Most of us are in the privileged position of having a job. And yes, it is a privilege. Some people work for larger corporations, some work for smaller companies and some folks, like me, are self-employed. And if you’re a full-time, stay-at-home parent, that’s probably one of the most important jobs of all. We all work in some fashion or another and we all bring a certain set of skills, talents and expertise to the work that we do.

If you work in the kitchen of a restaurant, you’re probably pretty good with food. If you work for an accounting firm, you probably know a thing or two about numbers. If you’re a game developer, well, you’re probably pretty good at developing games. We all have our skills and talents. And some of your friends probably recognize that you might be the “go to” person to ask for professional advice. This opens up a dangerously slippery slope that is certainly not easy to navigate.

Especially when it comes to entrepreneurs who run their own businesses, do you ask for advice from friends who would otherwise charge for that same advice in their professional lives? Conversely, would you charge your friends for professional advice that would normally be billable to just about anyone else? There are no easy answers.

Several of my friends work in the visual arts. Sometimes, I may ask for their opinion, as was the case when I was getting a cover designed for my book or when I was thinking about variations to this blog’s logo. That feels like fair game, because I want to leverage their artistic “eye.”

However, when it came time to hire a photographer to shoot my wedding, I did not expect to receive this service for free. The photographers had to follow us around all day and then spend many more hours afterward to process all the pictures. I paid for that service.

More recently, I decided that it was finally time for this blog to get a new look. I had considered doing it myself, grabbing a free or premium theme that I would then tweak, but I also recognized this would be far too time-consuming. This is especially true since I’m not nearly as artistic or as technical as someone who is far better qualified. So, I’m paying for this service too, albeit at a discounted rate.

Tangentially, this relates back to the conundrum of a friends and family discount, but the issue is even more complex. Where do you draw the line?

Friends have asked me to clarify some confusion about grammar. That sounds like fair game. Friends have asked me to compare the wording of two sentences, asking which I liked better or if I would reword it another way. That’s reasonable. I’ve also been asked for advice on what smartphone to buy or what restaurant to visit. But if these same friends asked me to proofread an ebook or to “clean up” a project proposal email, I’d hesitate. I’d normally charge for this service, but I can also feel uncomfortable asking for money from a friend.

Just because a friend happens to be a realtor, can I expect her to research a list of available properties that fit a certain criteria and not charge me for it? Can I expect my notary friend to draft up some legal documents for free? If a friend works in technical support, should I expect him to spend the next several hours with me to troubleshoot my computer woes? What about my friend who owns an auto mechanic shop? Can he help me diagnose and fix a problem with my car? Can my homemaker friend babysit my daughter for a few hours on a moment’s notice?

I don’t know. And I also recognize my own hypocrisy on the matter.

What do you think? How have you handled this kind of situation in the past, both as the person asking for professional advice and as the person receiving the request?