When I delivered the 2025 commencement address at Chatham University, I was standing on stage receiving an honorary Ph.D. 39 years after walking away* from my first try at college.
It wasn’t lost on me that this has been a nontraditional journey for me to get to that stage.
Back then, I did what many of my generation did. I followed the advice of people who meant well. “Go to a state school. Study business.” Play it safe was the undertone.
So I went.
It’s not like I looked around and picked the school. There were no “college trips” with my parents, there was no discussion about where I would want to go, which school matched my interests. I had no idea what I would like to study. And no confidence to study what genuinely interested me. So I applied to the one school my parents thought made sense. I got in.
And I hated it.
Not because the education wasn’t solid—but because I couldn’t see the connection between what I was doing and who I could ever imagine being. Also, I was at college with a lot of friends I’d been with all throughout my childhood and high school years.
So I left at the end of my sophomore year. I walked away. And by “left/walked away”* I mean I deliberately flunked out. Seven F’s and a B+. I loved my Spanish phonetics class so much that I couldn’t stay away. But I knew I had to leave that school in a way that I couldn’t go back.
Looking back, it was a bold move. My parents were furious, especially my father. They made it clear that I was on my own, completely and all the way. I moved from Durham, New Hampshire to downtown Boston. My first apartment was in the Fens, the neighborhood behind Fenway Park (home of the Boston Red Sox). And it didn’t last long. My roommate and his boyfriend got into a fight stabbing each other with forks, the police were called and I eventually moved out.
I spent much of my 20s bartending, waitressing, writing, exploring different industries—gathering metaphorical flight hours, though I didn’t know it yet. That nonlinear path gave me a hell of an education and one that has served me ever since.
These five rules come from that journey.
Whether you’re just starting out, starting over, or just trying to stay the course—these are for you. Because at some point along the way, you will question yourself and I am hoping you can lean into parts of this narrative to realize that you will figure it out. No one interesting has it easy.
1. Your Values Are Your Compass
Your values are your most important career tool.
Not your GPA.
Not your résumé.
Not even your network.
Your values determine how you show up in the world.
They shape your decisions under pressure.
And when your job, your boss or your environment goes against them – yikes, you feel it in your body first.
I’ve worked in places where I was asked to defend decisions that didn’t sit right with me. Where I felt like I was playing a part instead of doing my part. Every time I stayed too long in a place where values clashed, the cost was high: in energy, in health, in joy.
Values alignment isn’t soft stuff. It’s the foundation. When there’s a gap between your values and the organization’s values, to the negative for you, make a plan to get out. Do it shrewdly but find a way to leave on your own terms. That may take some time. But know you can find something better.
I waited too long in one high-stakes situation and the decision was made for me.
So if you haven’t defined your values—do it now.
Ask yourself:
- What do I believe in?
- What am I not willing to trade, no matter the offer?
- Which line will I never cross?
- Where do I feel most like myself?
I am a glass half-full person, an optimist. I love working with and learning from others. And I believe all problems can be solved with creativity and other people. I am miserable in a job/role where curiosity is not a strength and where no one states the obvious so problems are never clearly identified.
Your values are your internal flight plan. Use them to set a course to find what you like and/or what you can learn from where you are. Use the values to find mentors and colleagues you like and/or learn from.
2. Your Skills Get Sharper With Every Flight
I spent my 20s in jobs that didn’t make sense on paper.
Years ago when I was in what some considered to be a “real job,” a colleague complained that she had nothing to learn from me because I had “all those lost years.” As if there was only one path. I never felt lost. I felt I was on my way to something, I just didn’t know where I would end up.
I learned to understand people from their point of view from behind the bar.
I learned diplomacy by waiting tables.
I learned how to communicate in new (to me) industries by writing press releases.
And I learned how to build trust working with clients as a consultant in countless countries and cities across four continents.
None of that would have been on anyone’s career plan.
But every one of those jobs sharpened a skill I use today as a CEO.
That’s the thing: some of us undervalue experience because it doesn’t fit neatly on a résumé.
But leadership isn’t about developing skills in a straight line manner. Leadership is about readiness for anything and everything. And it’s messy. The more you have to draw upon for experience and skills, by figuring out how to figure things out, the better prepared you are as a leader.
