Here's a take from an individual: I was recently unemployed (January)[0]. I signed up for COBRA right away. Within about a month, I had offers and I ended up

Here's a take from an individual: I was recently unemployed (January)[0]. I signed up for COBRA right away. Within about a month, I had offers and I ended up narrowing it down to two. I was having a really difficult time choosing between the two jobs. One was a local company, not large, but not small that was doing really exciting things but would end up with me taking an "in the office" position (I had been working at home for about a decade up to now). The other was a very small outfit, out of state, which was directly in my unique area of expertise. The salary offers were the same but the smaller business was so small that they didn't offer insurance so I'd have to buy it on "the exchange". I ran the numbers. I was paying $1,500/mo[1] for COBRA coverage (family) and discovered that because I had signed up for COBRA, I couldn't join an exchange plan until November. This, alone was a deal breaker. I went back to the small business and asked for additional compensation to cover it (and it was offered). I ran the numbers again. Going off of this years rate, I could get a plan for around $1,200/yr. This "plan" came with a $12,000 deductible. Incredibly, it was not eligible for a Health Savings Account. And the way the laws are setup, all of the monthly costs of coverage and the $12,000 spent toward medical coverage would be after taxes until it reached 10% of my annual earnings. Very quickly, a well paying job became a huge downgrade in salary from my prior position. And that was this year's rate. I anticipated at least a 10% increase come November and that's probably low. At the other job, I had three options for very good healthcare coverage that was the cheapest I've ever encountered. One of them was a High Deductible plan with the minimum deductible required to qualify for a Health Savings Account[2]. The cost of the plan was such that despite their initial offer being exactly on-par with what I was making at my prior employer, I ended up taking home a few thousand more every year. And the coverage is better than my last employer (and mountains better than the $12,000 plan ... from the same health insurer ... the exact same health insurer -- same state, same administrative unit, same brand).[3] [0] I mention this only for context, not as a judgement of the company. They took great care of me and the circumstances behind the layoff had to do with changing of the focus of the company to things that I wasn't working on. The unique nature of the position I filled made it impossible for me to effectively transition to this new kind of work without moving to another country... something I cannot do. [1] For those who are unfamiliar, COBRA allows you to keep your former employer's insurance at the same price that it was at your former employer but it's got one big gotcha. Your employer usually pays a percentage of that monthly cost. In my case it was somewhere around 80% of that cost. It was a good deal while I was employed, but turned into a pretty terrible one when I was no longer employed. Companies often continue to pay/fund part of the COBRA costs for a period of time after an employee is let go and because I'm not entirely sure what I agreed to keep confidential with the NDA that I signed when I was let go, and out of respect for my former coworkers/managers, I am neither confirming nor denying that they helped out here. I certainly wouldn't have expected them to if they did and wouldn't have been upset if they didn't. Sufficiently vague enough? [2] HSAs are pre-tax accounts that carry over to the next year (they work a lot like a 401K that allows you to take money out any time for qualified medical expenses). I love them both because they have always saved me money in the long run and on the principal of them. I hate our broken healthcare system. It's the worst kind of "fake capitalist" arrangement there is. Ask yourself what the last prescription you filled actually cost, or that last trip to the doctor. Most people have no idea what doctor's visits, medications, hospital trips, and medical tests cost so there's no shopping around and therefore no reason for "the system" to optimize prices. A high-deductible plan changed my behavior immediately. For unimportant things, like "where I fill my prescriptions", I do my research (and man does it take time -- try to get the price of a drug out of the drugstore in less than an hour) and I fill things where I know they are cheapest. I used to just go to urgent care when I got sick, never realizing it's twice the price and half the quality (at least where I'm from). I never realized that I could call my physician and get a same-day appointment on week days (I've never been turned down and though I end up having to wait a little bit, it's never as long as the wait at Urgent Care). [3] I just want to clarify, I kept the discussion about healthcare due to the post topic. This certainly wasn't the only reason I went with my current employer. They are really doing awesome things and I was very excited to have been given an offer here. I'm also very glad that I took it. I can't say that I wouldn't have chosen them, anyway, simply because the work looked (and turned out to be) exciting. I mean that, though. I really can't say. The healthcare issue was such huge thing that it took the other option completely off the table.