It’s open enrollment season for health coverage. If you’re self-employed, you can’t afford to ignore it

Open enrollment season can be a time of trepidation for the self-employed.

The stakes are especially high because if you need to buy individual or family coverage, the next few weeks could be your only chance for 2024, barring certain exceptions such as moving to a different state, getting married, divorced or having a child.

“For most people, the nationwide open enrollment period for individual and family coverage is your best shot to review your options and enroll in a new plan,” explained Anthony Lopez, vice president of individual and family and small business plans at eHealth, a private online marketplace for health insurance, in an email.

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Here’s a look at more coverage on what to do finance-wise as the end of the year approaches:

Picking health insurance on your own — without the help of a human resources department — can be daunting. Instead of throwing up your hands in frustration, here are answers to questions self-employed individuals often have about open enrollment.

Healthcare.gov and other options for information

Freelancers, consultants, independent contractors and other self-employed individuals can visit www.healthcare.gov to research and enroll in flexible, high-quality health coverage, either through the federal government or their state, depending on where they live. You can also choose to work directly with an insurance agent or with a private online marketplace to help you wade through options. To be considered self-employed, you can’t have anyone working for you. If you have even one employee, you may be able to use the SHOP Marketplace for small businesses.

The deadlines you need to stay on top of

Most states set a deadline of Dec. 15 for coverage that begins Jan. 1, so don’t delay when it comes to signing up for benefits, said Alexa Irish, co-chief executive of Catch, which helps self-employed individuals choose health-care plans. Also, remember to pay your first month’s premium before your health care is supposed to start or you’ll be out of luck as well. “If you miss those deadlines, there’s no wiggle room,” said Laura Speyer, co-CEO of Catch.

If you are already enrolled in a marketplace plan

Those who were already enrolled in a plan last year can make changes by Dec. 15 for coverage that begins Jan. 1. Doing nothing will mean they are automatically reenrolled in last year’s marketplace plan.

Qualifying for tax credits and other savings

Many people assume they won’t be entitled to savings, but they should still investigate their options, Irish said. Indeed, 91% of total marketplace enrollees received an advance premium tax credit in February 2023, which lowers their monthly health insurance payment, according to data from the Centers for Medicare & Medicaid Services, a federal agency within the U.S. Department of Health and Human Services.

Credits and other eligible savings are available based on an applicant’s income and household size and can be estimated even before they officially apply. It’s advisable to check for savings possibilities every year, Irish said.

What to consider in making coverage decisions

The thought process will be similar to what you went through when picking health insurance offered by an employer. Whether you are signing up for the first time — or deciding whether to renew your existing plan or choose a different one — you’ll want to consider factors such as who in the family needs the coverage and for what purposes, and how different plans compare in terms of coverage options and cost. This analysis needs to take into account copays, prescription drugs you take or may start to take, whether the plan covers your doctors, and out-of-pocket maximums.

If you’re self-employed and aiming to grow your business in the coming year, possibly by hiring employees, it’s good to know you can enroll in a small business plan at any time of the year, Lopez said. “Small business group plans aren’t governed by the same open enrollment rules as individual and family plans. So, you can enroll in an individual plan today, then switch over to a group plan in mid-2024 if you add a couple employees and want to provide them with health benefits,” he said.

How much health insurance costs the self-employed

Cost will vary, depending on the plan you choose, who is covered and what subsidies you’re eligible for. But, as a general guide, the average total monthly premium before tax subsidies in February 2023 was $604.78. The average total premium per month paid by consumers after the tax subsidies was $123.69, according to the Centers for Medicare & Medicaid Services.

Self-employed individuals may also be eligible for a cost-sharing reduction, a discount that lowers the amount paid for deductibles, copayments and coinsurance. You’ll find out what you qualify for when you fill out a marketplace application, but keep in mind, you need to enroll in a “Silver” plan, one of four categories of marketplace plans, to get the cost-sharing reduction.

Wading through policy options, working with an agent

You don’t have to go through the process alone. There are assisters who are trained and certified by marketplaces to help you apply and enroll. If you want more specific help, you can also choose to work with an agent or broker who is trained and certified to sell marketplace health plans in the state they are licensed. Agents can advise you and give you more detailed information about the plans they sell, and since health insurance premiums are regulated by your state’s Department of Insurance, you don’t have to worry about paying more by working with an agent.

A few things to note: Some agents may offer other plans that aren’t available on government exchanges, but that comply with government requirements. However, to take advantage of a premium tax credit and other savings, you must enroll for a plan through a state or federal marketplace, on your own or through an agent.

The risk and reward of high-deductible plans

Marketplaces offer multiple plans to choose from and they will vary in terms of coverage and price. One option that’s becoming more popular, especially with young entrepreneurs, is called a high-deductible health insurance plan. This type of insurance plan comes with higher deductibles in exchange for lower premiums, which could be a good choice for people who are healthy and don’t visit the doctor much. Another benefit of a qualified high-deductible plan is the ability to contribute to a tax-advantaged savings vehicle known as a health savings account, or HSA.

When deciding whether to choose a high-deductible plan, individuals should take into account factors such as how often they visit the doctor, how much they can afford to pay out of pocket, whether their doctors are in network and what the out-of-pocket maximums are. It’s also important to know you have the means to cover a high-cost medical event, should the need arise. If a high-deductible plan makes sense for your circumstances, you can then consider an HSA.

Lopez recommends people don’t delay when it comes to reviewing their coverage options, which may also include dental and vision insurance. “The last week or so of open enrollment can be a busy time for licensed agents too; if you want the best chance of talking to an agent to get your personal questions answered, don’t put it off.”

