When the Islanders drafted Matthew Schaefer first overall and effectively handed the future to an 18-year-old defenseman this past year, I paid attention.

What I did not expect was that watching him would make me think about imposter syndrome in the workplace.

There is a quote attributed to Albert Einstein that shows up often in leadership and business conversations: “If you can’t explain it simply, you don’t understand it well enough.” I’ve always loved this quote and I use it regularly. Clear thinking usually does lead to clearer explanations. But after years of watching how communication actually plays out in executive rooms, I’ve come to think we’ve taken it too literally because it stops short of what really matters in leadership settings.

Spend five minutes in a leadership meeting today and you will hear some version of the same concern.

How can we adopt AI faster? What can we do to get a better return on our AI investment? What new AI-tools will transform our business?

That all makes sense. AI has changed how work gets done. It has leveled access to information, accelerated analysis, and raised the baseline of what “good” looks like..

There is no shortage of conversation about AI investment and ROI, but far less attention is paid to how people feel underinvested in. I’ve recently seen how powerful it is when that imbalance is addressed.

I sit in a lot of meetings. Client meetings. Leadership meetings. Team meetings. Planning meetings. Some in person, many virtual. And within the first five minutes, I usually know how it’s going to go.

The good ones feel prepared and thoughtful. The bad ones feel thrown together and disorganized. Too many people. Too much information to cover. No clear sense of why everyone is there. The clock starts running and somehow nothing is really accomplished, except a vague agreement to “circle back.”

A few days ago, Dr. Jennifer Byrnes and I delivered the first session of The Whole Leader Program. The program intentionally blends two complementary perspectives. I bring decades of experience leading businesses, driving growth, building client relationships, and operating under pressure. Jennifer brings deep clinical psychology expertise, along with a clear understanding of behavioral science and mental wellness.

That combination brings business reality and human reality together.

I’ve heard this phrase for as long as I can remember, almost like it wasn’t meant for me.

“If I’d known then what I know now.”

It came from grandparents talking about work and money at the kitchen table. From my parents, usually when they were reflecting on big decision points that shaped our family. I heard it from senior executives I worked for, late in the evening, when the office had emptied out and they were offering advice that felt more personal than professional.

I remember exactly where I was the first time I heard this saying and it really had an impact on me. I was on an airplane with two of my sons coming home from a golfing trip. We were all talking about my favorite hockey team. Actually, it’s my favorite sports team of all sports - the New York Islanders. I had just gotten a news alert that the Islanders best player, John Tavares, was leaving the team to fulfill his childhood dream of playing for his hometown Toronto Maple Leafs. I was devastated and figured there was no way we would ever recover from the rejection.

A few minutes later I read an interview with the Islanders general manager Lou Lamoriello. Lamoriello started by praising Tavares saying that he wasn’t just a great player. He was the captain, the centerpiece, the face of the franchise. However, Lamoriello didn’t sound defensive or rattled.

There is a short stretch of time every year that most leaders don’t plan for, but almost all of them feel. It lives between Christmas and New Year’s Eve, when the calendar loosens, the pace finally slows, and the constant pressure to respond, decide, and produce eases just enough to let quieter thoughts surface.

For people who spend most of their lives in motion, that pause can feel unfamiliar. And sometimes, a little unsettling.

Looking back on these first six months of running The Schuckman Group, a few highlights stand out. These experiences shaped the work I want to keep doing, and they might spark ideas for you or your colleagues as you plan for 2026. There is room for more coaching clients, more leadership work, and more proposal and growth support next year. If anything here feels useful, let’s have a discussion.

In the early months of building my business, I caught myself paying a little too much attention to a few specific people I hoped would become clients. They were strong fits, and I knew I could help them. But they weren’t moving at the pace I wanted. I kept refreshing my email. I kept wondering when the conversations would pick up. And each time they didn’t, I felt a small and unnecessary dip in energy.

Meanwhile, I was actually doing quite well. I had new clients coming in. I was doing interesting and challenging work that was sharpening my skills as both a coach and consultant. I was gaining momentum each month. I was learning how to run a business after nearly forty years inside a large organization. My revenue was growing steadily. Everything I truly wanted from this new chapter was happening right in front of me.

Every coach has moments that stay with them. Not because the situation was dramatic, but because something real surfaced. I had one of those moments recently with a client who had been holding more than most people realized. They looked steady on the outside, as many high-performing professionals do, but underneath they were juggling a mix of work pressure, family responsibilities, and the quiet fear that they were starting to come apart.

Since retiring from PwC and launching The Schuckman Group, I have built a new flow to my work. I have new clients, created new systems, and developed new ways to be creative. One constant surprise has been how much I have learned from artificial intelligence.

I treat AI the same way I used to treat a promising young staff person. It is eager, bright, and fast but not perfect. When I give it clear direction, it performs beautifully. When I am vague, it gives me exactly what I deserve. In that way, AI has made me a better manager. It rewards clarity and punishes sloppy and lazy direction.

Conference season always seems to arrive with a rush. The name tags, the coffee lines, the quick “How have you been?” exchanges that fill every hallway. After attending hundreds of these gatherings over my career, I’ve come to realize the most interesting part isn’t the content on stage. It’s the people in the room.

Spend time with any corporate tax department and you hear the same story. There are no quiet months. Filing deadlines overlap, reporting never stops, and new regulations arrive before the old ones are fully implemented. Expectations are constant, and the pace keeps rising.

Tax teams sit at the crossroads of the business. They manage compliance across jurisdictions, national and local taxes, direct and indirect obligations, and complex transfer pricing documentation. They are expected to deliver transparency, control, and precision while creating value through planning, structuring, and process efficiency. Leadership expects predictability. Regulators expect speed.

Lately I have been speaking with many recent retirees, including former partners like me, who are stepping into consulting or coaching after long careers. I am also spending time with fledgling entrepreneurs I have been networking with and sometimes coaching as they build their first book of business. And I am staying close to my Hudson Institute colleagues, a group I completed an intensive executive coaching program with this year, many of whom are starting practices of their own.

I’ve spent most of my life leading teams, advising clients, and helping people win business. Those moments were exciting and meaningful. But the joy I’ve found in coaching feels different. It’s quieter, deeper, and somehow more lasting.

A few months ago, I started coaching a partner who everyone in his firm would describe as a star. Sharp, reliable, respected. He had built an impressive book of business and was the person clients trusted to handle the most complex issues.

But he was also exhausted. His days started early and ended late. He led multiple teams, reviewed endless work, joined every client call, and never missed a deadline. His calendar was full and his inbox overflowing. On paper, he looked like the model of productivity. In reality, he was stuck.

He had built the career he always wanted, but it no longer felt like the life he wanted.

The one thing holding him back wasn’t skill. It was space.

The first Monday after I left PwC was quiet. Too quiet.

For decades, my mornings started with a wall of emails, nonstop calls, and a calendar that left no space to breathe. Then suddenly, it was just me, my laptop, and silence.

I had planned for this new chapter. I thought I was ready. But the truth is, no amount of planning prepares you for stepping into a new identity.

I’ve been in every seat you can take when it comes to training. Early in my career, I was the participant scribbling notes, hoping something would stick. Later, I was the leader approving budgets, expecting a return that rarely came. Then I was the trainer at the front of the room, trying to make the material come alive. Today, as a creator and facilitator of training programs and executive coach, I meet people weeks or months after they’ve been through a program. By then the question isn’t just whether they’ve been able to use it. Sometimes it’s whether they even remember it. And rarely is the question whether the training created measurable change in behavior or helped them improve results for clients and colleagues.