30 Conversations | Conversation #9 | Look Up and Look Around

What if instead of looking for the job that matches our qualifications, we looked for the problems that need our qualifications?

This week, I had the privilege of sitting down with Ian Sharp, Principal Lawyer, as part of my 30 Conversations project—a personal research initiative exploring the intersection of finance, strategy, venture capital, commercial law, innovation, and leadership.

I was particularly excited for this conversation because of Ian’s extensive experience as a surface landman and his ability to operate at the intersection of law, agriculture, energy, and land development.

His career offered a perspective I hadn’t yet explored in this project:

What happens when you stop looking for a career that fits your education and start looking for where your knowledge can create value?

A little about Ian

Ian didn’t exactly plan to become a lawyer.

In fact, when he was making his career decision, he had two things on his mind: money and fame.

Law didn’t quite deliver the level of notoriety and riches he imagined.

But somewhere along the way, it became something much more valuable: a passion.

Today, Ian combines his legal expertise with his upbringing as a fifth-generation Albertan from a large farming community to work in surface land—helping companies navigate land negotiations and secure the rights needed to access, explore, and build on property for energy, utility, and infrastructure projects.

In many ways, his career sits between two worlds:

the world he grew up in and the world he studied.

And that intersection turned out to be his advantage.

Three ideas that challenged my thinking

💡 1. Look up and tell me what you see.

Early in his career, while articling in downtown Calgary, Ian remembers looking up at the buildings around him.

But instead of seeing law firms, he noticed the names of oil and gas companies.

That moment changed how he thought about his career.

Rather than simply asking, “Where can I practice law?”, he started asking, “Where is the growth? Where is the opportunity? And how can my legal expertise serve it?”

That shift led him toward a niche at the intersection of law, agriculture, land, and oil and gas and eventually toward highly specialized knowledge that became valuable because it bridged multiple worlds.

This challenged how I think about career planning.

We’re often taught to start with ourselves:

What did I study?
What jobs match my degree?
What titles am I qualified for?

But what if we started somewhere else?

What industries are growing?
What problems are emerging?
Who needs the skills I have?
And what can I bring that helps move something from its current state toward its potential?

Maybe career exploration isn’t just about finding where you fit.

Maybe it’s about looking around and finding where you can create value.

Reflection:
What opportunities might I be missing because I’m looking for jobs instead of problems to solve?

💡 2. Your “random” interests might not be so random.

One of the themes I’ve noticed throughout these conversations is that people often build careers around something deeper than a job description.

For Ian, that something was agriculture.

His upbringing gave him an understanding and appreciation for the industry that he continued developing over time. Eventually, something that started as part of his background became part of his professional niche.

It made me think about the interests we tend to dismiss because they don’t appear relevant to our careers.

The hobbies.
The communities we’re part of.
The things we’ve spent years learning about just because we’re curious.

What if those aren’t distractions from our careers?

What if they’re inputs into them?

Especially in traditionally structured professions like law, finance, accounting, and engineering, I think there is something powerful about asking:

What parts of my life outside of work could make me better at the work I do?

Maybe the goal isn’t to leave our different interests at the door when we enter our professions.

Maybe it’s to figure out how to bring them to the table.

Reflection:
What knowledge or interests have I dismissed because I assumed they weren’t “career relevant”?

💡 3. Adaptability is a professional skill.

Before finding his niche in surface land, Ian spent the early part of his career practicing family law.

It wasn’t necessarily the environment he envisioned for himself long term, but it gave him something valuable:

information.

It showed him what practicing law actually looked like, what environments suited him, and what didn’t.

Ian also spoke about the importance of adaptability and tolerance—the ability to recognize that the real world rarely follows the clean path we imagined.

Plans change.
Circumstances change.
Industries change.
And sometimes, our assumptions are the thing that needs changing.

It made me think about how easy it is to approach our careers with an idealized picture of how things should work.

But perhaps one of the most valuable professional skills is being able to hold two things at once:

Have a vision for where you want to go—and remain flexible enough to respond to what you discover along the way.

That balance between conviction and adaptability may be one of the hardest parts of building a career intentionally.

Reflection:
Where am I being appropriately determined—and where might I be confusing conviction with rigidity?

My biggest takeaway

Every conversation in this project has reinforced that careers are rarely linear, but they can be intentional.

The lesson I’ll be taking with me from this conversation is:

“Look up and look back more often.”

We’re often taught to start with ourselves:

What did I study? What jobs match my degree? What am I qualified for?

But what if we looked up first?

What industries are growing? What problems are emerging? Who needs the skills I have?

And then looked back.

What experiences have shaped me? What interests have followed me? What skills have I developed—inside and outside of work?

Ian’s story reminded me that some of our most valuable career opportunities may sit at the intersection of what the world needs and what we uniquely bring to it.

It also made me rethink the things I sometimes consider “unrelated” to my career. Ian’s agricultural upbringing became part of his professional advantage. Our hobbies, communities, experiences, and seemingly random interests may not be distractions from our careers—they may be inputs into them.

How I’m applying this

Learning only matters if it changes how we think or act.

Because of this conversation, I’m going to:

• Connect the dots between my education, professional experiences, interests, hobbies, and communities.
• Research emerging industries and the problems they’re trying to solve—not just the jobs they’re hiring for.
• Pay closer attention to where my existing skills could create value in unexpected environments.
• Identify where I may be approaching career decisions with unnecessary rigidity or idealism.

I’m excited to see how these small changes shape my own career journey.

A thank you

Thank you, Ian, for your generosity, openness, and willingness to share your experiences.

I truly appreciate your time and the perspective you brought to this project.

Conversations like these remind me that sometimes the most valuable career insight comes from looking at something familiar from a completely different angle.

Help me reach 30 conversations

This is Conversation #9 of 30.

My goal is to speak with professionals across:

• M&A & Commercial Law
• Venture Capital
• Investment Banking
• Corporate Development
• Corporate Strategy
• Innovation & Entrepreneurship
• Family Offices
• Economic Development

If you work in one of these areas—or know someone whose perspective would add to this project—I would love an introduction.

Every conversation is helping me better understand how organizations create value through capital, strategy, governance, innovation, and people, and I hope these reflections provide value to others exploring similar career questions.

Who do you think I should speak with next?

Nine conversations down. Twenty-one more opportunities to learn.

#30Conversations #CareerDevelopment #Leadership #CommercialLaw #MandA #VentureCapital #CorporateStrategy #Finance #Innovation #Mentorship