Essential Guide to Open Enrollment for 2026

September 30, 2025 — Sam H. Fawaz

As we approach the annual open enrollment period for most employers (typically October through November 2025), now is the perfect time to review your employee benefits and make informed decisions that will impact your financial well-being throughout 2026.

Why Open Enrollment Matters More Than Ever

Open enrollment is your once-a-year opportunity to make changes to your employer-sponsored benefits. Outside of qualifying life events (marriage, divorce, birth of a child, etc.), this is likely your only chance to:

• Switch health insurance plans or carriers

• Adjust life and disability insurance coverage amounts

• Modify flexible spending account (FSA) elections

• Review and update beneficiary information

• Evaluate supplemental benefits like vision, dental, or critical illness coverage

Key Areas to Review During Open Enrollment

Health Insurance

Health insurance, especially catastrophic health insurance, is not optional for anyone, as healthcare and hospitalization costs continue to skyrocket.

• Compare your plan options carefully: Don’t automatically re-enroll in your current plan. Premiums, deductibles, and covered providers may have changed.

• Consider your 2026 healthcare needs: Are you planning any major medical procedures? Do you have ongoing prescriptions? Select a plan that matches your anticipated usage.

• Network providers: Verify that your preferred doctors and hospitals are still in-network for your chosen plan.

• Supplemental Insurance: Analyze the real total cost of dental and eye care insurance by comparing total out-of-pocket costs with and without insurance. With meager benefits, limited payments, and high co-pays or co-insurance, the premiums may not be worth the coverage provided, and you therefore may want to forego coverage.

• Total cost analysis: Look beyond monthly premiums to include deductibles, co-pays, and out-of-pocket maximums. Are you a good candidate for a high-deductible health plan (i.e., you’re generally in good health and have minimal consumption of healthcare), which makes you eligible for a health savings account (HSA)?

Life and Disability Insurance

• Life insurance: Review your current coverage amount. Has your income increased? Do you have new dependents? Consider whether your current coverage adequately protects your family’s financial needs. Consider whether you really need accidental death and disability insurance and whether it’s worth the extra cost.

• Disability insurance: Evaluate both short-term and long-term disability options. Your income is likely your most valuable asset—protect it accordingly. For most people, maximizing available disability insurance coverage is a great idea.

• Supplemental coverage: Group rates through your employer are often more affordable than individual policies purchased elsewhere.

Flexible Spending Accounts (FSAs)

• Healthcare FSA: Estimate your out-of-pocket medical expenses for 2026, including prescriptions, dental work, and vision care.

• Dependent Care FSA: If you have qualifying childcare or eldercare expenses, this pre-tax benefit can provide significant savings.

• Remember the “use it or lose it” rule: Most FSAs have limited carryover provisions (some plans require you to use all amounts by December 31; others give you a few extra months), so plan and understand your elections carefully.

Smart Decision-Making Tips

1. Gather last year’s data: Review your 2024-2025 healthcare spending, insurance claims, and FSA usage to inform your 2026 decisions.

2. Calculate total annual costs: Don’t focus solely on monthly premiums. Add up premiums, deductibles, and expected out-of-pocket expenses for a comprehensive view.

3. Consider your family situation: Changes in marital status, number of dependents, or family health conditions should influence your benefit selections. Compare benefits and costs if both spouses work, and make choices that fit your family’s needs.

4. Think ahead: Are you planning a family addition, major surgery, or a career change in 2026? Factor these into your benefit choices.

5. Update beneficiaries: Use this time to ensure your beneficiary information is current for all accounts (e.g., 401(k), 403(b), 457, 401a plans) and insurance policies.

6. Ask questions: Don’t hesitate to attend employer benefit sessions or contact HR for clarification on plan details.

We’re Here to Help

Navigating open enrollment can feel overwhelming, but you don’t have to do it alone. We are available to consult with you on your benefit elections and help you make informed decisions that align with your financial goals and family needs.

To ensure we can provide timely guidance and help you meet enrollment deadlines, please contact us before your employer’s enrollment period closes. Many companies have strict deadlines in late October or November, and missing these dates could mean waiting until next year to make changes.

Take Action Now

• Mark your calendar: Note your employer’s specific open enrollment dates

• Gather your information: Collect recent medical bills, current benefit summaries, and family health information.

• Don’t procrastinate: The best benefit choices require careful consideration—start planning now.

Your employee benefits are a significant part of your total compensation package. Making thoughtful, informed decisions during open enrollment can save you money and provide better protection for you and your family throughout 2026.

Sam H. Fawaz is the President of YDream Financial Services, Inc., a fee-only investment advisory and financial planning firm serving the entire United States. If you would like to review your current investment portfolio or discuss any other tax or financial planning matters, please don’t hesitate to contact us or visit our website at http://www.ydfs.com. We are a fiduciary financial planning firm that always puts your interests first, with no products to sell. If you are not a client, an initial consultation is complimentary, and there is never any pressure or hidden sales pitch. We begin with a thorough assessment of your unique personal situation. There is no rush and no cookie-cutter approach. Each client’s financial plan and investment objectives are unique

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How Much Health Insurance Do I Need?

January 25, 2015 — Sam H. Fawaz

How Much Health Insurance Do I Need?

The answer is simple: enough to ensure that if you (or a covered family member) get sick or injured, you’re not footing the entire medical bill on your own.

If you receive health insurance through your employer, your choices are limited. Some employers will offer plans from multiple health insurance providers, but most limit their offerings to one provider. Additionally, most employers offer one or more of the following: an HMO, a PPO or a traditional plan.

