Seamanship as a compass to larger life
FewGoodMen Sailing Retreat in Netherlands
Even though I never met my grandad from my mom’s side, from what I heard an archetypal, wild and adventurous sailor of commercial ships, I obviously inherited the need and appreciation for sailing adventures.
I can’t think of a more precise, complex, effort-requiring and useful discipline to be used as a metaphor for, and actual embodiment of the man’s midlife passage.
It keeps me humble, vigilant, and yet excited—always yearning to learn more. I’ve come to realize how every element, both the vessel itself and the art of sailing, mirrors the inner work I’ve gone through and now share with other men. The words below have also proven highly effective for explaining the basics of sailing to beginners.
Never “From To” but always “From Towards”
Skilled sea farers would always indicate their navigation as “from - towards”. A successful journey to a larger life does not mean that life becomes permanently calm or that all challenges cease.The true destination is the mastery of the vessel of the self, and the reward is the profound and ongoing joy of skillfully sailing the open sea of life.
For the individual in the first half of life, the unknown can be a source of anxiety. But for the person who has navigated the midlife, who has weathered storms, learned their vessel and become a capable sailor, the horizon became a symbol of freedom, and limitless human potential. It presents the open-ended unwritten story of the second adulthood, a future to be sailed with trust, skill and confidence.
Always Humble
My first attempt of renting a sailing boat ended up with me sponsoring KNRM, watching the boat being pulled up on the crane. For those not living in Netherlands, KNRM is essentially a volunteer based organisation of skilled individuals and fast boats that comes to save your backside when you manage to screw up in the waters of Netherlands. There were two of us, myself with my fresh off the print license holder, and my girlfriend whose qualification were movies of the Pirates Of the Caribbean. Suffice to say that such a duo is not great to operate a for-racing modified sailing vessel. Which I did not ask for just to be clear but received form the above to ensure the lesson was administered well. After the initial adrenaline rush of doing almost 9 knots of speed, the wind started to pick up even more and I realised we need to turn back at some point. Several mistakes and decent amount of panic later, I realised one of the lines is stuck in our propeler, and we are being carried uncontrollably towards the bird island. It was then I discovered the armaggedon-looking like crew of KNRM. At the end there was no damage to the boat, just to my ego.
What a beautiful example of a man moving from the heroic thinking in which the young ego sets out to conquer the world, believing it can bend the universe to its will through sheer force and determination. To realistic thinking which seeks not to control the universe but to establish a humble but dignified relationship with it. This is the central philosophical maturation of midlife. It moves the locus of control from an impossible attempt to manage external outcomes to an empowering focus on managing one's internal state and response.
The “death of my ego” installation aka Sailing Boat Pulled Up on Crane to remove the jib sheet, Medemblik
The Vessel of the Self
To become the captain of one's life, one must first become an expert on one's own vessel, to embark on the journey of self-discovery, finding who he really is beyond his work, roles, possessions.
The hull is the watertight, structural body of the boat, the very thing that defines its form and keeps it afloat. A perfect symbol for our core self, the integrated essence of who we are. Below the hull is the keel, a heavy, flat blade that serves two critical functions: it prevents the boat from being pushed sideways by the wind, and its weight (ballast) provides the stability to keep the boat from capsizing when it heels over in a strong breeze.
The keel is a powerful metaphor for our deepest, non-negotiable values and convictions. These are the principles that give us stability in times of turmoil, keep us true to our course against countervailing pressures. And these are the ones we need to revisit first when doing the inner work.
Taking Responsibility for One’s Own Life
The rudder is the movable blade at the stern used to steer the vessel. Controlled by a tiller or a wheel, it represents our capacity for conscious choice, personal agency, and deliberate action. To "take the helm" is the quintessential act of assuming command. In the context of the midlife passage, you are being called to life, to take responsibility for it. This means moving from a passive state of being blown about by the winds of circumstance and cultural expectation to an active state of steering a chosen course. It is the act of taking full responsibility for one's journey, however frightening or uncertain it may seem.
Revisiting Your Support System
This entire structure represents our personal framework—our physical and mental health, our key relationships with family and community, and our financial and professional stability. These are the essential support systems that hold up our ambitions (the sails) and allow them to function under pressure. Midlife often involves inspecting this rigging for what no longer serves us and for what needs better care (usually ourselves and our body).
Changing the “Acquired Persona” for Better Sails
The sails are the engines of the boat, the curved airfoils that capture the power of the wind and propel the vessel forward. They symbolize our strengths, talents, skills, and the energy we invest in our ambitions and purpose. Just as a sailboat carries different sails for different conditions - a powerful mainsail, a versatile jib, a large spinnaker for downwind sailing - we must learn which of our personal strengths and skills are best deployed in the various circumstances of our lives. The "acquired persona" of the first adulthood can be seen as an ill-fitting or damaged sail, effective in light airs but dangerously inadequate in the stronger winds of the midlife passage, needing to be reefed, repaired, or replaced with something more authentic and robust.
Harnessing the Winds of Change
The sailor's fundamental relationship is with the wind—an unpredictable, uncontrollable, and powerful external force. Life, like the sea, is a force too great to argue with; the sailor's task is not to command the elements, but to respond to them with skill, patience, and grace.
This skillful partnership is embodied in the art of sail trim. Trimming is the constant, dynamic process of adjusting the sails' shape and their angle to the wind to optimize performance and propel the boat forward efficiently. A sailor who tries to carry full sail in a gale is not brave; they are reckless, and their pride will lead to catastrophic failure. True resilience is not about how much punishment one can absorb, but about the skillful and proactive management of energy.
Tuning into your Intuition
To guide these adjustments, sailors use telltales—small strips of yarn or ribbon attached to the sails that make the invisible airflow visible. When the telltales are streaming smoothly backward on both sides of the sail, the trim is perfect. When one side is flapping or turbulent, it signals that the sail is incorrectly angled to the wind, and power is being lost.
Being able to listen to our internal states - feelings of anxiety, gut feel, restlessness, or our heart - represents immediate feedback signalling that our life's "trim" is off, that our current approach is inefficient or misaligned with the "wind" of our circumstances, and that an adjustment is required.
Finding Your Inner Compass
Once the inner mastery has been acquired, the vessel of self upgraded and refurbished, the time has come for the midlife task of deep reflection to chart a course toward a renewed sense of purpose. This will be supported by you uncovering your unique gift, or talent during the inner work, and perhaps a vision of what wants to happen through you. Together with your values this will become your guide to day to day choices to stay true to the long-term course.
Taking Time for Yourself
Finding a calm, protected harbor to drop anchor allows for rest, replenishment of supplies, reflection on the journey thus far, and planning for the next leg. I cannot stress the necessity of building intentional pauses into the fabric of one's life. On a retreat or during a men circle you might feel strong and put together but in the weather of real life, things are sometimes moving too fast and we tend to forget to take care of ourselves. Taking time for yourself is not a luxury, it is necessary. So that you can be the best version for yourself and others. Whether through a short meditation, journaling or simple contemplation of quiet time, these periods of "anchoring" are essential for integrating experiences, recharging emotional energy, and regaining the clarity needed to set a new, conscious course.
A sailor's journey is never truly over; there is always another voyage, another weather system to navigate. And so is our inner work. If you feel called to your own adventure, join us or schedule a complimentary call.
