• DC @ Young Adult Money says:

    As I’ve mentioned in the past I work in health insurance, but in accounting not in the sales side. One option that people will have very soon is purchasing through the health insurance exchanges (Enrollment for 1/2014 starts in just a couple of months). I think this will become the go-to place fore self-employed in the future.

    • John says:

      I can understand that DC, though I would tend to be leery of saying that especially with the delay that was announced a few days ago. I am hopeful that something like that would work, but we all know how things get when the government gets involved.

  • Holly@CLubThrifty says:

    Greg took a month off in between his old job and his new job AND his new insurance doesn’t start until Sept. 1st anyway. We bought a short term Anthem policy to cover us for a few months and I was surprised to find that it was quite painless!

  • Roger @ The Chicago Financial Planner says:

    Good post John. Among the major reasons that my wife works is for the health insurance (the extra income also helps with college costs). Your advice on using a broker is right on. I did exactly that to help a self-employed client find insurance that was right for her and far cheaper than COBRA.

    • John says:

      Thanks Roger! We would’ve been lost without a broker. I can’t imagine what it would be like having only COBRA as an option. It’s an option, but certainly an expensive one – generally speaking.

  • Alexa says:

    I work for an insurance agency and they don’t off health insurance to their employees…..go figure. My exhusband and I both have jobs without health insurance. A couple of years ago he had a false heart attack and they ended up care flighting him to a large hosptial and putting a stint in. He stayed at the hospital for 3 days and we got a bill for $50k and didn’t have insurance. You don’t realize how bad you need it until the unexpected happens!

    • John says:

      Wow, that’s a kicker! Wow, so sorry about that story, though it just goes to show you how expensive anything medical is. I toyed with the idea of not getting coverage for myself, but it is playing with fire not to get it.

  • AverageJoe says:

    I’m with you on this one: find a good broker who can limit your choices. I totally get paralysis whenever I compare health insurance plans. There’s just WAY too much information, and much of it I’m unsure how it affects me….even though I’ve worked in financial planning for 20 years!

    • John says:

      That’s saying something Joe – that it’s way too much to process. I am so glad there are people out there who can understand it and boil it down for people like me. 🙂

  • Matt Becker says:

    Great info here. I think the decision to go with a broker is a great one for a decision as complicated as this. I’m also very jealous of the HSA option. That’s definitely something I wish we had.

    • John says:

      Thanks Matt! Yes, a broker is a God send for situations like this. I am just glad there are people out there who understand this stuff and make it easier for simple people like me.

  • SuburbanFinance says:

    Luckily we are in Canada so don’t really need health insurance, except for with dental stuff. It’s likely cheaper to just pay for a cleaning every six months rather than pay into insurance for it, but I guess that depends on the size of your family, too.

    • John says:

      Yea, I am a bit envious. 🙂 We actually don’t have dental coverage as it’s just so expensive here in the States. We would be paying more per year than the value we’d be getting.

  • Grayson @ Debt Roundup says:

    When I was self-employed, I couldn’t get health insurance because of a pre-existing condition. Now that would be different with the new health law, but I had to go onto my wife’s plan. It worked for us, but I would have been in trouble without it.

  • Brian @ Luke1428 says:

    We’ve had an HSA for several years now and love it! We are relatively healthy so we have been able to save a great deal in our account. It just takes the discipline to put money in the account every month whether you are sick or not. is a great website for anyone wanting to learn more about these plans work.

    • John says:

      We do as well. We’re generally healthy as well, so it’s nice knowing we can build up a nice cushion in case anything were to happen. Thanks for pointing out that site, I’ll have to check it out.

  • Sam Gill @ Digital Spikes says:

    Thanks for the insights, Yeah one can easily get carried away with the different features when you compare, It is better to have a genuine broker who can understand your needs and get you the best

  • Budget and the Beach says:

    I agree it’s very complicated and frustrating trying to figure it all out. And the paperwork with applying is so daunting. My piece of advice to everyone is keep good health records if you ever plan on making the switch because I can’t remember every single doctor visit or that prescriptions they might have given me. I also used a health insurance broker which made it a lot easier. And I didn’t know you could do a HSA. I need even had one when I worked full time but that’s something I should look into more.

    • John says:

      I could not agree more Tonya, it can be very daunting. Great point on the good health records – those are key to have. Yes, as long as you have a HDHP, as far as I have read, you can have an HSA. It’s well worth it, if you’re able to have one.

