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Oh My Dollar!

137 EpisodesProduced by Oh My Dollar!Website

Lillian tackles your money overwhelm with practical, approachable financial advice (with a dash of glitter.) This is budgeting advice from someone that doesn't assume you're straight with a salary, retirement account, 2.5 kids, or a white picket fence. You'll get helpful advice for folks left out by… read more


Open Enrollment is like playing Dungeons & Dragons… with a drunk dungeon master

We have two listener questions this week for health care month: Anna wants to know how to fix an accidental over-contribution to her HSA without getting a penalty (time stamp 01:34), and Allison wants to figure out how to switch health insurance when the open enrollment periods don’t line up between the two plans (timestamp 5:32)

We talk about why navigating the open enrollment stacking is kind of like playing magic or playing Dungeons & Dragons with a drunk Dungeon Master (timestamp 10:34)

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Reasons you can switch insurance outside of open enrollment – otherwise known as a “special enrollment period” 
    • You have lost health coverage (you lose your job, or don’t qualify anymore at work, or you turn 26 on a parent’s plan)
      Please note that this does not apply if you lose coverage for non-payment of your premium (but if you’re behind on co-pays or co-insurnace, not premiums, your coverage shouldn’t be cancelled)!
    • You get married or divorced
    • You don’t lose coverage, but your hours are reduced to below 30 hours a week at work – then you can enroll in a plan
    • You adopt or give birth to a child
    •  You have moved out of state or your zip code (and you’re on a plan)
When Moving qualifies you for a special enrollment period
  • Moving to a new home in a new ZIP code or county
  • Moving to the U.S. from a foreign country or United States territory
  • If you’re a student, moving to or from the place you attend school
  • If you’re a seasonal worker, moving to or from the place you both live and work
  • Moving to or from a shelter or other transitional housing
How to cancel health insurance
  •  Generally you can cancel your plan at any time, and it usually takes effect immediately (sometimes it will be the 1st of the next month). You can do so online at or by calling your insurance company
  • If you want to cancel an employer-provided health insurance plan, talk to your HR department or the person at your company that handles benefits.
How to get health insurance during open enrollment – Sign up at work if you qualify – Sign up at a partner’s or parent’s work (the later if you’re under 26 years old) – Enroll at your state’s exchange, which you can find at

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