I'm Jen Klassen 

Part 1: Ambition

When I received my Executive Coaching certification in 2021, I had big dreams for how my career would take off —but I underestimated how much my own insecurities would shape my path.

At 46 years old, I had just graduated with a BA in Leadership (my late-in-life decision to go to University is a story for another time) and earned my coaching certification that same year. I was ready to finally step into work that felt meaningful and true to who I was becoming after years of dreaming of something ‘more’.

Or so I thought….

I was not prepared for how brutally my insecurities would derail my ambition. As I look back now and reflect on that time, I’m able to recognize with absolute clarity the many things I couldn’t see then. And with the gift of hindsight, I can appreciate the ways in which I was reaching for an identity that wasn’t mine.  

After graduating from University where I’d thrived as a big fish in a little pond of adult learners, I entered an executive coaching program—an international cohort filled with people who already had thriving corporate careers and advanced degrees. I felt lost, and for the first time, I encountered insecurities I hadn’t known were there.

Here’s an excerpt from my journal from that time:

I feel lost and unclear about who I am in this space. My self-doubt is paralyzing in this new classroom— everyone has more professional experience than I do, more education than I do, and everyone is smarter than I am. They understand the professional, corporate culture and environment, but I’ve only recently been introduced to it. I am way out of my depth. My insecurity is a roadblock that I am unable to break through. I feel like I have nothing to bring to the table. I have no career legs and I can’t seem to sparkle and charm my way into a place of belonging here. No one in this cohort has given the slightest hint that I don’t belong; it’s me. This is coming from inside me and I am unmoored, grasping for a place.

At this point, I was not ready to turn toward my anxieties with any level of curiosity or kindness. So, I did what I typically do when I feel afraid or uncomfortable: I tried harder. I hustled for a place at the table — studying more, reading more, listening to podcasts, learning new language and concepts, and working tirelessly to earn my seat.

Here’s what I know now that I was unwilling to admit then: it wasn’t my table.

And the longer I sat there, the further I drifted from myself. My table was never going to be in the C suite. Not because there’s anything wrong with that world, and not because I was starting too late in life, but because it asks for a version of me that isn’t true. What is true is that I am not meant to lead from the top down, but from the inside out.

And I thrive in spaces where being fully myself is the qualification.

Looking back at that 46-year-old version of myself, I can see with absolute clarity that I wanted two things: I was drawn and attracted to courage and authenticity, and this is how I’ve always wanted to show up as a person, a coach, and a woman— not as ideals to admire in others, but as ways I longed to inhabit my own life.

At the same time, I wanted safety. I was not ready to turn towards myself; to explore the depths of what lay hidden because I knew that road would require me to change everything.

My masks kept me safe and protected, but at the same time they kept me from being known to myself and others.

I was born to lead from the inside out, but pursuing top down meant I could show up without having to make myself vulnerable. The cost to me was that the woman I wanted to be — courageous and authentic— could not emerge as long as I refused to shed my masks.

However, seeing myself with complete honesty meant unravelling a life I’d spent decades building.

Everything I had built— the family, home, and persona —was my Roman Empire. And who was I without that?

So, how did I resolve this moral dilemma?  I gave up on my coaching dream and walked towards a brand-new table. Another table that wasn’t mine and one that, again, required that I drift farther and farther away from myself in order to succeed (what I walked towards is another story for another time).

As they say, lessons in life will be repeated until they are learned.