As Leaders, Are You Settling Up or Settling Down?

By Drew Dudley

Updated Over a Week Ago

Minute Read

I’ve always had tremendous admiration for leaders and engineers.

The ability of engineers to pull apart problems, and their commitment to the exploration of multiple possible solutions, are skills I’ve tried to emulate in numerous leadership roles.

And, of course, they can actually build things.

That’s a talent that has always escaped me.

Throughout my youth and teenage years, whenever the tools would come out, I’d ask, How can I help?” the answer would always be the same: “Don’t touch anything!”

It’s humbling knowing that the best help you can provide is not to try to help.

So I’ve always admired those leaders whose minds were able to pick things apart from the way my engineer friends could.  People who could apply fixed truths and unbendable laws to make flexible, creative—even artistic—solutions to seemingly impossible challenges.

Personal Leadership

I want to share the story of how an engineer taught me a powerful lesson about personal leadership.

I met Caleigh in the late afternoon of the 3rd day of a cross-Canada train ride.  Earlier that day, I had been given an amazing lesson on the power of the question, “Why are you on this trip?”  And after we struck up a conversation, I decided to pose it to her.

She immediately blushed, then sat back in her seat and looked at me as if considering whether or not I deserved to hear her story.

Finally, after a moment, she said, “Okay, but before I tell you where I’m going and why I need to tell you a story.”

“I love stories!” I said.  “In fact, this whole trip has kind of turned into a chance for me to hear as many peoples’ stories as I can!”

“Well,” she said.  “This one’s a love story.  An engineering love story.”

“Ah!” I said. “Is it yours?”

“That comes next,” she replied. “This one is the story of the Roeblings. You ever hear of them?”

“No,” I said.  “But generally, my students have to explain everything pop culture to me these days.”

She laughed out loud.  “Well, these guys haven’t been pop culture since the mid-1800s.”

I was intrigued.  “Alright, let’s hear it.”

The Roeblings

The Roeblings Leadership

“Well,” she said.  “During my first year in engineering, a professor told us the story of the Roeblings.  And for some reason, it really stuck with me. During the Civil War, one of the best engineers in the world was a guy named John Roebling. In particular, he built huge suspension bridges. Bigger than any bridges that had ever been built before. After the war, he and his son came up with an incredibly unique design for the biggest suspension bridge in the world. You know which one it was?”

“No idea!” I replied.

“The Brooklyn Bridge – linking Manhattan to Brooklyn. Getting it across the East River meant building a bridge 50% longer than any suspension bridge in history. But he and his son had come up with all these innovative designs, and they went for it.”

“Obviously, it worked out!” I laughed.

“Well, not so much for them, actually,” she replied. “Even before they started building it John Roebling was killed in a freak accident at the river, and then his son Washington actually ended up getting the bends, which partially paralyzed him.”

“How do you get the bends while building a bridge? Doesn’t that come from diving?”

“Usually, yeah,” she said.  “Because it’s actually known as DCS or decompression sickness, which you’re usually only subjected to through diving.  But its original name was actually ‘caisson disease’, because that’s the name of the huge towers that are built underwater into the bedrock to hold up big bridges.  When they first started building them, they had no idea the danger the pressure difference could have on workers, and a lot of them died from the bends.  Washington Roebling was almost one of them.”

True Engineering Love Story

“So where’s the love story come in?” I asked.

“Well that’s just it,” she said.  “Washington Roebling was incapacitated to the point he couldn’t directly oversee the project anymore, but his wife, Emily Roebling, actually ended up learning everything about building bridges.  She was the only one who saw Washington, and she’d carry messages back and forth between him and the onsite engineers.  Eventually, he taught her so well that people figured a lot of the big design decisions being made were actually hers. Which is pretty amazing because she wasn’t allowed to officially study to be an engineer; it was all her and her husband learning, teaching, and working together.”

“I had never heard that story before!” I said, amazed.

“Yeah, they even tried to pull her husband off the project as Chief Engineer when they realized how big a role she was playing, and she went to bat with politicians, funders, the American Society of Civil Engineers, everyone.  This was 12 years into the damn project – and she managed to keep both he and herself in charge of the project.”

Caleigh leaned back and smiled. “She spent hours with him every day working on making that bridge a reality.  She taught herself to be an engineer for the two of them and that bridge.  She built the damn thing.  And she was the first person to walk across it.”

