Childhood Lessons from Painting Flagpoles

" Desire is a contract you make with yourself to be unhappy until you get what you want. – Naval "

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How my Dad taught me to take risks.

" The imprint of the father remains forever on the life of the child. – Roy Lessin "

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It is often so easy to underestimate the impact of a father’s actions – however small they may be – on our lives. For me, watching my father work with flag poles taught me so much about how to run a business, particularly in observing the risks he took to put food on the table.

Putting on the Entrepreneurial Hat

In the following excerpt from my upcoming book, you’ll learn about how much I deeply love my parents. I’ll also discuss my father – a man who found himself on the wrong end of unemployment during the 1980s and who, during that period, taught me so much about risk, reward, and the importance of doing a good job. Here are some lessons I gleaned from him during my childhood.

Excerpt From Flag Poles

By 26, I had founded and built a successful commercial real estate management company – maintaining schools, stores, office buildings, hospitals, and corporate campuses – with over 400 employees.

Born into a loving two-bedroom home in Corpus Christi, Texas with amazing parents and sister, I was blessed to witness my parents struggle, work, and trust. My Mom worked two full-time jobs plus an extra part-time overnight job at one point, while my Dad put on his entrepreneurial hat to help pay the bills while out of work during the lean 1980s. After leaving his military police career before I was born, he had mostly worked as an oil tanker inspector and armored truck driver.

I recall us packing the van on the weekends to drive up and down Texas’ salty coast looking for rusted flag poles for my Dad to paint. He had made a neat contraption of wood and rope to shimmy up and down flag poles. We’d go to banks, funeral homes, and anywhere else with a flagpole to offer his services.

He promised us the work was safe, but we knew when he painted a nautical flagpole it was otherwise. The nautical pole is used to hang three (or more) flags and was therefore cross-shaped about two-thirds the way up. The two flags on either side hung downward; the middle flag flew above.

A cross-shaped flag pole must be traversed at the intersection. And the harness and sling where he sat must be detached from the pole, just below the crossing, then reattached above, before he could access the upper portions. While remaining suspended.

Prep on the rise, paint on the fall. And so it was. Risk with the reward of another meal and a little gas money.

And one thing I learned is that I could either do the job right, or I could make it seem right. For the metal rope that held the flag through the pulley could be run with an uncoated wire rope or a vinyl-coated wire rope which would stand up against the salty air for months and years. No one ever checked. When your life’s on the line, you understand more clearly doing the job right is more important than cutting costs. And my Dad always did the job right. 

And so when I ended up founding a small and running a moderately-sized commercial real estate business, working most days at coffee shops, I did not know where to turn for help. I needed a mentor who would know my next three moves.

I had never met anyone else with hundreds of employees. No one to identify with what I was trying to do. No way to network to find solid advice from someone who had been where I had gone.

I was detached from my now and my future. 

" A strong defense eventually detaches to maintain the offensive ascent. "

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Risk is right when ascending flagpoles to feed your family. The hungry see. 

Three Takeaways

First Takeaway – Always Do the Job Right

For as wonderful as my father was, he often took unnecessary risks when working on the flag poles. It was never enough for him that the job “looked” right without it being right. I learned from this – cutting costs will always be secondary to doing the job well. Not just for the literal risk to life that can be created by cuts – as I mention in the excerpt – but due to the reputational aspect.

Get it right and more opportunity will follow.

Second Takeaway – Look Beyond Those Close to You For Mentors

" Our chief want in life is somebody who will make us do what we can. – Ralph Waldo Emerson "

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My father was a great man in many respects, but he was never the man who would run a business of 400 people. That’s not him. I could look to him for advice in almost all areas apart from this. So, I sought a mentor who could guide me in my next three moves when I founded my own company. The lesson here is simple:

Only a man who is a step ahead knows what it took to get there.

Third Takeaway – Risk Leads to Reward

I learned this lesson in a roundabout way from my father. For him, the risk lay in doing the job in a way that looked right without necessarily being right – a risk to ensure our next meal and gas for the car. He had to do the job right and that meant additional risk. The cable had to be the expensive kind. The ball at the top of the pole had to be properly sanded and double-coated, even if you can’t tell from the ground. 

I saw this and tuned it to my own agenda, seeing that risk was more about allowing yourself to be vulnerable enough to recognize your shortcomings and brave enough to attempt to overcome them.

Fulfillment only comes when you are willing to take risks. Risk is right. 

And the opinion of the One who sees the top of the flagpole is the only opinion that really matters. So do the job right – especially in that place where only One person can see if you did.