Adjusting my sails: A life lived in many ports

I joined a six-week journaling circle. Just to see whether that would inspire me to write again. This week the prompt during our session was, in brief: if your life metaphorically was a boat, what kind of vessel would you be traveling in?

Others in our group spoke about being in a canoe, pleasure boat, even barges. I settled on a sailboat. Not a small dinghy sailboat, but a larger one that needs two or more hands on board to navigate.

What made me choose the sailboat was its versatility, its maneuverability—constant motion over great distances, island-hopping or gliding along a coastline, with the ability to enter various harbors and anchor in ports along the way. Each port is a metaphor for a chapter of my life, whether defined by a place or a mission.

We cannot direct the wind, but we can adjust the sails.

Thomas S Monson

When asked about anchors, I mentioned that in each of the ports I’ve visited, there were new friends and colleagues whom I onboarded into my life, new projects to develop, and new challenges to meet. An anchor, to me, was the commitment I made in each port to see something through to its natural conclusion.

Today, some days after our zoom session, I opened the PDF with the prompts given to us to reflect and write on and realized I may have misunderstood the original question. Perhaps she meant it to be: what kind of boat represents your life? Sitting with that for a while, I came to the same conclusion—a sailboat, and for pretty much the reasons I’ve given. It’s a vehicle I could handle, yet not alone, with the help of many along the way.

I’ll journal here in response to a few of the meaningful prompts given to us.

About journaling

Before diving deeper into my sailboat journey, a word on why I journal this way. I suspect there are as many ways to journal as there are journalers. For many, if not most, journaling is a private activity, much like the diaries I tried to start as a teenager but never continued for long.

I’ve used various ways to record the events of my life, from photographs to day planners, calendars, and annual newsletters. Writing clears my thinking. I’ve written long explanatory letters to people with whom I was in conflict when I’ve wanted a calm resolution that didn’t burn bridges, and I’ve kept copies of those letters.

Most recently, I started this online journal to record my journey with cancer treatments and any internal changes I might notice along the way. My aim here, in part, was to shift from my natural tendency for too much logos (analytical) to more eros (emotional)—in brief, a shift from head-centered to heart-centered journaling. (Whether I’ve achieved that aim may be fodder for a separate essay.)

If you’ve followed my journal, you may agree I’m quite open and I harbor few secrets. So, while others prefer to keep their thoughts and feelings close to their hearts, I’m comfortable sharing most of mine.

Why would I? For people who know me IRL (in real life), my musings may bring added connection. Other readers may gain needed information, empathy, or a new perspective on shared human experiences. Finally, perhaps this journal can serve as a historical or legacy record, offering insights into my values, life lessons, and beliefs.

Let’s end the notion that ideas have no value unless they turn into a business or have some other practical use. Save them all in a beautiful book like Leonardo did. You might want to give them away someday, perhaps to someone who needs an idea. Or your great-great-grandchildren might love knowing what a fascinating mind you had. Or your biographer might be very happy after you’re gone.

Barbara Sher

Back to my sailboat—and what I mean by not navigating alone.

From a very early age, I was neither a loner nor a follower. My mother told me that as a six-year-old I was already directing my ten-year-old friends how we were going to play. And as the eldest of her five children, I was sometimes tasked with looking after them. It earned me a reputation for being bossy. I’ve self-servingly chosen to reframe that as pointing to my independence and leadership qualities. Regardless, rarely did I navigate my sailboat alone.

Since my teens, I’ve relished belonging to a community of females. The groups changed every time my sailboat entered a new port, but each group has played an important part in my early development of self, or, as Carl Jung, founder of depth psychology, would say, my ego development—the first steps in establishing my sense of personal identity and navigating the metaphorical seas. In later adult years, these women, individually and in groups, were, and still are, my steadfast support, who kept/keep my sailboat on an even keel through both calm and stormy seas.

The human heart is like a ship on a stormy sea driven about by winds blowing from all four corners of heaven. 

Martin Luther

Two life partners have played an outsized role in keeping my sailboat in best condition. The first accompanied me from the young age of 17 to 27 and nurtured me while I tested uncharted waters. The heavier storms came later, and these I’ve crossed for the past four decades with my soulmate, a true partnership of equals. We have complementary skills and interests—we like to joke that I’m the software queen and he’s the hardware king. We adore doing things together, and we’re at ease doing our own thing. I know deep in my heart that my boat is in hands I can trust—physically, mentally, and emotionally. (You may get more insight into our relationship when I wrote about our love languages.)

Calm seas do not make a skilled sailor.

Portuguese proverb

Among the more brutal storms my sailboat has weathered are the times I chose to sever a significant relationship. The first time was with my first life partner—that was heart-wrenching for both of us. Later, three different times over 24 years, I ended significant partnerships in businesses that I had helped create and/or build. While the details varied, at the core each time was an unbridgeable conflict in strategy that was fundamental to how we operated our business. Each time, my partners were shocked, while my heart ached at the loss of something I had poured my time, talents, and soul into.

What I learned, over and over, is that an end is not an end; the journey continues and another opportunity shows up. Perhaps more importantly, I learned that I was able to sever the roles cleanly and clearly without breaking the personal relationships. After my first partner married, we remained in touch, and he asked me to be the godmother of their daughter. Two of my business partners were family, and our familial relationships were not broken. I am still in touch with the third partner.

Compared to those storms, my heroine’s journey through cancer treatments was gentler on my heart. I do not feel I’ve suffered a great loss, and throughout the past few years, I’ve had the loving support of my soulmate and friends, as well as various competent and kind health professionals, all of which I’ve documented in this online journal.

But where, after all, would be the poetry of the sea were there no wild waves? 

Joshua Slocum

What does your boat look like? And what are the people and ports that keep you navigating?

Ardis Mayo, my friend who facilitates this legacy journaling circle, gave us many more meaningful prompts I may yet tackle. But I offer you this as an appeteaser to her brilliant work. You can learn more about Ardis on her website, The Reflective Pen, or join her Facebook private group: The Reflective Collective Daily Prompts.

PS. If there’s any topic in this online journal that resonates with you, may I invite you to sign up to get notified when I post? Go to and click on the hamburger (three horizontal lines) at the top right of the page and submit your email. Your address is safe with me.