — the year you reach age 72.

A Roth IRA is like a traditional IRA flipped on its head. You fund it with after-tax dollars, but you pay no taxes on the money when you withdraw it. 

You can withdraw the money you’ve contributed to a Roth IRA — although not the earnings on that money — at any time, with no taxes or penalties. You can also leave it in the account — and continue to make contributions — as long as you like.

However, you can’t contribute to a Roth IRA at all if your income is above a certain limit. In 2021, that limit is $140,000 for single people and $208,000 for couples. And you can only contribute the maximum amount if your income is below $125,000 ($198,000 for couples).

The IRS sets limits on how much you can contribute to either type of IRA. For 2021, the limit is $6,000. You can contribute an extra $1,000 if you’re age 50 or older. 

You can open either type of account through a broker like E*TRADE. If you choose an online brokerage, you can set up an IRA in minutes.

With an IRA, you can’t make regular contributions through a payroll deduction the way you do with a workplace plan. However, you can do the next best thing by setting up an automatic savings plan.

To do this, divide your maximum annual donation into monthly contributions. To contribute $6,000 for 2021, you would set aside $500 per month. Then set up an automatic transfer of that amount from your bank account to your IRA each month. This makes saving for retirement effortless.

Plans for the Self-Employed

IRAs are available to anyone. Even if you already have a full-time job with its own workplace retirement account, you can have an IRA as well. However, if you’re self-employed, you have several additional options. 

These plans are a little harder to set up than a traditional or Roth IRA. However, they can allow you to set aside more of your income tax-free.

Solo 401(k)

A solo 401(k) is for self-employed people with no other employees. It works just like a workplace 401(k) plan, with one key difference: You are both the employer and the employee. 

As the employee, you can contribute up to $19,500 per year in 2021. If you make less than 19,500 in a year, you can contribute 100% of your earnings. And, as the employer, you can contribute up to 25% of your earned income on top of that.

The total limit on how much you can contribute to a solo 401(k) is $58,000 per year for 2021. In addition, you can contribute an extra $6,500 if you’re age 50 or older. You can set up a solo 401(k) in just minutes with Rocket Dollar.

Roth Solo 401(k)

This is the Roth version of the solo 401(k). You contribute after-tax dollars, then withdraw the money tax-free in retirement. However, unlike a Roth IRA, a Roth solo 401(k) doesn’t allow you to withdraw money early with no penalty. 

Both types of accounts require more tax-related paperwork than an IRA. You have to fill out one additional form each year, called Form 5500-EZ. You can complete it by mail or electronically. However, most tax software doesn’t include it. 

SEP Plan

A Simplified Employee Pension Plan, or SEP Plan, has the same contribution limits as a solo 401(k). However, a SEP is easier to set up and maintain. 

Tax-wise a SEP works like a traditional IRA. There is no Roth version. One downside is that if you have any other employees besides yourself, you’re required to contribute to their SEP Plans as well. 

If you’re interested in a SEP Plan, you can open an account with TD Ameritrade.


For small-business owners, a Savings Incentive Match Plan for Employees, or SIMPLE IRA, can be a better choice. With this plan, you don’t have to fund your employees’ plans all by yourself, although you typically have to make a matching contribution. 

However, the annual contribution limits for this plan are much lower. For 2021, the limit is $13,500. People over 50 can make an additional $3,000 catch-up contribution.

Defined Benefit Plans

Old-fashioned pension plans that pay you a specific income in retirement aren’t entirely dead. It’s still possible to get one by funding it yourself. Defined benefit plans can allow you to set aside more pretax dollars each year than any other type of plan. 

However, they’re complicated and costly to set up and maintain, and only a few brokerages offer them. And, if you have employees, you must contribute to pensions for them as well.

3. Do-It-Yourself Sick Leave

If you have a full-time job, your employer probably allows you a certain number of sick days per year. If you catch a cold or sprain your ankle, you can take time off to recover and still get paid. 

But when you work for yourself, that’s not an option. You have to make the stressful choice between trying to work while you’re sick, which isn’t always possible, or losing income.

