Building Your Expeditionary Skill Stack

Introduction

Scott Adams popularized the idea of a skill (aka talent) stack in his book “How to Fail at Everything and Still Win Big.” It’s hard to become the very best at one thing. Very few people get into the NBA, NFL, or PGA tour. But it’s possible to combine a pretty good golf game, conversation skills, and knowledge of persuasion and psychology to launch a successful sales career. Adams could barely draw and had no idea how to actually color his cartoons when he began his career as a cartoonist. He argued that a willingness to take risks and an inability to be embarrassed by having your mistakes revealed in public, combined with solid (but not great) abilities in several skills that work well together, goes a very long way towards success.

Expeditionary Skill Stacks

Can the same idea be applied to expedition success? The Oxford dictionary defined an expedition as follows:

A journey undertaken by a group of men with a particular purpose, especially that of exploration, research, or war.
Oxford English Dictionary

So expedition success can be measured as newly discovered lands, important scientific discoveries, or military victory.

But what if we limit our focus to light expeditions, short journeys that let us venture into pristine, beautiful, wilderness spaces? What travel skills get us there, keep us (mostly) comfortable and well fed along the way, and get us safely back?

Can we build an expeditionary skill stack that might not get us to the top of Mount Everest, but does get us to exquisitely beautiful and private spaces that we can briefly own?

Saint Croix River near Grantsburg, Wisconsin.

The answer is yes. Consider the best expeditionary YouTubers: what do they have in common? They combine multiple skills to get them to remote wilderness spaces most people could not possibly reach.

RoKKiT KiT: Australian Catch and Cook

RoKKiT KiT combines small boat skills; an understanding of local weather, navigation, and islands; and fishing/spearing plus cooking skills to execute multi-day trips to deserted barrier islands in Australia. RoKKiT KiT also records his trips via GoPro and then posts the edited video to his YouTube channel. As of May 2021, his relaxed, engaging, you-are-there dialogue and beautiful locales have led to 343,000 subscribers.

The Baird Brothers: Canadian Wilderness Experts

Similarly, Jim Baird combines whitewater canoeing, bushcraft (including camping, cooking, and survival skills), and videography and editing to create and record his unique journeys in Canada’s wild North country. His brother Ted Baird is also highly accomplished in bushcraft and wilderness travel and has his own YouTube channel.

A Latter Day Viking Sailor

Expeditionary sailors like Erik Aandrea bring core sailing skills but up their game in navigation, heavy weather training, automation, and safety to achieve extraordinary sailing journeys within modest means. Erik has sailed the North Sea during winter numerous times, and recently completed a circumnavigation of the Norwegian Sea.

Building Your Own Expeditionary Skill Stack

Here’s an introduction to how to evaluate the best skills for expeditionary travel. First, you need a travel mode. Sailing, canoeing, boating, hiking, and climbing are excellent choices. Sailing in particular gives you tremendous mobility in open water without the need to constantly re-fuel (assuming you can wait out the slow or no wind days). Canoeing provides excellent flexibility including the ability to traverse lakes, rivers, and short stretches of land (known as portages). Canoes can also traverse highly technical whitewater rapids while carrying a ton of gear. And with canoes, you can always portage around falls and rapids to difficult to cross.

Once you’ve chose a travel mode, you need to learn basic camping skills. How to set up a tent and tarp for shelter, how to choose the right location for camp, cooking meals, avoiding bear encounters, getting water, lighting a fire, and more. Strong camping skills allows you extended stays and multiple day trips to remote spaces. The basics are relatively easy to learn, and the quality of camping gear in general has increased exponentially in the last 3 or 4 decades.

You Can Travel, Camp, and Cook. What’s Next?

Now you can move about in the wilderness and stay for extended periods of time via basic camping and cooking skills. What’s the next skill you should considering adding to your stack?

The next most important skill is judgement based on experience. My advice is to do multiple trips that feel comfortable to you based on your skills. This gives you a chance to experience adverse conditions, including weather, bugs, and gear failures, under controlled conditions. As your experience grows, you can start increasing the length (number of days) of your trips. You can go to more remote places and push the envelope on the level of whitewater rapids while canoeing or storm levels while sailing. Do this gradually and don’t get cocky, but be willing to push the envelope somewhat as you gain experience.

