A Simple Plan: How to Stay out of Trouble

“Never fly in any airplane unless I say it’s an airplane, and only then if I’m the one flying it.”

--My father, Capt. Robert P. Littlefield, Jr., Distinguished Flying Cross recipient, World War II, upon seeing an “ultra-light” experimental aircraft flying over our house

“And he’s long gone/When he’s next to me/And I realize/The blame is on me/’Cause I knew you were trouble when you walked in”

--Taylor Swift, “Trouble”

Because I’m 43, I’m always amused to get emails from the local bar association inviting me to their Young Lawyers Division events. It would be more accurate to say that I’m a lawyer with a young legal career. Although I’ve only been in practice for five years, I’ve noticed a certain trend. I hope I can describe this trend, because I believe my theory can save all of us a lot of heartache.

In addition to my full-time “real” law job and my law practice that I do on the side, I have donated legal services to more than one organization. Plus, I’ve taken notice of my own mistakes and those of my family and friends. This small amount of legal and life experience leaves me with this observation: Most legal problems don’t start out as legal problems—they are life management problems, and I believe they result from not one lapse in judgment but from a series of smaller errors.

Airplane crash investigators will tell you that airplane crashes are never the result of one catastrophic mistake. Instead, they are a series of small mistakes that lead the pilot down the wrong path until it’s no longer possible to pull the airplane out of the death spiral.

For example, when John F. Kennedy, Jr., crashed his Piper Saratoga off the coast of Martha’s Vineyard in 1999 (killing himself, his wife, and her sister), the official cause of the crash was “pilot error.” That’s true, but it’s more accurate to say that the crash result from this series of errors: 1) The three passengers were running late, and 2) Kennedy chose to take off after sunset anyway, even though he was 3) tired, 4) stressed and distracted, 5) inexperienced with night flying, and 6) was not instrument-rated and therefore should not have been flying so close to dusk. Further, it was 7) hazy, 8) he had recently injured his foot, and 9) he failed to file a flight plan and ask for advice, and 10) he had selected incorrect radio frequencies. It’s easy to see how these smaller errors set him up to make the one large fatal error: He became disoriented while flying over the featureless, darkening Atlantic Ocean, which in turn caused him to crash the airplane into the ocean as he prepared to land.

Fine, but unless we’re pilots, what has that got to do with any of us?

Most of the legal problems that I’ve untangled during my brief career have followed the same path. It’s never one large mistake; it’s a series of lapses in judgment, growing ever larger until the person (now known as "the Defendant") is in serious (and expensive) trouble. Sometimes, this path resembles a rabbit hole, and we find ourselves making bigger and dumber mistakes to try to correct our course while we tumble ever-faster toward our fate.

The smart way to avoid this tumble, of course, is to avoid making the very first mistake. I made a list of the “first mistakes” I’ve observed (and made in one or two cases here), and I welcome additions to this list:

How to stay out of trouble:

1) Don’t do hard drugs or prescription drugs, go easy on the weed, and limit yourself to one or two drinks per outing. Don’t drive even then. (Helpful side note: You may also want to put your phone away during late-night party time.)

2) Stay away from criminals. Similarly, if you notice that a person no longer speaks to his close family members, former military colleagues, past business associates, or church members, proceed with extreme caution. No, in fact, do not proceed at all. Stay away.

3) Don’t date, befriend, hire, or work for people whose values are markedly different than yours. Avoid people who blame their problems on other people. If anyone describes himself as "misunderstood," run!

4) Don’t marry someone whose financial philosophy varies from yours. If you marry them anyway, keep your finances as separate as possible and try not to have children with that person.

5) Don’t marry someone with children unless the children’s other parent is out of the picture permanently OR has a Swiss-like diplomatic relationship with the person you’re dating.

6) Never buy anything or invest in anything when the person who is selling it cold-called you (over the phone, via email, through direct mail, etc.) Likewise, don’t rent-to-own anything at all. In fact, if a real bank or similar institution won’t give you a loan for it, it’s a bad investment and you should not buy it.

7) It’s often a bad idea to go into business with another person, but if you must, make sure everything’s in writing and everyone has equal exposure to loss. Never agree to anything called a “handshake deal” or a “gentlemen’s agreement.”

8) Surround yourself with honest, blunt people who have your best interests at heart and will tell you when you’re about to do something stupid.

9) Do not enter into a contract of any kind without walking away, thinking about it, and probably talking to an attorney. If you find yourself explaining to other people (often in an excited, rapid tone of voice) why it’s such a good idea, this is a sure sign that you’re trying to convince yourself.

10) Let go of the idea that you’re special. I mean, we’re all special in a “Mr. Rogers’ Neighborhood” way, but don’t let someone tell you that you can make a lot of money without hard work, sacrifice, and probably some education. I’m thinking here of multi-level marketing and similar scams.

11) Don’t enroll in any college that advertises on TV. Seriously, avoid any college that is not accredited or can be described as “College, Inc.” You’ll know these by their locations in charmless office parks near interstate exits. Your college should have at least one quad.

12) Don’t do anything “under the table.” This includes hiding money from the government in order to qualify for Medicaid or Food Stamps or to avoid paying taxes. These strategies rarely work and always end up costing more money than they save. Happily, the price of honesty is very small.

13) Get your affairs in order, and make sure your close family members have their affairs in order, too. This includes—but is not limited to—making a valid will. Avoid schemes that include transferring property or money into family members’ names unless you intend to make a gift outright.

14) If it matters to you, put it in writing.

Can anyone add to this list?