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Thanks to Sean O. — Unsplash

My Grandfather, Bill O’Brien (Pa), never went to college. He moved from his parent’s apartment in Yonkers, NY to the United States Marine Corp back to New York to “Ma Bell” (That’s the old telecommunications conglomerate now known as AT&T, Verizon and a bunch of other “Baby Bells” for you post Gen-Xers out there).

Although he wasn’t an educated man, he was as smart as smart gets. We were pretty close, especially as I got into my teens and beyond. Whenever he was about to give me some hard-fought wisdom, he’d invite me for a walk.

We’d talk about growing up in Yonkers and his expectations of me. He taught me you should be decent to people, even when they don’t give you the same consideration. I learned about hard work and integrity and that character meant doing the right thing, even when no one was looking. I also learned about how fortunate I was (and am).

When I graduated from college, while basking in the glow of my new college graduate awesomeness, I was invited on one of Pa’s famous walks.

I remember this one, in particular, as if it happened 15 minutes ago.

“This is a good day. I’m proud of you.”, he told me. I was the first of his clan to graduate from college. It was, indeed, a good day.

“Thanks Pa.”

Then he asked me a rather interesting question, “You think know a lot now, don’t you?” I thought for a moment and replied, “Well, it’s a good school and they just handed me a diploma. So, yeah, I guess I do.” For the record, I was a C student.

“Do me a favor, over the next 6 months, when you see someone with gray hair, talk to them. Take a couple of minutes and ask them about their life, their family, their opinions and their perspectives. We’ll talk when we see each other at Christmas.”

I’m a bit of an introvert. Talking to people I didn’t know, sort of freaked me out. I thought he was trying to get me to break out of my shell. I agreed.

To be honest, I wasn’t really fired up about it. But I did what he asked of me.

Over the next 6 months, I struck up conversations in the line at the grocery store. I sat at the counter at restaurants and talked with people I’d never met before.

Some people thought I was nuts. I certainly felt a little nutty. More than a few people engaged and we had a nice chat. Not long ones…3 minutes here…5 minutes there. The more I did it, the more comfortable I got and the more I enjoyed it. Over those 6 months, I probably talked with 90–100 people.

When Christmas came around, I headed up to the Cape (Cod) to see my family. Back in those days, that meant walking into a house full of music, laughter, the smell of my Grandmother’s Halston perfume, the equally sweet smell of my Grandfather’s pipe and a whole bunch of aunts, uncles, cousins and friends.

Pa saw me. We made eye contact. He smiled and went back to his task, helping my Grandmother with something in the kitchen. I said my hellos, with hugs and kisses for everyone. I ran up to the bedroom I usually crashed in. As I threw my bag on the bed, I heard Pa’s deep bellowing voice, calling me back downstairs.

“Let’s go for a walk.” I knew what was coming. As we cleared the front steps, Pa threw an arm around my shoulder. “How’s work?”

“Good, I get to do a lot of different things and I’m learning a lot.” I’d gone to work for a small software company in Edison, NJ. I was selling the company’s software products and writing their marketing brochures for their new products.

“Did you do what I asked you to do, back at your school?” Pa clearly knew the answer before he asked the question.

“Yes, I did.” I expected to hear about how becoming a little more extroverted would help me in my career, or something to that effect.

“So, how many people?”, he inquired.

“Oh, had to be at least 90. I was initially really uncomfortable doing it, but over time, I came to really enjoy it.”

“Good. So…still think you know a lot?” A big smile came across his face.

Wow…not what I expected.

“No sir.” I paused, appreciating the impact of his question. “I have a lot to learn.” I smiled as the light bulb went off in my head.

“Good,” he replied, a smile forming around his gritted teeth as he puffed on his pipe. The smoke billowing a cloud around and above his head.

“A lifetime of experience can be learned in just a few minutes with someone, if you’re willing to check your ego, ask the right questions and more importantly, listen to them and apply their advice.”

Of the many lessons I learned on my cherished walks with Pa, this was one of my favorites.

The bottom line…Understand, you’ll never know everything about a topic, a job, a business, etc.

· Be curious
· Be humble
· Network your tail off
· Talk with people who are smarter than you
· Find mentors who have done what you aspire to do
· Soak in every nugget of advice, big or small
· Model those mentors

Written by

Dad, Husband, Coach, ‘Nova BBall fanatic w/an addiction to real estate. Founder @ Clark St Properties & Co-Host of the CTREIA Podcast.

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