Dear J.T. & Dale: I will be completely honest about myself and my situation. First off, I’m what doctors call obese (flabby is more appropriate, but I am working on getting unflabby). Next, I have numerous medical conditions that allow me to walk short distances, but a wheelchair is often necessary. Then there is the fact that I have not worked as a paid person in my field (accounting/financial services), ever. I have eight years of volunteer work and internships. And, last but not least, I am fast approaching 50. How can a person like me find a career? — Cynthia

Dale: You started out by saying you are going to be completely honest, and let me do likewise. Hiring someone who has never worked is always a risk for an employer. (Does the person have the self-discipline? Is she willing to take supervision? Does she understand office rules, etiquette and policy?) And most employers feel that hiring someone with health issues is likewise risky. (Will the person have multiple absences? If things don’t work out, will they be able to fire the new employee without accusations or lawsuits?)

J.T.: If your goal is to discourage Cynthia from even trying, you’re off to a ripping good start.

Dale: No, no … what I’m trying to discourage is trying a traditional job search. When it comes to entry-level jobs, employers have a lot of choices, and few are going to take a chance on a risky hire. So, bypass the traditional resume-spraying job search. Instead, go to all those people you’ve met in your eight years of volunteer work and offer them the gift of your honesty: Tell them that you understand that you are not a typical new hire, but you’re looking for someone to take a chance on you, and in return you will give them loyalty and exceptional effort.

J.T.: Yes, and also try to find other ways to minimize their perceived risk — offer to start as an intern, temp, part-time or trial employee. But in what field? You mentioned a career, not just a job. There’s a career coach who specializes in helping people manage and grow their careers in spite of chronic illness — her name is Rosalind Joffe, and she calls her process “sick-proofing.” For instance, she suggests that you look not just at the entry-level job, but at the entire career path — to anticipate what obstacles you will encounter and map your path accordingly. I urge you to visit Joffe’s Web site, cicoach.com, and to read her book “Women, Work, and Autoimmune Disease.” I can sense that you not only are open-minded, but a person who has a wonderful can-do attitude, and Joffe’s work will inspire you.