However, you can make this choice easier by planning ahead. There are several strategies that can help.

Plan for Sick Days

No matter how careful you are, you can’t eliminate all risk of getting sick. What you can do is assume you’re going to need a certain number of sick days and factor them in when you plan your work schedule. 

For example, let’s say you expect to miss eight days of work due to illness in an average year. And at your current hourly wage, you need to put in an average of 30 billable hours of work each week to make ends meet. 

If you boost that to 31 hours per week when you’re healthy, those extra hours will add up to about eight days’ worth of work over the course of the year. That’s enough to make up for eight days off when you’re sick.

Create a Sick Leave Fund

Take the money you make from that extra hour of work each week and set it aside in a separate bank account. You can use a high-yield savings account so it will earn interest. This will be your sick leave fund. 

When you have to take time off from work, you can take money out of this account to keep the bills paid until you’re back on your feet. Alternatively, you can add to and withdraw from your emergency fund for this purpose.

Keep Your Schedule Flexible

Even if you have plenty of money in the bank, it’s hard to take a sick day if you’ve got a big deadline looming. To avoid ending up in this situation, try to plan a little leeway into your work assignments. 

If you think a job will take you five days to complete, promise to have it done in seven. That way, you won’t miss your deadline if you have to take a day or two off.

Stay on Schedule

Of course, having extra time in your schedule won’t help if you use it as an excuse to put off getting started on a project. If you’re not sick, stick to your work schedule and avoid procrastination

If you expect an assignment to take you five days, work on it steadily for five days. Getting it done early isn’t a problem; turning it in late is.

4. Do-It-Yourself Vacation Leave

If being self-employed makes it hard to take a day off when you have a cold, it makes it even harder to take a whole week off for a vacation. However, working all year without a break isn’t the best solution for your health or happiness.

There are many benefits to taking regular vacations. They can reduce your stress level, prevent job burnout, and even protect you from illness. A 2000 study in Psychosomatic Medicine found that yearly vacations reduced the rate of death from all causes for men at risk of heart disease.

To  free up time and money for vacations, follow the same strategies as for sick days. Block out time in your schedule for vacations and plan work assignments so they don’t overlap with your time off. To make up for the lost wages, put in extra hours at other times throughout the year.

Along with your sick leave fund, create a special vacation fund. Use it to cover both the expense of a trip itself and the cost of your lost wages. To stretch this money further, look for ways to save money on your vacation so you won’t need to work as many extra hours to pay for it.

Bonus Tip: Consider Both Long & Short Trips

If your job allows you to telecommute and set your own hours, there are a couple of additional ways to squeeze in some vacation time without significantly reducing your income.

If you plan it right, you can enjoy a long weekend away without actually missing any work hours. In the workweek leading up to the long weekend, work longer hours to get five days’ worth of work done in four days.

You can also put in extra time the following week to make up work if needed. And three or four days off is a short enough period that you don’t have to worry about missing anything too important.

Alternatively, you can go to the other extreme and take long working vacations. You may not be able to take a month away from work, but if you can take your work with you, you can work during the day and play tourist in the evenings and on weekends.

Instead of living out of a hotel room and eating every meal out, book an apartment on Airbnb and cook most of your meals in. Or take it a step further and check out ways to travel the world for free to learn how you can save on accommodations, transportation, or both.

Final Word

Right now, the majority of American workers are still able to get benefits from their jobs. However, many economists expect this to change in the future as the gig economy continues to grow.

Already, many companies are outsourcing large portions of their business to subcontractors. These individuals or small companies don’t offer the same benefits as big ones. 

If this trend continues long enough, figuring out how to fund your own benefits won’t just be an important skill to succeed as a freelancer. It will be vital for all workers.


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Amy Livingston is a freelance writer who can actually answer yes to the question, "And from that you make a living?" She has written about personal finance and shopping strategies for a variety of publications, including,, and the Dollar Stretcher newsletter. She also maintains a personal blog, Ecofrugal Living, on ways to save money and live green at the same time.