Food and Aesthetics

Once you’ve built up experience and can routinely travel where most people cannot, what’s next? My suggestion is to learn photography and videography. Modern GoPro cameras and drones are inexpensive and when combined with simple video editing tools the allow you to create high-quality videos of your trips that you can share with friends and family on social media.

The possibilities with today’s miniature portable cameras like GoPro are endless.

As you gain more experience cooking outdoors, you can build up your repertoire of possible meals. Portable refrigeration is becoming lighter and more mobile so that for short, 3 to 4 day trips, you can cook almost as you do at home with similar ingredients. Beyond 4 to 5 days, you need to dehydrate meat and other perishables to reduce weight and increase wilderness “shelf” life. For short trips, grilling is ideal because it is quick, can leverage campfires, and results in fewer dishes to clean up afterwards.

Outdoor grilling can create awesome meals in the wilderness.

Conclusion

An expeditionary skill stack is a force multiplier. You can go farther than 90% of the sailors, canoeists, and backpackers who strictly focus on their own specialty. Adding more skills to help you safely navigate and traverse remote wilderness areas means you get more solitude and can experience nature’s beauty without the noise, ugliness, and distractions of modernity.

To learn more about light expeditions and expeditionary travel, here are some previous blog posts you might find useful:

The Power of Light Expeditions

The Best Skills to Master for Light Expeditions

Light Expeditions, Lake Superior Style

How I Got To Heaven in a Sea Kayak

A View of Heaven

What does Heaven really look like? I was about to find out as I pushed my kayak from shore. I needed to cross 6 miles of big water with strong wind blowing to get to a bay my sailor friends had described as “Heaven”. Read on and you can find out if I made it and what heaven really looks like.

In previous posts I’ve described several boat camping trips on Lake Sakakawea and a sea kayak trip down the Missouri River. Here I describe crossing Lake Sakakawea in a sea kayak on an overnight trip. My goals was to connect with sailor friends at a place they told me was Heaven.

The Trip Plan for Lake Sakakawea

I had done a few short day trips in my sea kayak on Lake Sakakawea to help build up more big water experience. Lake Sakakawea stretches 180 miles from the dam near Pick City in central North Dakota to Williston, on the border with Montana. The lake is the second largest reservoir by surface area in the US after Lake Oahe and it averages between 3-4 miles in width. It has 1320 miles of shoreline. That’s longer than California’s coastline. This article in the New York Times provides excellent descriptions of the lake and its shoreline.

My goals this trip were to do my first overnight camping trip in the sea kayak, and do an open water crossing where I wasn’t just hugging the shoreline as I traveled. My reward was a the chance to stay in one of the prettiest bays on the lake while connecting with my good friends who had sailed there ahead of me.

Heading Into the Open Water

The trip occurred over a weekend in June 2015. I traveled to Indian Hills resort and boat landing on the north side of the lake, about 30 miles due south of Parshall, North Dakota. My destination was on the south shore, roughly 7 miles southeast from the entrance to Good Bear Bay, where Indian Hills resides.

And this is where things got interesting. At this point my sea kayaking experience was very limited. Large waves in open water were new to me. In fact, I had abandoned several previous attempts to connect with the sailors because it involved 8 to 10 miles of sea kayaking over open water against a big wind. But today, as I worked my way out of Good Bear Bay to the big lake, I had decided no matter what, I was going to cross the lake.

The shoreline on Good Bear Bay where I started the journey across the lake.

On my way to the open lake a peninsula on the edge of the big water was perfect for lunch. The wind to that point had been light, about 5-7 knots, but it was gradually increasing to 12-15 knots from the west. The waves were building to 2 to 3 feet rapidly across a fetch (stretch) of 10+ miles. Should I go, or not?

