No Time Like the Present

Dear Short Answers: I really don’t like my job and am freelancing on the side, hoping to one day be my own boss. When do I take the plunge to freelancing full-time? I’ll never have enough money saved up since I have a lot of college loan debt. Stuck Dear Stuck: If you are good [...]

Talk is Cheap; Money Is Dear

Dear Short Answers: I have a very good friend who is constantly spending more money than she can possibly afford. She is behind on her mortgage, her credit cards are maxed out and constantly buys her family and friends lavish gifts. I am VERY worried about her. How can I get her to come to [...]

Day Late/Dollar Short

Dear Short Answers: My brother makes a LOT of money and is very generous. He helps support a number of family members including our parents who are in their middle 80′s. I’m far from poor but just finished putting a child through college. I haven’t contributed in the same way. He never asks for help, [...]

Early Retirement

Dear Short Answers: I’m 60 years old and have been out of work for over 3 years. I doubt that I will ever work again. Money is tight but not too bad because I have a military pension and veterans benefits and my wife is still working. My problem is that my wife won’t stop [...]

Share the Pain, Share the Gain

Dear Short Answers: Ever since the recession, my husband has gotten incredibly cheap. He canceled our HD cable and ordered basic service. He mows the lawn himself and fired the cleaning woman. He refuses to buy new clothes for himself, me or the kids. He has strictly limited the kids cell phone minutes. And now [...]

Casseroles for the Crowd

Dear Short Answers: My husband and I have lived in the Berkshires for over 20 years and we’re about to start the fall season of GUESTS. We love showing off this area to old friends and relatives. But this year, neither of us are working and the budget is tight. In years past, we paid [...]

Spare the Rod; Spoil the Child

Dear Short Answers: My husband has been out of work for almost 2 years and I only work part-time at an insurance office. Unfortunately, this means that our two kids have had to go without a lot of things that other kids seems to have. I could live with that but lately they seem to [...]

Common Cents

Dear Short Answers: How much debt should you go into to send your kids to college? My wife and I have totally different perspectives. What makes cents Dear What: We don’t think it makes ANY sense to jeopardize your own future to send your kids to college.  And to do so puts inappropriate pressure on [...]

Looks Like Up to Me

Dear Short Answers: I have a criminal record and after 10 yrs, I received a pardon.  My problem is when I apply for jobs, that I know I can do and that I am qualified for, I can never get a interview or they won’t call me for one or they say that they are [...]

Staying Connected

Dear Short Answers: I am married and currently work 7500 miles away from my family, my contract expires in 3 months should I renew my contract and remain separated from my family or should I return home and try and find work so I can be with my family? Secondly being able to provide for [...]

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