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The Route You’re Looking for is Straight Through the Woods

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The next time you’re walking down a well-trodden footpath through a wooded area, give a thought to the first person (or deer) who took that route.

Some determined being came through here when there was no path. They went straight into the woods. They didn’t circle around to try to find an easier way.

At any time you’re on a path, you can recreate the trailblazer’s ordeal by turning 90 degrees and walking straight into the messy, wet undergrowth that bounds the path now. If you do, you’ll immediately discover how much ease and comfort a path offers. From the first step, the dangers and costs of movement multiply.

For one thing, you aren’t sure where it’s safe to put your feet. You can easily roll an ankle or hook your foot on a low root, so you have to slow down and concentrate, feeling out each footfall.

Discomfort is unavoidable. Wet ferns soak your boots. Nettles scrape your legs. Dirt stains your clothes. It’s laborious and sweaty. And there are bugs. If there are snakes, you won’t have any warning. Moving through virgin terrain is mentally, emotionally, and physically taxing — everything a path is not.

The first person to go that way took on all those discomforts at once. By picking through the tricky terrain like that, they broke off branches and tamped down undergrowth, leaving a slightly less taxing route behind.

A hero

By the time you’re an adult, most of your life is spent traveling on paths of your own creation. In your youth, there’s frequent branch-breaking and ankle-rolling, because everything is new. This friction is unavoidable, although the adults in your life can guide you along.

You had your first nerve-wracking day at school, first swimming lesson, first wobbly bike ride, first awkward date, first time using the floor polisher at work. You had to step carefully, and you still endured scrapes and stumbles, went in circles, and got bitten by bugs. All of this carves paths you’ll use for life.

Years later, you mostly travel along the huge network of paths you’ve made. You have ways of talking to people, ways of conducting yourself at your job, ways of getting things done, ways of coping with uncertainty, ways of eating, sleeping, problem-solving, and learning — worn trails that allow for quick and easy movement.

Come by anytime bro

Quick and easy movement is good, and the larger your path network, the more places you can go.

But there is a paradoxical problem with having all these paths. The more paths you’ve carved out, the less necessary it feels to head into the woods again.

The problem is that well-worn paths aren’t just a little easier to travel on than non-paths. They’re something like ten times easier – ten times less discomfort per mile. Walking a path is so much more attractive than traversing a non-path that we end up following paths even if they’re not going where we want to go.

Say you’re trying to learn a language. You’ve learned things before, so you follow the well-worn paths you’ve always used to learn: you read books, take lessons, and do exercises.

Like a warm bath, even when you don’t need one

However, it doesn’t get you where you want to go. What you really need is to go out and have conversations in the new language – because the goal is to have conversations in that language. But you don’t have a well-trodden, comfortable path for that. How do you even find someone to converse with? Won’t you be embarrassed? You can already see the waiter’s impatience as you try your French on him. You know you will feel like a child.

So you look for a nearby path to take. You go back to the apps and flash cards, and ten years later you cannot speak the language.

It can only work this way, because even the enormous path network of a skilled and experienced adult doesn’t reach everywhere that person wants to go. In fact, none of your paths reach places you haven’t been, because they were all created only by your own feet.

Lurking just off the trail

It’s not effort that’s missing

Extra effort will not make a path go where it does not go. Going to a new place requires the specific act of choosing the untrodden, 10x-more-uncomfortable wilderness route over the clean, inviting path that’s right there waiting.

The path is so much easier to traverse than the woods that it doesn’t even seem like you’re at an intersection at all. And hey, maybe this path winds around to the place I want to go eventually. (It doesn’t.)

I feel like we’ve taken this path before

People try that all the time though – putting in a lot more effort or mileage on an established path, to avoid heading directly (through the woods) to the destination.

You get inspired to write your book, to hit it big. You’re prepared to do more, and go farther, than ever before. You know it’s an ambitious goal and you’ll have to put in unprecedented mileage to get there.

You will never get there though, because no matter how many miles you travel on those paths, they do not go to that destination. You cannot get to a new place if you do not subject yourself to the sticky and unyielding undergrowth between you and it.

Surely our path goes there at some point

Taking the long and fake detour can be such a trap. You can walk a thousand miles looping around the same paths to avoid a one-mile trudge through the woods.

This is because the human mind is guided by a million years of conditioning, screaming at you to STAY ON THE FREAKING PATH. Get away from the snakes and brambles! You have enough food, you have an insulated place to sleep, you aren’t currently gushing blood. SO WHY ARE YOU LEAVING THE PATH?! DO YOU WANT TO DIE?!

The mind will do anything but tell you to enter the woods

The mind will do anything to trick you into staying on the path. You might read this post and feel inspired to try harder, to go farther, to do the thing for real this time. That is also staying on the path. You’ve gone this way before, haven’t you?

The mind also steers you towards familiar — and therefore more “comfortable” — forms of discomfort. Entering new territory requires new forms of discomfort. You might already be accustomed to the discomfort of doing a lot of cardio, or working late nights. But saying no to needy clients is a deep, untrodden wood for you.