Decision Time and the Margin of Safety

If the wind continued to increase, the waves would get even bigger. But the forecast was for winds around 15 knots, which I was seeing. Sailors use the Beaufort Scale to gauge wind speed from sea state and conditions ashore. But wind forecasts are often inaccurate, and the wind speed could increase. Going downwind and warm water (meaning I could swim for it for hours if necessary) reduced the risk. If I ended up in the water I would have to get back in and bail out the kayak. My VHF marine radio could be used to contact boaters and the first responder station in Twin Buttes if things went south. A high quality PFD and equipment to get me back in the boat increased the margin for error.

There were literally thousands of these spiders on the shoreline.

Pushing off from shore and within a few minutes and the kayak was in the larger waves. But the kayak surfed the waves easily. As I headed south-southeast, I quartered on them to enhance stability. My 17-foot Wilderness Systems Tempest 170 sea kayak was stable and comfortable to paddle. There wasn’t much paddling necessary as the waves drove me towards my destination.

The Trip in Open Water

I traveled more south than southeast to get closer to the south shore as quickly as I could. The compass bearing was 110 degrees from my starting point to Heaven Bay, based on my map and the GPS coordinates the sailors had given me. Heaven Bay and that part of Lake Sakakawea’s shoreline were new to me. Often one bay looks like the next one on the big lake.

GoPro video from my crossing. Here I am about mid-lake.

After about an hour, I had covered four miles and was about 300 yards from the south shore, but further west from Heaven Bay. This is a common practice when navigating: taking a bearing and then deviating to one side or the other as you travel towards your destination. Once you reach shore, you travel in the direction to recover from your deviation, and you can methodically travel looking for your specific destination. This is exactly what I did and it worked perfectly.

Arriving Near the South Shore

The waves had become smaller as I approached the south shore, and fortunately the wind and hence wave sizes didn’t change during the crossing. I had gambled and won.

The only real problem is that I had trouble connecting the features I was seeing on the south shore with the topographical map. I tried haling the sailors on the VHF radio but they were behind several hills and couldn’t hear me. (Always bear in mind VHF marine radios work best when there is direct line-of-sight to the other radio.) One of them climbed the hill, we connected on the radio, and he provided good directions. With my binoculars I could also see a sailboat entering the bay when I was about 3 miles west of the entrance. I navigated towards a landmark on shore (in this case, a distinctive cliff face).

Arrival at Heaven Bay

The Tempest sea kayak with sailboats Sovereign, Avalon and Czechmate II tied to shore.

Left to right, sailboats Sovereign, Avalon, and Czechmate II.

A large, beautiful, rounded butte guarded the entrance to Heaven Bay. As I turned into the bay, I saw three sailboat masts standing tall and knew I had made it. A few minutes of paddling and here were my sailor friends enjoying the sun and the mid-day heat. It was exhausting and exhilarating, not so much from the few hours of paddling, but more from the adrenaline and stress caused by this being my first big crossing. It was also my first encounter with 3 foot waves in the kayak.

I pulled the kayak up on shore, greeted my friends, then jumped in the water to cool off. After swimming for about 20 minutes, I sat down and did what sailors usually do in port: poured a drink and savored the great company and the beauty of Heaven Bay. I thanked my friends for sharing it with me. After catching up and relaxing for a bit, it was time to get back to work. The gear from my kayak was unloaded. The tent was set up on a small, flat peninsula.

Heaven Bay’s Geography and Geology

Indian Hills and Heaven Bay are in the middle of the lake. Further west the lake turns north towards the huge Van Hook Arm and also south into the Little Missouri arm. It’s ideal for sailing because you can choose the direction you go to optimize your travel based on the wind direction. Heaven Bay is unusual for this portion of the lake in that it is an outcropping of the badlands that dominate the lake shore in the Little Missouri Arm further west. These badlands were formed when ancient volcanoes spewed ash over the swamps that covered North Dakota 65 million years ago. Runoff from ancient mountains added sand and mud. After the buildup stopped, these formations have been slowly eroding to create the badland’s buttes and valleys we see today.

This butte’s face was more pillowy, in contrast to others in Heaven Bay with nearly sheer vertical walls.

