Balancing Life’s Checkbook

There is an unusual, yet really powerful heuristic for leadership that I’ve subconsciously used throughout my life, and it’s what I now call “balancing life’s checkbook.”

Today, some people still use checkbooks, but there are now far more who have never used one. So, if you’re in the latter group, here’s an example so you can fully understand the essence of what I’m about to tell you:

Let’s say you had to pay your phone bill this month. Using a checkbook, you would write the amount of your phone bill on a check, sign your name, and mail it out. Then, in the back of the checkbook, you would go to the ledger, or the “register,” fill in how much you paid in one column, and subtract it from your current balance in the next column. You would do this for any bill you had to pay that month. And at the end of the month, according to standard practice, you would go through and verify every transaction you recorded against your monthly bank statement. If all deposits and withdrawals were accurate, you would draw a line under the last transaction of the month and move on to the next. You successfully balanced your checkbook.

I always try to take a similar approach to life and leadership. In every day of every year of every generation, there are transactions made by everyone on earth in the form of deeds, lessons, failures, and accomplishments. The first 30 years of my life have been full of those transactions, and like many of my peers growing up, I learned to learn from those instances very quickly. The lessons, and failures in particular, were very instructive for me, and if I ever saw someone else dealing with those same difficulties, I would do everything in my power to help them avoid the pitfalls I had faced. In essence, I was acting as the monthly bank statement who had already seen those transactions happen to me. And by guiding others through, I would be helping them to balance their checkbook.

When I was in high school, I was really good at math (remember those workbooks I stole in elementary school??) So, as a freshman, I was placed in the pre-calculus class with all sophomores and juniors. I was the only freshman there, and I stuck out like a sore thumb. But as the year went on, my older classmates began to come to me for help with each homework and before each test. And by helping them through the same challenges that I had previously overcome, by teaching them, I learned even more than I would have otherwise, I made some really good friends, and I was recognized with the school’s annual award given to the highest performing student in the subject of math. It was there that I learned a key pillar of my leadership philosophy. And by helping others, by shining the light on the path I had already been down, by balancing life’s checkbook as I saw it, I would find meaning, fulfillment, and enjoyment for myself and for others.

When I began to work for a living, I learned often how not to manage and lead employees from the steady barrage of bad bosses I had (which I’ve often written about). So, when I first got the job to build and run a brand-new restaurant, I made a promise to myself: “I’m going to build this into a place where I would have wanted to come work every day as a college student.” And from day 1, we cultivated an atmosphere of accountability, of consistency, and of fun. It was a culture that everyone wanted to be a part of, that rivals admired, and at which customers marveled.

When I left the restaurant after two years, I received a flood of texts from my former employees about how much my leadership and management philosophy meant to them. They were able to make a lot of money, they did their jobs correctly, they had fun, and they enjoyed coming to work every single day. Many remarked that it was the best job they’ve ever had. For two years, I’m happy to say that I was able to balance the checkbook of miserable work.

In the online writing course Write of Passage, I currently serve as an alumni mentor to over 300 students who are learning how to accelerate their careers by writing consistently online, and at a high level. For many returning students, each 5-week cohort, run twice a year, is a reunion of sorts. But for the new students, the first week can be a pressure cooker. Seeing a flurry of activity, doing intense writing assignments, and feeling out of the loop in a lot of conversations among returning students can be quite intimidating and demoralizing. I know that for a fact, because that’s how I felt when I first took the course.

So, as an alumni mentor, I’ve taken the approach to personally reach out to every single student in the course and offer them the most finite of all resources, my time. Because when the going gets tough, and they want to quit, they at least have that welcoming, familiar face that they can go to for any questions they have or any help they might need. By opening that door to everyone, I’ve provided an opportunity that I didn’t quite have when I first experienced the course. By opening that door, I’ve provided a guiding light for them—to avoid the pitfalls I’ve run into over the past year—as they venture out to publish their thoughts, on their own websites, to the world for the very first time in their lives. As a mentor, I’m attempting to balance the checkbook of online opportunity and creation.

If there’s one word that you can boil my checkbook heuristic down to, it’s empathy. It’s the realization that the challenging childhood I had, the series of bad bosses I had, and the year of toiling in relative digital obscurity I had—those were necessary for me to become who I am today. Using those experiences, I’ve taken it upon myself to try to step in where others won’t, correct imbalances, fix discrepancies and help people in the times when I would have needed help the most.

Human progress slows considerably if every new generation has to learn the same exact lessons from scratch, so my approach to leadership has always been to help, guide, and lead people around the deserts, over the swamps, and through the chasms that I’ve encountered so that they can focus their time on solving new challenges for the world.

That is the essence of human progress.

That is the essence of leadership.

That is the essence of drawing the line in your check register at the end of every month.

If you don’t yet know how to lead well, start with balancing life’s checkbook.