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Periodic work to pay for health insurance
Old 05-11-2017, 01:27 PM   #1
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Periodic work to pay for health insurance

My tentative plan is to retire at age 60 in four years. I will need to purchase my health insurance until I am Medicare eligible at 65. With the current battle field over health care, I can only conclude that the cost will be much higher than today's prices, especially if preexisting conditions are not covered.

I am considering using COBRA for a year or so and then return to work intermittently. I am thinking I could work 6-9 months, part time for my current employer, and be eligible for employer health coverage. I would winter in a warmer climate for 3 months, again using COBRA coverage. My job classification is in high demand (but marginal pay) with my employer, and the nature of the work could be accomplished in 6-9 months. My employer allows health coverage (with employee paying part) for 20 hour per week employees. Obviously the boss lady would have to see the benefit of this for it to work.

Another option would be to not work as many hours to be eligible for employer provided health insurance but use the job income to pay for the private health insurance. I could work intermittently in both the north and south either several months per year or several days per month.

My question is: Have others worked intermittently to either be eligible for employer sponsored insurance or to produce extra income to pay private health insurance? How did you do it?

P.S. This is not a post about the future of Obamacare vs Trumpcare.
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Old 05-11-2017, 01:43 PM   #2
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This is what my sister has been doing in the last few years. On and offfor healthcare. She is doing contract work.
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Old 05-11-2017, 02:06 PM   #3
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Might be a good plan.

I have thought about doing some substitute teaching to pick up some fun money or to help offset healthcare costs until 65. I might be able to contract with my current employer part time as you plan to do. I have a co-w*rker who retired from here in August. They just brought her back as a contractor to do some pop-up w*rk that no one remaining with the company can do as efficiently as she can. She says retirement is WONDERFUL, but she doesn't mind doing this part time for 3 month here and 6 months there.
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Old 05-11-2017, 02:41 PM   #4
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In the pre-ACA days, many small companies were set up with the (unstated) purpose to establish eligibility for small group or even "group of one" health insurance policies.

Sure seems simpler than taking and quitting a job every 18 months just to punch the Cobra eligibility watchdog timer.
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Old 05-11-2017, 03:17 PM   #5
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Originally Posted by Fedup View Post
This is what my sister has been doing in the last few years. On and offfor healthcare. She is doing contract work.

Thanks for responding.

How does your sister like this arrangement? Any pros and cons?
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Old 05-11-2017, 03:34 PM   #6
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If you are self employed, every penny of your health insurance premiums is deducted off your AGI. Keeps your taxes low and saves the anxiety of how to pay for health insurance. But, if things change eventually getting coverage may again be a problem.

As a self-employed person you should be able to quit and take breaks whenever you want.
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Old 05-11-2017, 04:39 PM   #7
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I have no desire to w*rk again, but this thread got me thinking. So, if you really needed some kind of job just to get insurance, can you do something like being a professional blogger and say you are self employed? So what if you earn peanuts and have a really really short schedule, to earn good money really isn't the purpose. As I said, I'm not looking but just curious is such a job for insurance possible.
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Old 05-11-2017, 05:06 PM   #8
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Thanks for responding.

How does your sister like this arrangement? Any pros and cons?
Pro is that she gets paid for OT. Con is when she can't find work as a contractor and has to be permanent like now. They abuse her, she has to work like 12 hours a day without OT. She has converted to contracting work for 40% more pay, through contracting house for years. So during the downturn she often went for months or years, maybe 2 years max, without work. Another con, she is over qualified for some jobs. She is an accountant with lots of experience so she gets hired to fix problems or somebody's mess.
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Old 05-11-2017, 06:26 PM   #9
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Originally Posted by easysurfer View Post
So, if you really needed some kind of job just to get insurance, can you do something like being a professional blogger and say you are self employed? So what if you earn peanuts and have a really really short schedule, to earn good money really isn't the purpose.
If you actually setup a business (LLC, EIN, business filing with the state, dept of revenue, etc., licenses), then that should qualify. You list yourself, and spouse perhaps, as members of the LLC.

I don't believe there's any profitability bar, or hours to report. I have a small business I started from jewelry making, and plan to run my HI thru it after I'm off employer severance. But I also plan to meet with a business/tax/attorney for a deep consult before setting that part up and ensuring I'm taking full legal advantage.
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Old 05-11-2017, 06:38 PM   #10
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If I am understanding https://www.irs.gov/uac/is-your-hobb...rofit-endeavor properly, your business has to show a profit 3 out of 5 years.

