Leah’s Story


A personal trip to Costa Rica to investigate retirement and investment housing in 2006 steered Leah Dobkin into an encore career of freelance writing. She wrote an article for Kiplinger’s Retirement Report about the Costa Rica experience and has not stopped writing since. It has led her to fascinating people in unusual places, including an American expatriate who built a public library in the jungle, and an old fashioned horse logger in the deep Wisconsin woods. Her encore career also led her to unusual experiences, such as constructing a hand-built log cabin, and hitchhiking a passage on a 600-foot cargo ship through the Great Lakes. She has contributed articles to Kiplinger’s, AARP, and other regional, national and international magazines and websites.

Ever since her broken-down sailboat drifted up against the docks in Milwaukee’s harbor, Leah Dobkin has been enthralled by the evolution of the port and the city so firmly moored to it. Based on a feature article for the Milwaukee Magazine, Leah Dobkin authored the book Soul of a Port The History and Evolution of the Port Of Milwaukee. The book takes an unconventional look at a Port through the eyes of the people who work there. It is a tapestry of characters, their stories, and observations about the inner workings of the port. The people interviewed for this book come from all walks of life – crane operators, captains and crew of a cargo ship, and tug boat and ferry captains, as well as pile drivers, and a ship wreck hunter, to list just a few. Their stories are often funny, sometimes tragic. From collecting their stories, she discovered her love for capturing people’s stories, harvesting their wisdom and transferring that wisdom to the next generation.

Leah Dobkin is a versatile and creative writer, covering environmental, housing, social, consumer and business issues. She skillfully weaves compelling human-interest stories for print and online articles. She has written extensively about creative solutions and opportunities in an aging society. Prior to freelance writing, Ms. Dobkin was in the aging and nonprofit field for more than 35 years, with a strong focus on intergenerational programming.

It Came To Me In A dream.

In early spring 2011, I literally woke up from a dream about helping people write their Legacy Letter. I thought my gerontology professional background, and writing expertise was a powerful combination to take on this venture. I was so excited I called my editor at Kiplingers, and told her about the idea. She told me that the idea has been around a long time, and asked if I had Googled it. Embarrassed, I acknowledged that I had not Googled the term, but thought it was an original idea.

Not only was my idea not original, it turned out that the tradition dates back to 3,500 years ago when the prophet Jacob called his sons to his deathbed and verbally shared his ethics and values, creating the template for Legacy Letters. One of Jacob’s wives was my namesake, Leah . Was this a sign steering me in a new direction, a new venture, a new adventure?

Just as I was kicking-off Legacy Letters, announcing Legacy Letter writing workshops and writing services on a NPR radio interview, the unthinkable happened. It is the worst thing to hear. You have cancer. I know that dizzy, knock you off your feet experience. I was diagnosed with Ovarian and Uterine Cancer on March 25, 2011. I canceled all my Legacy Letter workshops, speaking engagements and writing until I could regain my health and strength. I was treated at Froedtert Clinical Cancer Center in Milwaukee, Wisconsin. After months of surgery and chemotherapy, I am happy to share that September 15, 2011 was my last chemo session and I am Cancer-free.



After (my real hair came back)


In the autumn of 2011, I was chomping at the bit to continue my Legacy Letter social enterprise. I started to reschedule my canceled workshops and agreed to do more workshops, speaking engagements and legacy writing assignments. My first Legacy Letter writing workshop was for fellow cancer patients and survivors. Froedtert Hospital Foundation funded the workshop making it free for patients. The feedback was so positive that they have scheduled other workshops and classes. I have “graduated” from saving my life to helping people share theirs. At the time, I hoped that the shine on my baldhead shed light, demonstrating that there is life during and after cancer treatment and encouraging everyone to celebrate their lives–and write their Legacy Letter now rather than later.

Upcoming Workshops!

As I started to recover from the cancer and chemo, and gain more strength and hair, I discovered many powerful applications for Legacy Letters. I was working with a wide variety of organizations and individuals, and gaining traction with my business.

Knocked Down Again


On March 6, 2012, five months after my last cancer treatment, a few hours after my 54th birthday, my smart and beautiful daughter, Hannah Rose, died at age nineteen. I struggle every day to wrap my brain around this tragedy; to make sense of her death. I have decided my most important challenge is to figure out meaningful ways to honor her life; to make sure her death was not in vain; to live twice as hard for both of us.

I am a professional writer, so it is not surprising that writing, particularly poetry, has helped me to learn how to endure my daughter’s death. I did write my daughter a Legacy Letter before she died. When I wrote a Legacy Letter for my daughter, I thought I was writing the letter because I would die before her. Never in a million years would I ever have anticipated the reverse. So, if I seem impatient when I urge you to write your Legacy Letter to your children or grandchildren, you can better understand my urgency. No one knows who will still be with us tomorrow.

My ultimate goal is to wake up in the mornings and remember she lived, not just that she died. I want to keep her memory alive. I want to make sure the abbreviated story of her life- why she was so special to so many people– is not lost, but told and retold. I want to make her smile and laugh, wherever she is right now.

To honor Hannah and others loved one, lost to soon, I decided to offer a specialty Legacy Letter called “Honoring Your Angel” Legacy Letter. This special letter or book captures the stories, memories and unique qualities of your deceased loved one or friend. It entails the same process as crafting a Legacy Letter, we just consume a little more tissues.

I am recovering from my daughter’s death, knocked down, but not defeated. I don’t know what is around the corner. I’m just glad there is a corner. My crazy journey continues. I am more motivated than ever to help you write your Legacy Letter. It was difficult to write, but I hope revealing my personal story motivates you too.
Leah's Signature

Leah Dobkin’s Ten Beliefs

  1. There is no such thing as an ordinary person; everyone I interview or teach is extraordinary.
  2. It is a unique time in history. Because of increased longevity, we have more people with more life experiences and lessons to share than at any other time in history.
  3. Because of accelerated change, it is very difficult being a young person today. The youth need us more than ever.
  4. Stories are the most powerful way to teach and transform our youth.
  5. With the privileges of increased longevity comes the responsibility to share our life stories and wisdom and to foster deeper roots for young people.
  6. A Legacy Letter is one effective tool to help develop unparalleled inner growth to release the sage we all have inside of us.
  7. Writing a Legacy Letter is not for the fainthearted. It takes courage and commitment to confront and reflect on one’s life and mortality.
  8. There’s an old saying that every time an older person dies without sharing his or hers stories it is like a library burning.
  9. Our society cannot afford for this to happen. Older people are a very important untapped resource to make the world a better place for all, to create a road map for our children and grandchildren.
  10. Lastly, the young and old can forge special bonds to help change the world at a critical time in our society.