The evening was fantastic, with eagles, vultures, and night hawks entertaining us with their flight and the setting sun painting the tops of the butte in a beautiful soft light.

The Trip Back

The next morning I awoke early to take some golden hour photos. After breakfast and coffee, I said my goodbyes to my friends and headed back across the lake to Indian Hills. There was no wind. The lake was still, a flat calm. After three hours I arrived in Good Bear Bay once again, and traveled up it to the Indian Hills take out.

New Indian Friends

While packing up for the drive back home, I met two young Indian men. The Fort Berthold Indian Reservation contains the middle section of Lake Sakakawea where I was traveling. Most of the locals are Native Americans.

While taking my kayak out at Indian Hills boat ramp none of the other boaters were very friendly. This is expected. Fishermen just want to get their boats in or out of the water and get going.

However, the two Indians from Mandaree asked me if I fished from my kayak and said they really liked my boat. I told them the eskimos did use the original kayaks for hunting, and modern sea kayaks were just pale imitations of the original sea kayaks the Indian’s made. The Indians told me how they use their kayaks for fishing. We had a good chat and then shook hands and parted. I need to figure out how to connect more with my new Indian brothers the next time I’m out sea kayaking on the reservation.

Early morning golden hour shot I took around 5am.

Observations

The rounded butte on the right center of the photograph guards the entrance to Heaven Bay. This is the view to the north out of the bay.

Margin For Safety

It could be argued that it was too risky to make this crossing the first day. In fact, many sailors who ply the lake were concerned as they had seen the lake at its worst. As I mentioned, the sea kayak was much more stable in the 2-3 foot waves (and occasional 4 footer) than I expected. I’m not sure what it’s rated for, but I think I could handle up to 5 foot waves if I can quarter on them and the waves are mostly regular. More experienced sea kayakers are welcome to provide their thoughts in the comments.

Gear Improvements

One thing I changed after this trip is the system I used to tie gear down on the deck. There was too much gear not properly tied down and just hanging from my neck, and if the kayak had flipped, it would have been painful getting it all back in place.

For longer trips over open water, a compass on the deck above the bow is a necessity. It’s almost impossible to both paddle and look at the compass often enough to stay on track.

Privacy and Ease of Camping

Two other things struck me about this trip. First I was surprised how easy it is to camp on Lake Sakakawea. There are beaches and flat prairie everywhere, lots of dry driftwood for fires, easy access to water, and privacy. It turns out that fishing boats and power boats are often reluctant to cross the lake, and Heaven Bay is quite far from any boat ramps on that portion of the south shore of the lake. So except for the occasional sailboats, it’s a private place.

Prints of the Photographs

If you would like to get prints of any of these photographs, you can do so by going to this web site.

The Expedition That Reunited a Family

How teamwork during a sailing expedition rebuilt a family

In 2015, my kids were entering their mid-20s and due to divorce, moves, remarriage, and other changes, we were becoming strangers. I needed to own that.

So how to fix it? Answer: A sailing expedition.

My plan? Get them interested (and trained) in sailing with the carrot of a week’s vacation in the Caribbean.

We lived in Minnesota, so warm weather was the right bait.

It turns out through the magic of sailing certifications, training, and the bareboat charter industry, you can fly to the Caribbean, provide a credit card, and you effectively own a 20,000-pound, 40-foot, twin-hulled sailboat for a week.

This trip was the first where I was the captain and my kids were the crew. Sailing and operating the boat were 100% on us.

We were ready for the challenge.

But we had a lot to learn. And we had been sailing through darkness, for years.

Truth is, we didn’t know each other anymore.

We landed in the Charlotte Amalie, USVI, then transited via ferry to the British Virgin Islands where our boat was located.

To be honest, the boat and the environment were very intimidating.

Although we had sailed in the BVI the previous year for training, the boat was now my responsibility, 100%.

All 10 tons of it, and although the BVI is a the world’s most popular cruising ground, the seas get big, 4-8 ft is common.

But that’s the essence of an expedition: you are pushing past your comfort zone into an unknown. Even if it’s known for others. If it’s not known to you, then it’s a (light) expedition.

