The Money Paradox

A while ago, I had the chance to return to my small hometown as a volunteer when I was asked by a local non-profit to spend a week teaching high school kids about money. I knew being in the classroom would be great, but I was really impacted by something far less expected… the hallways. Walking through the hallways that I had graduated from years before was like a magic eraser that evaporated all of my adult years. For more than a second, I fully expected to see my old Jeep sitting in the parking lot and to hear Bruce Springsteen playing in the background.

The most stirring part of that time warp wasn’t a fit of nostalgia for my glory days, but the confirmation of a long-held suspicion that my career as a financial advisor had turned me into a modern day Dr. Jekyll and Mr. Hyde (just not as sinister). Let me give you some background... You see, growing up I was about as laid back as a kid can get. And while it isn’t uncommon for most kids to be able to relax and enjoy the moment, I was actually able to master the skill for quite some time. I managed to coast my way through high school with a planning horizon that never extended past Friday night.

I continued to ride my happy-go-lucky wave all the way into college, and had I been graded my freshman year on social skills and fun optimization, I would have passed with flying colors. Unfortunately I wasn’t. So by the end of the year, I found myself on the verge of academic probation. The university told me that if I wanted to get into the business school I had only one semester to bring my grades up. This, coupled with the fact that I was also working forty hours a week to pay for school, facilitated what was likely my very first long-term goal: to not to be a telemarketer for the rest of my life (my all too glamorous vocation at the time). So, sitting in the guidance counselor’s office, I made the commitment to myself to make it happen.

Over the first four months of my sophomore year my friends all started to notice a shift as I went from being a social butterfly to essentially living in the library. Christmas vacation marked the end of the semester, and I’ll never forget the small envelope under the tree that I had wrapped for my mom. Inside was the only gift I’ve given her that has made her cry: a report card full of straight A’s.

Sure enough, the old cliche rang true: I set my mind to it and I achieved it. I had gone from C’s and D’s to a 4.0 and the sense of empowerment was something I’d never had a taste of... and I was hooked! I made the dean’s list every semester from there on out and my new found foresight even fueled me all the way through to a master’s degree in accounting (for those of you who haven’t had the privilege of reading tax law for two years, let me tell you that it’s no easy feat).

It turned out the new me liked planning for the future so much, I thought, “why not make a career out of it and become a financial planner?” Which is exactly what I did. Day in and day out over my career, I’ve helped clients fast forward into the future to plan the steps necessary to turn their dreams into a reality. While the act of doing so is just as rewarding as it might sound, the problem is I got a little too good at it.

A few years ago an attorney I know told me that because lawyers spend all day examining people, they develop a tendency to carry that approach into their personal lives. Because of this habit of always putting loved ones on the proverbial witness stand, lawyers have a much higher than average rate of divorce. I have no idea if that’s actually true, but the theme really rang true with me. To a carpenter with a hammer, everything starts to look like a nail.

The repetition of how I approached my job began to evolve into a lens that colored how I saw everything in my world. While living in the future might work wonders for your finances, I’ll be the first to tell you when it comes to your ability to enjoy life, it sucks. I found myself running on the treadmill of life chasing carrots on the stick of “I’ll be happy when…”, which somehow never seems to come when you’re always stuck in the future.

Even worse than my inability to live in the moment was what came along with repeatedly explaining to clients the dreadful reasons for which they might need life insurance, emergency funds and disability policies. The more I honed my skill of predicting worst case scenarios, the more my personal life started to feel like Matt Damon in this scene from “Good Will Hunting.” My tendency to see every possible negative down the road began to overtake my ability to see the good in my situation at any given moment.

After being smacked upside the head with these realizations, I began to make a concerted effort to draw a line between how I went about my professional and private life. Enter Jekyll and Hyde...

While my new found outlook allowed me to drastically improve my quality of life, it still presented a few problems. The first of which was it was still very hard to switch hats so frequently, and something about it also felt very hypocritical. As I was working with clients I began to notice the financial planning process pulling some of them into the same traps I had once fallen into.  

As I struggled with this for quite a few years, my dilemma basically came down to this: On one hand, if there were ever a consensus among philosophers, gurus and mental health experts as to the best thing you can do for your happiness, it would be to live life in the moment. On the other hand, if you were to ask any given money expert the worst thing you can possibly do for your finances, it would also be to live life in the moment (ie not plan for the future).

My ah-ha moment in reconciling all of this was when I realized that I was looking at it in the entirely wrong way. It isn’t a linear issue where you have to choose to fall somewhere on a spectrum of living in the moment on one end and planning for your future on the other; it’s a paradox. The choices aren’t mutually exclusive, I don’t have to choose between being the overachieving planner and happy-go-lucky high school version of myself, nor do I have to compromise each to meet in the middle... I can strive to be the best of both. And I’ve come to see the beauty of a financial planning is that, done correctly, the road map created will allow you to put your financial decisions on autopilot for a time, enabling you to live for today and focus on what’s really important in life.