Here's how I approach open enrollment every year — the decisions most people make on autopilot that deserve deliberate attention.

Health insurance: compare actual premium costs plus the maximum out-of-pocket between your plan options. If the HDHP premium savings plus the employer HSA contribution exceed the deductible gap, the HDHP is almost always worth it.

Life insurance: employer-sponsored life insurance is cheap but usually not enough. Run the 10-12x income rule. If you have dependents, the $50k policy through your employer is probably not the full picture.

Disability insurance: this is the most commonly underselected benefit. Long-term disability that replaces 60-70% of income is worth maxing out at employer rates, which are almost always better than individual market rates.

FSA/HSA: if you have an HDHP, max the HSA and invest it. If you have an FSA, estimate carefully — unspent FSA money is forfeited at year end in most plans.