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Be the hero of your own story.


Part 1/5


My career trajectory, much like a Hero's Journey, unfolded in unexpected ways, offering valuable lessons along the way.


Graduating from HBS (2001) at the tail end of the dot-com bubble, I was fortunate to join Goldman Sachs' high-tech investment banking group.


Yet, as the bubble burst lasted longer than anticipated, I found myself laid off—wrong place, wrong time. But, I quickly pivoted, securing another investment banking position in NYC.


Banking, however, wasn't for me.

Yearning to work on the buy-side, I transitioned to a hedge fund, starting as an analyst before becoming a portfolio manager.


The buy-side appealed to me for its directness

—you invest with conviction in undervalued assets and reap the rewards of your insights.

It was here, in the right place at the right time, that I thrived.


Life seemed perfect. I met my husband, started a family, and settled in Greenwich, achieving my goals faster than I'd ever imagined.


But then, everything came crashing down.

Not because of the 2008 financial crisis, but due to a personal crisis in my 40s.

Sleepless nights, deteriorating health, and a lost edge in the stock market left me feeling out of sync and disillusioned with the game of investing.


Climbing to the top only to feel like a failure led me to question,


"What's next?"


A turning point came with a quote from Oprah Winfrey, spoken to Harvard's class of 2013:


"At some point, you will stumble; you will fall. And when you do, remember this—there is no such thing as failure. Failure is just life pushing us in a new direction."


This perspective helped me pivot towards a new path.


Here are the top 1 out of 5 lessons I learned from my journey:


Make a Plan and Set a Goal:


Initially, the turmoil within left me directionless. I realized the pain of working for others and the pain of lacking control over my future were signs pointing towards my dream: launching my own firm.


Yet, envisioning such a significant goal was daunting. 


William James, a renowned philosopher and psychologist, once said,

"Your hopes, dreams, and aspirations are legitimate... They are trying to take you airborne, above the clouds, above the storms, if you only let them." (Thank you to Thomas Oppong for your blogs)


James suggests that our goals can lift us above the challenges and difficulties we might face in life, much like an airplane rising above the clouds and storms in the sky.


It takes courage to go after your dreams, but make a plan and set a goal. #entrepreneurship #financialplanning


Stay tuned for lesson 2 / 5 next week!!


Reach out if you want to discuss your goals and develop a plan!


Thank you for reading!


Tiffany Kent

Your Friendly Wealth Engagement Guide,


Disclosures: Past performance is not indicative of future results. This material is not financial advice or an offer to sell any product. The information contained herein should not be considered a recommendation to purchase or sell any particular security. Forward-looking statements cannot be guaranteed.


This commentary offers generalized research, not personalized investment advice. It is for informational purposes only and does not constitute a complete description of our investment services or performance. Nothing in this commentary should be interpreted to state or imply that past results are an indication of future investment returns. All investments involve risk and, unless otherwise stated, are not guaranteed. Be sure to consult with an investment & tax professional before implementing any investment strategy. Investing involves risk. Principal loss is possible.

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