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3 Lessons That Shaped My Early Career

Leah Ri (Progress Residential) shares lessons from her early life and career that have shaped her professional trajectory.


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1. Never fear the possibility of rejection.

One of the first lessons I learned was at the age of 5 years old. My Godmother took me to her company’s “Bring Your Kid to Work Day”. At that point in time, she worked at CNN as a teleprompter. As soon as I walked into the CNN building, I was mesmerized. I remember the building brimming with men and women dressed in fancy business suits, walking on the marble floors, and rushing into big fancy elevators. 

The best part, however, was when my Godmother showed me her office. And let me tell you, 5-year-old me was thoroughly impressed. Especially by the jar full of candy sitting on her desk (Tootsie Rolls to be specific). That was the day I decided I wanted to become a businesswoman. 

Perhaps it was the professional atmosphere, or maybe it was the chocolate milk that I had while my Godmother sipped on her morning coffee, but I was compelled to begin my first business venture right then and there. After some convincing, my Godmother allowed me to acquire all of her Tootsie Rolls which I proceeded to sell to the inhabitants of every surrounding office. I called it “Penny for a Tootsie”. By the end of the day, I had a pocketful of change and few remaining Tootsie Rolls to share with my siblings when I got home. 

Although that business venture lasted for only a few hours, I remember taking away a very important lesson. Never be afraid to ask for what you want. Although I was ecstatic that my Godmother encouraged my entrepreneurial spirit, I will never forget the euphoria I felt when people purchased the candy that was free just moments before. I like to think it was because I gave one hell of a sales pitch, but in hindsight, I would probably donate a couple dollars to a kid that’s that bold too. 

20+ years later, “asking for what I want” has developed into the ability to effectively communicate, negotiate, and advocate for my industry, my company, and for myself. I have found that, if done in a professional manner, asking for what you want can propel you in your career faster than just waiting for the opportunity to come. And in the moments that I find myself hesitating, I think back to that bold 5-year-old girl and I remind myself even she knew the worst they could say is no.


2. Growth is rarely comfortable.

Another lesson that has shaped who I am today is one I learned at the age of 12. One blistering summer, my older brothers and I decided to try and make a little extra spending money by operating a Kool-Aid stand at the entrance of our neighborhood. Yes, a Kool-Aid stand, not a lemonade stand. 1) Because it was more cost effective (even back then lemons were “expensive”) and 2) it was less time consuming to produce. (Do you know how many lemons you must squeeze to get enough lemon juice to make one gallon of lemonade? 8, sometimes 10 depending on the size of the lemons. Just take my word for it.) 

Anyways, we charged 25 cents per cup of this warm Kool-Aid. In retrospect, our neighbors must’ve just felt bad for us. There we were, these young children, sweating in the sweltering summer sun selling lukewarm Kool-Aid. And I don’t care what you say, there was no way our customer service was worth the $3-5 they were dropping in our tip jar. 

After a few weeks of this rigorous work, we circled up as business partners to decide what we should do with our proceeds. Although there were debates on whether we should spend the money on candy or a trip to the movie theatre, we ultimately came to a collective decision to invest the money into an ice shredding machine. 

The ice shredder was $25. It was small, white, and plastic, but it was one of the most innovative contraptions we had ever seen at that age. With this innovation, we were able to upgrade our business to a shredded ice Kool-Aid stand and increase our price from 25 cents to $1 (a 300% increase in revenue).

Today I relate this to the importance of continuously reinvesting and utilizing innovative strategies to enhance any business, but as a pre-teen, my biggest takeaway was that growth is going to require a little sweat equity, and a little sweat never hurt anyone. 


3. Compassion makes a great leader.

From the time I was old enough to work, I worked every summer doing various jobs ranging from lifeguarding, running a nursery, to selling fine jewelry. I even dabbled in my own entrepreneurial endeavors like partnering in a fix and flip, opening an online retail store, and day trading crypto currency and FX. Although I learned and developed important skill sets such as time management, problem solving, and (what I like to call) “failing gracefully” while doing those jobs, the most important lesson that I’ve learned thus far is one that I learned while working at Crown Asset Management.

In 2017, I began my professional career in finance at Crown Asset Management. By the end of the second year of my career, the world was capsized by the COVID-19 pandemic. As the pandemic progressed, I had the opportunity to witness leaders both within and outside my organization navigate their companies. In observing them, I discovered what I believe to be one of the most important qualities any leader or future leader can possess. The ability to lead with empathy. 

Since its onset, the COVID-19 pandemic has allowed many workers to rethink their careers, work conditions, and long-term goals, which is why many businesses are experiencing what business professor, Anthony Klotz, coined as the “Great Resignation”. Many analysts predict that the workforce will begin to gravitate towards companies whose leadership not only allows for flexible work schedules, but whose leaders and culture display genuine interest in the well-being and professional development of its employees. Needless to say, I’m proud to work for a company whose leaders have exhibited this quality since the day I started. 

Throughout this experience, I’ve learned that being a true leader isn’t just about having the technical knowledge or the most decorated resume. To become a great leader, you must become someone that others would be proud to follow. 

In conclusion, although my story has quite a way to go, I hope what I have shared inspires you to lean into every aspect of your life and reflect on how it has influenced you into becoming the person you are today and the leader you will become tomorrow.