What Matters Most

quoted author avatar
Written by Dane McDonald 2 years ago

Being a CEO can be a daunting, humbling and lonely endeavor. Daily stresses are numerous and the ever present possibility that the house of cards is suddenly going to come crumbling down can become petrifying. Burn rates, runway, revenue, hiring, firing, receivables, payables, are employees happy, is the team working together, are investors satisfied…the list goes on and on. As my father would say, “Being an entrepreneur is a lot like being the plate spinner for the Ringling Brothers. No matter how hard you try, there is always going to be some plate of responsibility that needs a serious amount of attention.” It can be difficult to find time to eat and even harder to sleep, and in this onslaught of responsibility, it is far too easy to become lost in the day-to-day trappings of startup life.

Days fly by, weeks sometimes even faster, and hobbies slowly change into “former interests.” More often than not little time is left to those things that should in theory mean so much: family, friends, laughing, crying, and living. We do this under the guise that we’re working towards something: money, fame, a catalyst of change, some thing that makes us all tick. We believe that at some point our hard work is going to result in a form of success that will systematically remove all of our stresses and those of our loved ones. This hope is one of my greatest day-to-day motivations and often times makes my job so satisfying. The belief that we, as a team, are working toward resolving some fundamental flaw in our industry, and are doing so, in hopes of bettering our own lives along the way. But while we focus on this goal, it’s possible and all too common that family and friends can become impatient, distant or even lost.

This isn’t to say that monetary and social success isn’t attainable, quite the opposite in fact, but the reality is that reaching these goals often damages the relationships we so heartily work towards strengthening in the first place. Never intentionally of course, but certainly indirectly due to the natural requirements imposed on all early stage employees. And while we thrive on the constant influx of challenges that entrepreneurship provides, we all secretly fear what we know will eventually befall us. At some point, we’re going to receive a knock on the door from a stranger informing us of some catastrophic loss, or have to handle a scratchy telephone line with a parent who can barely control their emotions. Some news that results in an uncontrollable shift in our daily routine, a situation that drops us to our knees and renders us human. Try as we may to control and compartmentalize our lives, we are abruptly reminded that it’s completely out of our hands.

In early September, amid the twilight hours of a beautiful Labor Day, I was notified by my father, scratchy voice and all, that two of my very dear relatives were in a horrific car accident. All that was known at the time was that my aunt had passed away at the scene of the accident, and my uncle had been medevaced to the nearest hospital in hopes of saving his life.

As is common in these situations, information continued to trickle in over the next couple of hours, and it turned out that my uncle, who had been in the Emergency Room for a number of hours, was transferred to ICU. The doctors notified my family, who by that time had all arrived at the hospital, that he would most assuredly not last the night. Family gathered around his bed, and while everyone took the time to say their goodbyes, he slowly drifted away.

My aunt and uncle were married at the age of 19, they had two children, and after having worked his entire life for one company, my uncle Ken retired at the age of 65 on Friday August 29th, 2014, two days before his death.

Years had been spent planning a retirement filled with travel, hobbies, events, etc… and in one seemingly preordained moment, all of their hopes and dreams were wiped away forever.

The instant prior to receiving my father’s call informing me of the situation, I was buried neck deep in email, focused on things that certainly could’ve waited until the next day to be addressed. While I could have been spending quality time with the people I was surrounded by, I was instead focused on the things that are superficially important. In that moment, I realized I had run adrift.

In recognizing my error, my mind momentarily drifted away back to one of a thousand times that my grandfather and I were alone together talking about life. We used to spend countless hours discussing everything from his war experience, to children, love, hatred and everything in between. I can’t stress how formative this relationship was for me and how much it still effects my daily thinking. But of everything that stands out among the many lessons learned, his general mantra has, and I hope will, always stay with me, and it’s especially poignant to this story.

Among his many sayings, witty remarks, and often hysterical viewpoints on life, he taught me from a very early age to “treat every decision as if you are on your death bed.” That is to say, if the result of a decision isn’t going to enter your mind during the final moments of your life, it probably isn’t worth worrying about. If it is, then be thoughtful, be calculating and never waiver on a decision for fear of the outcome. The point is simple, think consciously about the few decisions you actually have control over. It’s far too easy to get lost in the background noise of our daily lives, fail to take a step back, and look at the current opportunities we have to make key decisions on things that will ultimately change the direction and happiness of our lives. 

“Think consciously about the few decisions you actually have control over.”

Externally, I continually find myself in conversations with startup CEOs that are telling me they’re “killing it,” yet the half-second delay and tentative stare at the ground before answering my question of “How are you doing” belies their actual feelings and their inherent need to talk about the shit they’re dealing with.

This most recent situation in my life certainly rattled my cage, forced me to step out from the trenches of “fucking killing it” and back into the reality that none of this is guaranteed and that NO ONE is actually “fucking killing it.” We’re all dealing with serious issues, whether professional, social, emotional, or physical, we’ve all got something. The important thing to remember is that sometimes there are decisions to be made that will have a dramatic impact on our path and our story of life. I know how easy it is to look at the week ahead on the calendar and say “I’ve just got too much going on to take a break right now,” but the reality is you’ll regret it for the rest of your life that you didn’t take the time to go see a loved one fighting a losing battle with terminal illness, gather with the family during holidays, or simply turn off the phone and enjoy the “normal” moments.

My intent isn’t for this post to be some macabre sermon to tell everyone to run away from their professional aspirations for fear of missing out on life or to never sign up to become a CEO. That would be a gross misrepresentation. I love my job, in fact I’m obsessed with the challenges it presents, but that same obsession caused me to get derailed. I’m merely hoping to remind everyone how easy it is to get lost in the tumult of day-to-day life and to forget how precious every day really is. There is no guaranteed ending to this path you see before you, and as my father would say in the case of the plate spinner, “eventually, everything comes tumbling down. Don’t fret, they’re just plates. You can always get more.” Some things however, aren’t replaceable.


As an aside, I spent five days in early October interacting with 20+ amazing CEOs from around the country during Reboot.io’s most recent CEO Bootcamp. I can’t recommend the program enough, and I guarantee that if you participate in one of their classes your experiences with Jerry Colonna and his incredible team will last forever. The program isn’t cheap, but the reward is priceless. In any event, I’ve decided that I’m going to write at regular intervals about my experiences as a first time CEO. I hope my ramblings will provide at least some solace to those dealing with many of the same issues.





comments powered by Disqus