The Career Mentors You Never Knew You Needed
I recently had Carl Seidman, a man of many titles, on my Breaking Beliefs podcast, and he shared something that's been rattling around in my brain ever since: "If you don't know what you don't know, where are you going to learn it from?"
Think about that for a second. How many times have we all been stuck because we didn't even know what questions to ask?
This hits home for me because Carl and I teach the Fractional CFO and Advisory Mastermind together, and we see this all the time—brilliant professionals who are technically excellent but missing crucial pieces they don't even know they need.
This question applies whether you're trying to switch careers, level up in your current role, or build something entirely new. Carl's journey from pre-med student to financial advisor shows how we often limit ourselves to the paths we can see, until someone or something opens our eyes to what else is possible.
The Problem with Following What You Know
"It wasn't that I wanted to be a doctor. It was all I knew," Carl told me.
His dad was a pulmonologist in Detroit. Carl would go to the hospital sometimes and watch people light up when they saw his father. But what Carl really noticed was how his dad treated people.
"He'd get on the phone with people. If somebody needed help, he'd get on the phone. He wasn't billing people for their time."
That stuck with Carl. Medicine thirty years ago was different - less business, more connection. His dad would work until 6:30 or 7:00, come home for dinner, then head to his home office until 11:00. The work ethic was intense, but so was the care.
Taking a Different Turn
Carl started college as pre-med. Made sense. Doctor father, academic success, clear path forward. Except he was miserable in those science classes.
"I decided I wanted to go into finance, and realized through that experience that what I was learning was directly relevant to the kind of work that I wanted to do."
How did he figure that out? Pure accident. He took an economics elective and wandered into a business fraternity booth. That random moment changed everything.
"I said, 'What is this?' They said, 'You should rush this fraternity.' I said, 'I don't know what that means.'"
When he finally went to the events, he discovered an entire world he didn't know existed—students studying supply chain, marketing, human resources. "I don't know anything about this," he realized.
The Note That Mattered
During Carl's journey, certain moments created lasting impressions. When he interviewed for a PwC internship, something unexpected happened.
"I still remember to this day, he wrote me a handwritten note after the interview. He was like, 'I know you're not sure about this. I know you come from a finance background. I want you to come here for this internship."
At the end of the internship, that same partner wrote another note: "Thank you for trusting in me. Thank you for trusting in us."
Twenty years later, Carl still remembers those handwritten notes. A Big Four partner taking five minutes to acknowledge an intern - that's the kind of leadership gesture that shapes how someone views their entire career.
When Numbers Meet Reality
The 2007 recession changed everything. Carl moved from PwC into turnaround restructuring - basically helping companies that were drowning. This wasn't academic finance anymore.
"Half of it is business and half of it is therapy or counseling," he explained. "You're taking a look at numbers, but the numbers represent somebody's salary. When you get rid of that salary, the company saves money, but you have completely upended somebody's life."
He saw people at their worst. Companies falling apart. Employees losing everything. The numbers on the spreadsheet turned into real families facing real consequences.
"It forced me in some ways to grow some thicker skin, but also to sympathize as well as empathize with what these people are going through."
Breaking Away
Fast forward to Carl working 60-hour weeks, traveling 40 weeks a year. The turning point came during a brutally honest conversation with his girlfriend.
"I remember I was dating somebody, and she was like, 'I like you. I want to spend more time with you. I can't see you more than Saturday night.' I was like, 'I know.' She was like, 'I'm looking for more than a one-weekend night a week relationship.'"
That wake-up call coincided with something else—his clients started seeing what Carl couldn't.
"A couple of clients pulled me aside. They were as direct as they could be. They were like, 'Carl, why don't you go start your own firm? You don't need this firm.'"
When Carl questioned them, one client laid it out: "You're doing all the work anyway. What would you need this firm for?" Another went further: "I'll give you the work. I've got plenty of relationships I can introduce you to."
Carl had always been resourceful. He'd sold everything from eBay goods to entire home interiors during his career transitions. But this was different. His clients were essentially staging an intervention, telling him he had all the skills and relationships needed to succeed on his own.
So he did just that. He quit without another job lined up and traveled the world while building his client base. Carl worked from tiny internet cafés around the world, responding to emails while exploring new countries.
"Nobody had any idea that I was in Argentina, Thailand, the UK, and the Dominican Republic. I was all over the place."
