Recently, our Hill team gathered at Round Hill (a storied boutique resort) in Jamaica to mark an important milestone: 20 years of serving the families who have placed their trust in us.

It was a true celebration.

Yes, islands, especially Jamaica, have a way of slowing you down. But what made the time meaningful was the chance to pause together and reflect on what has been built over two decades and, more importantly, why it was built in the first place.

As I looked around the group, I kept coming back to something Rick Hill impressed upon me early on: great firms endure because of people who care deeply, take quiet ownership, and hold themselves to a high standard, whether anyone is watching or not.

That spirit was unmistakable throughout the trip.

There was plenty of laughter. Real connection. The kind of easy camaraderie that only develops over years of working alongside people you respect and trust. We also invited spouses to join us, and that added a dimension I did not fully appreciate until I saw it unfold. Our work at Hill asks a great deal of the people who choose this path. Having spouses there brought more context, more gratitude, and more heart to the experience. It reminded all of us that the strength of Hill is supported by families who quietly stand behind the scenes.

The pinnacle for me came on our final night together. One by one, team members stood up and shared their favorite memories from their time at Hill. Some were funny. Some were deeply moving. All of them pointed to the same thing: a group of people who genuinely care about one another and about doing work that matters.

In that moment, it felt like we had quietly crossed into a new level of shared commitment. Not a finish line. Something better. A deeper understanding of what we are building together and why it matters.

Each year, during our time together, we present the Rick Hill Award. It is one of the traditions we hold most dear because it honors the kind of steady, values-driven contribution that Rick modeled from the very beginning. I am excited to share more about this year’s recipient below.

20 years in, Hill has never been stronger. We remain focused, grateful, and energized about the road ahead.

If you have been with us for part of this journey, thank you. Your trust is the reason moments like this matter.

And the most meaningful part of the story is still ahead.

Take the long view,

Matt

“Rick, what are some interesting activities that others are doing that bring joy to their lives?” This is a question that many of my older clients often ask me. I suggest family vacations, volunteering at a charity, and being with your grandkids.

I would now like to recommend something that was never on my bucket list until COVID forced me to spend more time indoors – writing a book about my life!

This process started when my son gave me a Christmas gift in December 2021 called StoryWorth, a website that simplifies writing and publishing a book. Every week for 52 weeks, I received an email with a question. I then would answer that question. I could also eliminate their suggested questions and ask ones I felt were more relevant to me.

Below are some questions asked by StoryWorth:

–  Tell me about your parents and grandparents.

–  How is life different today compared to when you were a child?

–  How did you meet your wife?

–  What advice would you give to your children and grandchildren?

I added some of my own questions, such as:

–  Why was a trip to Russia on your bucket list?

–  What factors do you feel attributed to your long, continued marriage?

–  What is one of the scariest situations you’ve faced in your life?

You can add pictures throughout the stories. This motivated me to go through stacks of old photo albums, many of which were in black and white, of my parents, grandparents, and my younger self.

 My wife and two children were my editors. They added additional information and accuracy to my stories and added more pictures. The book is now 307 pages and includes many priceless photos.

Challenges of my experience:

• Takes time, especially for me, because I tend to write in bullet points, not paragraphs. However, there is no deadline to complete the book…it took me 18 months. The support group at StoryWorth was very helpful in answering my questions.

Benefits of writing a book:

• My grandkids and future generations will know more about my life stories, including several stories that were new to my wife and children,
• The book contains the “greatest hits” pictures rather than losing them somewhere in the basement or on someone’s iPhone,
• Immense personal satisfaction from having written a book.

My takeaway:

I wish my parents and grandparents had written a book about their lives and advice for me and future generations. Now, with current technology, writing a book is much easier. Being older is an opportune time to tell one’s life stories while we still remember them. This is also a perfect gift for parents and grandparents. If you want information on writing a book using StoryWorth, I would be glad to talk with you!