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Why did you retire early (or not)?

I retired early (at 55) for the following reasons:
1. Got tired of working the job and the day-to-day issues associated with it. I was managing a IT staff augmentation firm.
2. Wanted to quit and focus on my investments and make some income there. Have lots of interest in stock investing.
3. My retirement planner from fidelity shows that I can live comfortably until 71 (with conservative returns and over 80 with average returns in markets). I thought that's good enough for me.
4. Its been couple years since I retired and so far its going well as per the plan. I am ahead of the fidelity's retirement plan. So looks good. I do sometimes feel bored and aimless but that's temporary. I find my footing quickly by doing focusing on my financial investments and spend lots of time following the markets. Also focus on my exercise and diet and keep healthy.
My friends do tempt me to join back the work force but I am not at all motivated to do so. I don't know anybody in my peer group who is doing what I am doing (retired). So sometimes I feel lonely in my new path.
I am 56 and my wife is 52.  I believe my career has come to an end and I have saved much more than I had planned at an early age. The only thing holding me back is health insurance.  I noticed most of the replies are from folks under Medicare age, like myself. Can you share how you deal with the cost of health insurance and your approximate cost for two?

Any advice is appreciated.
Well put.  I am on a homeowner association board.  The Board has been sued by a small group of unhappy members and several of us have been personally sued.  Fortunately we had a great indemnification clause in place, and Directors and Officer Insurance. Don't ever join a Board without these things in place.  This has been going on now for about 18 months and it is a time waster and consumer.  The only reason that I am still on this Board is to protect my personal interests. 
Besides the lawsuit, there are too many people with too much time on their hands and nothing to do but complain.  The Board has taken the position of thanking the complainers for there "comments" and ignoring them, because there is nothing that can be done to satisfy them.  I am in OH and OH does not require open meetings for homeowner associations.  I'm about ready to close these meetings. 
HOA's and other groups desperately need direction from capable directors.  Congratulations for your helping.  But it is a thankless job.  People think that because they paid their assessment that they own you and you should be at their beckoned call.  They forget that the board is unpaid volunteers. 
This is way off topic, but I had to respond.  Separately, I will discuss why I am not fully retired although I could be.
My wife and I are very fortunate.  We continue to be covered for medical (and dental) by our former employer, albeit at a higher cost than when we were employed.  We also continue to cover my daughter, who only turns 26 next year, and then she is on her own.  I do not recall exactly (the coverage is actually through my wife), but the premiums work out to about $200 per month for each of us for the medical (including Rx) and dental, with the company paying much more.  Of course, the premiums are going to depend on the coverage/co-pays/deductibles, as well as the pool of people (our former employer self-insures and hires an insurance company to obtain a provider network and to administer the claims).  When we become Medicare-eligible at 65, then Medicare becomes primary coverage, with the coverage through the company being supplemental.  At that point the premiums for the company coverage are much lower (maybe half?).
The above is not going to help you, but maybe others can also comment and provide advice.
I suppose if I were in your shoes, I would research what kind of coverage is available in the market to get an idea of the costs/benefits.  Even if it is higher than you currently pay, you may be able to budget for it..
<p><p><span style='color: rgb(61, 61, 61); font-family: Helvetica, Arial, "Lucida Grande", sans-serif; font-size: 14px; font-style: normal; font-variant-ligatures: normal; font-variant-caps: normal; font-weight: 400; letter-spacing: normal; orphans: 2; text-align: left; text-indent: 0px; text-transform: none; white-space: normal; widows: 2; word-spacing: 0px; -webkit-text-stroke-width: 0px; background-color: rgb(255, 255, 255); text-decoration-style: initial; text-decoration-color: initial; display: inline !important; float: none;'>I am using Obamacare and it works out very affordable because of subsidies. Since I am retired I come under low income bracket and only costs around $300. So you may have the same situation depending on your income. When Obamacare enrollments opens up shop for insurance.</span></p><br></p>
bigal Sep 3, 2015 9:19 AM (in response to dbailey)
ACA may void my suggestions as we may have some grand fathering that I am not totally aware of.

I retired 4 years ago at 59 from self-employment as I sold my business. I owned an HSA with maxed-out deductible/savings account since 2004. Currently our deductible is 11k. But, our premiums are $450 per month and rising. Our saving account is over 100K now and from the on- set, we did not spend from it as we covered our expense on an out of pocket basis. I use Anthem, preferred provider. The savings are for health emergencies. If unused, it will later be applied to our prescription and services copay expenses. Need to stay healthy so the savings maintain and grow. My annual deposit now sit around $7500. Pretty simple if you are fairly healthy. The first year or two of an HSA are the scary moments of creating a savings basis and not spending it. Good luck.
I would not close the meetings. This will cause the complainers to then think greater misdeeds are afoot. As they have the resources to sue they will re-double their efforts. Let them in to vent. Think of it as the beating you need to take to protect your investment. Limit the venting to a small portion of time at the start of the Board meeting. Then allow them to remain and observe, but indicate they must now stay silent while the Board conducts its affairs. If they refuse then call an Executive Session and close the meeting. Indicate they have two options, gain insight into Board actions in silence or be in the dark. If they refuse either option continue the meeting at a private residence.

Given they are suing I'm surprised they have not mounted an effort to run their own slate of Board candidates. At the Annual Meeting they can represent their case and you yours.

My problem was more trying. The Board itself was the issue. Homeowner apathy prevented quorum thus different Board members could not be elected. The current slate continues to serve ad infinitum. As dues are relatively low Homeowners show little interest.

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