This was over a dozen years ago, way before digital nomad culture became a thing.
Teaching from Experience
Carl's shift into teaching started with a simple observation from a colleague who'd taken a financial modeling course.
"Carl, you should teach that," he said. Carl remembers thinking, "Was it that bad, or do you think I would be that good?"
Six months after submitting his resume to an online portal (thinking no one would ever look at it), Carl got a call. The education director said, "You're exactly what we're looking for."
But here's where Carl's approach differed from every other instructor. He wasn't retired. He wasn't primarily an academic. He was doing the work every single day.
"I would take vacation days away from work to go teach," he explained. "I'm teaching you how to do what I've done in my career. I'm not a retiree, I'm not a professor, I'm not a real trainer."
The traditional training organization had been using the same materials for years. When Carl suggested updates based on what practitioners actually needed to know, they weren't interested. "If it's not broken, don't fix it," they told him.
So Carl started building his own content—curriculum that reflected real challenges his students would face. He put this new material in front of companies, and the response was immediate: "Nothing like this exists."
"I was bringing more of a practitioner angle," Carl explained. "I'm teaching you how to do what I've done in my career."
This gap between academic teaching and practical application exists in every field. Whether you're in finance, marketing, technology, or any other profession, there's always a disconnect between what's taught in classrooms and what actually happens on Monday morning.
The Skill Nobody Teaches
Throughout our conversation, Carl kept referencing this quality he has: the ability to stay calm when everything's falling apart. It started showing up early in his career.
"When I was in that business fraternity, I remember I had gotten an award. That was the person you would most want to be next to in battle," he shared. "At the time, I was like, 'That's funny, it's goofy.' I didn't think much of it."
Twenty years later, that same quality defines his professional reputation. In the turnaround world, where businesses are failing and people are losing their jobs, Carl's steady presence becomes invaluable.
"When something bad happens, I tend not to overreact. I tend not to get angry. I tend not to lash out."
The beautiful irony? When I asked about his spiritual goals, Carl said he wanted to increase his calm and peace. He's seeking more of the very quality that already sets him apart.
"Carl is this steady, reliable, calm person who, in the face of crisis and chaos, I would want to be next to me," he reflected. "I don't know why I have it, but I do have that ability to stay calm in the face of craziness."
In finance work - especially crisis management - that calm creates space for better decisions. While others panic, Carl helps clients think through their options clearly.
Finding Your Own Path
Carl's big question—"If you don't know what you don't know, where are you going to learn it from?"—isn't just philosophical. It's practical.
His answer came from his own experience. When he started teaching, Carl noticed something—the most valuable insights weren't coming from textbooks or outdated training materials. They were coming from the work he'd done that week, the client challenges he'd just solved, the real problems practitioners face every day.
"Knowledge is power, experience is power, network is power," Carl says. "When you're so good with your skills, network, experience, and confidence, people can't ignore you."
But you need all four elements. Skills alone aren't enough. Experience without a network limits your reach. Confidence without competence is just bluster. You need someone who can help you develop all of these simultaneously.
That realization led us to create the Fractional CFO and Advisory Mastermind, a program where finance professionals who want to build their own practices or level up their advisory skills learn from people actively doing that work. Instead of theory, we share what's working in our practices right now. When someone asks about pricing strategies, client management, or building referral networks, we're pulling from current experience, not memory.
Because as Carl discovered, the best teachers aren't necessarily the ones with the most degrees or the longest tenure. They're the ones still in the trenches, learning and adapting every day.
Taking Control
Carl left me with this: "Many of us are more in charge of the direction of our careers, which ultimately means being more in charge of the direction of our lives."
Whether you're in finance, marketing, tech, or any field, the message is the same. You probably have more control than you think. You just might not know what you don't know yet. They're decisions about how you want to live, who you want to serve, and what kind of impact you want to make.
Carl learned from his father that excellence includes caring about people. He learned from mentors that small gestures create lasting impressions. He learned from hard experience that finance work is human work.
Now he's teaching others what he knows. Not from a textbook. From the work he did yesterday and will do tomorrow.
So here's my challenge: Where in your career are you stuck because you don't know what you don't know? Who could you learn from who's actually doing the work you want to do?
Want to hear the full conversation with Carl? Check out the Breaking Beliefs podcast. And if you're ready to learn what you don't know you don't know about building a fractional CFO or advisory practice, Carl and I would love to work with you in our mastermind.