Early in my career, I was completely consumed with making money. My self-worth depended on my income, the car I drove, and the vacations I could afford. But instead of fulfillment, I found exhaustion, self-doubt, and a relentless cycle of never feeling good enough.
I began my career in the mid-'90s at a small admin/clerical staffing firm in Chicago. This is where I ‘cut my teeth’ in the industry. 100 cold calls. Back-to-back sales meetings. Every day.
Money consumed all my thoughts and my energy. I had student loans and credit card debt. I was a youngster with a wife in graduate school (more student loans:), and we wanted to enjoy all the city of Chicago had to offer!
After completing graduate school, my wife was accepted to complete her postdoctoral research program at UMass Medical School.
The move brought us to Boston. It also enabled me to pivot to the technology industry.
Mind you, this all happened in the late 1990s in which the technology industry was exploding with internet startups, and a massive surge in demand for IT talent.
I took a job with an IT consulting and staffing firm. I was fired up.
I still remember pulling into the parking lot—BMWs, Mercedes, Lexus, Range Rovers, all lined up like a luxury car dealership. But it wasn’t just the cars that caught my attention—it was the people driving them.
A team of young, hungry sales and recruiting professionals in their late 20s and early 30s, all raking in high six-figure salaries.
I wanted in. If they could do it, why couldn’t I?
Then the bottom fell out.
The Nasdaq crashed over 70%. Overhyped tech startups vanished overnight. Then 9/11 happened. Then Enron collapsed, triggering a domino effect—Arthur Andersen, WorldCom, Tyco, and more.
Mass layoffs followed.
Somehow, I survived not one, but two rounds of layoffs—while many of those high-earning top performers did not.
That moment changed me.
For years, I thought their success was normal. I assumed I was the loser who wasn’t good enough or smart enough to figure it out.
Today, as I reflect back on those years I realize that kind of success is rare.
It gets our attention because it is so uncommon.
Which Path Will You Take?
Over the past 16 years, I’ve trained and coached thousands of professionals in the IT staffing and consulting industry. Along the way, I’ve noticed a pattern.
People tend to follow one of two distinct learning paths.
The first path I will refer to as growth-minded learning. These learners see challenges as opportunities to develop their skills and seek mastery over completion. Instead of just asking, "What do I need to do?", they ask, "How can I do this better?" and "What can I learn from this?" They embrace discomfort, take ownership of their progress, and focus on long-term development rather than quick wins.
The second path I refer to as "check-the-box" learning. Most people take this path.
These learners do just enough to meet the requirements and keep their manager off their back, but they never fully engage in the process of learning. They see tasks as hurdles to clear rather than opportunities to learn, grow and develop new skills. Their mindset is transactional—focused purely on completion over comprehension, and efficiency over excellence.
They lack curiosity – rarely do they ask “why” or “how can I get better?”
Why Most People Are “Check-the-Box Learners”
For a long time I thought “check the box learners” were lazy or lacked discipline, but now I know that is not the case.
People who follow the “check-the-box” learning path are simply chasing the wrong thing.
They want the end results, the money, the prestige, a promotion, a fancy car, but they don’t enjoy the process of getting there.
I know this because I lived this.
For too long, I was obsessed with the scoreboard—chasing outcomes, only measuring success in dollars, and growing frustrated when the results didn’t match my expectations. I resisted the hard, uncomfortable work of truly learning, growing, and embracing my mistakes as stepping stones rather than setbacks. I looked outward for answers, blaming circumstances instead of looking inward and sharpening my craft. The irony is, if I had fully leaned into the process—trusting that growth and mastery would naturally lead to success—I would have arrived at my goals far sooner and with a deeper sense of fulfillment.
I was chasing the wrong thing.
Carving Your Path-Why it Matters
If you’re a “check-the-box” learner, that is O.K. You can still pivot.
But you should ask yourself: "Do I actually enjoy what I’m doing? Or do I just crave the outcome?"
Because if you don't enjoy the daily work — the candidate sourcing, customer research, overcoming rejection, the customer & candidate conversations, the forever learning, and solving problems — you'll probably end up quitting. And that's okay, too.
But it’s better to recognize which group you fall into early on than to spend years forcing yourself down the wrong path because success comes from leaning in and enjoying the daily grind.
I never did “hit it big” during the .com boom. But despite my very average performance (IMO), I survived two layoffs. Many of my peers, those 3x to 10x more successful than myself, were not so fortunate.
So why did they keep me?
My management saw that I embraced the daily grind.
Over the next few months I went on to triple my book of business, despite market conditions.
The Bottom Line
At the end of the day, the most rewarding careers belong to those who love learning from their mistakes, the development, and the practice, as much as they do the winning. Your success is about finding something you enjoy enough to do everyday, for years to come, even when it is really difficult.