Best Open Enrollment Newsletters in 2026

NewsletterFIT tracks 3 newsletters that cover Open enrollment as a primary topic, all with posts in the last 90 days. By publicly shown subscriber count, the largest are Wendy Parker is Eternally Irritated. (2K).

Updated Nov 7, 2026 · sorted by publicly shown subscribers · methodology

  1. 1
    Wendy Parker is Eternally Irritated.2K subscribers

    SubstackSeveral times a week · last post 5 days ago

    From recent posts: Wendy Parker is Eternally Irritated publishes a mix of personal essays, satirical relationship advice, and linguistic observations from a single author. The content covers specific topics including Social Security…

    Likely audience: Retired individuals

  2. 2
    Thriving Freelance: Gigs & Growth—

    beehiivSeveral times a week · last post 9 days ago

    Hundreds of job opportunities sent directly to your inbox each week, plus timely resources to support you as you grow and evolve. The Harlow newsletter is a treasure trove for freelancers, creators, and entrepreneurs.

    Likely audience: Small business owners

  3. 3
    Health Coverage Chaos—

    LinkedInEvery two weeks · last post 15 days ago

    All of the ins and outs of the health insurance market new articles every 2 weeks!

    Likely audience: Individuals with employer-sponsored health insurance

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