When I was a kid, I assumed the adults around me knew everything. It was a blind faith that comes naturally when you’re young and surrounded by people who seem to have it all figured out.
To be fair, I had good reasons to think that way.
My dad is an orthopedic surgeon, my grandpa was a teacher, a business owner, and a county commissioner before serving as the mayor of a small town (in first grade, I would have told you he was the President). My grandma was a librarian, and my mom—arguably the smartest of them all—made education feel like an adventure, not just something to endure.
Growing up in that environment built a strong sense of intrinsic curiosity in me.
But curiosity has its quirks.
My self-imposed educational ambition meant that I wasn’t always a straight-A student, especially in the topics that I didn’t find to be of personal interest. I’d often find myself going down rabbit holes that had nothing to do with the original task at hand.
Why finish a physics homework equation when I could be researching why Galileo even started studying physics in the first place?
To me, the process was always more interesting than the answer.
The Unknown Path
In high school, the inevitable questions started to surface:
Where do you want to go to college?
What do you want to do with your life?
Surrounded by a family that represented the most American traditional professions—doctors, teachers, public servants—you’d think I’d have a clear answer. But medicine wasn’t for me (too much school, too much blood), and teaching or public service felt like someone else’s story to tell.
It wasn’t until a school interview project that my perspective shifted. I interviewed a friend’s dad who worked in Global Procurement and Supply Chain Management for an international corporation. I didn’t understand half the words in his job description, but one line stuck with me:
“You might find that you love doing something you don’t even know exists yet.”
That statement cracked open a new possibility that maybe, just maybe, there was a job out there waiting and it was up to me to go find it.
Falling Into Strategy
Looking back, I probably should have done more research into the field of marketing before I decided on my major in International Studies. But at the time, marketing was as foreign as learning to hunt without a mentor—it’s hard to just start if you don’t know anyone who’s already doing it.
My career began in ecommerce and omnichannel operations—not exactly marketing, but close enough to set a foundation. And it was a good one.
Others might disagree, but I think it’s important to know how the sausage is made before you start running ads for it.
After a few years and a global pandemic, I fell head first into content marketing. It was a move that taught me more about what not to do than what to do. Maybe one day I’ll write about that stepping stone stage in more detail—probably after a whiskey or three—but for now, just know that it was a messy but invaluable chapter in my career journey.
Now, I’m an Integrated Strategist and Insights Manager, a title that would have made zero sense to 16-year-old me. But it fits.
In simple terms, I get paid to think.
I joke that my job title should be “Professional Dot Connector.” Most of my days are spent finding the threads others miss, sorting needles out of mismatched hay, and weaving them into insights that actually mean something.
But the real trick is knowing which dots NOT to connect.
We live in a world where data overload is often encouraged. Everyone wants more metrics, more pivot tables, more analysis. But too much data is like too much of anything—it can quickly turn into noise.
I believe half the battle of strategy is restraint. Just because you CAN have more data doesn’t mean you SHOULD.
Restraint involves asking, “Does this really matter?” and not being afraid to say, “No. It doesn’t.”
The Importance of Critical Thinking
The older I get, the more I realize that the critical thinking skillset isn’t as common as I assumed. Some people just don’t have it—and if they do… they don’t use it very often.
These are the people who answer “Why?” with “Because.”
That’s never been enough for me.
I recently watched an interview with Mark Zuckerberg, who was asked, “What should kids be studying today?”
His answer: “I think the most important thing is just learning how think critically and learning values when you’re young.”
I found this laughable coming from the guy who singlehandedly created the biggest brain-rot platforms of our time.
But cynicism aside, he’s not wrong.
We’re in an age where we’re drowning in information and stimuli, and the only way to distinguish the shit from the shinola is our own intelligence, our life experience and our ability to think critically.
Critical Simplicity
Critical thinking isn’t just about separating good ideas from bad; it’s about looking at a pile of information or a cluttered plan and saying, “This is what matters, and this is what we can let go of.”
Real simplicity is elusive because it leaves you exposed. It forces you to commit to an idea without the safety net of noise or extra data to hide behind. It demands the courage to stand by your decisions, knowing that if you’re wrong, there’s nowhere to hide.
In the end, the world doesn’t reward complexity; it rewards results.
No one cares how many words you used, how many data points you pulled, or how many slides were in your deck. And the people who care about those things aren’t the ones worth impressing.
What sets you apart is your ability to cut through the noise, to think critically, and to make things clear.
That’s the difference between being just another voice in the room and being the one people remember.
Stay Curious. Stay Simple.
From My Desk:
What I’m Thinking About: Whitetail deer. That’s about it. Welcome to the rut.
On Deck for Monday: The upcoming week will be a pivotal moment in American history pending the results of Tuesday’s presidential election. It’ll be interesting to see how the world reacts to those results.
From The Field Review Archives:
The Field Review is a space for exploring the intersection of work, life, and the great outdoors. It’s about figuring ‘it’ out—whatever your ‘it’ might be.
Every Sunday at 10AM EST, I share ideas, insights, and conversations that help break through the noise, offering a real look at how we can all keep moving forward.
If you have any thoughts, questions, or topics you'd like me to explore in future newsletters, feel free to reach out!
Venture Onward,
Jack