View in the direction of your dreams

The kind of discomfort that takes you to a new place always has a quality of uncertainty. You can’t know the exact pains you’ll experience. You cannot get guarantees of how much discomfort will yield how much reward. This uncertainty around the new route will make the mind go “Ugh, no, let’s go any way but this way!”

That feeling is the signal to head into the trees. It’s subtle, but it’s happening all the time. Right when the mind goes “Ugh no not that!” you know you have an option to break some twigs.

It’s the feeling of knowing you should call but you send a sheepish email instead. When you know you should practice scales but then you just play Fur Elise again. When you know you should approach the guy but instead you raid the snack table and make an early exit.

There are more than two ways forward here

Some part of you knows that the direct route to your goal is straight through the seething, sweaty, mosquito-ridden undergrowth. Meanwhile, the mind is shouting at you to avoid exactly that at all costs — even the cost of a taking years-long detour that never gets there.

The route we’re always searching for is straight through the woods.

***

Waiter photo by pressfoto.

Tom Northcott August 1, 2025 at 10:16 am

Joseph Campbell’s interpretation of the Holy Grail story, as I recall, is that the Grail was surrounded by a forest, and that each knight “had to enter the forest at it’s darkest point”.

David Cain August 1, 2025 at 10:32 am

That’s perfect. The aversion isn’t just a thing to learn to overcome when it’s in the way, it’s like a perfect signal for the right place to push forward.

Another way to say it is “The obstacle is the path” — both eastern and western philosophies came up with this same, perfectly unintuitive insight.

Livio Accattatis August 1, 2025 at 10:20 pm

David.

I think this should be more qualified.

There is a necessary evolutionary advantage as to why we are so attracted to the well trodden paths most of the times (yet not always).

I don’t think we should just force ourselves to go through hardships for the sake of it and in the hope it will lead us to something great. It’s like hitting the head against the wall in the hope it will help us.

I subscribe more to an AA-equivalent philosophy: when there is something worthwhile to pursue, and we are blessed with the wisdom to figure what that is, then it’s helpful to prompt ourselves into putting in the effort.

What do you think?

Sally August 2, 2025 at 11:03 am

it’s scary. I’m too old. boy….I have some work to do.

David Cain August 5, 2025 at 9:02 am

I wouldn’t say the point is hardship for the sake of it. The point is to take the direct route to what you really want, instead of trying to get there by sticking to where the resistance is low.

John August 3, 2025 at 12:16 am

This comment was nice to see – I thought of the exact same thing when I saw the title. I’m glad to read it here as a partner to this essay!

Roman August 7, 2025 at 5:13 am

What a great post! It’s very timely as I am in the middle of a book project…funnily enough it’s about the hero’s journey. It has been going well, until I reached the stage of actually scheduling interviews. Then it became real! I have commitments now! And my first anxiety dream in a long time! I don’t NEED to write the book. I am retired and doing well with multiple volunteer projects I am working on. But…the path beckons and I am one who can’t resist adventure.

Cris T August 1, 2025 at 10:53 am

Wow! What a perfect description of all the discomfort of making a change in life. It’s a great indicator for when I begin a task/project that makes me feel uncomfortable but I know it’s what I should do. For me, part of the difficulty is finding the energy to make that change, head in a new direction.

David Cain August 1, 2025 at 4:53 pm

I often feel the same too, and I wonder if the need to “find the energy” is another subtle way of going back to the path. It is *kind* of a way of waiting for it to become easy, for the current patterns to somehow begin to take us to the new place of their own accord.

John August 1, 2025 at 12:23 pm

Great article, struck a cord. Even at 64, I am trying new endeavors that push me off the path. Don’t get me wrong, I love my comfort, but you articulated what I know can lead to greater life fulfillment. Thanks!!!

georgia August 1, 2025 at 2:04 pm

What a delightful metaphor. I love paths, brain science, and trees. I’d love to see you write more about the pathfinder, the trailblazer, the pioneer, and the value of lifelong learning plus the value of working on relationships so you have a friend who explores with you. Write about the joy of solitude, even when you have a friend nearby, “just in case” you need assistance.

Wendy Giffen August 2, 2025 at 1:52 am

IHalf the year I live and work on the Isle of Iona.A tiny remote Hebridean Island( the other half I live in the centre of the City of Cardiff Wales)There was no path that brought me here, though there was two ferrys!A lifetime of caring for others putting myself last and a deep desire to rediscover myself brought me here.I remember sitting on the last ferry with my backpack aged 59 feeling scared and exhilarated all at once.People thought I was crazy but I have never looked back.I love this life.Most of the island is rugged wilderness.Jagged coastline, ancient rocks hills, bogs tufted grass and…mostly no paths or mobile signals! If you fall and if you are found(!) the only way off is my helicopter .There is no doctor on the island.So you tread carefully and are hyper aware of where you have been even if you cant see where you are going.I feel at peace just being one little part of the landscape here .Walking with no path has liberated me.

