The Dispatch September 2026
Health Insurance
How to actually use open enrollment season
Most people pick their health insurance plan in under a minute and regret it for the next year. Here's a 30-minute method that surfaces the right plan for your specific situation.
Open enrollment is annual. The decision affects your healthcare for the next 12 months. Most people pick a plan in under a minute, based on the lowest premium or “what we picked last year.”
That habit is expensive. A 30-minute method surfaces a meaningfully better plan for most people.
Why “same as last year” is risky
Plans change every year. Even if your plan still exists under the same name:
- Premium changed (usually up)
- Deductibles changed (usually up)
- Network changed (a doctor or hospital may have dropped)
- Formulary changed (your prescription may have moved tiers or been removed)
- Specialty coverages changed (mental health, fertility, weight-loss drugs are frequent areas of change)
A plan that fit your situation last year may no longer fit. A plan that didn’t fit last year may now be the right one.
The 30-minute method
Step 1: List your expected medical year (5 minutes)
What do you know is coming?
- Specific procedures or scans scheduled or likely
- Prescription medications you take regularly, with names and dosages
- Specialists you see regularly
- Pregnancy or fertility planning
- Surgery or major procedures you’ve been postponing
- Mental health or therapy services
- Dental or vision needs (often separate plans)
If your year looks like “1 PCP visit + 1 dental cleaning,” your plan needs are very different than if your year includes “2 surgeries + ongoing physical therapy + 3 prescriptions.”
Step 2: Pull each candidate plan’s documents (10 minutes)
For each plan you’re considering, you need:
- Summary of Benefits and Coverage (SBC) — required by law to be in a standard format
- Provider directory — which doctors and hospitals are in network
- Formulary — which prescriptions are covered, and at what tier
- Network details — HMO vs PPO vs EPO; in-network vs out-of-network coverage
For employer plans, your HR portal has these. For ACA marketplace plans, they’re on the plan’s detail page on Healthcare.gov or your state exchange.
Step 3: Check the four hard filters (10 minutes)
Each candidate plan has to pass these checks:
Filter 1: Are your doctors in network? Search the provider directory by name for every doctor and specialist you see. If any aren’t in network, you need to either switch doctors or eliminate that plan.
Filter 2: Are your prescriptions on the formulary? Each prescription you take should be on the plan’s drug list, and ideally at a manageable tier (Tier 1 generic = cheapest; Tier 4 specialty = most expensive). If a medication isn’t covered or is on a high tier, calculate the out-of-pocket annual cost.
Filter 3: What’s your maximum exposure?
- Annual premium
- Plus annual deductible (if you might hit it)
- Plus max out-of-pocket (worst-case scenario)
- This is your worst-case annual cost
For most people, the worst-case annual cost is the most important comparison metric. A “cheap” plan with a $9,000 deductible could cost $13,000 in a bad year; an “expensive” plan with a $1,500 deductible could cap your annual exposure at $7,000.
Filter 4: Does it support your specific needs? Mental health coverage, fertility coverage, specific therapy types, gender-affirming care, and other specialty areas vary significantly across plans. Verify what you actually need is covered, not just “is there a mental health benefit.”
Step 4: Run the dollar math (5 minutes)
For your two or three finalist plans:
Total expected cost =
Annual premium
+ (Expected non-preventive care × cost share)
+ (Prescription costs)
+ (Expected specialist visits × copay)
For the worst-case scenario:
Worst case =
Annual premium
+ Max out-of-pocket
Pick the plan that wins on expected cost AND has acceptable worst-case cost for your situation.
Common mistakes
1. Picking the lowest premium without checking the deductible. A Bronze plan with $400/month premium ($4,800/year) and $9,000 deductible looks cheaper than a Gold plan at $600/month ($7,200/year) with $2,000 deductible. But if you have any meaningful medical use, the Gold plan costs less total.
2. Picking a plan based on “I never use insurance”. True until it isn’t. A surprise diagnosis, accident, or pregnancy can flip you from “I never use it” to “I’m at the max OOP” in one event.
3. Picking a plan based on the cheapest copay. Copays only apply for some services and only after the deductible in many plans. The headline copay can be misleading.
4. Not checking the network for in-network coverage on emergencies. Emergency rooms must accept any plan in life-threatening situations, but billing varies wildly. Some hospitals charge in-network rates only if the patient is admitted; ER-only visits are billed differently.
5. Skipping HSA-eligibility analysis. If a plan qualifies for an HSA (Health Savings Account), the HSA itself is a powerful tax-advantaged savings tool — triple tax-free for medical expenses. Even if you don’t expect heavy medical use, an HSA-eligible plan funded annually can be a long-term wealth-building tool.
HSA-eligible plans
If any of your candidate plans is HSA-eligible, give it serious consideration. An HSA:
- Is tax-deductible to contribute (or pre-tax through payroll)
- Grows tax-free
- Is tax-free to withdraw for qualified medical expenses
- After age 65, can be withdrawn for any purpose (taxable, like an IRA)
Max 2026 HSA contribution: $4,300 individual, $8,550 family.
A fully-funded HSA over 20-30 years can grow to hundreds of thousands of dollars, available for healthcare costs in retirement (which are often the largest line item). HSA-eligible plans pair best with people who can afford the higher deductible AND can max the HSA.
What to do at the end
- Submit your enrollment before the deadline. Late = you’re stuck with whatever you had (or no coverage if you’re new to the option).
- Set a calendar reminder for next year’s open enrollment — usually mid-October for employer plans, November 1 for ACA marketplace.
- Save the SBC and your plan documents so you have them when you need them.
The plan you pick affects every healthcare decision you make for the next 12 months. Thirty minutes upfront is good ROI.