Best Insurance Options for Gig Workers and Freelancers in 2023

A lady sitting on single sofa looking behind her with Gig economy written on the wall

Imagine the sheer joy of waking up each day, setting your own hours, choosing projects that resonate with your passions, and having the freedom to work from a quaint coffee shop or the serene corner of your home. This is the dream for many – the unparalleled liberty you get as gig workers or freelancers. 

The 2020s have indeed ushered in a golden age for this versatile workforce. Yet, as the sun shines bright on this liberating professional landscape, it casts a shadow of uncertainty. For amid the allure of flexible hours and self-determined projects lurks a pressing concern: securing reliable health insurance. 

As 2023 progresses, the weight of this concern grows heavier, with many freelancers finding themselves navigating the tricky terrain of insurance options, seeking that one coverage that fits just right.

Who is a Gig Worker/Freelancer?

A lady working on her laptop at home

A gig worker or freelancer is an individual who takes on short-term, flexible jobs either as a primary or supplementary source of income. Unlike traditional employees bound by the routine rigidity of 9-to-5 jobs, freelancers enjoy the freedom to choose when, where, and how they work. 

This could be the graphic designer crafting logos for a budding startup one week and illustrating a children’s book the next, or the writer who hops from blogging about tech innovations to penning heartfelt travel memoirs. It’s a dynamic, vibrant world, colored with diversity and fueled by individual passion. 

Yet, while the horizons of opportunity seem endless, they often operate outside the conventional safety nets of traditional employment, leading to unique challenges, especially in areas like health insurance.

Best Insurance Options for Gig Workers 

Navigating the ever-expanding world of insurance, especially as a gig worker, can be daunting. The landscape of coverage options is vast, but among them, a few stand out as champions for the freelance community. Here are three of the best insurance options for gig workers in 2023:


Trimble stands out as a beacon of hope for many gig workers, especially when reliable health insurance seems like a distant dream. Recognizing the unique challenges faced by the freelance community, Trimble crafts insurance solutions tailored to their needs. Beyond just providing coverage, Trimble educates its users about the intricacies of health insurance, ensuring that every gig worker can make an informed decision. With it’s innovative approaches and commitment to bridging the knowledge gap, Trimble has quickly established itself as a top contender in the realm of gig worker insurance. Find out more about their offerings here.

Policy Genius

While Trimble has made notable strides, there are other noteworthy players in the gig worker insurance sphere. Policy Genius offers an impressive array of plans that cater to freelancers’ diverse needs. Whether you’re looking for short-term coverage or a more comprehensive package, they have options to fit the bill. The company’s user-friendly platform and attentive customer support have earned it rave reviews from satisfied gig workers. Explore their services here.


Last but certainly not least, Bestow also caters specifically to the freelance and gig worker community, they understand the challenges of fluctuating income and unpredictable job prospects. Their flexible plans, competitive pricing, and commitment to transparency make them a favorite among many in the gig economy. Dive deeper into what they offer here.

Do I Actually Need Health Insurance?

Oh, the age-old question that seems to pop into our minds every time we’re pinching pennies or setting life’s priorities. Do I actually need health insurance? Let’s have a heart-to-heart about it.

Life, as they say, is as unpredictable as a summer rain. One minute you’re enjoying the sun, soaking in its warmth, and the next, you’re scurrying for cover as raindrops make an unexpected appearance. That’s exactly how our health operates. Today, you might be as fit as a fiddle, taking those morning jogs or devouring those green smoothies. But tomorrow? Who knows. A surprise illness or injury can hit us like that sudden rain, and without any warning.

Now, I’m not trying to paint a bleak picture here. Life is vibrant, thrilling, and filled with endless joys! But here’s the deal: having health insurance is a bit like having an umbrella in your bag. Most days, you won’t need it. But when that unexpected downpour happens? Boy, will you be grateful for it.

Think about it. Without health insurance, a simple trip to the ER could end up costing you an arm and a leg (figuratively, of course!). You’d be surprised at how quickly medical bills can pile up. We’re talking about X-rays, blood tests, medications, and so much more. It can be downright overwhelming, and honestly, a tad scary. Health insurance is your shield, your protection from these unforeseen costs.

But, more than just the financial aspect, there’s an emotional side to this. Knowing you’re insured brings a certain peace of mind. It’s like a comforting whisper that says, “Hey, I’ve got your back.” You can take risks, live boldly, chase after your dreams, all while knowing that should life throw a curveball, you’re covered.

So, to answer the burning question: Yes, you actually do need health insurance. It’s not just another box to tick off in the game of adulthood. It’s a safety net, a cushion, and, above all, an act of love for yourself and the people who care about you. Because, at the end of the day, your health and well-being? They’re priceless.

Gig Economy Companies That Offer Insurance

Alright, let’s dive into a topic that’s as buzzy as your morning espresso: gig economy companies offering insurance. Yeah, you heard that right. The world’s changing, my friend, and it’s not just about those snazzy apps on your phone or getting your favorite pizza delivered to your door at lightning speed. 

It’s about the people behind the scenes, the drivers, the freelancers, the everyday heroes of the gig economy. And guess what? Some companies are finally stepping up to give these champs the security they deserve.

1. Uber

Remember when Uber was just that cool app to get a ride? Well, they’ve revved things up a notch. For their drivers and delivery folks, they’ve started partnering with insurance companies to provide coverage. Because, let’s face it, while cruising around the city is fun, life’s little (or big) accidents aren’t. Uber’s making sure their crew’s got a safety net to fall back on.

2. Lyft

Not to be outdone by its biggest competitor, Lyft’s also joining the insurance party. They’ve got protection for their drivers in case of accidents on the job. It’s like they’re saying, “Hey, we value you. We’ve got your back.” And in this hustle and bustle of gig life, that means a lot.

