Author Topic: Aspiring Entrepreneur: Questions about Job, COBRA, Health Insurance  (Read 439 times)


  • Bristles
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I have a new job and in some ways its perfect and in some ways its terrible.  I enjoy my particular role and most of the people I work with on a day to day basis.  It's close to my house.  The work is mostly interesting, compensation fair.  The big drawback is that someone totally inexperienced (way, way, below my level) was promoted to a slot above me in between when I accepted the job and when I started.  In theory big boss does not think this is an issue because we are supposed to be responsible for different pieces, but the reality of course is that we interact on a daily basis.  I know others in the org are already frustrated with all the past issues (and resulting turnover) in our department (most of which preceded both me and my inexperienced colleague), are really happy I am here and just come to me directly for all sorts of stuff, so I work independently and then brush her off when she tries to bring me in on other things or try to step in on things I'm working on.  I have no idea how we will resolve issues if we give conflicting advice (we are both lawyers).  Presumably the business people will take my advice.  (Honestly, given her level of experience I am not sure what basis she would even draw from to offer advice but that is a different story.)  But big boss seems to like her (she is attractive, well spoken, just not knowledgeable about our industry and has very little real legal experience in any capacity).   For context, I also received a bunch of very mixed feedback about big boss from others in my industry before starting and knew it was a roll of the dice -- I took the position despite him and am trying to navigate it. 

I hired an executive coach laying all this out and my story (lots of savings, perpetual desire to one day do my own thing, walking away from promise of partnership in 6-18 months at one of the top firms in our industry to take on this roll of the dice).  First, she gave me "permission" to not go back to a big law firm.  Phew.  Second, she said that regardless of his or my long-term aims, she thought it was clear big boss was playing mind games (basically, fucking with me on purpose to show me place / see how I would react).  Her advice was to shut my mouth, work hard, have a big smile on my face, watch and observe, impress the other executives and plan my strategy / next move, but that if I was actually learning and working with the people I came to work with (director of finance, director of strategy), I should take what I can get even if it was short term.

My first impulse when all this shook out was first to walk out back in a huff to my law firm but I shut up in order to talk to this coach first -- good move.  But I keep thinking that my whole dream in law school was one day to start my own thing, and now I have experience, contacts, a reputation in my industry, and money, and in a sense big boss has given me a gift because by creating this dynamic he's made this a short term option for me and clearly shown me exactly why I wanted to be on my own all along -- I want to work hard and do good work, but I do not want to march to someone else's drum and make myself a round peg to fit into someone else's round hole.  I want to do the work I want to do, with the people I want to work with, and if I'm not satisfied I'll finish up the engagement, deal, whatever and then move on something else.  So the thought of leaving this place and trying to navigate some other bureaucracy with a whole new set of political issues makes me ill.  I want freedom.

The specific plan is to start a solo practice offering legal services within my industry and hopefully branch out to business consulting on industry matters and co-investing in / leading smaller deals.  Legal services should bring in immediate cash and contacts while I build out my vision in other areas. 

A major complication I need to sort out while I plan this is health insurance.  I am the sole breadwinner with a recently pregnant wife and two little kids.  Assume our savings can float us for many, many years, but I do not want to run up huge medical bills on substandard insurance.  Does anyone have advice on where to look for information about COBRA, individual health insurance plans, etc?   

I read somewhere that one day is enough for COBRA, so presumably if I do have an awkward conversation with big boss and it goes south I can use that, but then I need to pay both employer and employee share, right?

Thanks everyone!
« Last Edit: September 29, 2018, 08:06:28 AM by blinx7 »


  • Handlebar Stache
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Re: Aspiring Entrepreneur: Questions about Job, COBRA, Health Insurance
« Reply #1 on: September 29, 2018, 10:06:41 AM »
You can keep the insurance from your existing employer by paying COBRA for up to 18 months, then you are on your own to find insurance.
ACA is pretty much your only option.   I retired end of 2017 so COBRA runs out next June, keeping that insurance for 18 months is costing approx. $800 per month for myself and spouse.  ACA private insurance looks like it is going to run roughly $1,100 per month so that's just what we will have to do.