The Everyday Hero

Trey Whitaker
5 min readMay 28, 2023


Toddler Cherry in the Philippines

When we think about someone’s life, it’s typical to list their accomplishments along the way. When I think about Cherry’s lifetime, I start by considering the backdrop to her experience. For example, her parents began building their family in the midst of World War II during the Japanese occupation of the Philippines. It wasn’t a small family either. Cherry was born the youngest of nine children.

Some folks push off commitment until the ‘right time’. Others forge ahead no matter the circumstances. Cherry’s parents forged ahead.

Cherry getting pinned by her mother

The Philippines is the largest Christian nation in Asia with over 81% of the population being Roman Catholics. To this day, Cherry says her daily prayers, attends church each week and is a volunteer at her congregation’s soup kitchen. Cherry was a top student at Catholic institutions from elementary school through university. She was always receiving recognition and honors including graduating cum laude with a degree in Economics.

Cherry at the podium

Even though she was the youngest in her family, Cherry was often at the forefront of planning her family’s activities. She always had a word in what excursion the family would make or where they’d dine. While she was maybe 5 feet tall and 90 pounds on a good day, the size of Cherry’s influence was far greater than those measurements suggested.

Cherry the scholar

After graduating from college, Cherry moved across the Pacific Ocean to Los Angeles. In the hope of starting her career, she immediately began looking for work. In 1985, Cherry landed a position with Aetna and she relocated to their Hartford office three years later.

Woodland Hills crew

In the Spring of 1988, Lincoln Financial Group purchased a portion of the Aetna and Cherry’s career continued within a new organization. She was the founding member of Lincoln’s compliance team and became the brain trust of this group.

On Wednesday, after beginning her career in an office building in Woodland Hills, CA, Cherry will end her career in her home office in Kihei, HI.

Working for 38 years with any organization is an amazing feat and even more improbable in this day and age. It’s a clear testament to Cherry’s ability and dedication that leader after leader have trusted in her.

Family ties

Working nearly four decades for a company is an accomplishment in itself. It’s around 9,000 days of work. How many commutes is that through log jammed traffic and poor weather? How many thousands of meetings? How many days when illness was stifled by a shot of DayQuil just to make it into work? How many late evenings and how many hours of lost sleep working on last-minute requests with early morning deadlines? How many personalities navigated, managed and endured? It’s an extraordinary achievement.

Cherry and Caylee’s first photo together

What makes this undertaking even more impressive is that it was not done in a vacuum. It was done while living a life full of challenges, hurdles, wins and losses. For example:

  • The passing of parents, in-laws and siblings.
  • Pregnancy and the birth of a child.
  • Moving from Chatsworth, CA to West Hartford, CT to Manchester, CT to Hebron, CT to Tolland, CT to Kihei, HI.
  • The loss of family pets.
  • A husband with cancer (twice).
  • Countless hours spent driving to dance, piano, basketball and soccer practices.
  • Innumerable days spent standing on sidelines watching soccer games in freezing and scorching weather.
  • Watching your daughter’s team lose and win championship games.
  • Terrorist attacks, mass shootings, stock market crashes, recessions, elections, an insurrection and a pandemic.
  • Blizzards, hurricanes, earthquakes and week-long power outages.
  • Opening a business.
  • Becoming a U.S. citizen.
  • Proms, recitals, weddings, holidays, travel, parties, wakes and funerals.
  • Building homes, selling homes and relocating.
  • First days of school and graduations.
  • Countless dinners cooked, houses cleaned and loads of laundry folded.

Cherry has worked hard in every aspect of life. She’s our everyday hero.

Our Queen

Through all of this, Cherry never strayed away from the responsibilities of her work. None of these things were an excuse for her to neglect her role.

Even when she was home during the pandemic or 5,000 miles away in Hawaii, her focus never lessened. Here in Maui, she would sometimes rise as early as 3 AM for a meeting with workmates on the East Coast. Even in the final days of her long career, it was common to find Cherry working on her laptop late into the evening. She’s just as dedicated today as she was in 1985.

Cherry and I met during the early days of her career and, since that time, she’s been the ying to my yang. We come from opposite sides of the globe. She’s left-brained (e.g., analytical, logical) and I’m right-brained (e.g., spontaneous, daydreamer). She was the youngest child and I was the oldest. She was a decorated student and I barely passed. She’s a Lakers fan and I root for the Celtics. She’s talkative and personable and I’m, well, not.

Despite these differences, we’ve formed an unbreakable unit.

June 1989

After nearly four decades of perseverance and hard work, it’s now time for Cherry to reap the rewards of her hard work. To turn off the wake-up alarm. To linger a bit longer over her morning coffee. To take as many naps as Abbey. To spend time visiting her siblings in the Philippines. To enjoy the ‘CherBear’ life.

We love you, Cherry. Congratulations on an amazing career.



Trey Whitaker

Former CrossFit gym owner, corporate manager, paratrooper, youth sports coach and jujitsu black belt. Now a trail steward at Haleakala National Park on Maui.