Terry August 2, 2025 at 2:44 am

This reminded me so much of the core idea in Julien Smith’s book The Flinch… But a kinder, gentler, more human expression of it.

Your analogy of language learning is particularly resonant — I’ve been trying to learn Japanese for 9 years, in exactly the “easy-hard” ways you’ve written about: flash cards, textbooks, multiple apps. But I’ve avoided the one “simple-hard” thing that would make the most difference — conversations. And so I’m in exactly the same place that you said such methods would lead to after a decade. Sigh.

Thank you for articulating these things as evocatively, patiently and generously as you do. <3 I think it allows for more self-reflection than the aggressively-worded, masculine-coded self-help that abounds these days.

David Cain August 5, 2025 at 9:04 am

I think the language example is something most of us can relate to, because most people have probably tried to learn another language at one time or another, and few actually do. It would be interesting to talk to people who pulled it off and people who didn’t — I bet the reasons why would be obvious.

Terry August 2, 2025 at 3:11 am

The metaphor of paths through the forest is powerful!

As a parent to a pre-teen currently formulating his orientation to the world, I find this a very useful shortcut to understand the perils of helicopter parenting. i.e. either:
– pushing your child to follow paths that are familiar to you because you’ve done the work of clearing the path for yourself, without realizing that those might not be the path for them, or
– going in front of them and trying to clear their paths for them, rather than let them do the necessary work of developing the muscles and skill of cutting through the undergrowth.

Kendall August 2, 2025 at 9:43 am

This paradigm strikes me as fitting quite nicely within/alongside Jordan Peterson’s “chaos-order” phenomenological model of reality, which is his interpretation of how evolutionary biology, neuroscience, mythology, religion, and a multitude of psychological disciplines point to the same basic binary (chaos vs. order, explored vs. unexplored territory) underlying all conscious life (including animal life). He’s got the whole political thing going on (which can be off putting to some) but the bulk of his achievement, and the substance of his worldview, are definitely in this more “apolitical” category.

Just one example: because of our profoundly social nature (we are way more social than any other animal – consider the lengthy gestational period of children/adolescents, which is a marker of social dependency), the primary “territory” we interact with, and thus experience as having this dual aspect, is a basically social reality. Consider the primary determinant of survival and reproductive success of human beings (and most mammals for that matter): the capacity to successfully navigate, and thus to benefit from the resources provided by the social network we find ourselves in.

I appreciate your unique articulation of course. It was helpful to me, as much of your work is (I’ve been a regular reader for at least a decade). Thank you for your writing.

David Cain August 5, 2025 at 9:11 am

I hadn’t quite thought of the degree to which much of the challenge of the “forest” is navigating the social world. Many fears are ultimately social fears — the fear of failure, the fear of shame, the fear of making mistakes in front of others. Getting up early and getting to your desk does come with a lot of resistance, but I think yeah maybe most of it is social ultimately.

And yeah, there is basically a dichotomy between path and wilderness. Paths are the habitable order where there was once chaos (at least to the human trying to traverse it).

yorch August 2, 2025 at 10:23 am

I liked and enjoyed the article, thank you!

Deb August 2, 2025 at 8:22 pm

This was the right article at the right time for me. Thank you, David!

Pat August 3, 2025 at 7:25 am

What a beautiful metaphor! I’m working on a memoir for my life, and I’d love to quote you somewhere in the text. OK with you?

David Cain August 7, 2025 at 9:30 am

Sure, that’s fine!

ALH August 4, 2025 at 3:09 am

Thank you very much for this article, I found it a beautiful and helpful metaphor. It also reminded me of a TV programme I saw about the work of an air ambulance crew who rescued a woman who had fallen and broken her ankle on a very easy low level path, who had to be helicoptered out of the area because of the risk of her dying from hypothermia.

Arnold August 7, 2025 at 7:27 am

Be careful on the well followed route, last week I was following my regular mountain bike route, pedalled it dozens of times, a moment of distraction and the result is a broken collarbone. Now treading a new route to recovery and learning some physiology.

Hobrista August 12, 2025 at 10:37 am

So nice article.
I’ve found it useful, especially with mixing it with Hobrista’s Digital marketing

Nobody August 12, 2025 at 3:57 pm

Are you familiar with GeoWizard and his “straight line challenges” on youtube? He attempts to cross countries in an almost perfect straight line. To achieve this his often has to traverse woodlands in the most challenging ways imaginable. He documents his adventures with so much charm, they’re a joy to watch. Highly recommend them. You’ve put a nice philosophical spin on them for me.

Rebel13 August 26, 2025 at 10:09 am

Fortunately or unfortunately, aging will eventually force us to do this. The older I get, and the farther menopause progresses, the more my comfortable paths for doing the most mundane things become overgrown and impassable, and I have to find a new way through. Well, that, or realize the destination isn’t a possible one for me anymore and start practicing death.

David Cain August 26, 2025 at 2:29 pm

Shinzen Young has a saying to this effect: either you go to the monastery, or the monastery comes to you.

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