Fall Benefit Review:
Why Now Is the Time to Take a Fresh Look
By Ruthanne Monteleone, CFP® & Seth Borders CFP®, CPWA®
As we move into October, many employers are opening their annual benefit enrollment period. While the choices you make may feel routine, fall is an excellent time to step back and think about how your benefits fit into your broader financial plan.
At Plan & Prosper, we often encourage clients to review their coverage, contributions, and strategies before the window closes — because even small adjustments can have a meaningful impact on your financial health and peace of mind.
Why Fall Is a Good Time for a Financial Check-In
- Alignment with your overall plan: Your benefits — from health insurance and HSA contributions to retirement savings options — are a critical part of your financial picture. Reviewing them in the fall allows you to make choices that complement your other financial goals.
- Year-end strategy: Decisions made during open enrollment typically take effect January 1, which means your choices now can shape your 2026 tax planning, retirement contributions, and spending flexibility.
- Avoiding surprises: By evaluating your benefits early, you can identify gaps, redundancies, or opportunities you might not have noticed in the past.
Areas to Consider During Open Enrollment
- Health coverage: Are your plan options still the best fit for your needs and family situation? Consider premiums, deductibles, and out-of-pocket costs.
- Flexible Spending Accounts (FSAs) & HSAs: Funding these accounts strategically can help you manage medical expenses and reduce taxable income.
- Retirement plan contributions: Check that your 401(k) or other employer-sponsored retirement contributions align with your long-term goals. Even small increases can have a meaningful impact over time.
- Voluntary benefits: Disability insurance, life insurance, or other supplemental options may be worth reviewing in light of changes in your household, income, or goals.
Why a Conversation Helps
Even if you feel confident in your current elections, reviewing your benefits in the context of your overall financial plan can uncover opportunities to:
- Optimize tax efficiency
- Protect against unexpected expenses
- Align workplace benefits with long-term goals
We are reviewing accounts and planning strategies across our clients’ portfolios this fall, and we can help ensure your benefits choices work in harmony with your broader financial picture.
The Bottom Line
Fall benefit enrollment is more than a routine task — it’s a chance to align your employer-provided benefits with your personal financial goals. If you’d like to discuss your options and ensure your choices reflect your priorities for 2026, let’s schedule a conversation. Feel free to download, use and share our Open Enrollment Checklist: