Every now and then an “opportunity of a lifetime” will arise in your personal or professional life. How do you discern whether these situations are the “real deal” or “too good to be true”? Here are some tips I have compiled, which are drawn from reflecting on valuable lessons from classes I have taken in the “school of hard knocks.”

1. Don’t believe everything you hear. “Well duh,” you say. In theory, this principle seems simple enough. In practice, it is all too easy (if we’re not careful) to let ourselves be bamboozled by slick and smooth blowers of smoke. Savvy finance professionals learn not to be dazzled by ostensible brilliance or baffled by indecipherable nonsense. This leads to our second point.
2. Evaluate evidence and look for proof. If the sales pitch for this “opportunity of a lifetime” doesn’t make sense, be intellectually honest with yourself about this. Here’s a simple rule: Never pursue a product, job, or other type of situation that you do not understand. It is easy to become “desperate” to jump into something you don’t understand when you are driven by greed or fear. Therefore, you must maintain integrity and not get wrapped up in destructive emotions. Also, use your creativity to develop other opportunities for yourself so that you have “walkaway power” rather than allowing yourself to cast aside your better judgment and jump headfirst into a “too good to be true” scenario.
3. Develop “professional skepticism.” This is a principle from the audit profession. Young auditors must learn to dig into the subject matter and understand the numbers for themselves rather than subordinating their judgment to the client or even to senior auditors. You have your own mind, and you must take ownership of your thoughts rather than letting someone else program your evaluation process. Too many shady operators get away with shenanigans when others are afraid to question the so-called “wisdom” of experienced “experts.” But if you want to be a savvy financial professional, you should be willing to take scorn much like the little boy who declared the “emperor has no clothes.”

Following these tips is not easy. You have to learn to use uncomfortable words and expressions, such as: “No” or “Prove it.” Or sometimes you have to humble yourself and make the dreaded admission: “I don’t understand.” But you will add value to your jobs, your career, and your relationships if you bring intellectual honesty to the table. “Nail everything down” rather than letting yourself be manipulated into pursuing a disaster, cleverly disguised as an “opportunity of a lifetime.”