So there you have it! Gig economy companies are evolving, recognizing the heartbeat of their operations – the workers. They’re ensuring that amid the fast-paced deliveries and rides, there’s a cushion of safety. It’s a changing world, and it’s about time everyone feels a bit more valued and protected. Cheers to that!

Alternative Health Insurance Options

Alright, let’s chat about something that’s more important than our latest Netflix obsession: health insurance options! I know, I know, it sounds about as exciting as watching paint dry, but stick with me. Because, just like finding that perfect coffee blend or those sneakers that are both cute and comfortable, finding the right insurance can feel like a major win. Let’s dive into some alternative ways to score that coverage:

Through The Freelancers Union

Ah, the Freelancers Union. It’s like the cool club every freelancer wants to join. Not only do they have your back when it comes to fighting for freelancers’ rights, but they also offer health insurance plans tailored just for folks like us. It’s like that custom-made jacket that fits just right. 

Local Chamber of Commerce

Alright, this might sound a tad old school, like dial-up internet or flip phones, but trust me on this one. Your local Chamber of Commerce often has the inside scoop on group health insurance plans for small businesses and individuals. So, give them a ring and see what they’ve got cooking. 

Through Your State

Think of this as the friendly neighbor of health insurance options. Most states have their own marketplace where you can shop for plans. It’s like online shopping, but instead of adding shoes to your cart, you’re picking a health plan that fits just right. Plus, depending on your income, you might qualify for some discounts. Ka-ching!

Through Your Spouse’s Employer

Okay, we’ve all borrowed a sweater or two from our better halves, right? Well, think of this option as the health insurance equivalent. If your spouse’s employer offers family insurance plans, you can hop on theirs! It’s comfy, convenient, and can be a great way to save some pennies.

Go for a Private Plan

If you’re feeling fancy and want to go off the beaten path, consider a private plan. It’s like designing your own pizza with all your favorite toppings. You get to pick and choose exactly what you want, ensuring it fits your needs to a T. Just be sure to read the fine print and maybe compare a few options. After all, we want the best slice of the pie!

So, whether you’re a full-time freelancer, juggling side gigs, or just in the market for some solid health coverage, remember: you’ve got options, darling. And they’re as varied and wonderful as the ice cream flavors at your favorite parlor. Happy insurance shopping!

What to Look for When Comparing Health Insurance Options

medical insurance policy for gig workers

Navigating the health insurance maze can feel a bit like trying to pick the best ice cream flavor on a hot summer day. Do you go for the classic vanilla, the indulgent double chocolate fudge, or that newfangled matcha pistachio swirl? Similarly, with health insurance, the choices can be overwhelming, but knowing what to look for can make things a whole lot smoother. So, grab your metaphorical spoon, and let’s dive into the key things to consider:

1. Coverage Basics

First and foremost, what’s covered? Make sure the plan covers the essential health benefits like outpatient care, hospitalization, and prescription drugs. It’s the foundation, much like the creamy base of our ice cream.

2. Monthly Premiums

This is the amount you’ll pay for your plan, whether you use medical services or not. Think of it like an ice cream subscription – you pay each month to enjoy those cold treats. Ensure the monthly cost fits comfortably in your budget.

3. Deductibles

It’s the amount you pay for covered services before your insurance starts to pay. Imagine it’s like the waiting time before your ice cream order arrives; you want it to be as short as possible, right? Lower deductibles often mean higher premiums and vice versa.

4. Network Restrictions

Some plans require you to use a network of doctors, kind of like having an exclusive list of ice cream parlors you can visit. Make sure your preferred doctors and hospitals are in-network to avoid extra costs.

5. Out-of-Pocket Maximums

This is the most you’ll pay during a policy period (usually a year) before your health insurance starts to pay 100% for covered benefits. Think of it as the “safety lid” on your ice cream tub, ensuring you don’t over-indulge (or, in this case, overspend).

6. Co-payments and Coinsurance

These are your share of the costs for a covered service. It’s a bit like chipping in for toppings on a shared ice cream sundae. Understand how much you’ll have to fork out each time you visit a doctor or get a prescription filled.

7. Prescription Drug Coverage

If you’re on medications, ensure they’re covered. It’s like ensuring your favorite ice cream flavor is always in stock!

8. Additional Benefits

Do they offer free annual check-ups, mental health services, or maternity care? It’s the cherry on top of our ice cream – the extra stuff that can make a plan go from good to great.

9. Customer Service

Because when you have a question or an issue, you want it resolved smoothly and swiftly, much like when you’re hunting down that elusive ice cream flavor.

10. Reviews and Ratings

Lastly, look for reviews or ratings of the insurance company. It’s the equivalent of checking out those ice cream reviews before you try a new place – because nobody wants to end up with a bad taste in their mouth.

Choosing health insurance isn’t just about costs; it’s about ensuring you’re well-covered for life’s unexpected events. So, take your time, compare, and make sure you pick a plan that’s as satisfying as your favorite scoop of ice cream.


Choosing health insurance, much like selecting the perfect ice cream flavor, is deeply personal. Each individual has unique needs, preferences, and budgets. But, just as we all deserve that moment of pure joy when the first spoonful of ice cream hits our taste buds, we also deserve the peace of mind that comes with a comprehensive health insurance plan. 

It’s more than just numbers and coverage; it’s about safeguarding our future and the futures of those we hold dear. As you navigate the labyrinth of health insurance options, keep in mind that the best choice is one that offers comfort, assurance, and the freedom to live without the looming fear of unforeseen health crises. Because in life, just as with desserts, we should all be able to enjoy the sweet moments, knowing we’re prepared for the not-so-sweet ones. 

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