After adjusting to the boat and it’s idiosyncrasies, the first few days went very smoothly. We certainly enjoyed the 100+ degree temperature difference, from -20 F in Minneapolis in early January to 84F in the BVI.

We enjoyed all the delights of sailing the Caribbean’s finest cruising ground: wind, beautiful anchorages, and sunsets.

But the best part of the trip was the most stressful & challenging, and came on the third day, when we headed to Anegada, an outer island surrounded by reefs.

And this is where things got interesting. What we had experienced so far was idyllic; that was about to change. The skies darkened, the wind picked up, and we had to push through a big storm, big seas, and dangerous reefs to get to the best part of the islands: Anegada, and it’s endless, glistening white sand beaches.

During that part of the voyage, both my son and daughter played critical roles. My son stayed calm and found the outer buoy leading to the safe channel into the island’s only harbor. My daughter learned the right holding strategy from other boats when the visibility went to less than 100 feet (just hold in position, right into the wind, until the squall passes), and schooled us on it.

They tempered my worst tendency: to just stick with the strategy and force things, rather than adapt to circumstances.

We were soon rewarded with a gorgeous anchorage which, post-storm, was awash in rainbows and glistening white beaches.

Since this was an expedition, it required teamwork to complete the mission.

That teamwork reunited my kids and I, the success we had rebuilt trust and love, and the gorgeous natural surroundings cemented that love.

Conclusion

Most travel today is focused strictly on maximum comfort in known surroundings. Expeditionary travel is different: it’s about learning new skills, applying them in strange, unfamiliar environments, and adapting and growing in the process. It should be mentally and physically demanding, at a level that is appropriate for you.

Too much comfort is the enemy: it’s why we have an epidemic of obesity; it’s why being outdoors is so strange to so many of us; and why we focus so much on removing risk from our lives. The pervasive ill health we see today, including mental illness, is partly due to this incessant search for comfort.

By learning sailing skills and then applying them in challenging situations with some risk, a great thing happened. I was able to rebuild my relationship with my kids via the teamwork required in a difficult situation, build my own confidence, and most importantly, get ready for the next challenge.

Light Expeditions, Lake Superior Style

Part 3 of 3

In Part 1 of this 3 part series, I introduced light expeditions, journeys accessible to anyone willing to develop the necessary strength, courage, and mastery. A light expedition is a short, performable (in personal cost, preparation time and duration) journey with a purpose that leverages and develops the righ t skills and confidence while building self-understanding. It also affords opportunities to discover secrets and achieve firsts.

In part 3 of 3, I’ll provide several light expedition examples.

A Personal First: A Week-Long, 120 mile Long Canoe Trip in the Quetico

Cherokee Creek, Boundary Waters Canoe Area Wilderness. Photo by Matthew O’Keefe

My first light expedition was a week-long canoe trip in the Quetico as a teenager with 4 other Scouts and an adult leader. The Quetico is a large wilderness park in Canada that lies on the Minnesota border, adjacent to the Boundary Waters Canoe Area Wilderness (BWCAW). Together these two parks comprise 2.27 million acres. With no development allowed and highly restricted access and use, you can paddle and hike for days without seeing a single person outside your group. Six of us traveled 120 miles in canoes, nearly 20 miles a day, a brutal pace. The purpose of this trip was to put enough miles behind us that we would be alone and could experience the North American wilderness pre-settlement, and we succeeded: we saw only one other group of paddlers other than the days we left and returned.

And that was the last big trip I did for the next 22 years, as I built a career, a company and raised a family. I completely put aside this part of me, the need to explore the unknown and to push my physical limits. A divorce and the loss of my youngest cousin in a freak accident reminded me that my time on earth was limited, and that living life fully with my true friends and family required big changes. At the time it wasn’t exactly clear to me why what I now call light expeditions were so appealing and fulfilling, but they were.