“Nice,” I whistled. “You’re right; that’s the very definition of a true engineering love story.”

“Damn right,” she said. “And from the moment I heard it, it’s been the most inspiring thing in my life.  I want to be that passionate about my work and about someone else at the same time.”

Caliegh’s Love Story

“So you’ve found your engineering love story?”

“Well,” she said sheepishly.  “That’s what I’m doing on the train. I’m actually going all the way to Vancouver to see a guy.”

“Oh great!” I said. “Your boyfriend?”

She blushed.  “Well…sort of.”

“Sounds like a good story!” I said encouragingly.

“I guess it is,” she said, sitting back with a shake of her head.  “The fact is, we’ve never actually met in person. I met him on the internet.”

She cut me off with a wave of her hand before I could say anything.

“I know, I know.  Everyone thinks I’m nuts. But it’s been three years now, and we talk every day. Phone, email, texts, MSN. We know everything about each other, and we’re completely in love.”

“Man, how have you gone so long without seeing each other?” I asked.

“Well,” she said with a resigned smile, “We’ve got almost everything in common…including the fact that we’re both TERRIFIED of flying.  We’re both engineers, we both have huge loans, we both have new careers, and with neither one of us having cars, the only way we were going to see each other as if one of us took the train all the way across the country.  This is the first time either one of us has had the time or the money to make it happen.”

She leaned forward intensely. “Look, I don’t know if everyone in the world is entitled to a love story.  But I want one, and I’ll do whatever I have to do to get it.  And a lot of people think that’s nuts, and I have to be okay with that.”

“But let me ask you this, Drew,” she said after a moment. “How far would you be willing to go for the chance to be happier?”

How Far Would You Go?

That’s one of those questions that seems like a good one when it’s asked. But the longer you ponder it, the more powerful it becomes.

Long after Caleigh and I said goodbye that day, it stuck with me.  In fact, I remember it kept me up most of the night.

As I rode through the Rockies that night, I realized that for me the answer to that question was, “I’m not willing to go very far at all for the chance to be happier.”

You see, when I got on the train for that trip, I thought I had everything I was supposed to have to be happy.

I had a good job, I made good money, I had tremendous job security, and I worked at a prestigious university.  I knew work made me unhappy, tired, and bitter, but I figured it wasn’t because I didn’t have what I should want; it was because I didn’t appreciate it for some reason.

Almost everyone’s work made them unhappy, tired, and bitter, I figured, and many of them didn’t get the pay or the benefits I did, so who was I to complain?  I just needed to find a way to appreciate my good fortune and ignore these “silly” feelings of unhappiness.

Caleigh’s question brought me to a realization:

I wasn’t willing to risk making changes in my life to try to be happier if it meant risking what I already had.

That night I realized something, however. I didn’t even really like what I already had!  What I had was “okay.”  I was willing to settle for “okay” rather than chase the possibility of being happier.

I had never thought of myself as someone who would settle for “okay.” It was a moment of tremendous shock to realize that’s what I had allowed myself to become.

I don’t believe that it is possible to lead others if we are not willing to lead ourselves. And perhaps the first step to effectively leading ourselves is the willingness to honestly ask ourselves a single question:

“In What Areas of My Life Am I Settling?”

Are you settling for “okay” in your job?  In your relationships?  In your health?  In your level of hope and optimism?

I believe leadership means being honest with yourself about where in your life you are allowing yourself to settle and then making plans to ensure you don’t do it for even one more day.

I don’t care how old you are; you’re simply too young to settle.

Ask yourself, “How far am I willing to go for the chance to be happier?”  Then go there.  Right now.  Everything else leadership-related can only start to flow from there.

Are You Settling Up or Settling Down?

If you have ideas about settling up or settling down that might be helpful to readers, share them in the comments section below. Thanks!

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Drew Dudley
Drew Dudley
Drew is the Founder and Chief Catalyst of Nuance Leadership, Inc., and the former Coordinator of one of Canada’s largest leadership development programs at the University of Toronto.
  • Venki Prathivadi says:

    This is an outstanding article. I have read literally hundreds of books on Leadership but nothing gave me an insight as powerful as the question raised in this article – “How far would you go?”. Both the stories in this article are powerful, motivating and insightful. I now need to get on my train.

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