There is something quietly disorienting about walking a university campus with your son as he tries to figure out his future, knowing you stood at almost exactly the same crossroads nearly 40 years ago, just as certain, just as much in need of recalculating.
My wife and I have now toured Waterloo and Western with Will. He is only in Grade 11, yet his decision already feels very close. He is leaning toward math, with engineering still in the conversation. At Waterloo, the co-op pitch landed hard. The ability to gain real experience and a paycheque, especially after a frustrating stretch trying to land a part-time job, did not go unnoticed. At Western, same positive energy, same brochures read on the drive home. He commented that he likes Western’s campus layout more, which is about as much editorial as we got from him that day. For now, it is likely a pause until summer or fall, when things get more real.
On both drives home, my wife and I noticed he was quieter than usual, which, for someone who is usually the life of any road trip, said plenty. That told us more than anything he could say.
Watching all of this unfold, I kept thinking: I have been here before.
The Part Where I Changed My Mind (A Few Times)
In the late 1980s, I arrived at Dalhousie University having already revised my career plan twice. Mathematician. Then a veterinarian. Now an astrophysicist. Two years in, I switched degrees when I realized astrophysics meant pursuing a PhD I was not interested in, and I landed on a combined degree in Physics and Computer Science. It was the early 1990s, and while astrophysics would have taken me deeper into the universe, CS was quietly preparing to take me around the world, one slow dial-up connection at a time. 9600 baud, for those keeping score.
Did I need a physics degree to succeed in operations? Honestly, no. But I would not trade the way it shaped how I think. After graduation, I was even accepted to that same Waterloo campus we just toured for a master’s degree in computer science. I declined. I was ready to work.
Which brings me back to standing on that campus in 2026, listening to my son decide whether he wants to attend the school I once turned down. The symmetry was not lost on any of us.
The Part Where We Think We Have It All Figured Out (We Do Not, and That Is Fine)
Here is what the career planning conversation often gets wrong: it treats the initial choice as the variable that determines everything downstream. Pick the right path at 17, and the rest follows. Pick wrong, and you are somehow behind. It is a “wrapped in a bow” story. It is also largely fiction.
That has not been my experience, and I suspect it has not been yours either.
After Dalhousie? Ten years in IT. Almost two decades in operations across industries, I could not have imagined as a university student. Consulting since 2019, which has turned out to be the most direct expression of everything those years accumulated into. That is not a straight line. It is barely a line at all, unless you want to call a spaghetti diagram a roadmap. 🍝
But every segment connected to the next in ways that only became visible looking back. The CS foundation enabled the IT career. The IT leadership became the bridge into operations leadership. The operations depth became the consulting practice. None of it was planned in advance with that kind of clarity. It was built through decisions made with incomplete information, adjusted as better information arrived. Which is, when you think about it, just how most worthwhile things get built.
The pivot is not the anomaly. For most people, it is the pattern. You start somewhere reasonable, learn something real, and that learning quietly redirects you somewhere you did not expect. Sometimes it happens once. Sometimes it happens four or five times over the course of a career, and each time it feels like a detour until, eventually, you recognize it was the road all along.
This applies whether you are 17, trying to pick a university or college program, 25, realizing the job you trained for is not the job you want, or 40, wondering if the next chapter looks anything like the last one. The question worth sitting with at any of those moments is not “what is the perfect path?” It is whether the direction you are moving is building something that genuinely fits how you think, what you are good at, and what the world actually needs from someone like you.
If the path already looks different from what you planned, that is not a problem to solve. That is the process. The people who build the most interesting careers rarely draw a straight line from intention to outcome. They stayed curious, took the next reasonable step, and adjusted when the data (or their heart) changed. That is not a lack of direction. That is how it actually works.
Will is going to make a choice within the next year and will likely change his mind about something important soon after. That is not a warning. That is almost certainly just how this works. The kid who enters university to study engineering may end up in college to become an electrician. The young professional who starts in finance may find their passion in teaching. That is not a crisis. That is a person paying attention.
And if Will changes course a time or two along the way, that will absolutely be fine. I am living proof. So, probably, are you.