  • Michelle says:

    Great post! I have been looking into insurance and it is all just so confusing!

  • pauline says:

    The more I read about US insurance the more I am lost. I don’t have insurance, I just pay for what I use and get a free physical when I go back to France. With a family I would look for a plan, looks like kids break legs and have tonsils to remove all the time!

    • John says:

      You’re not the only one Pauline. 😉 Yes, kids do things all the time – thus the need to cover your risk.

  • Tanya @ The Heavy Purse says:

    Great timely post for me. I don’t have health insurance but it’s something I want/need. 🙂 It is confusing and I never though of going through a broker which sounds like a great idea. Choice is great but it can get overwhelming. I’ve been fortunate and healthy but I also don’t want to take the risk any longer. It’s not worth it in the end.

    • John says:

      Glad it is Tanya! I would respectfully classify it as a need. There are just so many things that could happen and you could be on the hook for thousands of dollars. It is confusing, but using a good broker will help you greatly. Ours gave us 5-6 plans that fit our needs and it was a simple decision after that.

  • Pension Retirement says:

    My wife and I have decided that if either of us do decide to go the self-emoployment route, that we’d always have the other at a “real” 🙂 job that offered insurance benefits, just because you never know when the poop is coming at you. I can’t imagine how complicated it is choosing plans, as I have enough picking through the options of my employer-offered plans.

    • John says:

      That is always a good route to take. You’re right, you never know what will be coming your way, thus why having insurance is so important. That said, using a broker makes it MUCH easier. Thanks for stopping by!

  • Deacon @ Well Kept Wallet says:

    I took the plunge earlier this year and health care costs did not play a huge role for me. My premium for a HDHP with a $5,000 deductible and Dental insurance is only $109 per month. Although that is higher than when I was working for someone else, it wont break the bank.

    • John says:

      That’s not bad at all Deacon. We decided against the dental insurance as it was just not worth the cost for us.

  • Jake @ Common Cents Wealth says:

    I’ve always heard how difficult (and expensive) getting health insurance can be when self-employed, but I’ve never had to personally do it. I think the exchanges in 2014 will make shopping for health insurance a lot easier. It’s supposed to be kind of like buying a car. We’ll see how that goes.

    • John says:

      It really has the potential to be Jake, thus why having a broker is so essential. I wish I had more faith in the exchanges, call me a cynic, but I’ll believe it when I see it.

  • Sean @ One Smart Dollar says:

    Insurance is easily the worst thing about being self employed.

  • anna says:

    I agree about spending accounts (though ours is FSA)! It can be a hassle with having to submit receipts (or rather re-submit when faxes don’t go through… but seriously, who uses faxes anymore?!), but still worth all the savings.

    • John says:

      I know, right? Why on earth do companies STILL use faxes? That said, that’s great you have an FSA, though I always hated having to spend money at the end of the year so we did not lose it.

  • John@MoneyPrinciple says:

    Well of course we don[‘t worry about that too much over here but the way the UK government is dismantling our health service, it may come to it. Generally for self employment you may take critical illness insurance which is where you get some income for very serious stuff but otherwise most depend on the NHS.

    • John says:

      That’s interesting. I had a family member who had to stay in the hospital for several days in London a couple of years ago and they thought it was a great compared to us here in the States. Hope it stays that way.

  • Pretired Nick says:

    It’s almost hard for me to read this because I hate the insurance system in the U.S. so much. What a scam! Fortunately my wife is still working so I can sponge off her for awhile, but someday this will become a big issue for us.

    • John says:

      As do I Nick! It’s as if it’s set up for us to be screwed…wait – it is! Glad you have coverage through your wife, that’s the important thing.

  • Kim@Eyesonthedollar says:

    I’ve had an HSA plan since right after they were first created. I had to go through a broker because no one knew much about them, and I still use him to this day. He calls every year on my anniversary and we review plans and make changes when necessary. It doesn’t even cost more than buying online. I would highly recommend finding someone you trust who can guide you through the maze of insurance. I am hopeful about the government exchanges, but as hard as Medicare and Medicaid have been to sort through for patients and providers, I’m not sure the government is the best answer.

    • John says:

      I would completely agree Kim about using someone you can trust as it can be one big headache. I am hopeful, as well, about the exchange, though the cynic in me is not buying it.

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