I am thinking I would have to earn more than the cost of the health insurance if I am going to be able to deduct it as a business expense.
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Old 05-11-2017, 06:55 PM   #11
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If you actually setup a business (LLC, EIN, business filing with the state, dept of revenue, etc., licenses), then that should qualify. You list yourself, and spouse perhaps, as members of the LLC.

I don't believe there's any profitability bar, or hours to report. I have a small business I started from jewelry making, and plan to run my HI thru it after I'm off employer severance. But I also plan to meet with a business/tax/attorney for a deep consult before setting that part up and ensuring I'm taking full legal advantage.

Thanks. Good to know as a just in case .
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Old 05-11-2017, 08:13 PM   #12
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If I am understanding https://www.irs.gov/uac/is-your-hobb...rofit-endeavor properly, your business has to show a profit 3 out of 5 years.

I am thinking I would have to earn more than the cost of the health insurance if I am going to be able to deduct it as a business expense.
Technically, you NEVER can deduct you and your families health insurance premiums as a business expense, ie, it is not entered on Schedule C for self-employed (or single member LLC). Thus, it does not reduce your self-employed profit nor the self-employment tax.

However, you can take an adjustment to income on line 29 of Form 1040, that reduces your AGI and thus your taxable income. The amount is limited by the amount of profit your Schedule C shows.

For more details, see: The Self-Employed Health Insurance Deduction: A Valuable Personal Deduction | Nolo.com
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Old 05-12-2017, 06:18 AM   #13
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Thank you for the clarification.

That is what I did for 2015 and 2016.

Thank goodness I had a "profit" on my Schedule C-EZ for both years.

2017 looks like it will be different since I don't have enough profit on my Schedule C-EZ unless I find a 1099 job.
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Old 05-12-2017, 09:45 AM   #14
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Go work at ups sorting packages a couple hours a day. Full health care...not sure what the hourly rate is...prob around $12/hr.
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Old 05-12-2017, 10:18 AM   #15
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Go work at ups sorting packages a couple hours a day. Full health care...not sure what the hourly rate is...prob around $12/hr.
Someone suggested this in another post recently.
Apparently it is fast-paced backbreaking work which I wouldn't doubt.
I know at my age, I couldn't handle it.
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Old 05-12-2017, 10:22 AM   #16
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Someone suggested this in another post recently.
Apparently it is fast-paced backbreaking work which I wouldn't doubt.
I know at my age, I couldn't handle it.
Ive also heard its tough work...and they work you hard! But if someone is retiring around 50 or so...there should be plenty of fuel in the tank for a couple years anyway.

If someone really needs healthcare and they're strapped for cash it would prob be better to just work a few more years...but if you're really stressed sorting packages at UPS doesnt require too much thought...and once you leave for the day thats it. Just something for people to consider.
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Old 05-12-2017, 10:55 AM   #17
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I am not concerned with health insurance costs at this point (I am more concerned with coverage availability). But DW was contacted recently by a company who wanted to hire her as a consultant and she took the job (max 140 hours of work per year up to 3 years). Because she commands a high hourly rate, she could make a substantial amount from the gig. We are planning to save that income in a separate account and use the money to help pay for future health insurance premiums (if our budget can't absorb premium increases any longer).
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Old 05-12-2017, 11:22 AM   #18
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Originally Posted by broadway View Post
Someone suggested this in another post recently.
Apparently it is fast-paced backbreaking work which I wouldn't doubt.
I know at my age, I couldn't handle it.
225 hours required over a 3 month period, assuming this page is accurate: UPS Part-Time Benefits | TeamstersCare 25. That's 5 hrs/day, or 3 full days/week. A lot more than "a couple hours a day". I don't know if this is right though. Just for funs I searched for jobs at a nearby UPS, and they listed part time sorter positions at 15-20 hrs week. Benefits unclear but seemed to include some medical. Not interested enough to delve deeper. Hours were anywhere from 3pm to 9am. You have to be able to lift and move up to 70 pounds.
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Old 05-12-2017, 12:16 PM   #19
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I worked at a UPS terminal during My Jr/Sr yrs of college, ~30 years ago. I sorted and loaded trucks. I assume a bit has changed since then, but no way in h*ll I would be able to do that job today. Especially loading, the packages seemed to come at you at warp speed, way too physically demanding for someone in their 50's+
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Old 05-13-2017, 07:21 AM   #20
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I worked at a UPS terminal during My Jr/Sr yrs of college, ~30 years ago. I sorted and loaded trucks. I assume a bit has changed since then, but no way in h*ll I would be able to do that job today. Especially loading, the packages seemed to come at you at warp speed, way too physically demanding for someone in their 50's+
Me too. Same job. They just forced 8 hours of work into 4 hours. I used to have sweat pouring off me!
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