Don’t overlook these 5 open enrollment elements

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At Dribbble, we’re privileged to help our growing community of talented designers be successful. Thanks to a wealth of design data that will soon be released from our annual design survey, we learned that nearly 75% of designers have freelanced in the past year, and more than 40% are currently freelancing. Designers have an incredible opportunity to refine their craft and build business, whether it be through occasional projects or as full-fledged, self-employed entrepreneurs.

Benefits for the self-employed stretch well beyond healthcare.

One of the most important aspects of building a business is ensuring the designer themselves is well-cared for, yet finding and planning for healthcare and benefits coverage can feel like one of the most daunting tasks. Benefits for the self-employed stretch well beyond healthcare, so we’re ready to break down the big elements you need to consider—from health insurance to retirement, and everything in between.

Open enrollment season ends on December 15 so make sure you get enrolled as soon as possible so you’re covered for 2020. Keep in mind these five important elements when walking through open enrollment.

1. Pick a health plan that works with your lifestyle

The healthcare questions are copious and important. You’ll want to figure out the nuts and bolts of not only what you need, but what’s a smart choice for your health needs next year. If you need an individual insurance plan, you can enroll and get those tax credits you deserve.

Some questions and considerations you may want to ask yourself to choose the right health insurance plan for you and your lifestyle:

  • Are you purchasing coverage for yourself or for a significant other/dependents?
  • Do you have upcoming, foreseeable surgeries or medical needs in the coming year?
  • Are you choosing a plan with in-network physicians that works for you?
  • High out of pocket with a lower deductible, or lower out of pocket with a higher deductible?

2. HSA, health expense savings

If you do choose a higher deductible health plan, do your due diligence and save for medical expenses that your plan doesn’t cover. Set up an HSA (Health Savings Account): a tax-advantaged account created for individuals to save for medical expenses that their high-deductible health plan doesn’t cover.

As long as withdrawals from your HSA are used to pay for qualified medical expenses (like deductibles, dental services, vision care, prescription drugs, co-pays, etc) that are not covered under your health plan, the amount withdrawn will not be taxed.

3. Retirement

It’s unlikely that you want to work forever, so start saving for retirement! Investing for retirement can feel like a big task, but it’s critical to secure funding for your future. With automated benefits services (like Catch), you can put a little bit in your retirement each time you’re paid so that your money can start working for you in an IRA built from a smart investment portfolio.

4. Tax withholding

Uncle Sam wants his money, don’t stiff him. With each paycheck, you should be setting aside what you’ll owe for state and federal taxes. Freelancers, contractors, and 1099ers should all have a plan for their tax withholding each year. Many benefits platforms have tax withholdings built into the set up so you can be sure you’re saving the appropriate amount come April 15.

5. Time off

What’s the golden rule in building a business? Pay yourself first! That includes paying yourself to take much-needed time off. Whether you’re planning for a vacation or preparing for the arrival of a new baby, calculate the number of days/hours you’ll need off and toggle your benefits platform to automatically save for your future time off.

We know that open enrollment can be a deluge of information and options, many of which can change year to year. We also know that when you take care of yourself, you’ll create your best work yet. Designers of all sorts, whether freelance, contract, or 1099: Research your options to make the most informed decisions for your health, your finances, and your future.


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