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Retire Early

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My wife and are started teaching in NY when we were 22. She’s now a director of technology in the teacher’s union and I’m a technology teacher. 

We work extremely hard with a second business and save 50-60% of our income.  

This is our 24th year of teaching and we’d like to retire after 30 years at 52 1/2 years old.  We know we won’t be able to access our NYS pension until our 55th birthdays 2 1/2 years later but we’ve been planning for this.  The kids both finish college when we’re 52. Their college expenses are both fully funded now and we continue to contribute to it for grad school should they pursue careers that require it  

Retirement to us means leaving teaching and “working” remotely on our business to continue pulling in an income.

The problem we’re facing is our districts will not not honor their health care contributions after “retirement” (60-70%) because as they say we’re not eligible for retirement.  

There is nothing in either of our contracts about the age of “retirement” or what constitutes retirement or the number of years you have to work for benefits.  

I have not asked if we can go on Cobra for 2.5 years and then our benefits kick in or if they would consider this a resignation and we’d be walking away from our healthcare benefit. 

Wondering if anyone has experience with this or any ideas how we might achieve our “early retirement.”


We both max out our 403s, 457s, backdoor Roths, 529 plans, fund a Defined Benefit plan through the business and contribute the rest to a taxable account. 

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First of all, congratulations on how well you have planned for early retirement. Well done. Health care is always the biggest concern in this country when contemplating an early exit (sigh). I wouldn't be able to comment on the language of your employer's health care policy, but have you looked at the "Obamacare" exchanges in your area? This could provide a bridge to eligibility. 

Dan Otter

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Hey Dan. 

Thank for the reply.  Search you email for my name. We’ve spoken before. 

My big concern is having a lapse in employment at my district and the district not honoring the retiree benefit.  It’s at least a $15K annual benefit.  I really had everything planned to go out at 52. Who knows. Maybe when I reach that age I won’t want to retire but it’ll be nice to know you can.  You know FU money.  Who am

i quoting.  

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I think COBRA allows you to continue your current district health care coverage but at the full premium being paid by you and the district.. Instead of your contracts, I would look to see what is stipulated in the District policy manual. What ever it states is probably law. Most of the specific rules on COBRA benefits can be found in that resource as well. Obamacare might be a possibility as well. If worse comes to worst, maybe one of you can work longer so that you can both get coverage until your pension kicks in.

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