Solo sailing around both poles in a figure-eight: lessons for leaders

Executive overview

Randall Reeves is 123 days into a solo, non-stop circumnavigation of the globe in a figure-eight pattern — looping Antarctica via the Southern Ocean, then the Arctic via the Northwest Passage, in a single year. No one has attempted it before.

Planning takes years and must be thorough. But once underway, every plan breaks. What keeps you going is execution discipline, not inspiration.

The moment you commit to something truly extraordinary, the work shifts from vision to endurance — one foot in front of the other, every day.

The figure-eight route

• Start and finish: San Francisco
• South leg: Pacific, around Cape Horn, full loop of the Southern Ocean (Antarctica), back to Cape Horn, up the Atlantic
• North leg: Greenland, through the Northwest Passage across Arctic Canada and Alaska, home
• Southern Ocean = sailing's Mount Everest; Arctic = only navigable for about ten years
• Combining both in one year, non-stop and solo, had never been attempted

The Southern Ocean

• The "roaring 40s" and "screaming 50s" — old whalers' proverb: "Below 40 south there is no law; below 50 south there is no God"
• Average winds 25–30 mph; gales (35–45 knots) roughly every other week
• Seas of 15–30 feet, cold, dark, no heat in the cabin
• A 40,000-pound boat can surf down a wave at 10–12 knots — a genuine capsize risk
• The birds in this region have likely never seen a human before

Why he did it

• Fell in love with solo sailing as a teenager; spent two years cruising the Pacific (2010–2012)
• In 2013 heard about Matt Rutherford's solo loop of the American continents — the idea clicked
• The Arctic route had only become viable in the last decade; combining it with the Southern Ocean loop was his own invention
• Wanted something genuinely unprecedented: not just hard, but never tried
• Motivated by Kennedy's moon speech and Daniel Burnham's "make no small plans"

Years of planning before departure

• Spent 2013–2017 planning before the first attempt
• Two years finding the right boat: needed to handle both ice-strewn Arctic shallows and open-ocean Southern Ocean storms — very different requirements
• Joined someone else's Arctic expedition in 2014 to gain firsthand experience; learned that only steel or aluminum hulls survive ice
• Chose Moli: a 45-foot aluminum expedition sloop built in 1989, simple and robust — no electric pumps, no fridge, no water maker
• Carries 200 gallons of fresh water (budgeted at 1 gallon/day), 1,000 lbs of canned goods, four propane tanks
• Planned food, clothing, and fuel in meticulous detail — filling the family living room with provisions

What the first attempt taught him (Figure Eight 1.0)

• Left late October 2017; called "the longest shakedown cruise in history"
• Lost both self-steering systems near Cape Horn; hand-steered for six days to reach port
• A massive breaking wave near the Crozet Islands threw the 40,000-pound boat sideways — punched out a pilot-house window, flooded electronics
• Lost communications and weather data; diverted to Hobart, Tasmania for repairs
• Completed a full globe circumnavigation in five months, then started again October 2018
• Key lesson: storm tactics books say "there is no one answer — every storm and every boat is different." You have to learn your boat by sailing it hard

Dealing with setbacks and failure

• Shame is natural when the boat does something it has never done in 30 years of high-latitude sailing
• The only response: bail out, repair, and go again
• Planning is priceless but "no plan survives contact with the enemy" (Moltke) and "everyone has a plan until they get punched in the face" (Tyson)
• Reframe failure as a shakedown: every breakdown surfaced something that needed to be fixed before the real attempt

Loneliness and mental endurance

• 123 days alone at time of interview; longest prior solo passage was 50–60 days
• The hardest stretch was near the antipodes — the exact opposite side of the world from San Francisco, 12 hours out of sync with his wife
• No single tactic; relies on routine and staying busy: tidy lines, empty bilges, regular meals, staying dry
• Inspiration is irrelevant mid-voyage: "How do you stay inspired in a marathon? You don't. You focus on one foot in front of the other."
• Knowing that people are tracking him live — friends, strangers — provides real emotional sustenance

The business parallel

• Big audacious goals attract a team, a community, and supporters in ways that modest goals never do
• The planning phase is rich and energising; the execution phase is grinding endurance
• The leader's job mid-journey: keep systems in good order, keep yourself healthy, stay focused on the finish line
• Setbacks are not failure — they are data about what needs to change before the next attempt
• A champion does not feel like a champion. They feel cold, tired, and unshowered. They keep going anyway.