We recently connected with Tiffany Kent and have shared our conversation below.

Tiffany , thanks for taking the time to share your stories with us today Can you open up about a risk you’ve taken – what it was like taking that risk, why you took the risk and how it turned out?

Growing up with my single mom in New Canaan, CT was a miserable experience.

I didn’t have a lot of friends;
I was small and shy;
I was held back in the 2nd grade, and
I was the only kid with divorced parents.

What made my childhood even worse,
was my mom spent a lot of her energy hating my dad.

She would tell me my father should have been more successful.

What I’m realizing now is that when my mom told me my dad wasn’t successful, I somehow internalized that I wasn’t smart.

My mother dropped out of college, meanwhile,
my dad graduated from Harvard Business School and climbed the ladder at IBM, and supported me and my mom financially.
In 1980s, I lived in two houses in an affluent town an hour outside of NYC.
While we didn’t belong to a country club, a girl teased me that I was a rich girl.

We all know that we are children, a product of our parents.

Kids absorb and interpret information in ways we, as parents,
don’t always understand and know.

Her criticism created an internal criticism inside of me.
I created a harsh internal judge who told me that I wasn’t smart.

I mean, who fails the 2nd grade?!

Listening to a podcast by Dr. Jim Joehr and Shane Parrish, I learned ….

Success isn’t about getting another degree but it’s about changing something inside.
Life is all about winning the mind game and the stories we tell ourselves.

I didn’t know I was holding myself back because of an internal voice until I broke the spell.

This is what happened.

I suffered a rejection at work five years ago. I shared this failure with my now-coach, who told me I should start my own firm.
Then my daughter told me to listen to the book The Secret by Rhonda Byrne. This is when I realized, “The more you think you can or think you can’t, you are right”—Henry Ford.
The last piece of the formula, I shifted my mindset from fear of failure to I have nothing to lose.

And so I broke the spell of the internal evil judge had over me and went for it 6 months later. That was almost 4 years ago.

So many of us, tell ourselves we can’t do something and this becomes our reality.
The secret is to stop the judge and just move forward and start to take action.

We have to stop working from fear of failure and learn to think that we have nothing to lose.

Today I have a high growth, successful investment management and financial planning firm with $90 million under management and 40 clients. I went from 0 to $90 million in 4 years.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

Tiffany Kent is the founder of Wealth Engagement LLC, an independent investment management and financial planning firm. With over 25 years of experience as a Wall Street equity research analyst and portfolio manager at esteemed institutions such as Goldman Sachs and Alliance Bernstein, Tiffany has established herself as a trusted figure in the industry. She is also a CERTIFIED FINANCIAL PLANNER™ (CFP) with a deep commitment to empowering individuals, particularly women and those navigating significant life transitions.

Tiffany’s primary focus is on promoting financial literacy and encouraging active engagement in wealth management. Her expertise lies in providing individuals with the knowledge and tools they need to take control of their financial futures. Through her work, she aims to equip her clients with the necessary skills to make informed decisions and build a solid foundation for their financial well-being.

Tiffany holds a Bachelor’s degree in Economics from the University of California, Berkeley, and an MBA from Harvard Business School.

Can you tell us about a time you’ve had to pivot?

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.”

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.

Learning and unlearning are both critical parts of growth – can you share a story of a time when you had to unlearn a lesson?

After navigating the ups and downs of the dot com bubble and landing well in NYC, getting my dream job, meeting my husband, and having kids,

There was much comfort in being in the rat pack.
It was a fun playground in NYC and then Greenwich, CT.

But then something weird happened to me.
I was in pain.
Life was hard.
Did I miss something?
I worked so hard, and for what?
I felt like a failure.

What is the purpose of wealth if it leads to becoming unhappy?

Does it mean I now have a paradox of choice?
Too many options and don’t know what to do?

What obstacle was I facing?
I couldn’t figure it out.
I had tons of anxiety.

Then I realized something at the peak of my despair…
I had stopped growing.
I had a fixed mindset.
I followed the rules and formula of success but didn’t know what was next.

I didn’t know what I wanted out of life or my career.
I had no goals, no dreams.
I hadn’t read a book in years.

But then I started reading, and
I discovered Carol Dweck’s book Mindset: The New Psychology of Success.

What is a true growth mindset?
Developing a growth mindset means embracing failure.

“You will only have some of the answers when you start something new.”
People with a growth mindset don’t look at failure as failure!
They see it as an opportunity to learn and improve.

Quickly, this book drove me to devour more non-fiction books and learn from those who’ve mastered their fields.

But it was this discovery that helped me start to forge a new path.

“Where the way is hardest, there go thou; Follow your own path and let people talk. “— Dante Alighieri

Always be growing.

The most rewarding journeys often involve overcoming obstacles and staying true to your convictions, even if it means going against the grain.

Contact Info:

• Website: https://Wealthengagement.com
• Linkedin: https://www.linkedin.com/in/tiffany-kent