Day Jobs and Night Gigs: Health Coverage When You Work for Yourself, Open Now Through Jan 15

Questions this episode answers

Key facts

• If you have a business that takes in income but has no employees, you can enroll through the individual Health Insurance Marketplace. That includes freelancers, consultants, and independent contractors (HealthCare.gov).
• Open Enrollment started November 1, 2026. Enroll by December 15 for coverage that starts January 1. The last day is January 15, 2027. If you enroll December 16 through January 15, coverage starts February 1 (HealthCare.gov).
• Put your estimated net self employment income for the year you want coverage, not last year. Net income is what you take in minus business expenses, sometimes called profit (HealthCare.gov).
• Update your Marketplace application as soon as possible if your income changes. If you make more than you reported, you could have to pay back some or all of the premium tax credits. If you make less, you could qualify for more savings than you claimed (HealthCare.gov).
• You get exact prices and savings when you fill out an application. CMS says more than 75% of people who buy through HealthCare.gov will have access to premiums at or below $50 a month in 2027 (official CMS estimate) (CMS).
• Losing job based coverage for any reason can open a Special Enrollment Period, so you can enroll outside Open Enrollment (HealthCare.gov).
• Call the Marketplace at 1-800-318-2596 (TTY 1-855-889-4325), or find trained local helpers through HealthCare.gov (HealthCare.gov).

Chapters

1. 00:00Voicemail: Rosa asks if she can sign up
2. 00:29Show open
3. 00:39Last time: VA pension, up to $17,441 a year (estimated)
4. 00:49Day jobs and night gigs
5. 00:57Open now, plans for $50 a month or less for many (estimated)
6. 01:13Welcome to Your Daily Benefit
7. 01:24The dates: Dec 15 and Jan 15
8. 01:35Who counts as self employed
9. 01:58Savings, Medicaid and CHIP
10. 02:18On the street: what people think
11. 03:08Three fixes
12. 03:37What income to put
13. 03:51If your guess is wrong
14. 04:06Losing job coverage
15. 04:16Where to get help
16. 04:32Benefit Bull helps you look
17. 04:43The answer for Rosa
18. 04:53Next time: LIHEAP heating help for families
19. 05:09AI voices note

Find help

• Full episode page with transcript
• All Your Daily Benefit episodes
• What Happens When You Apply (Benefit Bull guide)

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Sources

Full transcript

1. 00:00

   Rosa (voicemail): Hi, um... hi. This is Rosa. So, I clean houses. On my own, no boss, just me. And I don't have health insurance. My sister says there's a site where you can sign up now? But I figured that's, um, for people with a real job. Can somebody like me even use it? And my money goes up and down every month, so... what would I even put? Okay. Thank you. Bye.

2. 00:30

   Nayva: Okay, Rosa. Two good questions. Can you use it? And what number do you put? We'll get to both. Drew, quick catch up first?

3. 00:39

   Drew: Last time, VA pension. Some wartime veterans with low income may get up to seventeen thousand four hundred forty one dollars a year. Estimated.

4. 00:49

   Nayva: Today, health coverage. What do day jobs and night gigs have in common?

5. 00:55

   Drew: Nobody hands you a health plan?

6. 00:57

   Nayva: Pretty much. But here's the good part. Sign up is open right now, at HealthCare dot gov. And government numbers say more than three out of four shoppers there can find a plan for fifty dollars a month or less. Estimated.

7. 01:12

   Drew: Fifty a month?

8. 01:13

   Nayva: For many people, after savings. Not everyone. This is Your Daily Benefit.

9. 01:19

   Drew: And today is for people who work for themselves. Okay. What's the deadline?

10. 01:24

    Nayva: Sign up by December fifteenth, and coverage starts January first. The last day is January fifteenth. Sign up after December fifteenth, and it starts February first.

11. 01:35

    Drew: So who counts as self employed?

12. 01:38

    Nayva: You have a business that brings in money, and no employees. Freelancers. Contractors. People who clean houses, drive, or make things to sell.

13. 01:48

    Drew: So Rosa counts.

14. 01:50

    Nayva: Rosa counts. People like her can use the Marketplace. That's HealthCare dot gov, or your state's own site.

15. 01:58

    Drew: How does she know what it costs?

16. 02:00

    Nayva: She fills out an application. It shows if she may qualify for savings that lower her monthly cost. That's based on income and household size.

17. 02:09

    Drew: And if her income is really low?

18. 02:11

    Nayva: The application also checks for Medicaid or CHIP. That's free or low cost coverage, run by her state.

19. 02:18

    Drew: Before Rosa's other question. I took a mic outside and asked people about health coverage when you work for yourself. Take a listen.

20. 02:30

    Drew (on the street): Hey, sorry, real quick. If you work for yourself, can you get health insurance on HealthCare dot gov?

21. 02:36

    Man on the street: Uh... no, I don't think so? Don't you need, like, a job that signs you up? An employer?

22. 02:45

    Drew (on the street): Okay. Thanks.

23. 02:48

    Drew (on the street): Hi, excuse me, real quick. When you sign up, what income do you put down?

24. 02:53

    Woman on the street: Um, what you made last year? Like, off your taxes? Right?

25. 02:57

    Drew (on the street): Okay, okay.

26. 02:59

    Drew (on the street): Sir, one more, real quick, when does sign up

27. 03:02

    Second man on the street: Oh, that's over. That ended, like, before Christmas, right? You missed it.

28. 03:06

    Drew (on the street): Appreciate you. Have a good one.

29. 03:08

    Nayva: Okay. Three fixes. One. You don't need an employer. If you work for yourself with no employees, you can use the Marketplace.

30. 03:18

    Drew: Two. Last year's income.

31. 03:20

    Nayva: Savings are based on what you expect to make in the year you get coverage. So for this sign up, that's twenty twenty seven. Not last year.

32. 03:29

    Drew: And three. Did they miss it?

33. 03:31

    Nayva: No. Sign up started November first. The last day is January fifteenth.

34. 03:37

    Drew: Back to Rosa's other question. Her money goes up and down. What does she put?

35. 03:42

    Nayva: Her best guess for next year. Her net income. That means what she takes in, minus her business costs. Some people call it profit.

36. 03:51

    Drew: And if she guesses wrong?

37. 03:53

    Nayva: She updates her application as soon as she can. If she makes more than she said, she could have to pay back some or all of her savings.

38. 04:02

    Drew: And if she makes less?

39. 04:04

    Nayva: She may get more savings than she took.

40. 04:06

    Drew: Okay. And if she loses a job with coverage later?

41. 04:10

    Nayva: Losing job coverage can open a special time to sign up, even after open enrollment.

42. 04:16

    Drew: Good to know. Where does she get help?

43. 04:19

    Nayva: The Marketplace help line. One eight hundred, three one eight, two five nine six. HealthCare dot gov can also find trained helpers near you. And you apply yourself.

44. 04:32

    Drew: And if you're not sure what other help is out there for you, Benefit Bull dot com can help you look. You still apply yourself, on the real program's site or phone line. It just helps you find it.

45. 04:43

    Nayva: So, Rosa. Yes, you can use it. You put your best guess for next year, after costs. And you update it if things change. Thanks for calling.

46. 04:53

    Drew: Okay. What's next time?

47. 04:55

    Nayva: Help with heating bills for families. It's called LIHEAP. We'll walk through it.

48. 05:00

    Drew: I'll be here.

49. 05:01

    Nayva: See you next time. Take care of yourselves. And hey, this and a lot more, you can find at Benefit Bull dot com.

50. 05:09

    AI voices note: Quick note, the voices on Your Daily Benefit are AI generated.