In investing, we often talk about “buying the dip”—taking a chance on a company’s potential turnaround when its stock takes a hit. If it rebounds, it feels rewarding because you took a risk, believing in the company’s future success.
This investment strategy mirrors the timeless framework of the hero’s journey, outlined by Joseph Campbell. The hero’s journey is a cycle of growth and transformation: it begins with a call to adventure, followed by trials and challenges, and culminates in a return home with newfound strength and wisdom.
You’ve seen this framework everywhere—from The Matrix to The Lego Movie. The hero starts as untested and ordinary, thrust into extraordinary situations. Along the way, they face challenges, meet mentors, and learn to use their unique gifts to overcome obstacles. But the hero’s journey isn’t just for fictional characters. It’s a model for navigating the challenges of life, career transitions, and personal finance.
I didn’t fully understand the hero’s journey until I experienced it myself. During a period of personal and professional transition, the concept of “buying the dip” became my guiding framework, helping me navigate the ups and downs of my career in investment management—and ultimately discover my true calling.
The Paradox of Success
Early in my career, I climbed the ranks of investment banking and then investment management. By the time I was a hedge fund portfolio manager managing $175 million, I seemed to have it all. I lived in Connecticut, commuted by train, had a full-time nanny, and checked every societal box for success.
On paper, everything was perfect. Inside, I was restless, sleepless, and anxious. At my lowest point—my personal “dip”—I had a panic attack. Instead of confronting it, I buried my struggles and kept grinding. I thought I was living the life I was supposed to live, but I felt like I was unraveling. Then one day, I broke down and shouted at my husband, “I’m not happy!”
Instead of dismissing me, my husband empowered me in his own way, issuing a call to adventure: “You’re a f**ing Harvard MBA. Go figure it out.”
Breaking Free from the Rat Race
One of the most transformative scenes for me comes from Apocalypse Now, where Captain Willard, stuck in a hotel room, reflects:
“Every minute I stay in this room, I’m getting weaker, and every minute Charlie squats in the bush, he is getting stronger.”
This mirrors the internal struggle of anyone stuck in their own metaphorical hotel room. The longer you stay stuck, the harder it becomes to act. I, too, felt trapped—afraid to take risks, unsure of my next steps, and overwhelmed by doubt.
The Midlife Reckoning
Why do so many of us reach midlife and feel lost?
For me, the harsh truth was that I had become a commodity. In finance, commodities are interchangeable—one pound of copper is no different from another. That’s how I felt: interchangeable, replaceable, and stuck in a system of rules and expectations that didn’t serve me.
Much like Neo in The Matrix, I realized I was trapped in a script that wasn’t my story. I didn’t understand my mission. How do you figure out what you want? The paradox of too many choices left me paralyzed. Like all heroes at the beginning of their journey, I had a choice: resist the call and grind it out, or step into the unknown.
Facing My Fears
One of my biggest fears was financial ruin. I imagined myself divorced, broke, and living in a one-bedroom apartment with my kids. That fear weighed on me like a debt, compounding every day I avoided confronting it.
I decided the only way forward was to step into the fear and start moving. Like Emmet in The Lego Movie, I had to see the value in the ordinary. Emmet begins as a rule-following construction worker but eventually learns to embrace his creativity and become a “Master Builder.”
For me, reclaiming my power meant recognizing my unique skills and building a life that felt authentically mine.
Self-Awareness: The Foundation of Personal Investing
How do we become “The Special” in our own lives? It starts with self-awareness.
As Lao Tzu said, “Knowing others is intelligence; knowing yourself is true wisdom.”
Self-awareness allows us to assess our strengths, values, and goals, and make choices that align with who we are. For me, this meant asking hard questions:
- What do I really want? Ten years ago, I wrote down a dream: One day, I want to manage $1 billion. It was ambitious but directionless. I didn’t know how to get there, but admitting what I wanted removed my limiting beliefs. It gave me direction and created new energy.
- What am I willing to let go of? Reflecting on my strengths and limitations, I realized I needed to pivot. My old strength—picking stocks—was being overshadowed by the rise of index investing. Instead of chasing a misaligned goal, I leaned into a new path.
- What am I uniquely good at? I didn’t particularly like being one of the few women in finance, but I couldn’t change the path I had already taken. Instead, I looked for ways to make it work for me. Through freewriting, I uncovered a childhood memory: helping my single mom balance her checkbook. That small act planted the seed for my future path—helping women take control of their financial futures.
When something seems to hold you back, and you can’t change it, the key is to change your environment. What feels like a headwind in one situation can become a tailwind in another. For me, this meant pivoting from stock selection to becoming a trusted advisor and embracing being a woman in investment management. I went back to school, studied for five months, and passed the CERTIFIED FINANCIAL PLANNER™ exam to focus on building relationships with clients and offering personalized guidance.
The Hero’s Journey in Action
The hero’s journey isn’t just about overcoming external challenges; it’s about transformation. For me, the steps looked like this:
- The Call to Adventure: Realizing I was unhappy and needed change.
- Crossing the Threshold: Leaving the safety of a traditional career path and forging a new direction.
- Trials and Challenges: Building a new career as a financial advisor, confronting doubts, and redefining success.
- Transformation: Embracing my strengths and trusting my unique story.
- Return with Wisdom: Using my journey to empower others—especially women—to reclaim their financial independence.
The Path to Freedom
Looking back, I see how the moments of discomfort and doubt were necessary. They forced me to confront what wasn’t working and chart a new course. Now, I can confidently say: “I am exactly where I need to be.”
The hero’s journey teaches us that growth isn’t linear, but it’s always worth it.
So, what’s the secret to managing the ups and downs of life and career? It’s this: the greatest investment you can make is in yourself. When you align your life with your values, embrace self-awareness, and take bold, intentional action, everything else falls into place.
The time to start is now.