Anegada, British Virgin Islands. Photo by Matthew O’Keefe

I took up whitewater canoeing, sailing, and light backpacking with friends and family because I enjoyed them. Gradually I began to realize what Sir Wilfred Thesiger had said (quoted in Part 1of this series) was the key:

I went there to find peace in the hardship of desert travel and the company of desert peoples… It is not the goal but the way there that matters, and the harder the way the more worthwhile the journey.

Our true nature is to seek out ways to test our strength, courage, and mastery and to achieve some recognition (honor) for that. We’re never really satisfied until we’re suffering through a journey towards a goal, perhaps to be the first to achieve something or to reveal some secret, but more often just to find peace through the effort.

Here are a few other light expeditions to give you a better sense for the concept.

A First: Diving the Edmund Fitzgerald via SCUBA

The Fitzgerald is the best known Great Lakes shipwreck, going down during a horrific storm on November 19, 1975 with all 29 men. Their bodies are still entombed in the ship. The storm that sank the Fitzgerald was one of the worst gales ever recorded on the lake, with mountainous seas reaching 40+ feet. The wreck was studied first via remote cameras mounted on submersibles, and more recently by submarines manned by people.

In 1995, two expert divers drove a truck from Florida to Lake Superior. They were the first to dive the wreck of the Edmund Fitzgerald via SCUBA, taking only 6 minutes to reach the wreck at 530 feet, and 3 hours to return. They only had 15 minutes on the bottom.

Terence Tysall and fellow diver Mike Zee (a former student of Tysall’s) were not foolhardy thrill seekers. Tysall had performed more than 8,000 dives for the Navy, NASA, NOAA and other organizations. Yet, given their extreme skill levels in SCUBA diving plus experience and the simple logistics (they simply chartered a boat to take them to the wreck site for the one day they had a weather window), they were able to make the dive strictly with their own personal resources. The Fitzgerald dive was not only the deepest SCUBA dive ever in the Great Lakes, it was the deepest such dive to any wreck.

From a recent article on the expedition:

The two picked a date, arranged a team and drove a small pickup truck from Florida to Michigan, taking turns sleeping on the oxygen tanks in the truck bed. When they arrived in the Upper Peninsula, the weather gave them a window of one morning when the water was millpond calm for the expedition.

On the lake bed, the pair saw a hull towering above them, illuminated by heavy-duty lights they’d dropped on a camera line. The lights gave them about 60 feet of visibility on the bow area and of the iron ore scattered around the bottom. They floated up the hull side, past the words “Edmund Fitzgerald,” to the pilothouse.

“In an era when people can experience so many things virtually, Tysall said he considers diving a way to maintain a physical connection with history. “The Fitzgerald was another step in that for me,” he said. “I think it was important for us to be there.”

Looking for a Secret: Remote Surf on Lake Superior

Lake Superior is home to hundreds of shipwrecks that testify to the lake’s potential for destruction. It’s southwest coast near Grand Marais, Michigan is popular with surfers. The sheer number of ships sunk there led to that area being called “the Shipwreck Coast”.

Superior is also one of the few freshwater lakes on the planet that generates ocean-sized surf. Surfing requires water big enough to allow swells to develop, which means winds blowing over hundreds of miles of open water. The topography (bathymetry) of the lake floor must also be conducive to forming waves that peel rather than closing out all at once. Stony Point is a popular surfing destination for the lake, yet surfing there began only two decades ago.

Superior’s frigid waters require that surfers wear the thickest wetsuits possible because the best surfing happens in the coldest months, fall through spring. Rocky shores demand solid skills to avoid injury.

Stoney Point is close to Duluth, a medium-sized port town with an accessible airport. However, there is a lot of isolated shoreline in Lake Superior with high potential for surfable waves, yet these are usually so remote and inaccessible they have never been surfed. The problem is exacerbated by the sporadic nature of swells in an inland lake and the fog, high winds, and big seas that often accompany swell-generating weather. To understand these challenges while scouting for solid surf locations, a light expedition was needed.

Ryan Patin preparing to surf Isle Royale’s south shore. Photo by Matthew O’Keefe.