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It may take $10 million to achieve ‘financial freedom,’ say ‘Earn Your Leisure’ hosts

Troy Millings, left, and Rashad Bilal, co-creators of Earn Your Leisure.

Source: Tyrell Davis

Rashad Bilal and Troy Millings are among a growing class of financial influencers who want to help people be smarter about money.

The duo — a former financial advisor and a teacher, respectively — launched the podcast “Earn Your Leisure” nearly five years ago with a mission to promote literacy around money and entrepreneurship.

About 1 in 7 people lost more than $10,000 in 2022 due to a lack of financial literacy, according to a study by the National Financial Educators Council.

“I realized there were certain things that weren’t taught inside schools — financial literacy and financial education being one of them,” Millings said of the idea to create Earn Your Leisure.

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Today, Earn Your Leisure has expanded to create multiple podcasts, host live events and offer an online educational platform, EYL University. It has 1.4 million Instagram followers and another 1.4 million YouTube subscribers. Its flagship podcast has an average 3 million downloads a month, said Bilal and Millings. It’s also developing a financial literacy curriculum for high schools.

CNBC interviewed the duo — who have been friends since childhood — to talk about personal finance and financial literacy in the U.S.

This interview has been edited and condensed for clarity.

told CNBC last year that your “purpose is financial literacy and empowerment.” When it comes to financial literacy, what’s the No. 1 mistake you see people making with their finances?

Rashad Bilal: Not understanding the importance of investing, or [not] knowing how compound interest works.

For a long period of time, investing was something that people looked at more as a luxury, not a necessity, [thinking] if you’re able to invest then you’re in the top 1%, or you have to be wealthy to even consider that.

Investing is not just for rich and wealthy people. It’s for everybody. You can start with smaller balances and dollar-cost average.

Troy Millings: The relationship with money: People don’t understand what to do with it or how to save it. These are simple concepts we’re not taught. When we don’t know what to do, we do what we know, and that’s often spending outside our means. Mistakes are made because nobody is educated.

People may have heard that investing and compound interest are important but might not know why. Can you speak to that?

Bilal: The only way to really achieve financial freedom is if your money is growing without you working for the money. How to achieve that is through investing. One dollar will only be $1 if it’s saved in the bank. But $1 can become $2 if it’s invested.

Most people understand this without even fully realizing that they understand it because they have a retirement plan. The whole point of a retirement plan is investing. You put money into a 401(k), and that money gets invested with the expectation that when you’re 65, 70 years old you’ll have a nest egg you can draw from and live off of in retirement.

The only pathway to not working forever, to having money in abundance, is to find ways to make more money with the money you currently have.

What it takes to achieve financial freedom

Earn Your Leisure co-founders on the importance of financial literacy

Making it ‘cool to be educated’ about money

For the person who’s just starting out investing, how would you suggest they go about it?

Millings: When you’re young, you want to be as aggressive as possible, and when you’re older, you want to get more conservative. Risk mitigation is a huge part of that. We always tell people to start with indexes — an entire index or entire [industry] sector in an exchange-traded fund. That keeps you from having the volatility of watching a stock either appreciate — where you might get some upside — or depreciate, where the risk on the downside is far greater.

High school classes in financial literacy use real-world examples to teach budgeting

In a recent discussion with entrepreneur and musician Sean “Diddy” Combs, you mentioned that when he met you, he said you “make it cool to be educated.” How do you go about that?

Millings: We’re authentically ourselves, so there’s a natural relatability because people see themselves in us. When people talk about finance they try to make it a language that is upspoken to the masses. Our mission was to democratize it, to make it seem like something that can be very relatable and digestible. We show up the way we are, we wear sweatshirts, we wear hoodies. We represent everybody. It doesn’t feel like it’s only for the elite or it’s only for a select crowd.

It’s the same thing in the classroom: A student has to realize this is someone I can learn from and who I want to teach me. Our audience kind of feels that way when they look at us. We’re also very vocal that we’re learning as well. We don’t know everything, and we bring people on [the show] who can educate us.

‘Having money doesn’t alleviate the problems’

For your podcasts, you’ve interviewed several famous and wealthy people — pro athletes, musicians and entertainers, for example. Are there certain things about finance that seem just as confusing for the rich and famous as for the average person?

Bilal: Yeah, I think a lot of people don’t have a full understanding of finance. It doesn’t matter how much money you make. That’s a common misconception.

Having money doesn’t alleviate the problems, it just makes the problems even worse. Understanding money or having a good understanding of money isn’t something that’s correlated with how much money you have.

Financial literacy is something I think gets metastasized on the highest level. Those are the same issues that everybody else has, it’s just everybody else doesn’t have the opportunity to lose $30 million or invest $20 million into a bad investment and then it goes belly up. If given the opportunity they probably would, it’s just they don’t have it. It’s a bigger microscope on celebrities because they’re public figures.

Is that because wealthy people and celebrities have a capacity to overspend more than the average person?

Bilal: I think it’s not so much just a spending situation. That’s a common misconception also, that they go broke because they spend money lavishly. That’s one part of it. But another major part is they’re actually trying to do the right thing, they’re just misinformed.

You see a lot of people make bad decisions when it comes to investing. They’ll invest in things that might be Ponzi schemes, bad real estate deals, they’ll be led down a bad path when it comes to financial advisors or people they trust. They think they’re doing something productive with their money but they actually are losing money because the investments aren’t fully vetted, they don’t fully understand what they’re investing in.

So I think it’s a little more complicated than just spending habits. It all comes back to not having a basic level of understanding and education when it comes to money.

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