Open Enrollment 2026: Don't Just Click Re-Enroll

Most people click "re-enroll" and move on. That one click sets your health plan, your HSA, your daycare money, your disability coverage and a good chunk of your retirement savings for the next twelve months. Open enrollment was one of our most downloaded episodes of 2025, so Tom Kaminski, CFP®, is back with the 2026 edition, updated for the 2027 plan year. He walks through the benefits packet in the order it matters: your 401(k) (and the "Frankenstein" allocation most people never fix), how to actually compare a high deductible plan against a PPO, why your HSA belongs in your retirement plan, the dependent care and healthcare FSAs, short- and long-term disability, life insurance, and the page 37 extras like pet insurance, identity theft protection and legal plans. Plus what to watch for if your employer starts matching Trump Accounts. The short version: take an hour, read the 40-page PDF, and do the math for your own family. Links and resources IRS Publication 969, HSAs and other tax-favored health plans: https://www.irs.gov/publications/p969 IRS Publication 503, child and dependent care expenses: https://www.irs.gov/publications/p503 IRS Publication 926, household employer's tax guide: https://www.irs.gov/publications/p926 Social Security disability facts: https://www.ssa.gov/disabilityfacts/facts.html Medicare open enrollment: https://www.medicare.gov ACA marketplace open enrollment: https://www.healthcare.gov Our Trump Accounts episode (Season 1 Ep 21) Our original open enrollment episode (Season 1 Ep 2) Twin Robins Capital disclosures: https://www.twinrobins.com/disclosures This episode is for informational purposes only and is not tax, legal, or investment advice. Please consult qualified professionals before making any financial decisions.