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Wisdom in 17 sayings

by Brent Stewart on Tuesday, Nov 15, 2022

I grab onto quotes. Some I hold onto long enough to consider and they pop up in conversation at odd times. Others seem to bubble up consistently. To me, these favorite quotes are the compass that I use to retain my sense of direction in difficult times and circumstances.

Folks who have worked with me over the years will have heard versions of these sayings (and probably some that I am forgetting right now). Some may complain for hearing them too much.

I’m preparing for a new job and thinking about how I want to approach new responsibilities. I’ve never tried to compile a list but it’s a good time for reviewing these touchstones. I wanted to share that list with you.

So here are sixteen sayings pertinent to leadership, collected over about that many years of leading. I’ve tried to organize these into themes. I’ve researched attribution and exact quote where possible.


These sayings can be employed in a variety of circumstances.

I heard this first while teaching computer networking at Camp Lejeune. I was told it was an “old Marine Corps saying”, which I suppose is like the Klingons talking about Shakespeare “in the original Klingon”.

If you don’t know where you’re going, any road will get you there.

I had a wonderful boss in the early ’teens. He coached me on promotions and, as best I remember, here’s his advice.

If you want to be promoted, take responsiblity. Being responsible attracts opportunities, and eventually someone in management will say “get that guy a hat”.

I think I first heard this last one from 12 Rules for Life by Jordan Peterson. The metaphor, about self-discipline and being in control of yourself and your emotions, struck a chord.

When you get hurt, say, by an arrow, that is pain. . . However, there is a second arrow, which is your reaction to the arrow, the getting angry, the planning revenge, this is beyond pain, this is suffering.

On Preparation

Ideally, we’d anticipate possible issues and make plans to mitigate. These quotes deal with the issues and rewards of being ready.

These start with some cynical reminders.

Bad security looks just like good security until seriously attacked.

and one of my favorites in the same vein.

Everyone has a plan until they get hit.

Two of my former CIOs gave me solid advice about preparation that I’ve carried forward in my career. Mike said the first when talking about the constraints of budgeting, but it’s a good reminder to not over-commit.

You can only fit 5 lbs of sugar into a 5 lb bag.

Kap intimidated me in those days and I regret not getting to know him better. He had a very clear vision about the way the world works, illustrated below.

Play the cards you’ve got in your hand, not the ones you want.

I saved the best for last. I use this to encourage preparation and to commend it’s results. I saw Gregg Easterbrook attribute this to Bear Bryant in a Tuesday Morning Quaterback article, but it turns out the original quote is from Neyland.

Gentlemen, touchdowns follow blocking as sure night follows day.

As I recall, Easterbrook added the aside that “it’s a lot of fun to run a hundred yards when everyone in front of you is on their back.”

On Troubleshooting

Troubleshooting requires deep understanding. It is often denigrated, but I’ve always found it to require tremendous imagination and to reward patience and persistence. I’ve had many opportunities to mentor troubleshooting over the years and here are some of my favorite aphorisms.

This first was one of Dad’s favorites. As it has become well known, it’s grown a little trite but still makes a great point for technologists.

If you only have a hammer, you tend to see every problem as a nail.

Many times the way forward is not clear. Here I took an example from being a parent. This has always been solid advice because there’s always some technical cruft that can be cleared up and the act of cleaning either reveals the issue or puts the person in the right headspace. Although Peterson has a similar saying, mine preceeded his.

My kids would ask me if I’ve seen their favorite toy. I’d say, “No, but I bet if you clean your room you’ll find it”.

No one likes change, but sometimes troubleshooting presents opportunities to move forward.

You never let a serious crisis go to waste.

On people

Many of these, such as the “second arrow” also address dealing with other people. These are the two best quotes I have specifically on the topic of the trials of co-workers.

My father could be pithy and a little cynical, but he understood something about people.

If you went to the mall and gave out $20 bills at the door, someone would compain that you didn’t have change or were at the wrong door. You cannot make everyone happy.

I’ve carried around this quote since I was a kid. I think I picked it up from reading Robert Heinlein. It, or something like it, has been said in various forms for a long time.

Never attribute to malice what can be adequately explained by stupidity.

Extreme Ownership as a book is like a Mel Brooks movie - everyone remembers just the bits that hit it out of the park. Still, there’s an undeniable relevation about leadership in this quote and I repeat it when mentoring young managers.

It’s not what you preach, it’s what you tolerate.

On Gratitude

I finish with the subject that has most influenced my “mature” years. I’ve worked to become a grateful person and to recognize that I’m blessed in myriad ways. To list just three: I have a wonderful wife and amazing children, I have friends around the world who want nothing but good for me, and I have the opportunity to do meaningful work. Focusing on those gifts has brought a peace and happiness to my life.

When I was younger, I thought that Stoicism was depressing. I’ve come to realize that it provides perfect perspective for a grateful life.

Nothing is more honorable than a grateful heart.

and also

He is a wise man who does not grieve for the things which he has not, but rejoices for those which he has.

I sincerely hope that - if you take nothing else - these thoughts on gratitude will resonate and be useful. As a Christian, I’ll end with the most meaningful quote to me, taken from the end of the Sermon on the Mount.

Therefore do not worry about tomorrow, for tomorrow will worry about itself. Each day has enough trouble of its own.


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