Calm Seas Never Made a Skillful Sailor
This week I took my eldest daughter, Paige, to see Christopher Nolan’s The Odyssey in IMAX.
If you haven't seen it, the story is everywhere right now – Odysseus and his long, challenging journey home. What struck me most wasn't the monsters or the size of the spectacle. It was the trials. The kind that shape a man – even break him – and make him different on the other side.
I think that's why the story lands. Most of us know something about trials. About being stretched past what we thought we could take, and coming out changed.
A little over a year ago, I was in the middle of my own stretch.
So much of what I was doing was new – challenging my skills, my knowledge, pulling me well outside my comfort zone. There were moments the pressure was so heavy I felt like I could barely breathe.
It was right in the thick of that season that I came across a quote. I don't know who first said it, but it's stuck with me ever since:
"Calm seas never made a skillful sailor."
I’ve been thinking about that phrase, because we’ve gotten to experience it firsthand a couple of times over the past year.
A Family on the Water
We've lived just outside Seattle for 22 years, and one of the things I love most about this corner of the world is that we're surrounded by water – the fingers and bays of the Puget Sound, the rivers, the lakes.
For 20 of those years, though, we mostly admired it from shore. A ferry ride here, some stand-up paddleboarding on a calm lake there.
That changed last summer, when we spent five days on a sailboat up and around the San Juan Islands. Then this summer, we got another view of open water entirely – a 7-day Alaska cruise up the Inside Passage with my extended family. My mom is about to turn 78, and a family trip to Alaska was near the top of her bucket list.
Most of that voyage was protected water. But there was one day we ran exposed to the open Pacific, and you could feel it – the big swells rolling under the ship, lifting and dropping thousands of tons like it was nothing.
Calm water, and then not.
There are a few lessons I keep coming back to:
🌊 Lesson #1: The most turbulent times can bring the most growth, if you let them.
Struggle can lead to growth, if you are willing to let it.
Last year's stretch was good, but hard. Looking back on that and other challenging times, there are moments I wouldn't want to relive. But when I look back honestly, almost everything I'm most proud of came out of churning times, not the calm ones.
I’m reminded of a Charles Swindoll quote a coach gave me years ago: “Life is 10% what happens to me, and 90% how I react to it.”
When the rough waters come, how am I going to react to them? At some point, I stopped bracing myself, and started leaning in.
💡 Takeaway: The storm you're in right now may be exactly what's making you a better leader, a more empathetic person, a more resilient human being. Not around the storm – through it.
🌊 Lesson #2: Ebbs and flows are part of the rhythm of life.
Waves have rhythm. They rise and fall. Ebb and flow.
For a long time I treated the flows as the point and the ebbs as a problem to fix. Out on the water, you learn quickly that you can't have one without the other. The tide that carries you out is the same tide that brings you back.
Once you stop fighting the rhythm, the ebbs stop feeling like failure. They start to feel like part of the process.
💡 Takeaway: Plateaus and stormy seasons aren't proof you're doing it wrong. They're part of the rhythm. Learn to read them instead of resenting them.
🌊 Lesson #3: Ships were made for the sea.
A ship in a harbor is safe. But that's not what ships are made for.
I've written before about eustress – the good kind of stress that comes from playing up, taking on something just beyond your current reach.
The harbor might feel comfortable and safe, but it's also where nothing happens.
Every meaningful stretch of growth in my life has started with me leaving a harbor I liked.
💡 Takeaway: If everything feels safe and comfortable right now, that's worth noticing. Where do you need to leave the harbor?
🌊 Lesson #4: Pay attention to what's happening under the surface.
Sailing looks like a flurry of activity up top – lines pulling, sails filling, crew moving. But the real forces are underneath. Tides. Currents. Hidden shallows. The occasional submerged log big enough to sink you.
Our boat last summer had a deep, heavy keel – eight feet down. It made us watch the charts carefully in shallow marinas. But that same deep keel was exactly what kept us steady when the water got rough.
The things below the waterline – the ones nobody claps for – are usually what determine whether you stay upright.
💡 Takeaway: Don't just manage what's visible. Pay attention to the currents and the keel – the quiet forces under the surface that keep you steady or steer you off course.
🌊 Lesson #5: A supportive community makes all the difference.
Here's what surprised me most on the water: how generous the boating world is.
Pull into almost any marina and, before you've even tied off, someone from another boat wanders over to catch a line. Strangers, every time. When you need help, someone is usually already walking toward you.
You are not meant to sail alone. Neither the good days nor the rough ones.
💡 Takeaway: Who's in your crew this season? And just as important – are you showing up as crew for someone else?
Recurring Giving Is a Voyage, Not a Cruise
Here's where this hits home for our work.
We often talk about recurring giving like it should be one smooth, calm cruise – set the program, watch it grow, enjoy the ride. But that's not how it actually goes.
Growing steady, resilient recurring giving programs are a voyage. They have ebbs and flows. Plateaus. Rough patches where retention dips or growth stalls and you can't quite see why. The currents under the surface matter more than the activity up top. And the organizations that come through it strongest are almost never the ones sailing alone.
The turbulence isn't a sign you're doing it wrong. It's the sea doing what the sea does. The question is whether you've got the resilience – and the crew – to grow through it.
💡 Takeaway: Calm seas never made a skillful sailor, and they never grew a great recurring giving program either. The challenges are where the growth is.
You don't have to navigate them alone.
Until next week… Surf's Up! 🌊
- Dave