I met two Lake Superior surfers, Ryan Patin and Stefan Ronchetti (we all work for the same software company) who’ve surfed Lake Superior for years, almost since the beginning. They were passionate about finding new surfing locations on the lake, and had already executed several driving trips (light expeditions actually) to surf remote parts of the north shore of Superior in Minnesota. They were excited about the potential for surfing Isle Royale, an island 20 nautical miles offshore in the northern part of Lake Superior. The bathymetry looked very promising in the southeast portion of the island, which was also exposed to hundreds of mile of fetch (stretches of open water over which the wind can blow) from the southeast and southwest.

Matthew O’Keefe and Ryan Patin (left), Windigo, Michigan

Ryan and I traveled to Isle Royale, a national park, in July 2018 to scout potential surf locations. Over the course of three days were able to circle the island in my Zodiac 650 RIB (Rigid Inflatable Boat), mapping and photographing dozens of sites with solid potential. We also practiced getting a surfer in and out of the boat safely, and operating the Zodiac in the shallow reefs where surfable waves happen. Ryan even did a little surfing in a dying swell on our first full day on the island. Since this trip was in the summer, the weather was ideal for testing the logistics and scouting potential sites, but not ideal for surfing, which happens in the colder months.

This light expedition combined my boating and camping experience plus navigation skills, with Ryan’s surfing expertise and talent. Based on this trip, we are considering another trip in October or April timed to coincide with strong surfing potential based on Lake Superior weather forecasts and wave models. We will be able to refine the logistics and safety planning along with focusing on the potential surf sites with the most potential. Perhaps we will be able to find a huge wave where no one else has.

At Beaver Island, Isle Royale National Park.

The links below point to all three essays in this series on light expeditions.

Part 1: The Power of Light Expeditions

Part 2: The Best Skills to Master for Light Expeditions

Part 3: Light Expeditions, Lake Superior Style

The Best Skills to Master for Light Expeditions

Part 2 of 3.

In Part 1 of this 3 part series, I introduced light expeditions, journeys accessible to anyone willing to develop the necessary strength, courage, and mastery. A light expedition is a short, performable (in personal cost, preparation time and duration) journey with a purpose that leverages and develops masculine skills and confidence while building self-understanding. It also affords opportunities to discover secrets and achieve firsts.

What kind of journey’s make you better at being a man from the perspective of Jack Donovan’s male virtues?

And what journeys and skills have good masculine aesthetics and appearance, can be recorded and inspire creative works, and provide the chance to socialize with family, friends, and interesting women?

From my perspective, the pro-masculine skills to master for light expeditions should answer the following questions affirmatively.

(0) Are there low-overhead, low-cost ways of participating almost anywhere? This allows you to practice the skill regularly.

And can you start out with a one-time experience (e.g., bucket list checkoff) and then incrementally grow it to a hobby, from a hobby to proficiency, and from proficiency to mastery?

(1) Does the skill allow practicing to scale, so that practicing on a small scale applies at a large scale as well? Can you experience the skill at both small and large scales?

For example, sailing a dinghy (i.e., a small personal sailboat like the Laser show in this photo) is low-cost and easy to learn; can be done on almost any body of water, large or small; and yet it significantly improves your understanding of winds and waves. Racing dinghy’s also increases your understanding of race tactics for all types of boats and race courses.

(2) Are there upper limits to mastery, and who can reach them? Are there deeply experienced masters of the skill willing to teach you and are they readily available?

Skills to Master for Light Expeditions — Canoeing the Seal River during a forest fire. Photo: Hap Wilson.

(3) Can you get killed doing it if you don’t have a minimum level of mastery? This seriously reinforces the need for strength and courage.

(4) Can you test your courage with the skill by pushing beyond the limits of your current mastery to achieve more mastery, in ways that are prudent and not reckless? By doing so can you accrue honor in some form?

(5) Can the skill take you to remote places that few others get to see regularly? This is key to having unique explorations, and to finding secrets. It also likely means it requires some courage to make the journey there.

Master for Light Expeditions — Outer Island, Lake Superior. Photo by Matthew O’Keefe

(6) Does the skill easily allow you to bring others — friends, family, attractive woman, LTRs, etc. — to see places few others get to see, on explorations that excite the imagination?

