The Wild, Gritty, Brilliant World of Sailing
Unfurling the Big Idea
Sailors don’t just traverse the waves - we read them.
We turn chaos into direction. Uncertainty into motion.
And when it inevitably kicks off? We don’t panic. We adapt, control and communicate. Amongst a lot of back and shoulder excercises.
And when the wind dies… ha, most likely go make a sandwich down below and enjoy the moment.
Sailing is one of the oldest human crafts - and still one of the most demanding.
It's innovation by necessity, and leadership while in motion.
Every journey is a masterclass in risk, resilience, and resourcefulness.
In this world, we don’t wait for perfect conditions - we work with what we’ve got. You plan like hell, then surrender to the conditions. And through sheer effort and determination (and obviously ongoing education), we keep moving forward.
Making It Personal
Sailing gives us some great principles to instill.
Adjust our sails. Waiting on our motivation, some clarity, or someone else to go do it first? Umm. Let’s start with what's available in front of us. Micro-movements matter.
The ocean doesn’t care about my desires. Storms will come, some big and dark and ugly ones, and mistakes will happen. Growth starts when we let go of needing to be right, and focus on learning and acting fast.
Know your crew. Trust your gut. Beyond the separate point of who we invite in the first place, we know who’s onboard, and how we communicate with them under pressure is necessary. We also know when it’s time to listen to instinct over instruments. Although that precious data is mighty important!
We’re not in control, and that’s not a problem. Control is a myth. What matters is our response. How quickly we can adapt. This begs the question - how clearly can you think when the compass spins?
Moving the Work Forward
Alright, let’s bring it into our teams, clients, and leadership overall:
Check-ins like navigators. Plotting the course is not some half-assed task. Luckily most assumptions are identified and clearly marked out on charts. Not always though. And when the weather changes in our industry or market - what direction should we tack toward? Hopefully not rushing far off course to avoid some squall.
Operating rhythms like rigging. Everything in sailing is systemized but flexible. That’s your ops doc, your workflows, your communication culture. Strong, but built to shift. Capable systems with
Normalize lulls. No wind doesn’t mean failure. It means reassess, repair, restore. Build this into your sprints and cycles. Burnout isn’t brave - maintenance is.
Train for the storm. Don't just role-play success. What happens when the preverbial hits the fan? Practice recovery. Practice redirecting. Build resilience into your team muscle.
Sailing isn’t about dominating nature - when you play it there‘s a feeling of peotry. We dance with it. Same goes for life and work. We don’t need calm seas to move. We need presence, preparation, and the courage to keep adjusting the sails.
(I couldn’t resist) Boats don’t belong to remain in a port - I hope you chart that course, get those bearings, and bring it about!
