⛵ Beyond the Harbor: Four Leadership Lessons from Sailing
This week, I did something that I’ve never done in my life.
I sailed a boat. 😬
We are embracing the final days of summer break in the Raley household. School starts next week, so this past week as a family we struck out for adventure on the Puget Sound in and around the San Juan Islands, or as they are known in the PNW, the “San Juans.”
We didn’t go it alone, though. We were joined by Grandpa, and led by intrepid Captain K, an experienced sailor with decades of experience, who knows just about everything there is to know about life on the seas.
Above: Helmed by Captain K, ready for adventure on the Puget Sound.
Sailing requires a surprising range of knowledge, from marine biology, chemistry, fluid dynamics, tides, winds, currents, mechanical, rigging… and probably several other fields I don’t even know exist! Good thing we had Captain K.
For us, it was a time to invest in our family and to experience things we’ve never encountered before.
It was also a nice moment of calm before the storm for me professionally, as the stretch from August to October is intense – in addition to the organizations we’re working with to accelerate sustainable giving, these next three months are a metaphorical wave of keynotes, live events, workshops, podcasts, and hosting the Sustainable Giving Workshop. 🌊
So the time to get away, connect, reflect, and enjoy nature was something we looked forward to. Not to mention a first-time adventure!
Lessons from Sailing with Captain K
If you know me, you know I’m always up for a good wave-oriented metaphor. So for today’s Wave Report, I’d like to share four lessons I learned from our time with Captain K – lessons that you and I can apply to everyday life and leadership.
⚓️ Lesson #1: We aren’t meant to go it alone
Sailing, like life, is not a solo sport. The boat we were on was a 43’ sailboat, built for racing. The original owner had the boat custom-made to circumnavigate the globe, so it was no simple sailboat! There were more lines than I could count – lines for things like the jib halyard and jib furler, main sail, spinnaker, and so on (for those of you who know sailing – can you tell I have no idea what I’m talking about??).
But one thing I did learn well was that sailing isn’t meant to be done alone.
When Captain K and I were talking about our trip plan, we agreed that the most enjoyable approach would be for the family to board the boat at a marina near our house, just by the main crossing to the San Juans. The catch was that it would take a day of sailing/motoring from his home marina to get to that pick-up spot, and he explained that he needed a second set of hands.
While Captain K could handle navigation, running the helm, watching the tides, currents, wind, and so on, he needed help with rigging, docking, bringing out and trimming the sails, and so on.
That’s where I came in.
I have no clue what I’m doing, but Captain K is a patient teacher, and I’m a quick learner. In no time, he had me running spring lines, tying off bumpers, trimming the sails, and more. It was hard work, but satisfying to learn new things.
I quickly saw what Captain K meant by needing a second set of hands.
Sailing isn’t meant to be done alone, and neither is life or leadership.
💡 Takeaway: Who are you sailing through life with? Who is a part of your crew in this season? Are you trying to sail alone?
⚓️ Lesson #2: Smooth seas never made a skillful sailor 🌊
I love that waves have rhythm. They come and they go. Rise and fall. Ebb and flow.
Waves can be calming. Rhythmic. Beautiful.
But waves can also be scary. Overwhelming. Never-ending.
Waves create momentum. But it's not always about the highs. It's also about the moments of peace between the sets – the peace of an inner harbor.
This season has felt like a huge wave building. In my life, in my heart, in my mission. But truth be told, it's also been tiring. Stretching.
The stretch from February through May of this year felt like riding a set of incredible waves:
🌊 Welcoming 16 new and returning clients to grow Sustainable Giving at Imago Consulting.
🌊 Doing 46 keynotes, panels, interviews, webinars, podcasts.
🌊 Launching SustainableGiving.org.
🌊 Launching the Sustainable Giving Podcast.
🌊 Launching the Sustainable Giving Workshop.
The truth is, we grow the most when we are challenged. Stretched.
On the water this past week, in an environment I’m not familiar with, I was stretched. But not nearly as much during the times of peace and calm – it was when we hit strong currents, swirling eddies, rip tides, or when the wind shifted unexpectedly that I learned the most.
💡 Takeaway: Waves can be exciting, but overwhelming and exhausting too. As exciting as riding the waves can be, there is also time for rest. For space. For reflection. For calm. That's why after a long day, I was always grateful for the peace of being in the harbor.... Figuratively and literally.
While the peace of the marina is nice, just remember – a ship in a harbor is safe, but that's not what ships are made for. 🌊
⚓️ Lesson #3: Pay attention to what’s going on under the surface
When you watch people sailing, it can be a flurry of activity – ropes pulling, sails unfurling, waves crashing, crew scurrying about… But what is going on underneath the surface can be more powerful than anything we can see.
The tides and currents are powerful forces. There can be hidden obstacles under the surface. Surprising shallows and sand bars.
Captain K was constantly surveying the conditions and nav charts for shallows to avoid, tides, and current conditions. During one stretch, we motored closer to shore because he knew we could avoid the strong current brought on by the rising tide and ride the swirling currents to propel us forward. During another moment, the local Coast Guard radioed that there was a deadhead in our area – a submerged log so big that, if struck, could cause major damage.
Our boat, being built for ocean crossing and heavy conditions for sailing around the globe, had one of the deepest and heaviest keels available – extending 8 feet under the water, so we even had to be careful coming into marinas at low tide that we didn’t hit the bottom.
But that same heavy, deep keel provided stability. It was a good thing, too, because the forces going on under the surface were powerful.
💡 Takeaway: Don’t just pay attention to the conditions that you can see. Look for signals about what is happening underneath the surface, and respond accordingly – taking advantage of what you can, and avoiding hidden obstacles.
⚓️ Lesson #4: A supportive community makes all the difference
One thing we quickly noticed – boating is its own subculture and a community that is very supportive.
Every marina we arrived in, when people saw us coming in, one or two people would inevitably come over from other boats and offer to lend us a hand. We would toss them a couple of lines, and they would help bring us in safely.
When we needed help, there was always someone nearby willing to assist, give advice, or just offer a friendly word. We talked to people from all over the world, from all kinds of backgrounds. Some people in the community live for the marina life, while others enjoy the journey of getting from one destination to another.
No matter what, the community is there for each other.
💡 Takeaway: We all need community. Are you investing in being a part of community?
I’m grateful for time away, for learning new things, for making memories, and I’m ready to ride the wave that is the next few months. 🌊
Until next week… Surf’s Up! ⚓️
- Dave
About the Author | Dave Raley
Consultant, speaker, and author Dave Raley is the founder of Imago Consulting, a firm that helps nonprofits and businesses who serve nonprofits create profitable growth through sustainable innovation. He’s the author of the book The Rise of Sustainable Giving: How the Subscription Economy is Transforming Recurring Giving, and What Nonprofits Can Do to Benefit. Dave also writes a weekly innovation and leadership column called The Wave Report, and the co-founder of the Purpose & Profit Podcast — a show about the ideas at the intersection of nonprofit causes and for-profit brands. Connect with Dave on LinkedIn.
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