• An HMO (or health maintenance organization) is usually the lowest-cost alternative. As a result, enrollees are limited to doctors and treatment facilities within a limited “network.” These plans usually have no deductibles. Enrollees are required to make copayments when seeing a physician.
• A PPO (or preferred provider organization) allows enrollees greater flexibility. Enrollees can see doctors in or out of the PPO’s established network of providers. Deductibles usually apply and co-payments are required. A visit to an out-of-network doctor will trigger an additional charge.
• A traditional indemnity plan is usually the most expensive, as it typically gives enrollees the greatest number of choices in choosing doctors and facilities. But the deductibles can be high and the insurance company may cap the amount of money it will spend on the enrollee’s behalf over his/her lifetime.

Choices for the Self-Employed

If you are self-employed, you can comparison shop among the insurance providers licensed to do business in your state. It is a good idea to get as many estimates as you can because coverage and premiums vary significantly. Be sure you are comparing apples to apples: You want cost breakdowns for coverage with similar deductibles, copayments, prescription benefits, and physician access.

Beyond Standard Insurance

As you can see, even the best plan probably won’t provide 100% coverage for you or your family. If your employer allows, you can also fund a flexible spending account (FSA) or health savings account (HSA). An FSA, which is an employee benefit typically funded through payroll deduction, allows you to set aside pre-tax dollars to use toward copayments, out-of-network coverage, or other medical expenses. The drawbacks of an FSA: The maximum you can contribute is low and any funds not used during a calendar year are forfeited. An HSA, available to those enrolled in a high-deductible plan, has a higher annual contribution limit and no “use-it-or-lose-it” rules.

If you feel you need more coverage and can afford it, you can also buy supplemental health insurance. The three most common types are disease specific, accidental death or dismemberment, and hospital indemnity. Again, be sure to comparison shop before purchasing.

If you would like to discuss your health insurance or any financial planning matters, please don’t hesitate to contact us or visit our website at http://www.ydfs.com. We are a fee-only fiduciary financial planning firm that always puts your interests first.  If you are not a client yet, an initial consultation is complimentary and there is never any pressure or hidden sales pitch.

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I’m Self-Employed. How Can I Get Health Insurance?

November 18, 2014 — Sam H. Fawaz

Self-employment is an important career choice for many people, and it is an option elected by many seniors and baby boomers. But with this choice comes the need to provide your own health insurance, which can be a formidable expense. And, thanks to the Affordable Care Act, a necessary one starting in 2014. If you are self employed and are seeking health care coverage, here are your major options.

Piggyback on a Partner’s Plan

If you have a spouse or partner who is or can be enrolled in an employer-sponsored plan, joining this plan is usually the simplest and least expensive way to maintain coverage. Nearly all employer-based plans offer coverage to spouses and children, and many provide coverage to domestic partners as well.

Continue Coverage Through COBRA

If you formerly were employed by an organization that employed 20 or more people and made a group health plan available to employees, you may be able to obtain medical coverage through the federal Consolidated Omnibus Budget Reconciliation Act, known as COBRA. COBRA requires employers to make available to departing employees the option of continuing membership in an employer-sponsored group medical plan at the employee’s expense. You can continue your health insurance under COBRA for yourself and your dependents for 18 months, during which time you can search for the best option as a self-employed person.

Enroll in a High-Deductible Plan & HSA

High-deductible plans (HDPs), as their name suggests, involve a high deductible or threshold below which you must pay all costs.  For 2014, minimum deductibles are $1,250 for an individual and $2,500 for a family. In essence, a high-deductible policy provides coverage for catastrophic situations but does not generally provide for regular doctor visits and routine care. Such plans can involve complex cost-sharing arrangements in which certain procedures or visits are covered only in part. When considering this option, factor in not only monthly premiums but also the costs of partial out-of-pocket payment for different procedures.

Combining an HDP with a tax-free health savings account (HSA) can also save you in taxes. You deposit pre-tax dollars into your HSA, and use that money to pay medical expenses that aren’t reimbursed by your health insurance.

Enroll in a Group Plan Through a Professional Association

You may be able to save money by enrolling in a group plan sponsored by a professional organization. Check with any affiliations you may have (for example, the American Medical Association or a state bar association for attorneys) to see if they offer group rates for members. As with any plan, you’ll need to look at not only costs but also deductibles, co-pays, and how well the coverage meets your needs.

Enroll on Your Own Through a Health Insurance Marketplace

Many states now have health insurance marketplaces. The federal marketplace has an up-to-date list and provides insurance referrals to consumers whose states do not have their own websites.

Enroll in an HMO or PPO Plan

For many self-employed individuals, their best option will be to enroll directly in a health maintenance organization (HMO) or preferred provider organization (PPO). In general, HMOs tend to be more expensive than PPOs, but plan costs vary considerably with coverage options, so shop around. Also keep in mind that individual enrollment in a plan is likely to be expensive, often $500 or more per month for individual coverage, and that costs are generally not tax deductible.

When shopping for the right plan, make sure to do your homework. Compare premiums, coverage, deductibles, and copays. Also keep in mind that after you turn 65, you may be eligible for Medicare benefits, even if you remain self employed.

For More Information

Check out the Web resources listed below:

If you’d like to know more about health insurance when self-employed, or if you want to discuss other financial planning matters, please don’t hesitate to contact us or visit our website at http://www.ydfs.com. We are a fee-only fiduciary financial planning firm that always puts your interests first.

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