So if you’re in a job that doesn’t seem like it yet, ask:
- What am I learning?
- Who am I learning from?
- Which conditions bring out my best?
- How do I handle uncertainty and stress and chaos?
Every flight teaches you something. Stay curious. Stay airborne.
3. New Destinations Become Possible
Careers are often presented like preset itineraries:
Pick a major. Pick a path. Stick with it.
But that’s not how it works for most people.
And it’s not how it worked for me.
When I arrived at Pittsburgh International Airport (PIT) in 2015, 37 nonstop destinations were served. The airport staff was defeated from the previous 10 years of losing service (US Airways abandoned Pittsburgh as a major hub airport in 2004). Today, there are well over 60 nonstop destinations and every major domestic airline (except Hawaiian) serves PIT. That didn’t happen by accident. It happened because we stopped waiting to be chose and started showing who we are and what we can do.
We connected the community and the global industry to each other and to PIT.
We leaned into innovation and challenged expectations.
We let the airlines, our partners, look at us differently.
And when you do the same with your career, new destinations open up.
Because the truth is:
Your ideal job may or may not already exist. Either way, you are going to need to make sure whatever you do/create is in line with your values and your skills.
And then, the journey is the destination in itself.
4. Expect Turbulence
I had a great job before I came to Pittsburgh.
I was working for a global commercial aviation consulting firm, leading teams across Boston, New York, London, and Beijing working with clients all over the world.
It was fast-paced, high-impact and I loved it. It was just right for me.
Until it wasn’t.
Our boutique consulting firm got acquired.
Leadership changed. And we became part of a publicly-traded consultancy.
And two days before I graduated with my MBA from MIT, they laid me off.
I didn’t see it coming. Well, I did. But I thought I could control my exit without considering how they saw the situation or me.
Looking back, I can see my part. And I am glad they made the move. How they did it was bush-league and really cowardly but that made it more obvious that I didn’t belong there.
Really big value gap.
Turbulence is to be expected. It’s part of some flights.
It’s also part of growing.
Sometimes, the rug gets pulled.
Sometimes, the dream job feels like a nightmare.
Sometimes, it’s just time.
That doesn’t mean you’ve failed.
It means you’re in motion. It means you know what you don’t want.
When turbulence hits:
- Check your crew
- Check your altitude
- Adjust your heading
- And keep flying
5. Ask for Help
I got lost in the airport garage on my way in for my first day as CEO of PIT..
I had flown in the day before from Boston to get settled into the temporary apartment I would live in until my family joined me months later. (I know, I know – cut it super close. Not recommended btw).
I didn’t remember where I was supposed to park.
And just as I was about to spiral down the rabbit hole of “what was I thinking taking this job??” a bright yellow truck with the airport’s logo pulled up beside me. The man inside rolled down his window and said, “Do you need help?”
I said “yes, I do.” He said, “follow me.” And I did.
That moment stays with me, not because I got lost, but because I remembered that I was not supposed to know everything about the new job or even the new facility on the first day.
It’s okay to need help. It’s okay to ask. And it’s so much worse when you don’t.
No one is supposed to know everything. The people who act like they do, or worse, say they do. They are lying, mostly to themselves. And when people lie to themselves, they believe their lies so it becomes their new truth, which they will impose on others indefinitely.
Leaders don’t go it alone.
We ask questions.
We seek perspective.
We admit what we don’t know.
The best leaders I know—mentors, peers, rising stars—are curious. And they’re better for it.
Asking for help builds trust.
It accelerates clarity.
It deepens connection.
So ask. And receive.
Final Boarding Call
There’s a reason this speech was titled The Left Seat.
In aviation, the left seat belongs to the captain.
The person who takes full responsibility for the flight.
The one who calls the shots and knows when to call for help when needed.
You may not feel like you’re ready.
You may doubt whether you belong.
You may worry that you’ll make a mistake.
That’s normal. And it is not just for career beginners. We all struggle sometimes. And we all have the chance to figure it out.
You are in the left seat of your life.
You are flying your own route.
And you have what it takes.
Wheels up.
