Diane Sherwood

WHAT DO YOU LOVE MOST ABOUT BEING YOUR AGE?
In the strangest way, I love that I am approaching the end. I have lived life to the fullest, going all out on what I do. That being said, I am really looking forward to the final journey home.

DO YOU LIKE BEING 40+?
I like being a grown-up. I like being able to do what I want, when I want. I like being responsible.

WHEN IN YOUR LIFE, SO FAR, HAVE YOU FELT MOST CONFIDENT, AND WHY?
Confidence for me has been a rollercoaster. As soon as I think I am all that, I am appropriately humbled once again. I have accomplished so many things that I never even imagined I would do and felt at the top of my game, only to find out that I am just me, flaws and all.

WHAT BRINGS YOU THE MOST JOY AT THIS AGE?
Freedom and adventure have always brought me the most joy.

WHAT IS YOUR SUPERPOWER?
I am fearless. I will try almost anything. I have done almost everything. I am an adventurer and tread where most have not. I have traveled the world and to the depths of my soul. I have walked on hot coals. I have skydived. Few animals or foods scare me. People don’t generally scare me. I walk in the love of my God and his angels, knowing I cannot go where he has not been.

WHAT DO YOU CONSIDER YOUR GREATEST ACHIEVEMENT?
I have accomplished so much in my life. After college, I got my law degree. After my law degree, I got my Master’s degree. I became a vice president of my family business, then left to start my own business. I have always worked on my own. I began mediating family law matters, then began filing divorces. I have been on many boards of directors and committees. However, my greatest achievement was being elected as the president of the Wesley E. Brown chapter of the American Inns of Court.

WHAT IS YOUR GREATEST EXTRAVAGANCE?
My greatest extravagances are probably my mani-pedi, massages, hair, and skincare. I get a manicure about every three weeks, a pedicure every six weeks, and a massage every month. I color my hair every three weeks. I also subscribe to a personalized system that sends me shampoo and skincare products monthly.

WHAT IS YOUR MOST TREASURED POSSESSION?
My most treasured possession is a series of sculptures by Fredrick Hart that I have in my home. I got them in 1998 while traveling with my nephew in San Francisco.

WHAT’S YOUR FAVORITE THING YOU HAVE CHECKED OFF YOUR BUCKET LIST?
The one thing that has been on my bucket list for over a decade, maybe even two, is traveling to Africa, which I am doing in June 2025. I am going on a mission trip with my church to Kenya. Then, my bucket list will be complete. All other future events will only be gravy to an amazing life.

WHAT IS YOUR IDEA OF PERFECT HAPPINESS?
I don’t believe there is a “perfect happiness”. Happiness is a fleeting emotion. All emotions should last only a matter of minutes at most. If you hold on to emotions, you are not living in the present. However, I generally only hold on to negative emotions and am working hard on letting those go too.

WHAT IS A TRAIT YOU ARE MOST PROUD OF?
I think that the character trait I am most proud of is my integrity. That was my top character trait when I was studying them in 1988, and it has remained so over my life, especially as I have met others along the way who have shown themselves to lack moral principles and ethical values. Always, always, do the right thing. Doing anything else will always catch up with you and haunt you.

WHAT HARDSHIPS HAVE YOU ENDURED THAT YOU FEEL HAVE MADE YOU STRONGER?
Hardships are a very personal journey. Each one is self-created to make you stronger. In the 1970s, I studied in Germany as an exchange student. In the 1980s, I dated interracially. In the 1990s, I got a law degree and married a man with three children. Then, I went into business for myself. In the 2000s, I returned to school and got my Master’s degree while being self-employed, married, and raising a family. In the 2010s, I buried my mother. Every decade has made me stronger.

WHAT ADVICE WOULD YOU GIVE YOUR YOUNGER SELF?
Stay on your path. There are no wrong decisions. Only decisions that send you on a new path.

DO YOU HAVE ANY WORDS OF WISDOM FOR YOUNGER WOMEN?
You are braver than you believe, stronger than you seem, smarter than you think, and loved beyond measure.
There will always be someone prettier than you, smarter than you, and funnier than you. You just have to hope that in that critical moment, she is not standing beside you.

WHAT IS YOUR MOTTO OR FAVORITE QUOTE?
“Wherever you go, there you are.” Every problem you have is of your own making and a different version of one you have already faced. You have another opportunity to conquer it. And if you don’t conquer it this time, you will face it again in a more tumultuous fashion. Don’t run away or try to start anew because “wherever you go, there you are.”

WHAT DO YOU MOST VALUE IN YOUR FRIENDS?
I like smart people who like to help other people.

HOW DID YOU CHANGE OVER THE YEARS?
I generally believe that a person’s character is created by about age 30, maybe earlier. Barring a major life event, you are who you are. Thereafter, you are only changing in shades of yourself.

IF YOU COULD CHANGE ONE THING ABOUT YOURSELF, WHAT WOULD IT BE?
I have always thought I was too fat. I remember, in college, I weighed 128 pounds and tried to lose that last 5 lbs. Oh, what I wouldn’t give to weigh 128 pounds again or at least lose those same last 10 pounds. I would change, always finding fault with the way I look.

WHAT DO YOU HOPE FOR THE FUTURE GENERATIONS?
I just hope people will eventually learn how to treat each other kindly and that we will stop killing each other and the planet.