By Cliff Ennico

Twice a year, I host a program for the New York State Bar Association targeting young lawyers who are looking to set up solo law practices.

These people ask a million questions, and while there are clear answers to many of them, there are some that simply cannot be answered because there aren’t clear legal precedents.

Believe it or not, as comprehensive as our legal system in the U.S. appears to be (just look at the 2,000-plus pages of the federal tax code, and the 20,000 pages of regulations interpreting those 2,000 pages, and the millions of pages of case law interpreting those regulations), there are still a lot of legal “grey areas” out there where there is no clear answer to the question, “what should I do?”

The last time I gave my State Bar talk, I spoke at length about one of these grey areas, affecting attorneys who practice out of home offices. One of the attendees, apparently neurotic about the fact that there wasn’t a clear answer, requested the State Bar to give an “ethics opinion” on the matter to get some clarification. Unsurprisingly, the State Bar took the most conservative position possible, and now there is authority on the books (at least in New York) that you cannot or shouldn’t do the thing I spoke about.

Far from being considered a hero (or heroine) for doing this, I think this young attorney should frankly surrender his or her license and go into another line of work.

Frequently, clients of mine get into legal and ethical “grey areas”. Remember, my clients are primarily entrepreneurs:

  • For whom the normal rules do not apply (or who cannot work within the normal rules);
  • Who challenge the existing order of things,
  • Who are looking for creative new ways to solve problems; and
  • Who are sometimes frankly pains in the you-know-what who never learned to color between the lines when they were kids.

I was told many years ago by a reliable authority (a law professor in fact) that if the major fast-food chains complied strictly and to the letter with every federal, state and local rule and regulation that applied to their business, the cost of a hamburger would be between $10 and $15 (without fries).

Being an entrepreneur does not, of course, excuse illegal or unethical behavior. But complying too strictly with our ever-expanding legal system and being overly concerned about strict compliance can be a serious handicap to an entrepreneur’s growth and success.

“Grey areas” can sometimes be an entrepreneur’s best friend. “Grey areas” mean you may be able to do something and get away with it for a while until so many other people are doing it that legislatures and regulatory bodies feel the need to develop regulations and rules for that behavior (with your business possibly being “grandfathered” and excused from compliance).  “Grey areas” mean there may be opportunities for a little business to get a leg up on bigger competitors, who will be advised by their overly-paid army of neurotic lawyers that the opportunity is “too risky”.

Listen to successful entrepreneurs saying in interviews “I would rather beg for forgiveness than ask for permission” or “I was too dumb to know I couldn’t do X.” Big companies (and neurotic attorneys) ask for permission; entrepreneurs take the shot.

Now, I understand completely why professionals (not just attorneys) may be tempted to get an advance ruling from some legal or ethical authority when giving “grey area” advice to a client. They are concerned about their malpractice liability. They don’t want to tell the client “it’s a grey area, so go do it,” for fear that if the activity is regulated in the future they will be blamed (or sued, or stripped of their license) for giving the client bad advice. In an increasingly litigious and hostile world, those fears are not unjustified.

Nevertheless, professionals who take the view that “I can never be sued for telling a client not to do something” are failing their clients and not doing their jobs out of cowardice. Here’s what I think professionals should say to their clients when confronted with a “grey area”:

“Hi, Joe. Listen, I really cracked the books and I couldn’t find any clear authority saying you can’t do what you said you wanted to do. Now, that doesn’t mean it’s okay to do it – you’re in a grey area here and if you do proceed there’s a risk somebody who doesn’t like what you’re doing will try to shut you down. If you’re going to do it, I would be extremely cautious and take it one step at a time. But I can’t find anything at least today that says it’s prohibited.”

That way you have covered your you-know-what and empowered the client to decide whether or not to take the desired action. Just make sure you put it in writing . . .

Cliff Ennico ( is a syndicated columnist, author and host of the PBS television series ‘Money Hunt’. This column is no substitute for legal, tax or financial advice, which can be furnished only by a qualified professional licensed in your state. To find out more about Cliff Ennico and other Creators Syndicate writers and cartoonists, visit our Web page at COPYRIGHT 2014 CLIFFORD R. ENNICO. DISTRIBUTED BY CREATORS SYNDICATE, INC.