Discretion may be the purview of a gentleman but hyperbolic modesty is not something to be proud of. I am a competent outdoorsperson, having spent decades and lot of time and effort becoming one. Cast your net across the broad enough range of outdoor pursuits and do them all long enough to learn more than a little and you’ll see that they have a lot in common. People who do them well, whether it’s backpacking or climbing or boating, have figured this core skillset out at least well enough to see the full picture, and can thus cross-apply skills from one to the other. If you’re starting from scratch and have set as a destination the point where the necessary skillset for any given outdoor adventure is both not a mystery and reachable, then read on.
1) Learn to rock climb
Experience ice climbing is handy but the technical, physical, and mental aspects of rock climbing are the best starting point for anyone seeking outdoor expertise; even if climbing itself holds little interest and especially if you’re acrophobic. Secret: everyone is afraid of heights, just like everyone is afraid of death, failure, and grizzly bears. Learning to manage rational, foundational fears is not a basic outdoor skill, it is a basic life skill, and I know of no better way to do it than while climbing. Not sport climbing either; proper, traditional climbing. A good goal would be to become a solid 5.9 climber before you retire, solid meaning you could onsight 95% of the climbs given that grade in the US, be they offwidths at the Creek or in the Valley, runout eyebrow slabfests at Looking Glass, or sandbagged thuggy roofs in the Gunks. Take moves you know are at 80% of your capacity, assume that estimate is 10% short, then put those moves at the top of pitch four 35 feet out from a blue alien and #5 stopper, and you’ll figure out how to function well, even (especially) when you really don’t want to. Over the years quite a few people have gotten annoyed with me when, upon being faced with a chossy traverse at the end of a stressful and tiring day, I tell them not to slip or kick any rocks loose. How do you guarantee that, they ask? The same way you don’t drive into the ditch in the way to work everyday: you don’t fucking do it. Humans have an amazing capacity to get the job done when it needs to be done, and being able to flick that switch at will is vital to every outdoor pursuit I can think of.
Mastering the various knots and having a couple thousand hours of mechanical practice at properly weighting bad flakes and wet moss smears are good, too.
2) Learn to walk
A good second step, because while most climbers get pretty good at some aspects of walking while carrying heavy packs up poor approach paths, the I-won’t-hike-unless-it’s-to-a-cliff mentality endemic to climbing will not teach you to embrace walking for the glorious, instinctual activity which it is. Thankfully the educational perscription here could not be simpler: get good at walking by walking a lot. The particulars of Gladwell’s 10000 hours thesis may be pop rubish, but the raw math works out in his favor. Learn what a 30 mile day on good trail feels like, then what a 40 mile day feels like. Then learn how a 15 mile day across slickrock and sand is way harder than either. The end result should be an intimate knowledge of fatigue, how far you can push beyond certain levels, and what it will cost you in the days after, as well as a bulletproof 2.5-3.7 mph trail autopilot and a good injury-preventing foundation of strong connective tissue.
3) Learn to navigate
Proficiency at navigating cross country is akin to learning to write poetry like Emily Dickinson or e.e. cummings; first you painstakingly learn all the rules in exacting details, then you ignore as many as possible. For the beginning map reader topo lines are little more than a printed jumble, just as for a beginning writer the effects of words and sentences are random. When you’ve correlated enough lines on paper with terrain, you can keep the compass in your pack almost all of the time, and bring fewer and less detailed maps. Just keep in mind that being able to shoot a close bearing, just like the ability to write a sonnet, never goes out of style.
Map and compass work is one area where good instruction really makes a difference, as does field practice, and is money well spent. Running orienteering courses in Boy Scouts, looking for numbered milk jugs in thick mid-summer Ohio woodlands, is a fond childhood memory and was time very well spent. This foundation will blossom into deep knowledge when repeatedly tested year after year on trip after trip, ideally in as many different terrains as possible.
Shameless plug: my on-trail route finding article remains (in my opinion) the best technical thing I’ve ever written. I’ve learned a lot since I wrote it, and there’s hardly anything I’d change.
4) Learn water
Waterways are, rightfully, regarded with fear by many backcountry travelers. Achieving expertise in wilderness travel, even if you never use a boat, requires becoming informed enough to know what to fear about water and why.
Take stream crossings as an example. These can generally be broken into three levels: easy ones, scary looking ones which aren’t actually that hard, and dangerous ones. Being able to cruise through most of the second category has more to do with confidence than anything else, which in turn has mostly to do with familiarity. Spending a lot of time wading and boating is the key here, and of all things fly fishing has done the most to build my abilities. So get out in the water on foot and in a boat, learn to read water in both circumstances, and build a body of experience from which the least fear-based decisions can be made.
5) Learn the system
Outdoor activities take place in the modern world, and all the knowledge and skills which can fit into one brain are of purely academic worth if they don’t get out and help shoes get muddy and eyes see astounding things. Familiarity with what makes a good route and a good trip, everything from planning with maps and sat photos to getting applicable permits and finding the best post-trip eats, is as much the hallmark of experience as not making wrong turns through densely forested valleys. Finding good camps, hitting the rivers at the best levels, and bringing close to the right clothing and shelter all make a good trip into a great, and there is no higher satisfaction than going to a brand new area and nailing a creative, varied, new route.
Lastly, I would counsel patience with all of these things. Outdoor adventure is a discipline, in that intelligent shortcutting of the learning is only possible and desirable to a limited extent. Beating your head against the wall with the same mistakes year after year is no good, but the effort in/reward out correlation is a pretty damn linear one, regardless of discipline. Adventure is a lifelong enterprise; better to learn things well the first time, given how much there is to see.
Bedrock & Paradox 
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