How AI Helped Me During Open Enrollment for Benefits

Open enrollment can feel confusing. There are so many plans, rules, and small details that are hard to read and even harder to compare. This year, I used AI to help me sort through everything and choose the medical plan that made the most sense for me. It made the process way less stressful.

Why I Needed Help This Year

I had to choose a new medical plan because my usual provider was no longer in-network. On top of that, my company moved to an ICHRA (Individual Coverage Health Reimbursement Arrangement). That meant I had to shop for my own plan on the Marketplace instead of picking from a smaller list of employer options. It gave me more freedom, but also more decisions to make.

What I Shared With the AI

To get useful and accurate help, I provided:

• My recent paystub
• My expected healthcare needs
• My past usage (how often I go to appointments, what I usually spend)
• The Marketplace plans I was comparing
• Details about my employer benefits starting January 1
• My financial goals for next year

Giving real numbers made the AI’s breakdowns much clearer.

The Types of Questions I Asked

I kept my prompts simple, like:

• “Which plan saves me the most money over the full year?”
• “Explain these plans in simple terms.”
• “How will this affect my paycheck?”
• “Do I need to adjust my tax withholding?”
• “Is an HSA or FSA better for my situation?”

The AI helped me understand the math, the rules, and what each plan actually meant for my wallet.

What I Had to Think About

The AI didn’t choose the plan for me. But it helped me think through:

• How much I use healthcare in a normal year
• Whether my favorite providers were in-network
• My income and tax bracket
• Total yearly cost (not just monthly premiums)
• How much risk I’m comfortable with
• Whether to save more in my 401(k)
• If an HSA or FSA made more sense

It also helped explain tricky things like “use-it-or-lose-it” FSAs, how HDHPs work, and how pre-tax deductions lower taxable income.

What I Learned

Using AI during benefits enrollment saved me time and gave me a much clearer picture of my choices. It broke down complex documents, compared costs, and pointed out details I would normally miss. I still made the final choice myself, but I felt informed instead of confused.

The big lesson?

AI is great for tasks that involve math, charts, and fine print. It won’t replace a professional adviser, but it can help you understand your options so you can make smarter decisions.

Open enrollment is still a lot—but having AI explain things step-by-step makes it feel manageable. If you’re stuck or overwhelmed, it’s a tool worth trying.