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Oct 21, 25
10 min read

What To Do When Your Job Doesn't Offer Health Insurance: Step-by-Step Guide

Lost employer coverage? Step-by-step guide to getting healthcare without a job. Find your path: subsidies, DPC, COBRA, or special enrollment.

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No employer health insurance? You're not alone—64.7% of uninsured workers are employed by companies that don't offer health benefits. Whether you're self-employed, working for a small business, or between jobs, you need coverage now. This guide cuts through the confusion with specific action steps based on your situation.

Source: Kaiser Family Foundation, "Key Facts about the Uninsured Population," December 2024 (using 2023 data). https://www.kff.org/uninsured/issue-brief/key-facts-about-the-uninsured-population/

Remember: Any coverage beats no coverage. Medical debt remains the leading cause of bankruptcy. Pick something, even if imperfect, then optimize next year.

Start Here: Find Your Path

Which describes you best? Choose the path that matches your situation:

Not sure about your income? Use last year's tax return as a starting point, then adjust for changes. For subsidies, it's your Modified Adjusted Gross Income (MAGI) that matters.

Path A: The Subsidized Path

Income under $62,600 individual / $128,600 family

Your Best Options (In Priority Order)

Check Medicaid First. It's Retroactive!

The opportunity everyone misses: Medicaid can cover medical bills from the past 3 months if you would have been eligible. This could save you thousands on recent emergency room visits or hospitalizations.

Income limits vary by state:

  • Expansion states: Up to 138% of Federal Poverty Level ($21,597 individual / $44,367 family of 4)
  • Non-expansion states: Varies widely, often much lower
  • Some states have higher limits for pregnant women and children

Action step: Apply at Healthcare.gov or your state Medicaid office. It takes 20 minutes and could save you $10,000+ on recent bills.

Source: Code of Federal Regulations, Title 42, Section 435.915 - "Retroactive coverage." https://www.ecfr.gov/current/title-42/chapter-IV/subchapter-C/part-435/subpart-J/subject-group-ECFR8fa41d2938b8fd6/section-435.915

Path B: The Optimization Path

Income over $62,600 individual / $128,600 family

When you don't qualify for subsidies, traditional insurance becomes expensive. Here's how to optimize.

Your Best Options (In Priority Order)

DPC + Bronze HDHP - The Clear Winner

The math without subsidies:

  • Bronze HDHP: $380-420/month
  • DPC membership: $75-100/month
  • Total: $455-520/month
  • After 2026 HSA tax savings: $350-415/month net cost

Compare to alternatives:

  • Unsubsidized Silver: $497/month (with worse access)
  • Unsubsidized Gold: $587/month
  • COBRA: $600-2,000/month

Why this wins for healthy high earners:

  • Better primary care than any insurance plan offers
  • Protected against catastrophic events
  • HSA triple tax advantage
  • Predictable costs
  • No insurance hassles for routine care

Real example: A 35-year-old software engineer in Austin pays $85/month for DPC + $395/month for Bronze HDHP = $480/month total. With HSA contributions in the 24% tax bracket, the effective cost drops to $367/month. His DPC includes unlimited visits, and he pays $4 for a 90-day supply of his allergy medication.

Sources:

  • DPC Frontier Mapper, "Direct Primary Care Practice Mapper." https://mapper.dpcfrontier.com
  • Healthcare.gov, "See 2025 health insurance plans & prices." https://www.healthcare.gov/see-plans/
  • Example based on Texas DPC practices including Euphora Health (Austin). https://euphorahealth.com

Path C: Special Timing Situations

These create special enrollment periods outside normal November-January window

🎂 Turning 26—Your Healthiest Years Need Smart Coverage

Your timeline:

  • Employer-sponsored plans: Coverage ends on the last day of the month you turn 26
  • Marketplace/ACA plans: Coverage lasts through December 31 of the year you turn 26
  • 60 days before and after losing coverage to enroll in new Marketplace plan
  • Can use parent's address for subsidy calculation if still dependent

Source: U.S. Department of Labor, "Young Adult Coverage Under the Affordable Care Act." https://www.dol.gov/agencies/ebsa/about-ebsa/our-activities/resource-center/faqs/young-adult-and-aca

Your best options at 26:

Option 1: DPC + Catastrophic Plan (Under-30 exclusive)

  • Catastrophic plans: ~$350-370/month average (only available under 30)
  • Add DPC: $75/month
  • Total: $425-445/month
  • Perfect for healthy 26-year-olds who want doctor access via text
  • Note: Premium subsidies cannot be used with catastrophic plans

*Sources:

Option 2: Stay on Parent's Plan

  • Costs them: $200-400/month extra
  • Worth it if: They're willing to pay and you need specific specialists

Option 3: DPC + Bronze HDHP

  • Total: ~$350-450/month depending on location
  • Builds HSA savings early (huge benefit compounding over time)

Action: Start shopping 30 days before birthday. Don't wait until you age off.

🚨 Just Lost Your Job—You Have Options

Your critical timeline:

  • 60 days to elect COBRA (can be retroactive)
  • 60 days for Marketplace special enrollment
  • Medicaid available immediately if income dropped

Source: U.S. Department of Labor, "FAQs on COBRA Continuation Health Coverage for Workers," 2025. https://www.dol.gov/sites/dolgov/files/ebsa/about-ebsa/our-activities/resource-center/faqs/cobra-continuation-health-coverage-for-workers.pdf

📦 Moving to New Area

Your opportunity: Moving triggers special enrollment + potential cost savings

Price variations to consider:

  • Vermont Silver: $1,277/month
  • New Hampshire Silver: $325/month

Action before moving:

  • Check new area's Marketplace prices
  • Research DPC availability
  • Consider state Medicaid if moving to expansion state

Timeline: 60 days after move to enroll

Source: Healthcare.gov, "Qualifying Life Event (QLE) - Moving to a new home." https://www.healthcare.gov/glossary/qualifying-life-event/

👶 Pregnancy or Planning—Special Rules Apply

If pregnant:

  • Immediate special enrollment in all states
  • Medicaid income limits often higher (up to 200-300% FPL)
  • Coverage can be retroactive

If planning:

  • Enroll during Open Enrollment for January 1 coverage
  • Choose Gold plan if possible (lower deductibles)
  • DPC generally doesn't cover prenatal/delivery

Source: Healthcare.gov, "Having a baby? You can sign up for health insurance." https://www.healthcare.gov/coverage-outside-open-enrollment/special-enrollment-period/

How to Actually Enroll

Documents You Need Ready

For Healthcare.gov:

  • Social Security Number
  • Income documentation (pay stubs, tax return, or self-employment ledger)
  • Current coverage information (if any)
  • Employer coverage info (even if not taking it)

For DPC Enrollment:

  • Insurance card (for your HDHP)
  • Medication list
  • Medical history summary
  • Payment method for monthly membership

Estimating Income—The Most Critical Step

If employed:

  • Use year-to-date pay stub
  • Project forward including expected bonuses
  • Include spouse's income

If self-employed:

  • Use last year's Schedule C as baseline
  • Adjust for known changes
  • Can use bank statements if needed

Critical: Underestimating income means paying back subsidies. Overestimating means missing out on help. Update if income changes more than 10%.

When Coverage Actually Starts

Marketplace plans:

  • Enroll by 15th of month → Coverage starts 1st of next month
  • Enroll after 15th → Coverage starts 1st of month after next

Source: Healthcare.gov, "When coverage starts & ends," 2025. https://www.healthcare.gov/quick-guide/dates-and-deadlines/

DPC membership:

  • Usually starts immediately upon payment
  • Some practices prorate first month

COBRA:

  • Retroactive to day after employment ended
  • Must pay all back premiums

Source: Department of Labor, "COBRA General Notice," 2025. https://www.dol.gov/sites/dolgov/files/ebsa/laws-and-regulations/laws/cobra/model-general-notice.pdf

Payment Timing Gotchas

Common mistakes:

  • Marketplace requires first payment before coverage starts
  • Auto-pay sometimes fails first month—set reminder
  • DPC bills separately from insurance
  • HSA contributions can't exceed annual limit even if starting mid-year