Freelancers and side hustlers know the drill. No employer means no benefits package. You’re on your own for health insurance, and the options can feel overwhelming.
Picking the wrong plan costs real money. We’re talking thousands in premiums or surprise medical bills that wreck your budget. But here’s the thing: you don’t need to be an insurance expert to make a smart choice.

Comparing Individual, Family, and Short-Term Plans
Individual plans cover just you. That’s it. They work great if you’re single or your spouse has coverage through their job. Family plans bundle everyone under one policy. Usually cheaper than buying separate plans for each person.
Short-term plans exist too. They bridge gaps when you’re between jobs or waiting for permanent coverage to kick in. Not ideal for long-term use, but they serve a purpose.
Here’s where a broker helps. Companies like Custom Health Plans compare options across multiple carriers at no extra cost to you. They show you plans you might miss on your own. And they explain the fine print without the insurance jargon.
Family coverage makes sense once you’re covering two or more people. Do the math. Add up individual premiums versus one family plan. Many families pair a higher deductible with a Health Savings Account and save money that way.
The Health Insurance Marketplace offers subsidized plans if you qualify. Your income determines the tax credit. Open enrollment runs November through mid-January most years. Miss it and you wait, unless you have a qualifying life event like losing your job or getting married.
Using Health Savings Accounts to Build Wealth
HSAs are tax magic. You put money in before taxes. It grows tax-free. You take it out tax-free for medical stuff. Name another account that does all three.
You need a high-deductible plan to qualify. That means at least $1,600 deductible for individuals in 2024. Families need $3,200. The lower premiums usually offset the higher deductible if you’re healthy.
Contribution caps change yearly. The IRS sets these limits at $4,150 for individuals and $8,300 for families in 2024. Over 55? Tack on an extra $1,000. Smart savers max these out because the tax benefits compound over decades.
Treat your HSA like a retirement account. The money never expires. After you hit a minimum balance, you can invest in mutual funds or stocks. Some people pay medical bills out of pocket and let the HSA grow untouched for 30 years. Pretty clever.
Finding Affordable Coverage When Self-Employed
Self-employed means you pay the whole premium yourself. No employer chipping in half. This makes shopping around critical.
Start with your expected doctor visits for the year. Rarely go? A high-deductible plan with cheap premiums might be your best bet. Frequent visits? Pay more monthly for lower copays.
Check the drug formulary. That’s the list of covered medications. Some plans cover your prescriptions cheap. Others charge a fortune. Generic versions almost always cost less than brand names.
Network size matters. Narrow networks limit your doctor choices. Great if you live in a city with tons of providers. Not so great in rural areas or if you travel for work. Make sure your current doctors take the plan before you sign up.
Deductibles protect you from bankruptcy. Say yours is $3,000. You pay that first, then insurance covers most costs after. The out-of-pocket max caps your total spending each year. Pick numbers you can actually afford if something bad happens.
Evaluating Coverage Features Beyond Monthly Cost
Everyone stares at the premium and calls it a day. That’s a mistake. The monthly bill tells maybe half the story. Your actual healthcare spending depends on how the plan handles everyday stuff like doctor visits, prescriptions, and routine care.
Copays and Coinsurance Add Up Fast
Copays hit you every time you see a doctor. One plan charges $30 per visit. Another wants $75. See your doctor monthly? That’s $540 versus $900 per year. Not exactly pocket change.
Coinsurance works differently. Instead of a flat fee, you pay a percentage after meeting your deductible. A plan might cover 80% while you pay 20%. That sounds fine until you need a $10,000 procedure and owe $2,000 out of pocket.
Specialist visits usually cost more than primary care. Some plans charge $50 for specialists while others hit you with $100 or more. Need regular specialist care? Track those copays across plans before deciding.
Prescription Drug Tiers Matter More Than You Think
Drug coverage varies like crazy between plans. Insurance companies use tiers to categorize medications. Tier 1 drugs cost maybe $10. Specialty medications in tier 4 can hit $500 per month.
Look up your regular prescriptions on each plan’s formulary. That’s the official list of covered drugs. Your diabetes medication might be tier 1 on one plan and tier 3 on another. Same drug, wildly different costs.
Generic versions save money almost every time. If your doctor prescribes a brand name, ask if a generic exists. Most plans charge way less for generics. We’re talking $10 copays instead of $75.
Mail-order pharmacies offer another savings angle. Many plans discount 90-day supplies ordered through mail. You might pay for two months and get the third free. Worth checking if you take maintenance medications.
Preventive Care Should Always Be Free
Annual checkups, vaccines, and certain screenings must be covered at zero cost under most plans. This includes things like flu shots, mammograms, and colonoscopies at recommended ages.
Use these benefits. Catching high blood pressure or diabetes early beats paying for complications later. Free preventive care is probably the best deal in health insurance.
Some plans throw in extras like gym memberships or weight loss programs. Nice perks if you’ll actually use them. Don’t let bonus features distract from core coverage though.
Telehealth Saves Time and Often Money
Virtual doctor visits exploded during the pandemic and stuck around for good reason. You can see a doctor from your couch for minor issues. No commute, no waiting room, no taking half a day off work.
Check what your plan covers for telehealth. Some charge the same as in-person visits. Others cost less. A few plans offer unlimited virtual visits for a flat monthly fee.
Most telehealth works great for simple stuff. Sinus infections, rashes, medication refills. Anything requiring physical examination or testing still needs an in-person visit.
Making Coverage Decisions That Fit Your Situation
Run the numbers for your actual life. Take last year’s medical bills. Add them to potential premiums and deductibles. Compare a low-premium, high-deductible plan against a high-premium, low-deductible option. Which one costs less for how you actually use healthcare?
Life changes open special enrollment periods. Got married? Had a baby? Lost your job coverage? You get 60 days to enroll in something new. Miss that window and you’re stuck waiting until November.
Review your plan every year during open enrollment. Your health changes. Your budget changes. Last year’s perfect plan might be terrible now. Spend an hour comparing options. It’s worth thousands in savings.
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