I left my full-time job to pursue a freelance career a few months before my 26th birthday. Talk about bad timing. I was about to lose access to my parent’s health insurance and I was giving up the benefits that come with full-time work.

The good news is that ticking clock was the push I needed to figure out my own benefits, from health insurance to retirement savings and time off. Here are four key benefits you should consider as a freelancer.


I began my search for health insurance at HealthCare.gov which led me to my state’s marketplace (you can find your state’s marketplace here). Based off your income and your needs, you should be able to find a plan that is a good fit for you or your family.

Vision and dental insurance may not be included in your marketplace health insurance plan. If these are important to you, you can choose a stand-alone plan. Dental is typically offered separately through the marketplace; however, for stand-alone vision plans you’ll need to contact a third-party. Vision coverage for children, however, is included in all marketplace plans.

Just like with a full-time job, you can only enroll for healthcare during the open enrollment period unless you qualify for a special enrollment period. Losing employer sponsored coverage is typically one of those times (you can learn more about Special Enrollment Periods here).


Saying goodbye to an employer-sponsored 401(k) can be tough (especially if it came with a company match), but there are other options to save for retirement if you’re self-employed.


An Individual Retirement Account (IRA) is a common retirement savings option that offers tax advantages. IRAs come in two varieties: traditional or Roth. The major difference between the two is whether you’ll pay taxes upfront on your contributions (Roth IRA) or when you withdraw them in retirement (traditional IRA). Both grow tax-free.

There are also limits to how much you can contribute to your IRA (both traditional and Roth). As of 2019, you can’t contribute more than $6,000 a year ($7,000 if you’re 50 or older). Plus, if your income exceeds certain limits, you can no longer contribute directly to a Roth IRA. You also may not get a full tax deduction for traditional IRA contributions if you make too much money.


These are a different form of an IRA available to small businesses.

With a Simplified Employee Pension (SEP IRA), you can contribute as much as 25 percent of your net earnings from self-employment, not including contributions for yourself, up to $56,000 for 2019.

A Savings Incentive Match Plan for Employees (SIMPLE IRA) lets you put all your net earnings from self-employment up to $13,000 into the plan (plus an additional $3,000 if you’re 50 or older), plus either a 2 percent fixed contribution or a 3 percent matching contribution.

Solo 401(k)

A Solo 401(k) allows you to make contributions today without paying taxes. Your money will grow tax free and then be taxed when you withdraw it in retirement.

When you’re self-employed individual you can open a Solo 401(k) and contribute both as the employee and employer. For 2019, you can contribute up to $19,000 (plus an additional $6,000 if you’re 50 or older) as yourself. Then, you can also make employer contributions up to 25 percent of your earnings. Your total contributions can’t exceed $56,000.

Beyond these plans, you may also consider a variable annuity to help save for retirement, which can play a key role in helping make your money last for decades.


Your employer likely provided you with life and disability insurance. But now that your employer won’t be funding these benefits, you should look into your own coverage.

Disability insurance, can replace a portion of your income if you find yourself unable to work due to illness or injury.

If you have a family, life insurance can help replace lost income if you pass away. And, depending on the policy you choose, it can also provide benefits that you can use throughout your lifetime, including cash value, which you could use down the road if your business dips and you find yourself strapped for cash.


While one of the perks of being self-employed is the flexibility you have with your schedule, paid time off (PTO) simply doesn’t exist. If you’re not working, you’re not making money.

As a freelancer I try to keep my schedule as flexible as possible. If I need to take off an afternoon for an appointment, I know I can catch up on the work I missed that night. If I’m taking a short vacation, I may work a bit on the weekends leading up to my trip to get ahead. However, you can’t always manipulate your time and workload to take time off without missing a paycheck.

If you’re not working, you’re not making money.

When calculating my income goal for each month, I also plan how much time I’d like to take off in the future. While a day or two here and there can be easily balanced out, taking extended time off over the holidays or for longer trips is something I have to plan and save for.

I also try to keep my workload as flexible as possible. I avoid working with too many clients who give short lead times on projects or who need me available at certain hours. When traveling, I’m happy to catch up on emails at the end of the day or work while at the airport. I can only pull this off, though, if I work with clients who don’t require my services at specific times. When choosing your clients, this may be something you want to keep in mind if flexibility and time off is important to you.


When I first left my job to be self-employed, I had a simple goal of making as much per year as I did at my last salaried job. Spoiler alert: That was not a sustainable plan. Because my salaried job also included all the above benefits. If I wanted to be able to make a similar salary and afford traditional benefits, I needed to make more money, which meant increasing my rate.

Employers save a decent amount of money when they work with freelancers. Not only do they not have to employ them for a set number of hours or pay them overtime, but they also don’t have to pay for benefits, payroll taxes or office space and supplies. Since you need to cover these costs, you should take them into account when you set your hourly or project rate. After researching your different benefits options and making your selections, calculate how much your benefits will cost each year, then calculate factor those costs into your hourly rate.

This publication is not intended as legal or tax advice. Financial Representatives do not give legal or tax advice. Taxpayers should seek advice based on their particular circumstances from an independent tax advisor.

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