If You’re Fortunate

Trey Whitaker
2 min readSep 14, 2021


If you’re fortunate, you can look back at life and note some significant moments. I’ve been very fortunate:

1959 — Born in Manchester

1977 — Joined the U.S. Army

1981 — Began financial services career

1985 — Moved to California, met Cherry

1986 — Ran first marathon

1989 — Grandmother died, turned 30, grandfather died, got married

1993 — Purchased a home

1997 — Caylee born

2009 — Father died

2011 — First cancer surgery

2012 — Second cancer surgery, jujitsu black belt test

2015 — Mother died

2016 — Left corporate life

2017 — Opened TCF

2019 — Caylee graduates UVM, trip to Paris, 30th wedding anniversary

2020 — Pandemic

2021 — Caylee moves to Maui

Prior to the opening of Tolland CrossFit, I’d spent 39 years in the military and the corporate world. The past five years have involved planning for TCF’s opening and then working most every day in support of the community.

It has been both the hardest and most satisfying thing that I’ve ever done. A dingy warehouse became the home of a vibrant, diverse and supportive community. My life has been enriched a million times over through my interactions with each of you. I’m truly in love with this community.

After 36 years with the Lincoln Financial Group, Cherry is planning to retire sometime in the not too distant future.

When TCF opened, it was always my intention to retire when Cherry made her exit from the corporate world. We’ve both worked hard for a long time and we’re looking forward to beginning a new chapter together.

During the coming year, I’ll start my own transition into retirement by identifying someone interested in taking over my share of TCF and transitioning my accountabilities with the goal of ensuring that TCF thrives for years and years to come.

In the meantime, I’ll give you everything I can and enjoy every moment shared with you.



Trey Whitaker

Former blogger, CrossFit gym owner, corporate manager, paratrooper, marathoner, youth sports coach and jujitsu black belt. Now happily retired in Maui.