(7) Are the aesthics of the skill good and is your expedition worth recording, either in photos, film, paintings or drawings?

(8) Are new technologies continually changing the sport keeping things interesting, requiring more mastery, offering more chances to push your current mastery envelope and the state-of-the-art to gain honor via accomplishing firsts and finding secrets?

What skills emphasize the masculine and male virtues and provide the richest experiences? With these questions in mind, I’ll make my case.

Some Good Skills for Light Expeditions

Sailing: In sailing, more strength and more stamina translates directly to better performance: trimming sails, grinding winches, heaving anchor, and overnight watches all can be performed better with more pure muscular strength and stamina.

Moving heavy boats (or small ones) in big seas requires experience (mastery) and a calm demeanor (courage). As your mastery increases, you can push the envelope on the size of waves and wind your willing to sail in, but new, tougher conditions almost always require increased courage to overcome the sailor’s initial nerves when facing the new situation.

Sailboat Riva completing the Pacific Cup Race, 2010.

New, challenging conditions can happen suddenly (wind gusts, storms, lightning, etc.) and must be faced and mastered. Honor can be won in sailing via achievements in competitive races, either inshore or offshore, and by completing long, difficult voyages against your current level of skill. As your mastery increases, your courage and strength become important as you push the level of difficulty.

Whitewater canoeing and rafting: Strength, courage, and mastery all play a role in successful whitewater canoeing and rafting. Mastery is required to plan properly based on your current skill level across a spectrum of required tasks: logistics, routing, navigation, paddling technique and form, reading and running rapids (or not), lining, packing, camp-craft etc. Depending on the area, you may need to contend with bears (black, polar, or grizzly) or other aggressive wildlife.

Attean Lake, Maine. Photo by Matthew O’Keefe.

Canoeing scales up and down quite well, as experience gained on local waters, even flat water, translates directly to trip expertise. Finding whitewater can be tougher than finding flat water, depending on where you live, but modern air travel and support from canoe and raft outfitters on the best rivers can easily overcome this.

Surfing: Strength, courage and mastery are all critical in surfing, for safety reasons and to be able to push the envelope on the size of waves you can surf. The skill scales up quite well, and the search for the perfect wave or to be the first to surf some remote, beautiful, undiscovered location with huge waves (a form of secret) is intoxicating.

The best Master Skills to for Light Expeditions — Stony Point, Lake Superior. Photo: Surfing Magazine.

In addition, taking family and friends to the beach always gets a positive response, and there is no question surfers are thought of as masculine by many women. Surfing aesthetics are excellent, and it can be practiced with friends and family nearby.

Hunting: Hunting is an ancient sport and one that early men performed in small groups. It requires all 4 masculine virtues, and provides intense socialization with other men. In some cultures, deer hunting is something the whole family does together. It’s rather mysterious but the male bonding the comes from a joint, successful hunt is primordial and seems to tap into something deep in the male soul. Fishing has similar characteristics. Hunting and fishing are also excellent ancillary skills for light expeditions, even if they are not the end purpose of the trip.

Motorcycles: Motorcycles have great masculine aesthetics, are associated with small gangs of men, and are legendary for the variety and depth of the journeys one can achieve with them. Given the dangers to bikers on the open road, it requires and signals a base level of courage to even ride them.

You might think that my emphasis on aesthetics is superfluous, and yet… we are entering a golden age for gifted amateurs to record and artistically express what they have accomplished on light expeditions. Incredibly cheap yet sophisticated digital cameras like GoPro’s, combined with cheap film editing tools like iMovie and Final Cut Pro allow literally anyone to beautifully record their light expedition.

Although this list is not complete, these four skills are excellent for developing masculine traits and performing light expeditions. I hope this essay has you thinking about other potential skills that could be leveraged for light expeditions. The links below point to all three essays in this series on light expeditions.

Part 1: The Power of Light Expeditions

Part 2: The Best Skills to Master for Light Expeditions

Part 3: Light Expeditions, Lake Superior Style