Q: I have been a tax and accounting professional for the past 10 years. My mentor left the company, along with some others with whom I worked very well. I was asked to advance to a higher position under a man with clear personality problems, so I asked for a package as a buyout. I am 10 years away from retirement age, so with the buyout, I now have time to get another job.

I am highly respected in my field and already have contacts calling me for various positions, which may seem great, but here's the catch. My husband is more than 20 years older than I and has excellent retirement benefits with ongoing insurance. If I don't work, I can be placed on his insurance. If he passes away, which I don't like to think of since we've been married since my 20s, I will remain on his insurance until I am old enough to receive Medicare. If I get another job with insurance benefits now, I must accept that insurance. If my husband passes during my new job, I lose the chance of being on my husband's policy, which is a great one. The odds are against him living into his 90s. Do you recommend taking another professional job as a step higher in my career or taking time off to relax and enjoy being on my husband's insurance? We don't live an extravagant lifestyle, but the children are grown and we don't need my income.

A: You have several choices, depending on tax laws and the wording in your husband's retirement and insurance policy. Hire a private lawyer concentrating in employee benefits to confirm your husband's benefits and insurance policy cannot be changed, whereby you could lose your privilege of being placed on his insurance as long as he survives. If that is so, don't accept another full-time position where you will be forced to accept the company's insurance.

Starting a new position in your 50s is risky due to multiple variables. You already know one man with whom you did not want to work, so much so that you left the company; the odds of that happening again increase with a new job in a new company. If your husband passes away in the interim of finding a job or working in a job you don't like, you will be forced to work full-time for insurance or to join a health insurance policy under Obamacare.

Many baby-boomer professionals become independent consultants to maintain their independence from any one company. Check to ensure you can be included on your husband's insurance if you work as an independent contractor, and whether incorporating or filing as a sole proprietor will make a difference. If everything is in your favor, it sounds like you have maintained enough contacts in your field to introduce a successful consulting business. Another choice may be to join your husband's insurance policy, which offers you permanent health insurance, and find a part-time job where you will not be allowed on a company's health insurance policy. Either of these choices can help to eliminate the stress often present in a corporate position, and the opportunity for you to stay current in your field until you reach Medicare age, whatever that may be in 10 years. As you age, a secure health insurance policy may be a much-valued asset compared to a full-time job that furthers your career.

Email your questions to workplace expert Lindsey Novak at [email protected] and follow her on Twitter @I_truly_care. To find out more about Lindsey Novak and to read features by other Creators Syndicate writers and cartoonists, visit the Creators Syndicate website at www.creators.com.